Hearing stories of the legendary parties that Victor had been throwing when he was supposed to be writing finally pushed his publisher past the breaking point. “We’re going to sue you,” they said. “You have six months to deliver, or we’ll fine you 1,000 francs ($13,000 in modern dollars!) a week.”

So Victor came up with a solution: He had his butler lock away all his clothes until he’d finished the novel. He couldn’t attend or host social events without risking embarrassment (and arrest).

It worked! He wrapped himself in a large gray shawl (gotta stay warm to write), and set pen to paper every day until the novel was finished – two weeks before the date of the first fine.

The solution to procrastination is nudity, you heard it here first.

But fortunately, scientists have learned a lot more about the neuroscience of procrastination in the last ten years, to say nothing of the last 150! Thanks to the techniques that have come out of that research, you can procrastinate less AND keep your clothes on.

What Science Used to Think

I’m a lifelong procrastinator. I have vivid memories of playing Fantasy General until 1am when I was supposed to be writing my English thesis in high school, and despite dozens of attempts to break the habit, I still procrastinate today.

I’ve done two deep dives into procrastination research before, trying to find something that would transform me into someone who starts the work the day it was assigned. I tried once in college, spending a couple weeks I really should have been working on my projects diving deep into the research. The team and I tried again in 2010 when we created the Email Game at Boomerang, hoping that gamification could short-circuit the part of my brain that loved putting things off (it kind of did!)

Back then, the conventional wisdom was that procrastination stemmed from lack of time management skills and poor planning. The solutions involved getting better at making schedules and breaking up projects into the right sets of smaller steps.

None of it worked, and in retrospect, it was obvious that it never would.

I know how to make a schedule. It’s not hard to block out “6:00-6:30 PM: dinner, 6:30-7:15 PM: work on part one of project.” The problem came at 6:30 PM when it was time to start working on part one of project. Suddenly, I discovered articles on the internet that needed reading and bookshelves that needed organizing. I just couldn’t make myself do the work. Improving my planning skills was a solution to the completely wrong problem.

What Science Knows Now

Research from the last five years reveals something completely different: The fundamental issue in procrastination isn’t failures of scheduling or planning at all. It’s about emotional regulation and avoiding bad feelings.

When you’re not doing something, it’s because the task makes you feel a negative emotion, like anxiety, fear, stress, or boredom. So you avoid the task to avoid that feeling. And things like social media, with an instant drip of dopamine, have made it easier and more tempting than ever to procrastinate.

Neuroscience shows that procrastinators tend to have brain structures that are more susceptible to this effect for a number of reasons:

1. Larger fear center (amygdala): Procrastinators feel the pain and fear of tasks more intensely than non-procrastinators.

2. Weaker connection to the prefrontal cortex: The planning and emotional regulation part of your brain can’t effectively override the fear center because the connection between them is weaker.

3. Reduced error alarm response: Non-procrastinators’ brains light up more intensely when they think about the future negative consequences of not completing a task well and on time. Procrastinators’ brains light up more intensely thinking about the current, at-this-moment pain rather than the future consequences.

Real Solutions, Not Colored Pencils

The dividend from all this research is a set of techniques that genuinely can shift us away from procrastination.

Solution 1: Borrow From Acceptance and Commitment Therapy (ACT)

This approach is particularly effective for neurotic people who procrastinate due to anxiety – basically, people like me!

Since we recorded the podcast episode, I’ve been trying these techniques, and they’ve genuinely been helping. If you procrastinate out of an unsettled feeling that your work won’t ever get done or won’t ever be good enough or that you will take the wrong approach, it might work for you too.

ACT, or Acceptance and Commitment Therapy, is a technique used by therapists to help patients work through all kinds of issues. And I am absolutely unqualified to use the technique as a therapist or teach anyone how to use it that way. But to use these ideas to take on procrastination, you don’t need a therapist.

The core of this approach is that when you’re feeling a negative emotion, you don’t have to change your behavior because of it. You can feel the negative emotion and do absolutely nothing about it.

The metaphor the researchers used is surfing a wave. The feeling will come, you’ll observe it and name it, and it will pass. Meanwhile, you can wait it out, or just keep working through it.

Research from a consortium of universities in the Netherlands gave PhD students a 30-minute-per-week self-guided web course on using ACT principles for procrastination called the Get Started Program. After seven weeks, plus two brief sessions with a coach (not a therapist), the students saw a 30% reduction in procrastination that persisted after the program ended.

The approach rhymes with Cognitive Behavioral Therapy (CBT) in the sense that you focus on thinking about your feelings, but it’s subtly different. With CBT, you’d typically analyze whether the anxiety you are feeling is rational or based on a distortion of reality. With ACT, you skip that step entirely. You don’t ask if the fear is grounded in reality. Instead, you:

1. Acknowledge, observe, and name: “I’m feeling anxious right now.”

2. Even if it feels uncomfortable, you do the thing anyway as you wait for the feeling to pass. If it’s too uncomfortable, wait in stillness and continue to observe until is passes enough for you to get started.

It kind of matches one of Moah’s sayings about her childhood: Cry and do it anyway.

According to the study, practicing these techniques helps you become more comfortable with negative feelings and with operating normally even in their presence. You’re rewiring the neurons so the fear center doesn’t control you as much, so it gets even easier with time and practice.

Solution 2: Mental Contrasting and Implementation Intention (MCII)

This approach works well for people with lower conscientiousness who just need help with follow-through - like my cohost, Moah!

To use MCII, you need to pre-plan for obstacles that could come up and how you will work around them. There are three steps you’ll want to follow.

Step 1: Define Outcome in the form of “If I accomplish [X], the best reasonable outcome is [Y]”

Planning out the desired outcome as an if/then statement crystalizes the benefits in your brain and helps you with the next steps. At this stage, you want to think about the best reasonable outcome rather than thinking about what could go wrong.

Example: “If I go to bed on time, the best outcome is I’ll be in bed by 11 PM and get eight hours of sleep, so I’ll wake up with energy and no brain fog.”

Step 2: Define Obstacles “The main things that could stop me are me are [A, B, C]”

If you define things that could prevent you from accomplishing your goal in advance, you can plan for how to short-circuit them up front. Listing internal obstacles are especially important.

Example: “The obstacles to me going to be on time are that: social media is addicting, and I lose track of time, that I won’t have my teeth brushed on time, and that one of the kids will need something”

Step 3: If-Then Plans “If/when the obstacle appears, I will [do this specific thing]”

Example: “At 10:30 PM, I will turn off internet access on my phone. I will brush my teeth right after I eat. I will plug in my phone if I need to comfort a nightmare-frightened child”

When you know exactly what you need to do as soon as something comes up, it makes it easier to follow through than if you have to react in the moment. And even if something comes up you didn’t foresee, the planning you already did gives you an edge. As the inventor of the Eisenhower Matrix once said, “Plans are useless. Planning is indispensable!”

Studies on revenge bedtime procrastination (more later!) found this approach very effective, and it only takes about three minutes of planning to see the effects.

Solution 3: Temptation Bundling

This is the easiest quick win in our toolbox. Pair something you don’t want to do with something enjoyable, making the task feel good RIGHT NOW.

Katie Milkman’s research showed that people who only allowed themselves to listen to addictive audiobooks at the gym increased their gym attendance by 10-15%, and the effect lasted beyond the study period.

Hate writing performance reviews? Moah does it while getting a pedicure.

Solution 4: Commitment Devices

If you tend to honor social pressure and external commitments more than internal ones, a commitment device might be just the thing to help you beat procrastination.

Remember Victor Hugo and his locked-away clothes? That’s one commitment device! External consequences and accountability often can provide the extra motivation you need to tackle something you’ve been putting off, even when you’ve tried everything else. Some devices that I’ve used include a midway project review with a senior colleague or my boss that require me to have started on the thing so I have progress to show, asking a friend to check in, or using something like Flow Club to provide faces who might wear disappointed expressions if I don’t do what I said I would.

Procrastination That Isn’t Procrastination

We’ve talked a lot about why we procrastinate, but I want to make sure to note that not all forms of delay are really procrastination. There are two cases where what feels like procrastination is actually smart, and it’s important not to ACT and MCII your way out of them.

Creative Incubation

When you’re working on a creative task, what looks like procrastination can actually be your brain doing background processing. Right before the deadline, you’ll come up with a spurt of what seems like inhuman creative productivity. Behind the scenes, your brain was working on it unconsciously the whole time.

Mozart once took this to an extreme. He delayed and delayed on writing the opera Don Giovanni, so much they had to delay the opening. The morning of the already-delayed premier, his wife Constance woke him at 5 AM to remind him: “Hey, you have an opera opening tonight. Maybe you should finish that?”

He wrote from 5 AM until the performance. When the musicians got their music sheets, the ink was still wet. They never had time to practice. But the opera is one of Mozart’s most famous works and widely considered one of the greatest operas ever written.

Mozart wasn’t “just” procrastinating. His brain was giving itself time for incubation.

Strategic Delay

Sometimes people mistake prioritization as procrastination. Everyone has some “one day maybe I’ll get around to this” projects that have never made it to the top of the pile. And that’s because they never became as important as the projects that did.

Here’s an example from Boomerang’s history.

Google typically announces API changes 6-18 months in advance. Early in our company’s history, our CTO Mike (our co-founder who is by far the most conscientious of the three of us and who does not have a procrastination problem) would start work on preparing for the changes soon after they were announced.

Then, a month before the deadline, Google would often say, “Actually, we’re not ready, it’ll be another 18 months and work a little differently than we announced” or sometimes cancel the change completely.

Though Mike’s cortisol level went up a bit1, we learned to delay working on this type of project until much closer to the deadline. By then, we had more confidence that the changes would happen as as announced, and someone else will have already figured out the path and written about it, so we could do it faster.

We do the same thing with our company’s tax returns. We file with an extension every year, even though we’re usually owed a refund, which means we forego some interest income. Why? Because the product and strategy work we do in Q1 every year has way more impact on the company than the interest we’d earn on a small tax refund. That’s using time wisely, and even though it looks similar, it couldn’t be more different than scrolling TikTok because we can’t face doing our work!

The New Doom Loop: Revenge Bedtime Procrastination

Just what we needed - a new kind of procrastination!

“Revenge Bedtime Procrastination” (delaying bedtime to gain a sense of control) is a phenomenon that’s emerged since the smartphone. It was first described on the Chinese social network Weibo, among workers on the “996” schedule (9 AM to 9 PM, six days a week). The phenomenon is also common in Western societies, especially among parents of small children, college students, and anyone else who works too much.

It’s called revenge bedtime procrastination because it’s getting revenge against the people who control your schedule by taking it out on your own body. Instead of going to sleep, we stay up scrolling on our screens, extending our limited free time by sacrificing sleep.

Revenge bedtime procrastination creates a vicious cycle:

1. Revenge bedtime procrastination (scrolling on your phone late into the night instead of going to sleep)→ not enough sleep

2. Not enough sleep → less executive function the next day

3. Less executive function → more procrastination on other things

4. More procrastination → less caught up → less time to yourself

5. Less time to yourself → more revenge bedtime procrastination

Research shows that 74% of people go to bed later than planned at least once a week. And three habits correlate strongly with procrastination in other areas of life: not getting enough sleep, not getting enough exercise, and (surprisingly) skipping breakfast. So if there’s one place to stop procrastinating first, it’s probably keeping a consistent bedtime.

Applying the Tools

Don’t procrastinate on getting started using these techniques! But if you do, one important thing to keep in mind is that you need to extend grace and forgiveness toward your past self while you’re trying to make changes like this.

One study found that students who forgave themselves for procrastinating on one test procrastinated less on the next test. Kicking themselves just created a doom loop.

It is more possible than ever to get a handle on procrastination. All of these approaches showed results in randomized controlled trials. The effects lasted beyond the initial intervention for all of them. And best of all, these new anti-procrastination tools don’t require a behavioral step change. You don’t need to start a full ACT therapy program or spend a month reworking all of your workflows.

Just start paying attention when you feel the urge to procrastinate and observe and name what you are feeling. Or just spend a minute thinking through what mental obstacles will keep you from your goals and how you could work around them. Or, if all else fails, go for a pedicure and then throw away all your clothes!

To hear the full discussion, listen to Episode 18 of Less Busy Lab. Have questions? Want to share a procrastination story or a technique that’s worked for you? Send them to questions@lessbusylab.com

Microsoft’s massive scale and distributed customer base gives them data that nobody else has. And these reports have been both timely and well-executed, providing the most up-to-date information about work trends we’ve seen.

Unfortunately, every single slide in the report is about AI. And to be fair, AI came a long way in 2025 (and looks poised to go even further in 2026), but we were hoping to get to talk about new trends in hybrid work, or how chat and remote meetings have continued to evolve. But there’s still enough in this report to be interesting, and we’ll supplement it with some non-AI topics from our own product usage data that might surprise you!

The Good News: AI Can Make Us Better

The most optimistic finding in the report comes from a Harvard Business School study conducted at Procter & Gamble. Researchers put about 700 people through a product development brainstorming exercise and tested four different configurations: individuals working alone, individuals working with AI, two-person pairs (one from commercial, one from R&D), and two-person pairs working with AI. Judges evaluated all of the ideas using measures of novelty, practicality, and potential business impact.

The two-person teams with AI assistance came up with the best ideas, by a solid margin. So AI helped make people better, but as an extra teammate, not a replacement for either of the humans.

This suggests AI’s biggest value is still augmenting human teams, which fits the “this is a new productivity-enhancing tool in our toolkit” story that has taken us from subsistence farming to modern life. Though past technological shifts have been disruptive, we’ve gone through them before and come out wealthier and with better lives on the other side.

For those of us worried about AI replacing workers wholesale, this is reassuring.

But AI Is Already Better Alone, Sometimes

That said, the report includes some research that makes me feel both anxious and excited at the same time.

One of the most credible-seeming studies referenced in the report looked at doctors making diagnoses across a variety of specialties and evaluated how frequently the diagnoses were correct. When doctors worked alone, they got the right answer 75% of the time. When they used AI optimally (making their own diagnosis first, then using AI to challenge their assumptions rather than just provide answers), accuracy jumped to 84%. That’s great news for AI-assisted medicine, and that was the lead message in the report.

But looking past the headline and diving into the data showed something even more interesting: AI alone got the right diagnosis 90% of the time.

So if you’re a patient, this is (probably) very good news! After all, AI medicine was able to improve diagnosis accuracy from 75% to 90%. That means you’re less than half as likely to get treated for the wrong thing, which is an unequivocally better outcome.

But if a core competency of doctors, one of the hardest professions humans have, can be done better by computers, what else will be left? We’re certainly not at the point where human doctors are obsolete, but something that seemed impossible even a year ago suddenly seems… maybe on the horizon? It’s a stark reminder that AI capabilities are advancing fast.

Consider the Source

Before we take all these findings as gospel, it’s worth noting where the data comes from. A significant majority of the AI-favorable statistics in the report are sourced from OpenAI, Anthropic, or Microsoft’s own Copilot research. And all of these companies have a lot of reasons to want you to believe that you need to buy AI tools.

So what I didn’t see anywhere in the report were many of the studies showing that AI costs people extra time. And those exist. We talked in a previous episode about studies showing the overhead of reviewing AI output, checking for hallucinations, and fixing subtle errors sometimes taking 15-20% more time than just doing the task outright.

Though the headline from Microsoft’s report was basically “AI saves everyone time on almost everything,” the reality is not so clear. So I’m going to take the optimistic findings seriously, but not take them as gospel.

A Non-AI Trend: More Meetings than Ever

In past years of the report, Microsoft’s team summarized research that showed how people work, which tools they use, and how they spend their time. This year, we didn’t get any of that, so we’re going to take a quick break from the Future of Work report to discuss some findings from a study we did from our own Calendar Insights tool in Boomerang.

During the pandemic, it felt like I lived in Zoom. Every time I wanted to talk with a colleague in real-time, I had to put something on the calendar so we could join a virtual meeting. Admittedly, lots of work that might have been done in meetings or work sessions got done over Slack or Email instead, but when even game nights with friends were virtual, it certainly felt like we had more meetings.

But the data showed us the pandemic actually triggered a decline in the number of meetings that were on our calendars. Turns out, a lot of those meetings could have been an email! And when it was time to mask up, they were.

But like many pandemic trends, this one’s reversed. We’ve since added all those meetings back, plus more. There were more meetings on average in 2025 than there have ever been before.

Like entropy in the universe, meetings trend toward infinity.

We also looked at trends for when people schedule the most meetings. Conventional wisdom holds that the summer tends to be a dead time, with kids out of school and vacation on everyone’s mind.

The data shows that “summer” - at least as far as people’s meeting habits, really means “August.” June was actually a busier meeting month than average, with July in the middle. December, as you might guess, had the fewest meetings of all due to the holidays.

Opportunities Are Knocking

The report did a nice job of identifying a few areas that are going to need new workflows or new tools to help us work more effectively with AI.

The first opportunity is multiplayer AI. Right now, most AI tools are designed for individuals. You have your ChatGPT session, your Claude code instance, your Gemini app. These are personal. They don’t know what your teammates are working on, and they can’t participate in group dynamics. And while you can share chat histories with someone on your team, there’s not a good way to collaborate on prompts or provide extra context in either direction.

The report points toward a future where that changes. Imagine AI that participates in meetings thoughtfully, knowing when to interject and when to stay quiet. That AI could know when to be a devil’s advocate, when to mediate a disagreement, or when there’s something going on in another team that would have a meaningful impact on the discussion. That AI could also handle meeting handoff, summarizing what finance needs to know from what was discussed in the marketing meeting without anyone having to write it up. The research suggests people are surprisingly open to AI playing these roles, as long as it does so respectfully.

Another major opportunity is making tools and workflows for reviewing work at scale. For most of human history, creating things was harder than reviewing them. It took longer to write a report than to read and critique one.

With AI, that’s flipped. AI content creation is fast. You can generate a grammatically correct 10 page document in seconds. This creates a new problem, which the report calls “work slop.” Even content that is pure garbage now looks professional, so our shortcuts for identifying high quality work no longer serve us. We’re going to have to figure out how to work in a world where the bottleneck is now identifying quality and reviewing details.

For example, in software, there are literally thousands of code editors, likely tens of thousands. But good code review tools are few and far between. The industry has invested heavily in making production easier, but the tools for reviewing code output are still primitive. Now that AI is writing a lot of the code, the value of a great code editor has diminished a lot, and the value of a great code review tool is much higher. Hopefully we’ll see a lot more effort put into tools for code review as we move forward!

Tips of the Week

Though a lot of the report was theoretical rather than practical, there were a couple of useful takeaways for interacting with AI that I haven’t seen before.

One useful finding: the practice of “grounding,” or giving extra context to AI in your prompt, improves AI outputs.

AI chatbots are designed to give you a lot with little effort. Type a short question, get a comprehensive answer. That’s the interaction style that creates the most engagement. But it’s not the style that creates optimal output for you. The more context you give AI, such as what you’re trying to accomplish, what constraints you’re working with, what you’ve already tried, what information you have, etc. the better results you will get.

If you’re not sure what’s relevant, ask the AI to ask you questions. “I want to write a proposal for X. What questions would you need answered to help me write it well?” Let it interview you first, then ask for the actual proposal. AIs don’t behave like this by default, because it increases friction and reduces usage. But when the output quality matters, it’s a good technique to keep in your back pocket.

The report also talks about how to engage with AI while still building/maintaining your skills. Again, it’s not as easy as type in a short question and get a comprehensive answer - you have to use the AI to challenge your own thinking rather than outsourcing the thinking to it.

But “deskilling” is a real risk for anyone incorporating AI into their workflow. One of the studies cited in the report showed that doctors who used AI assistance, when later tested without it, performed worse than before they started using AI. Their diagnostic skills had atrophied from disuse. Doctors who used prompts like “Here’s my approach. What are the weaknesses in this thinking?” did not see the same effect.

The bonus is that this approach also produces better outputs. AI is trained to be agreeable. Ask “Is this good?” and it will tell you that you’re brilliant. Ask “What’s wrong with this?” and you’ll get genuinely useful feedback.

Whew! That’s hopefully it for AI for a little while. We hope y’all are keeping your New Year’s resolutions into February.

To hear the full discussion, listen to Episode 17 of Less Busy Lab. Have questions? Send them to questions@lessbusylab.com

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It’s the second Friday of January. If you made a New Year’s resolution, today’s the hardest day of the year to keep it.

Back in 2019, fitness app Strava coined the term “Quitter Friday” after analyzing their user data. They found that the second Friday of January shows the biggest drop-off in activity from the New Year’s bump. People are tired. Happy hour is calling. The gym can wait until Monday!

If you can push through today, you’re way more likely to make it another week. And another. And another. Until that resolution becomes an actual habit. So if you’re waffling on your resolution, let this be the signpost you need to stick with it!! Here are a few more ideas around habits and goal setting to help you get through Quitter Friday without quitting.

The “What the Hell” Effect

One of the biggest threats to your resolution is what researchers colloquially call the “What the Hell” effect, best pronounced in a thick Southern drawl.

In a famous study conducted at Northwestern University in 1975, researchers set up “an ice cream taste test” experiment where some of the participants were randomly chosen to drink a milkshake before eating ice cream. The researchers weren’t actually interested in whether or not drinking a milkshake changed the way the ice cream tasted; that was just a pretense so they could surreptitiously study the amount of ice cream people were eating.

Overall, the results were boring. People ate less ice cream if they drank a milkshake before they ate ice cream. Duh.

But the participants in the study who happened to be on a diet at that time did not behave the same way! Instead, dieters who first drank a milkshake ate more ice cream than the dieters who had not pregamed with a milkshake did! The thinking was probably something like: “I already had a milkshake. My diet’s ruined for the day anyway. What the hell, let’s have all the ice cream I want!”

After thinking about my own experiences with breaking diets, I’m not that surprised. When I’ve been trying not to snack, and I already lapsed with a cookie, I was way more likely to reach for a second one than I was to reach into the bag in the first place. What the hell, if I’m eating cookies why not eat a lot of them? Same for workout habits - as soon as I’ve “broken the chain,” I’ve failed, so why bother anymore?

Beating Perfect-or-Nothing

There are, fortunately, a number of ways to fight the “what the hell” effect and keep making progress toward your goal even when life gets in the way.

Structuring your goals to build in flexibility is one good option. Instead of “I will run every single day,” try “I will run five days a week.” That way, when you miss a day, you haven’t failed at all. And when you hit a six day or seven day week, it will feel really good and reinforce the positive feelings you associate with the goal.

There’s no character limit on how long a goal can be. If you need to interrupt your goal during a work trip, rewrite the goal to say that you will run when you’re home.

There’s also compelling research that shows that being kind to yourself makes it way more likely that you’ll pick back up your goal after a slip up. Beating yourself up doesn’t make you more motivated. To me, this is always a fine line to walk. Too much self-compassion makes me complacent, but apparently there is a Goldilocks amount. So instead of thinking that you’re “a weak person who can’t stick to anything,” think of yourself as “a runner who didn’t run today” or “a healthy eater who took a cheat day.”

The structure I used there was intentional. Incorporating your goal as a (small) part of your identity (“I am a runner” or “I am a healthy eater”) has a lot of positive knock-on effects. Aside from making it more likely that you will keep your goal, it also helps make your overall psyche more robust. And the part of your identity that’s associated with this goal doesn’t have to change because of one bad day.1

Finally, as we mentioned last time, preplan your comeback. Before you even slip up, decide what you’ll do when it happens. What’s your recovery plan? If you miss your morning run, what will you do instead?

The Quitter’s Comeback

If you’ve already fallen off the wagon, don’t abandon hope. Today is the best day to restart. It’s Quitter Friday - the gyms are already empty again!

But before doing exactly the same thing that didn’t work last time, take a few minutes to think about what went wrong. Was your trigger not strong enough? Was the habit too ambitious? Did life just get in the way? Then, use what you’ve learned from the lapse to build a better plan.

Maybe your trigger needs to change. Maybe you need to make things more visible. Or maybe you need to make the habit tinier or structure your environment a little bit differently so that it’s easier to do.

Whatever you decide, improve your habit and restart it. You’ll be glad you did in a few weeks.

Sleep and Reminders

If you’ve already optimized your triggers and your behaviors but are still finding it tough to keep your resolution, there are a couple other factors to consider.

First, there’s evidence that our sleep affects how well you can build habits. The light sleep stages help stabilize procedural memory, which is the kind your brain uses for skills and routines. Better sleep means stronger neural pathways for your new habits. The paper is kind of dense (what’s a sleep spindle? do you wind sleep threads on them?) but if you want to go deep, be my guest!

There’s also some compelling research around structuring reminders, in case you’re using technology to help you with your triggers. The research shows that the most effective technology-based reminders try to help you remember your trigger rather than your action itself. So, if your trigger is to run after lunch, you’re more likely to keep the habit if you set a reminder at the start of lunch that says “after lunch, go run!” rather than setting a reminder at 12:30pm that says “it’s time to go running!” when you’re supposed to actually head out. Neat!

Tip of the Week

If you’re still on track with your resolution, congratulations. Stay the course. Watch out for the “What the Hell” effect and remember that one slip doesn’t erase your progress.

If you’ve already fallen off? Welcome to the Quitter’s Comeback, picking up where you left off with better information about what works for you.

Either way, take a moment today to think about how your resolution is going and to update it to make it a little bit more robust in some way. If you don’t have any ideas, maybe incorporate a technology-based trigger reminder for the next few weeks, until the habit is fully cemented.

Don’t quit on Quitter Friday!

To learn more, listen to the full podcast episode.

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In general, people are deeply pessimistic about resolutions. We all know that guy who sneers about how “the gym’s totally empty by February 1, har har har!” Surveys show that only 3% of people believe New Year’s resolutions in general are very likely to succeed. Another 20% have some optimism, thinking resolutions have a “somewhat likely” chance of working out.

But when you ask people about how their own resolutions went, you get a dramatically different answer. After a year, 55% of resolution-makers feel like the resolution was a success in at least some way. And 18% report that their resolutions were a “total success!”

That gap tells you something important. Even when people don’t fully hit their goals, for example losing three pounds instead of the seven they set out to lose, they still moved in the right direction. The resolution gave them a push they wouldn’t have had otherwise. And they’re three pounds lighter than they would have been without it! That’s a big win!

Research on “Dry January” found something similar: people who committed to a month without alcohol reduced their baseline consumption for the rest of the year, even after they started drinking again. So even if a resolution isn’t a permanent solution or doesn’t solve all of your problems, it can trigger a lasting positive change.

Over the last ten years, I’ve had about ten “at least successful in some way” resolutions. Here’s hoping I can take my own advice and make this year “totally successful!”

The Fresh Start Effect

About 30% of people make a resolution on New Year’s Day in any given year, dramatically more than on any other calendar day. The most common resolution is saving more money, followed by a big cluster of health-related goals: exercise more, eat better, sleep better, be healthier. After that comes a bouquet of intellectual aspirations like learning something new, reading more books, or picking up a new language.

Katie Milkman, a professor at Wharton, wrote a book called How to Change that explores why certain moments make us more likely to attempt transformation. She calls it the “fresh start effect.”

Essentially, planning to change is most likely to work if it’s linked to what she called temporal landmarks. Temporal landmarks can be any point in time that carries special meaning. New Year’s Day is the biggest of these (after all, we start scrawling a new number at the end of all of our dates after we pop champagne), but it’s certainly not the only one. Your birthday works well. The start of a new month works a little bit. Even the beginning of a new week shows elevated rates of people trying to start something.

One of my favorite “landmarks” the research discusses is coming back from vacation. In addition to its temporal significance, vacations naturally provide a period of time where habits are necessarily different. You’ve been out of your routine, so you’re not fighting against the momentum of what you did yesterday. You’re starting fresh automatically.

The fresh start effect explains why people want to start things at these moments, and the data shows a slight boost in success rates when you begin at a landmark. But starting is relatively easy compared with following through.

The Problem with Resolutions

Most resolutions that fail are vague intentions, not specific behaviors. “Get more fit” is a worthy aspiration, but it’s not a good resolution. It’s not something you can actually plan to do on a Tuesday morning. And what does “get more fit” mean anyway? To me, maybe walking 30 minutes a day would count. To my crossfit-obsessed friend, a 30 minute lunch walk wouldn’t even register as exercise.

The resolution is too vague to act on, so it just floats around in your head until you forget about it. So a good resolution needs to tie your good intention to a specific behavior that you want to introduce. This is where habits come in.

The Science of Tiny Habits

The best research we’ve found on habit formation comes from BJ Fogg, who runs the Behavior Design Lab at Stanford. His book Tiny Habits lays out a framework that’s counterintuitive but effective. If you’ve heard of the book Atomic Habits, it’s based on the same framework.

Most people trying to build a new habit lean heavily on motivation. They psych themselves up, make vision boards, tell all their friends, visualize themselves succeeding, listen to motivational speakers.

Fogg’s framework is based on the acronym MAP: your likelihood of doing a behavior equals your Motivation times your Ability times a Prompt.

Motivation is the least controllable of the three factors. Sure, you can draw on pure motivation on January 1st, and even for a week or two after. But over time, the novelty will fade, the kids will bring home pestilence, you’ll have to travel for work, or would one piece of birthday cake really be that bad? It’s ice cream cake, come on!

So given that Motivation isn’t something you can bottle, you’ll want to increase Ability (make it easier to keep the habit) and find a really solid Prompt (something that reminds you to do it). To do that, you’ll want to simplify the habit and make it as easy as possible for you to do it, even on a bad day. Prompt-wise, you’ll want to tie it to some kind of behavior that you already do. The most common reason people fail at resolutions is really boring. They forgot. Life got busy, and one day they realized they hadn’t thought about their resolution in three weeks. A good prompt can help.

BJ’s representative example is flossing. People who fail at flossing habits often struggle because “floss your teeth” feels like a chore.

Fogg’s version? Floss one tooth. That’s the whole habit.

If you’re exhausted and need to get to bed, flossing one tooth takes two seconds. You kept your habit. And here’s the thing: 97% of the time, once you’ve got the floss out and it’s between two teeth, you’re going to finish the job anyway. But you don’t have to. The tiny version protects the habit on your worst days.

The second part of making it easy is setting up your environment. Don’t keep your floss in a drawer in the furthest corner of your house. Put it wherever you’ll actually see it.

BJ’s prompt for flossing is “after I brush my teeth” which is something that he already does every day, and something that naturally leads into flossing. It’s very easy to remember to grab the floss when you’ve already been working on your teeth.

Planning for Failure

The Fogg Behavior Model covers everything you need to know to form habits. But to make a resolution stick, you need one more thing. You have to plan to fail.

There’s a story that Jerry Seinfeld had a big calendar where he put an X every day he wrote, and his secret to writing was “don’t break the chain.” He later said he never actually did that. He just knew he needed to write every day. The “don’t break the chain” method sounds motivating in theory, but in practice, it can backfire. Once you miss a day, the chain is broken, and now you’ve got nothing to protect. “Don’t break the chain” is a recipe for a lost resolution. What you actually want is a system for getting back on track after you slip.

A year is a long time. A lot of things will happen. Even with strong motivation, a great prompt, and a simple tiny habit, there will inevitably be one day where the entire world comes together to block you from completing your new behavior. What happens then?

You’re most likely to be able to recover from a lapse in your habit if you’ve already preplanned what your recovery mechanism will be. When you’re choosing your resolution, spend a few minutes thinking through the most likely ways you could fall off the wagon. Then, think about how you’ll climb back up in each case. The higher the level of commitment for your recovery plan, the better. If you have a fitness goal and miss a day, booking a fitness class the day after will almost certainly bring you back.

There’s a myth that habits take 21 days to form. The actual research suggests it’s more like two months. The point is, you need to stick with it longer than you think. Those first few weeks aren’t enough. You have to plan for some bumps in the road along the way. Then, in March, you can put the habit on autopilot.

A Five-Step Process

We’ve taken the Fogg framework and our own addition and turned it into a five-step process you can follow.

Step 1: Pick a specific behavior.
Your intention is not a behavior. “Get fit” is an aspiration. “Walk for ten minutes after lunch” is a behavior. Find something you can commit to doing regularly that drives your intention forward. You have to translate the vague goal into a concrete action. Daily (or daily-ish) behaviors are easier to create habits around than “every few days” behaviors. Weekly ones can work if you can find a prompt that gives you an appropriate cadence.

Step 2: Make it easy.
First, make the behavior tiny. Instead of “go for a 30-minute walk,” try “put on my shoes and step outside.” Most of the time, once you’re outside, you’ll take the walk. But on terrible days when everything goes wrong, you can step outside, note that you kept your habit, and go back in. Second, reduce friction. Put your shoes by the door. Have your yoga mat already unrolled. Whatever you need for the habit should be as accessible as possible.

Step 3: Find a trigger.
The format is “After [existing routine], I will [new habit].” You don’t want to create a brand new neural pathway from scratch when you’re doing something that requires effort and commitment. Instead, attach to something that’s already automatic. After I eat lunch, I’ll step outside. After I turn off the living room light, I’ll floss one tooth. The trigger should be something you already do reliably, so you never have to remember.

Step 4: Celebrate.
This is the part I always forget, since it feels unnatural. I think that’s why so many of my habits have gone by the wayside over the years. Fogg argues it’s one of the most powerful pieces. You want to feel good about yourself when you do the behavior. It doesn’t have to be a pageant. His example is simply looking in the mirror and smiling. You could do a little fist pump. You could put on a favorite song. You could high-five a door. The point is creating a positive association with the behavior so your brain wants to do it again.

Step 5: Plan your reset.
Think through failure scenarios ahead of time. If your habit is an after-lunch walk and you’re at a conference with back-to-back sessions, what’s your plan? If you hurt your knee and can’t exercise for three weeks, how will you restart? You’ll want to make your reset as high-commitment as possible. Book a yoga class three weeks out. Put a calendar reminder for the day after your trip. Write yourself a note that says “I missed today, but I will do it tomorrow.” Anything is better than vaguely thinking “I should really start that again,” because that’s not enough to make you really start that again.

Two Examples

Let’s walk through how this works in practice.

Say your resolution is to get more fit. The specific behavior might be: after I finish eating lunch, I will put on my shoes and step outside. That’s the trigger (finishing lunch) attached to a tiny behavior (shoes on, step outside). Make it easy by keeping your shoes by the door. Celebrate with a high-five to the doorframe when you get back, or put on your favorite song while you drink a glass of water. Plan your reset: if you’re working from the office and coworkers drag you into a meeting right after lunch, you’ll do a five-minute walk after your last meeting of the day instead.

Let’s do a professional resolution too: you want to grow your network. Committing to going to an event every couple of months could work, but let’s find something daily, so we can make it more automatic. The behavior: after I close my work laptop, I will leave one comment on a LinkedIn post. It’s very tiny. You can just say “congratulations!” to whoever’s bragging about something on LinkedIn that day.

Do it at the end of the day so you don’t get sucked into the LinkedIn vortex when you should be working. Celebrate with a thumbs-up to yourself (LinkedIn’s already got the icon right there). Reset plan: if you forget, schedule a ten-minute calendar appointment for the next afternoon to remind you.

Founding Fathers and Resolutions

It’s an achievement to create a new habit. Creating a complete lifestyle transformation in one fell swoop, though, needs a lot stronger temporal milestone than a new date.

If you want a historical model for habit formation, look at Benjamin Franklin (He of the 35 illegitimate children, a Less Busy Lab recurring dispute!)

Franklin tracked himself against thirteen virtues: temperance, industry, order, and so on (not chastity, never chastity!) But even with thirteen goals, he only focused on one virtue per week. He’d rotate through all thirteen, giving each one dedicated attention before moving to the next.

This is why we recommend focusing on one habit at a time. You can still have multiple resolutions. Just stagger them. Use Boomerang to send yourself an email in March saying “time to start habit #2.” Put a task in GQueues and use our nifty new snooze feature to put it out of mind for two months. Stack your habits over time rather than trying to change everything at once.

Our Resolutions

In the spirit of practicing what we preach, here’s what we’re committing to.

Moah’s intention is to sleep better, and the specific behavior is getting morning sunlight for at least ten minutes within the first hour of waking up. The trigger is the kids leaving for school at 8:30. When they go out the door, she’ll put on her jacket and shoes and go out too. Most days when she’s driving somewhere, the sunlight happens automatically. For rainy days, she’s got a nice raincoat that might provide enough motivation. Her celebration is the checkbox itself. Tracking is rewarding enough. And she’s getting sun stickers for her calendar as a Christmas present.

My own resolution is to read more this year. I don’t feel any guilt about the nights I spend my few minutes with no responsibilities playing video games, but I still spend a decent number of them doomscrolling. Reading a book - any book - would be a lot better!

My specific behavior will be reading just one page after putting the kids to bed. The trigger is the kids’ bedtime routine finishing. I typically read on my Kindle, so I can load the books into my phone as well so they’ll always be accessible. If I miss a night because we’re traveling or out late, I’ll read the page in the morning instead to get back on track - and I just committed publicly that I’d do it, so there’s a little extra juice in the commitment. Celebration-wise, I’ve still got a couple of days to come up with something better than a thumbs-up in the book’s direction, but that’s a solid default.

The Bottom Line

Resolutions are good, but they’re even better when you turn intentions into a repeatable behavior. Most of them fail not because people lack willpower but because they never turned the intention into a system. The five-step process gives you that system: pick a specific behavior, make it easy, attach it to a trigger, celebrate when you do it, and plan how you’ll get back on track when you slip.

Eighteen percent of people keep their resolutions for a full year. Follow this framework, and you’ve got a much better shot at being in that 18%. And stay tuned for our next episode. We’ll be back just in time for “Quitter’s Friday”—the day when most people abandon their resolutions—with extra motivation to keep you going.

Happy New Year! To hear the full discussion, listen to Episode 15 of Less Busy Lab. Have questions? Send them to questions@lessbusylab.com

If you’re lost in a sea of acronyms and clickbait as you’re trying to figure out AI these days, join the club! At the risk of losing out on precious clicks, I’m not going to speculate on whether AI will deliver nirvana or extinction in the future. Instead, let’s talk about what AI can help you with and do for you today, in December 2025. And even more importantly, we’ll share how to get started so that you can get 90% of the benefits with tools you already have, without having to spend a week connecting things together, buying new subscriptions, and troubleshooting all of it.

Want a TL;DR? Gemini and Microsoft Copilot are built in to Google Workspace and Microsoft Office, they can already access your data, and get reasonably close to the best performance you’ll find even if you’re willing to do a bunch of work. If you have specialized needs, you may get some benefit around the edges from using the best-suited model, but for most things we do day-to-day, the easiest path is the best one. Try asking AI to help you brainstorm, summarize, critique, and make pictures!

What’s AI good for anyway?

AI is decidedly not human, so the tasks it can handle don’t map to our intuitive sense of how difficult they would be for us. It’s worse at counting than my five year old, but it can answer a question about a statistic buried in a document faster than a team of 20 library science PhDs.

AI geeks refer to this counterintuitive performance as “the jagged fronter” because it’s uneven and because the limits of AI are continuously pushing further out. So to find the places AI can help you in your workflow, you’ll have to be a little bit experimental. Some things will work great, others not so much. And the scope of what will work great is increasing quarterly.

The easiest starting point for using AI is brainstorming. AI is tireless, and it doesn’t (yet) get offended if you don’t like one of its ideas. You can ask for 20 taglines, expecting 10 will be terrible, 8 will be mediocre, but 2 might be great. The best thing about this kind of “breadth-first” search is that you don’t have to worry about hurting anyone’s feelings. You don’t owe it an explanation when you say “none of these work, try a different angle.” It will just start again, no feedback sandwich required.

AI is also excellent at shortening and simplifying dense information. In November, we used it for reviewing carbon capture research proposals. Every year, our company makes a donation to an academic research lab working on some kind of bleeding edge technology that could lead to economically-valuable carbon capture (this year, photosynthetic cement!) The proposals are only 1-2 pages, but they are hard to read for people who aren’t specialists in the field.

We asked Gemini to explain each proposal for a target audience of “smart college freshman,” and the dense technical papers became instantly accessible. It wasn’t perfect. There were some proposals where I read the summary and then read the actual paper and thought “that’s not quite the gist of it,” but it was pretty good, and plenty useful enough for deciding where to dive deeper!

Another strength is qualitative analysis. Earlier this year, we asked AI for help taking hundreds of survey responses and organizing them into themes. This used to require someone sitting in front of a spreadsheet for hours, reading each response and manually categorizing them, because users never describe the same problem with the same words. AI did it in less than a minute.

Again, at this stage, AI can do that initial sorting, but it might miss the nuanced cases where someone uses a word that seems like it belongs in one category but actually refers to something else entirely. You’ll still want human eyes on the results. But what used to take a couple days of laborious transcribing now takes only half an hour of human review.

And don’t forget pictures and videos and audio. Modern AI can work with visual content too, both in terms of “what might be wrong with this mechanical thing” or “what is this plant?” type questions. It can transcribe audio as well as most humans can, and read handwriting even better. It can also generate new pictures and videos, like the fun cat gifs that I generate as a way of motivating myself to write these blog posts!

One of my personal favorite use cases is using AI to write spreadsheet formulas. I don’t work in spreadsheets every day, so I’m never in the flow enough to remember the exact syntax for a complex lookup. The morning we recorded this episode, I needed to create a graph with a seven-day rolling average. Instead of spending ten minutes Googling formulas and syntax, I just told Gemini what I wanted. To get something that actually worked, I had to break it down into steps myself - first create a column with the rolling average, then verify it looked right, then create the graph, but it would have taken me a lot longer to do it the old way.

Where AI struggles is anything requiring nuance and subtext. A BCG study provides a quantitative example. 758 Boston Consulting Group consultants were asked to use AI to help them given realistic consulting work, like idea generation, problem‑solving, and writing. The consultants who used AI were more productive overall, but when the “right answer” required reading between the lines of what people said in interviews, AI led people astray.

AI also has trouble with things like precision math, even for things we consider basic, like counting. AI models semi-famously fail on tasks like counting the number of B’s in “blueberry.” But here’s a trick: if you ask it to write a script that counts letters instead of asking it to count them directly, it’ll produce working code in 30 seconds that you can run yourself. The model is better at coding the logic than performing the logic. Very different from us!

Incidentally, this blog post is not the work of AI (though the ones for Episodes 2-4 are). I am too persnickety about my tone and about making sure the ideas are represented on the page as they are in my mind to accept AI as a ghostwriter!

The Resume Screener

One of my favorite things we’ve done with AI came out of a hiring challenge.

As a 15-year-old company, we’ve come to value hiring people with a long enough tenure somewhere to have the experience of asking “what idiot did this work…” only to find that it was you, and you’d forgotten about it. Folks who’ve stuck around somewhere long enough to have a couple of those moments tend to have Chesterton’s fence embedded in their bones. They also tend to grant grace to other people’s work, since they can remember cases where their own fell a bit short.

In that spirit, we were looking for someone with at least three years of experience at the same company in a similar role. We posted the job to LinkedIn and got a flood of resumes, but very few candidates actually met that requirement. In the old days, sorting through the resumes one by one was a bottleneck in the hiring process.

Every morning, I’d open the folder, click through PDFs one by one, scan for dates, and do mental math. Nope, not this one. Nope, not this one. It drained energy before the actual evaluation work even began. Some (okay, fine, maybe most) mornings, I couldn’t face it at all.

So we wrote a script. Using Google Apps Script and Gemini, we processed all the resumes in our submissions folder and asked one simple question: “Does this person have three years of experience at the same company in this specific department? Yes or No.” The results went into a spreadsheet.

For the AI ethics folks reading this: we did not use AI to decide whether to hire anyone or to rank candidates. We only asked a binary, factual question. The AI was a filter to remove the obvious “nos” so we could focus our human attention on candidates who met our requirements.

It got it right about 95% of the time, which was better than our intern a few years ago did! It occasionally missed people who had been promoted within the same company (a good signal; we prioritized those people!) if they listed the two roles separately on their resume, so we spot checked it. But overall, it was remarkably good, and it made the mental burden so much lighter, all for free.

If you want to look at the script, we have a version here that you can copy and use! Feel free to ask Gemini for help making changes to it.

Who Benefits Most? The Novice Advantage

From our experience using it, it seems like AI helps less experienced workers more than experts. I get a lot more value out of Gemini in Google Sheets than our Director of Finance, who can write a formula as fast as he can type.

Some rigorous studies support this intuition! A study of 5,172 customer support agents at a Fortune 500 software company found that newer and lower-skilled agents were able to handle cases 30-34% faster to when given AI assistance. But the top-tier, most experienced agents saw almost no productivity gains, bundled with a slight decline in quality.

Much like my spreadsheet example, pairing the agents who were experts with a “B-player” assistant resulted in the agents taking as long to check and correct lower-quality work as it would have taken them to just do the work themselves.

Another research group called METR looked at AI’s effects on open source developers and found the same thing. They found that experienced engineers with five-plus years on a project were actually slowed down by AI assistance. The newcomers, though, got a significant boost.

Also interesting: the developers using AI thought they were going faster than they were without it. Their self-reported productivity was higher than their measured productivity. Much like keyboard shortcuts (users of keyboard shortcuts are slower than mouse users, but perceive themselves as being faster), there’s something about the type of cognitive load that working with AI produces that confuses our sense of time.

AI is like a great equalizer that pulls below-average performers up toward average, but doesn’t help (and may even hinder) people who are already operating at a high level. If you’re a great writer, ChatGPT might make your writing worse–and fill it with em-dashes! If your support team is super experienced and deeply knowledgeable about your product, they won’t see the gains that a new hire would.

Prompting Tips That Actually Help

Through our own experiments, we’ve found a few approaches that make AI more useful.

Breaking tasks into steps is probably the single most useful technique. Instead of asking for a final product all at once, ask the AI to do one piece, verify it looks right, then move to the next piece. This lets you catch errors along the way. Some people call working like this the “Centaur” model, where you’re the torso directing the work, and the AI is the legs making it go faster.

Asking the AI to act as a persona can help focus its responses. Instead of just asking “critique this podcast,” we’ve prompted AI to evaluate our podcast episodes with “You’re the producer of Freakonomics Radio—what are your notes for improving this episode?” (we ignored most of its advice; if you don’t like tangents, don’t listen!) These models are trained on the entire internet, so specifying a persona is like asking “which section of the internet should you draw from?”

Asking for emotional reads is underrated. “How does this email come across to a potential buyer?” gives you an objective tone check that’s hard to replicate, even from another person on your team. AI doesn’t have the background you have, or even the same shared experiences you’d have with a colleague.

For teams, setting up shared context projects is a game-changer. Using features like Gems in Gemini or Projects in ChatGPT, you can upload all your brand context, product details, and use cases one time, and use it over and over again. You can also create a shared “parent prompt” that you and your team can iterate on and improve. Then anyone on the team can run tasks without re-explaining everything from scratch. We built a custom GPT for sales discovery calls that knows all our features and use cases. You just type in a prospect’s email domain and it identifies their likely needs and generates a personalized demo script. No more generic “test email, test event” demos.

Finally, one note for early adopters. If you tried AI back in 2023 and weren’t impressed, it’s worth trying again. OpenAI’s data shows that people who started using their tools earlier use them less and trust them less than people who came later. That makes sense! If you showed up at the bleeding edge, tried tasks the models couldn’t handle yet, and got burned, you might never have looked back enough to see how far things have come. The models today are an order of magnitude more capable than the bleeding edge two years ago.

Tip of the Week: Connect Your Data

Our tip this week is simple: go beyond the chat window.

Go into your Google Workspace or Microsoft Office settings and enable the AI extensions for Gemini (Google, go to the gear menu –> Apps and toggle on Google Workspace) or Copilot (Microsoft, go to the gear menu –> Connectors and toggle on Outlook/etc.). You can grant permissions to both tools to access your actual documents, spreadsheets, and slides. This unlocks the ability to say things like “look at the project brief in my Drive and draft an email to the team based on the timeline.”

Your Workspace/Office subscription probably already includes some level of access to these AI tools. They already have well-tried paths to access your data, and because they’re part of the platform, they don’t present compliance/regulatory or security risks like hooking up a random new AI tool into your company’s data would.

You don’t need to know what RAG or MCP or MOE means, or spend a week connecting systems together to start getting value from AI today. The built-in options are good enough for 95% of the stuff you’d want to do, with only a minute or two of setup required.

Wrapping Up

You can get a lot of productivity benefits from AI you’re already paying for, with almost no up-front time investment, today.

AI is brilliant at some things and clumsy at others, and the line between them doesn’t follow human intuition about what’s “hard” or “easy.” So you’ll have to try a few things out to find the parts of your workflow where AI can really make a difference. If you don’t know where to start, try brainstorming ideas or shortening and aggregating information from documents.

Don’t wait for the perfect AI. The current models are powerful enough to be plenty useful already. And if you tried it a couple years ago and gave up, give it another shot. Things are different now.

To learn more, listen to the full podcast episode.

Listen to the Episode

From the length of their respective lines, though, the piece of art that sticks with the most Louvre visitors is the Mona Lisa. Peering through crowds to catch a glimpse of the famous painting, I could understand why. Is she smiling? Is she not? I didn’t know. But one thing I do know, is that she was never finished.

Leonardo Da Vinci never delivered the painting to the client who commissioned it. Despite creating what would become the most famous painting ever, he never thought it was good enough. He carried that canvas around with him for 16 years, adding layers, tweaking the smile, and adjusting the shadows.

Like painters, authors are famous for unfinished works. The Wheel of Time series was one of the bright spots in a not-great sophomore year of high school, but Robert Jordan had to die and hand over the pen to Brandon Sanderson to bring the series to a close. At 14 years and counting, it looks like Game of Thrones is headed the same way (come on George, stop making HBO shows and finish Winds of Winter!)

If geniuses can’t cross the finish line alive, what hope is there for the rest of us? I’m glad you asked!

Finishing a project is a different skill from starting it or working on it. Building that skill usually involves overcoming one (or more than one!) of three psychological roadblocks: perfectionism, boredom, and scope creep. By figuring out which one is blocking you on a specific project, you can build a strategy to get that project out of your hands and into the world.

Perfectionism: Murdering the Dream

Like many traits, perfectionism can be a virtue. A commitment to quality and doing good work is a good thing. However, when it comes to finishing, perfectionism can be rooted in fear instead.

Oliver Burkeman, author of a number of books that explore the philosophy of productivity, used the phrase “murdering the dream” to describe how fear leads to perfectionism, and perfectionism leads to never finishing.

When a project is still in your head or in the draft phase, it has infinite potential. In your imagination, your novel could become a bestseller, your software could be the next billion-dollar unicorn, and your research paper may be destined for a Nobel Prize. As long as it remains unfinished, it’s possible that this project, this very one, will be the work of your life.

The moment you declare it finished, however, it becomes real. And even if it’s good, even if it’s great, it’s never perfect. Nothing is. One of the characters is a little bit underdeveloped, you might have had to put in some inelegant code to deal with scaling issues, your bioengineered molecule might only be 10% better instead of an order of magnitude improvement.

By finishing, you are killing the perfect dream version of your work and replacing it with a real-world version that inevitably has the warts and problems that come with the real world. And the gap between the dream and reality can cause a kind of paralysis.

It’s even harder if you’ve already had some earlier success. The Hero’s journey from movies and books is mostly linear - even if there are a few setbacks, every achievement must be bigger and better than the last. So what happens if this project isn’t bigger and better yet? The pressure can stop you from shipping anything at all.

How to Beat It: External Pressure

I’ve rarely seen anyone use internal willpower to overcome perfectionism. Instead, bring in pressure from outside.

• Create deadlines, even if they’re artificial: For most of us, the boss (or maybe the board) is the source of most of our work deadlines. But in cases where that doesn’t work, there’s always a way to create a deadline. One strategy we’ve used with Boomerang was setting an “embargo date” with the press. We’d tell reporters, “We are releasing this feature on Tuesday.” Once we’d made the commitment, the conflict between making it perfect and having to go back to the reporters to walk back our plans pushed us to finally ship. You can replicate this by promising a draft to a mentor or to someone else you respect and don’t want to let down.

• Get an accountability group: Author Brandon Sanderson, who finished The Wheel of Time (and has written prolific numbers of very good novels in his own right), credits his writing group. When he was in writing school, he mentioned that all the students who were in his writing group finished a novel, even if it didn’t get published. Most of the rest of the class didn’t. If you’re struggling to finish something that’s not work-related, someone else is struggling with the same thing. Find them!

Boredom: The Slog of the Last 10%

The second reason we fail to finish is simple: the end is boring.

The final 10% of any project is rarely the most creative or exciting part. It is administrative. It is checking cross-browser compatibility, formatting citations, filling out tax forms, writing privacy policies, turning the research into 36 pages of dense scientific jargon. Because the novelty has worn off and the work is tedious, we tend to stall out.

How to Beat the Boredom: Small Area Hypothesis

When you are beginning a project, going from 0% to 20% done feels amazing. But when you are 90% done, the last 10% seems to stretch on forever.

To fix this, change how you visualize the work - instead of thinking about a project as being 90% complete, switch to a checklist with only the specific items left, as per the Small Area Hypothesis. If you have, say, five boring tasks left, checking off one item is 20% of your remaining workload. Reframing “the last 10%” as the first part of the final steps sometimes tricks your brain and makes it easier to approach.

How to Beat the Boredom: Engineer Excitement

You can also hack your dopamine levels by saving some part of the project you enjoy for the end. I like to leave one interesting, complex problem for the final phase so I always have something to look forward to.

If the end of the project is 100% paperwork, you will procrastinate. If it is 90% paperwork and 10% cool technical challenge, powering through the paperwork to get to the fun part becomes an option.

You might also try buying something you really want and putting it on display, but not allowing yourself to use it until the project is done. It serves as a visual reminder of the reward waiting for you. One of my colleagues at Boomerang did this with a nice hoodie, and it worked like a charm.

Scope Creep: “While We’re At It” Strikes Again

For team projects, scope creep (or gold-plating, as we often call it) is the bane of finishing.

You are working on a pricing page, and someone says, “While we’re at it, why don’t we localize this for foreign currencies?” It comes from a good place. After all, people don’t want to lose good ideas, and it is easier to go ahead and add something in while you’re already working in that area, rather than context switching later. But it keeps moving the finish line further away.

How to Beat It: Switch Modes

One of the techniques we developed over the years was to switch our definition of when something was done from feature-driven to date-driven once the end was in sight. When we started working on a project, we tracked its state by measuring how close it was to having the features and functionality that we wanted to add.

But when we started to approach the end of the project, we’d stop managing it by features and switch to managing it by a target release date. That way, there was a forced limit to how much we could goldplate and add on and “while we’re at it…” If we could get it done by the release date, we could build it. If we couldn’t, it would have to wait for the next version.

That target date was always a feature-freeze date, so we’d have some time left for fixing bugs or testing. But no new development! That mirrors a punch list approach that’s commonly used in the construction world. When a building is almost done, they make a list of minor fixes required before the owner takes possession. Nothing new gets built, nothing extra gets added, only the list gets fixed.

Key Takeaways

• Don’t wait for perfection: Finishing requires “murdering the dream” of a perfect project to accept the reality of a good, finished one.

• Use external pressure: You are more likely to finish if you have promised a deliverable to a mentor, a boss, or an audience.

• Change your view: In the final stages, stop looking at how much you have done. Make a short checklist of what is left to generate momentum.

• Define “Done” with a date: Agree on a feature freeze date. Any new ideas that can’t be done by that date go into a “Version 2” folder, not the current project.

Tip of the Week: Throw a “Finishing Party”

If you have a project that has been dragging on for months, stop trying to do it alone. Host a Finishing Party! One of our customers told us about doing this, and we thought it was brilliant.

How it works:

1. Invite at least one person: It can be a coworker (people have done these at work) or a friend who also has something nagging on their to-do list. The more the merrier, and in person is the best, but if it’s you and one other person, and even if it’s on Zoom, that’s enough.

2. Set a time limit: An hour and a half or two hours is usually the sweet spot. It’s long enough to get real work done but short enough to see the light at the end of the tunnel.

3. Add a reward: Have a specific celebration ready for the end, if you get something finished. I’m partial to beer and ice cream, but you do you - if you like mushroom tea and a few yoga poses, go for it!

4. The Rule: You are there to do the thing you have been avoiding. The social pressure of sitting next to someone else who is working can sometimes work magic.

Finishing is important for its own sake – if the world never gets to see your project, why bother doing ninety percent of the work at all? But finishing a project also lets you close all the open loops associated with it, freeing your mind to start whatever’s next. So get out there, and cross something off the to-do list!

To learn more, listen to the full podcast episode.

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But just spending money and being in a new place doesn’t bring out all the valuable aspects of an offsite. It takes a lot of deliberate, purposeful planning to create the kind of conditions where the magic can happen.

So in this episode, we talk about what we’ve learned from organizing more than 25 of these events over the last 15 years. We’ve held a mixture of strategic team gatherings and innovation-focused hackathons over the years, and some of our most successful products have come out of them.

If your role is more about attending an offsite than planning one, you may want to scroll on down to the part where we got input from our team about how to make the most of an offsite as an attendee.

What’s the point of this?

No matter what your stated goal for the offsite ends up being, the most valuable effect is likely to be that it strengthens informal social ties. Offsites remind everyone that they’re working with real people, not just boxes on a Zoom call. Even if you generally work in person, an offsite gives colleagues who don’t know each other super well a chance to connect about stuff that goes beyond work, and that makes a big difference.

These personal connections lead to better collaboration and communication long after everyone has returned home. A study conducted by Dartmouth’s Tuck School of Business found that after an off-site, attendees received almost 25% more incoming collaboration opportunities than before the event. There were spillover effects, too - employees in those departments who didn’t attend the offsite also received more invitations to collaborate.

Those connections are even more valuable when your team is remote or hybrid. Research from Microsoft has shown that remote work can decrease cross-group collaboration by as much as 25% because teams become more siloed. Offsites are a direct and effective way to counteract this by building “bridge connections” between different parts of the company.

Offsites also help align the team on vision and goals. As a former big company employee, I appreciated the opportunity to get a coherent quarterly plan in a document I could read. But it’s even better to have an opportunity to discuss it, ask questions, and see how everyone’s work fits into the bigger picture. Offsites provide a dedicated time and environment for this high-level strategic alignment, creating space to really engage with the material.

Finally, getting people into a new environment sparks creativity and fresh ideas. Breaking from customer tickets and fighting fires puts the team in a different mindset, one that’s more open to brainstorming and long-term thinking.

So even though the costs ($2000-$4000/employee, depending on location and logistics) can be steep, the intangible benefits make it, in our minds, well worth the cost.

Optimizing strategic offsites

A successful strategic offsite is built on a well-structured agenda that mixes together different types of work with deliberate opportunities to forge connections. Over the years, we’ve found a formula that works for us. Here’s how it works.

Start with psychological safety

At all of our strategic offsites, the very first activity is all about making people comfortable and creating psychological safety, especially for folks who are new to the team. A fun, low-pressure icebreaker encourages everyone to contribute.

We’ve done a number of different things over the years, and almost every icebreaker has worked well, at least for most people. Our most-frequently used icebreaker is a work-related rose, thorn, and bud exercise, where everyone goes around and shares something good, something that could be better, and something they’re excited about at work right now. We’ve also done a puzzle together, and a “deserted island” problem: if our plane crash-landed, what items would we bring? This gets people talking and sharing their perspectives in a quirky, fun way. The goal is to establish that every voice is welcome before diving into business strategy.

It’s also a good idea to establish rules of engagement at the outset. The obvious HR rules apply (and we generally don’t go over them), but for our team, we focus on being present. Laptops and phones should be put away unless they’re being used for a session. This signals respect for the time and sacrifice everyone made to be there. Then, it’s on to the strategy update.

Structure the agenda to follow energy levels

The flow of the day matters. Hit the big-ticket items, like the CEO’s strategy update, early in the day before focus starts to wane. That way, everyone’s energy levels and attention spans are high when the most important information is coming their way.

Brainstorming sessions are often most effective right after lunch when blood glucose levels are high. A core rule for brainstorming is that there are no bad ideas. We ask our team to always share their ideas, even if they aren’t that excited about them, and we write down every idea, always. We also ask the team never to say anything critical about someone else’s ideas during the brainstorming session.

The reason is that even a “terrible” idea might spark a brilliant one in someone else.

We also ask the team never to say anything critical about someone else’s ideas during the brainstorming session. The time for filtering and judging comes later; during the session, it’s all about “yes, and...“ thinking, a principle borrowed from improv comedy that increases creativity.

Team-led learning

An all-day marathon of strategy work and brainstorming can be completely exhausting, and deeply unproductive by the end. At the same time, offsites only provide so much time to spend together. So we like to incorporate sessions where team members can teach each other something. This can be work-related, like a deep dive into the company’s database structure, or something completely different. One session from our last offsite involved a team member from a region in China famous for its kite festival teaching everyone how to build their own kites. These hands-on activities build connections in a way that PowerPoint presentations can’t. They also make sure that the time spent feels valuable, but not so draining.

Finally, don’t overschedule. We learned the hard way that back-to-back sessions from 9-to-5 lead to pure exhaustion. Now, we always leave the last couple of hours of the day for dedicated small group work sessions. Small groups can collaborate on a project, catch up on customer support, or pair-program. This prevents burnout, gives teams a chance to build more social connection, and often leads to tangible progress on key initiatives.

Set up the space for success

The environment has a huge impact on creativity. (If you’re interested in a deeper dive on which physical environments are suited to different kinds of work, check out our previous post on the topic. Instead of a windowless hotel ballroom, look for a unique space with natural light and high ceilings, like a large rental house. If the house isn’t big enough for everyone to sleep in, find one near a hotel and have everyone who won’t fit in the house travel (ideally walk) over.

And don’t forget the tech. Almost everyone overestimates their WiFi. When you have 20 people connecting multiple devices at once, a standard residential connection will crumble. Ask for a screenshot of the venue’s upload speed or, better yet, bring your own powerful router as a backup. The same goes for A/V equipment—always have a plan B. We have a portable projector as our A/V-of-last-resort. It’s a cheap investment to guarantee that all the expense of the offsite won’t get ruined by a broken TV.

Hackathons: offsites for innovation

All offsites build connections, but hackathons focus on innovating and building instead of alignment.

Our first hackathon was born from a running joke that if we ever became profitable, we’d celebrate by going to Iceland. When we finally hit that milestone, we looked at each other and said, “Are we really doing this?” We did it!

But while we had a great time in Iceland, we weren’t able to point to a lot of company value from the work sessions we held there. We’ve since made a lot of changes:

1. From Cooking to Coding: We used to cook all our meals together to save money and build camaraderie. But we quickly realized that planning, shopping, cooking, and cleaning for a large group ate up huge chunks of valuable coding time. Now, we have food catered (or even get a chef) so the team can stay in a state of flow.

2. Opt-In, Not Mandatory: A hackathon requires a specific mindset. Forcing people who aren’t excited to tinker can be counterproductive. Our hackathons are now optional. Anyone who wants to go submits a short proposal for what they plan to work on. This ensures everyone there is motivated and has already put thought into their project.

3. Prioritize Flow Time: The schedule is designed for long, uninterrupted blocks of “maker time.” We always have one big group activity one of the afternoons, but the rest of the time is dedicated to focused work. Lunch is available, but optional—no one is pulled out of their work if they’re in the zone.

The goal of a hackathon is to step away from the reactive demands of day-to-day work and dedicate focused time to tinkering and innovation. Research shows that face-to-face interaction in a new environment generates more innovative ideas. Some of our most successful product features have come directly from the subsequent versions of these trips.

Attending an Offsite

If you’re attending an offsite you didn’t plan, it’s important to optimize your mindset and preparation. And it’s worth the effort: a long-term study of a law firm found that offsite attendees received 23.5% more incoming collaboration requests than non-attendees. These events are a powerful way to increase your visibility and impact.

• Before You Go: Clear your schedule of any nagging tasks so you can be fully present. Read the agenda to know what to expect and how to pack—you don’t want to be the only one without the right gear for bioluminescent kayaking! If it’s your first time, chat with a veteran attendee to get the lay of the land.

• During the Offsite: Participate actively. Listen, ask questions, take notes (especially any action items you want to follow up on) and keep an open mind. Step out of your comfort zone and contribute to brainstorming sessions, even if you think your idea is silly. For introverts, it’s crucial to manage your energy. Use the scheduled breaks to step away and recharge so you don’t burn out.

• After You Return: The work isn’t over when you get home. Follow up on the connections you made. Send that interesting article you mentioned or the notes you took during a session. Review your action items and plan to complete them in the coming weeks. Provide constructive feedback to the organizers through surveys. This helps solidify new relationships and makes the next offsite even better.

Tip of the Week

The biggest breakthroughs at an offsite often don’t happen during a formal presentation. They happen in the unstructured moments in between. The most impactful part of your offsite might be the hallway conversation while waiting for dinner, or the chat during a coffee break, or an idea that strikes you during the walk back to the hotel. These transitional times are where ideas cross-pollinate and true connections are made.

If you’re an organizer, intentionally build buffer time into the schedule. Things will inevitably run long, and creating space for these spontaneous conversations adds immense value.

If you’re an attendee, use these moments to connect. Instead of scrolling through your phone, strike up a conversation. Then, within 24 hours of returning, send a follow-up note to the new people you connected with. A simple message saying “Great chatting about X, here’s that link I mentioned” can turn a fleeting conversation into a lasting professional relationship.

To learn more, listen to the full podcast episode.

But a lot of time-tested workplace advice got turned on its head in the last five years. The pandemic and the resulting shift toward hybrid and remote work have impacted email as well. A lot of digital communication has moved out of asynchronous channels like email and into synchronous ones like chat and virtual meetings. Interruptions have become a more natural part of our work, which means they’re now something to manage rather than something to try to avoid.

So while the general techniques for “going through email” that we covered a couple episodes ago are still relevant today, the place email holds in our work lives has changed. Today, we’ll talk about how to navigate expectations around email and when to use email vs. another platform. We’ll explore how synchronicity can substitute for a lack of richness in a communications medium and help teams feel more connected, even when they’re not always together in person. This new reality requires a new set of guidelines and entire suite of tools—like Slack, Teams, and Zoom—that now define our workday.

The Richness of Connection

To understand why the old advice no longer fits, it helps to think about the “richness” of our conversations. A theory called Media Richness Theory explains that in-person communication is incredibly rich. When you talk to someone face-to-face, you get more than just their words. You see their facial expressions, can read their body language, and can hear the tone of their voice, without any lag time. So you have a much better idea whether that one-word response conveys passive agreement or biting contempt.

Email and chat, on the other hand, are much “leaner” channels. They strip away most of that non-verbal context, leaving only disembodied text on a screen. In an in-person office, where rich conversations happen spontaneously in the hallway, communicating via chat messages can feel like noisy, interrupting, contextless distraction.

As the CEO of an in-person company, I despised the proliferation of Slack DMs, feeling like they were the absolute worst of all worlds. The interruptions gashed productivity, there was no record of decisions outside of the private history of the participants, and the conversations we had there yielded less creativity and worse ideas than the ones we had when we took advantage of physical proximity to communicate in a richer medium.

But when teams went remote, conversation moved out of DMs and into channels, and those channels became lifelines. Suddenly, synchronous chat and frequent video calls became the primary ways to foster team cohesion. Research from the University of Mannheim found that for virtual teams, more synchronous communication led to a stronger sense of togetherness. Email, being asynchronous, had no impact at all on how connected teammates felt.

In 2025, “if you aren’t going to meet in person, use email,” is bad advice. Because they’re more synchronous than email, chat apps are now a richer default channel of communication rather than sitting in the uncanny valley of productivity. They’ve also replaced the water cooler, with custom emojis and casual conversations helping build culture from afar.

Why Veteran Teams Thrived (and New Hires Struggled)

Media richness theory was introduced almost 40 years ago. More recent research on communication channels gives us more insight into why chat and virtual meetings are now extremely valuable for collaboration.

The initial transition to remote work was surprisingly seamless for us. Despite a few hiccups, we kept shipping features, improving our products, and kept the lights on virtually. That was true for a surprising number of established teams.

The reason for this lies in a concept called Channel Expansion Theory. In short, the longer a team has worked together, the better they know each other. This shared history and understanding allow them to “expand” a lean channel like email or Slack, filling in the missing context.

When you read an email from a long-time colleague, you can almost hear it read in their voice. You can picture their expression as they wrote it. You’re mentally filling in the gaps because you have a rich, pre-existing relationship. This is why many teams felt they didn’t miss a beat. They were running on social capital built up over years of in-person interaction.

However, this has created a hidden challenge for new employees hired into a remote environment. Without that shared history, they can’t perform the same mental gap-filling. For them, a short Slack message is just a short Slack message, devoid of the rich context their longer-tenured colleagues automatically supply.

This makes it harder for them to integrate, build relationships, and feel like part of the team. And it also makes on-the-job learning harder and slower. Bridging this gap requires conscious effort, like scheduling more one-on-one work sessions and creating intentional opportunities for connection.

A New Look at Interruptions

Just as our view of communication channels has changed, so has our relationship with interruptions. For years, research painted a grim picture: interruptions increase stress, lower your effective IQ, and can even cause “email apnea“—a completely wild phenomenon where people unconsciously hold their breath while reading messages, depriving their brains of oxygen.

The consensus was that interruptions were always bad. If you’d asked me in 2018 how you should check email (and chat too!), I would have told you that you should pause your Inbox and turn off chat notifications. Check each one to three times a day, and otherwise spend your time trying to enter flow state and do focused work.

Post-pandemic, however, surveys reveal a more nuanced story. Many people now report that being responsive increases their job satisfaction and makes them feel more productive. In a remote setting, responding in a timely manner is a way to feel less isolated and more connected to the team. It replaces some of the lost richness with valuable synchronicity.

This doesn’t mean the pendulum has swung all the way to celebrating constant interruptions. Burnout among remote workers is significantly higher, largely due to the collapse of work-life boundaries. The key isn’t to be “always on,” but to understand that not all interruptions are created equal.

Research conducted at Microsoft highlights an important distinction:

• External Interruptions are the most costly. These are the unexpected pings and pop-up notifications that pull you out of a task without warning. Because you weren’t prepared, re-engaging with your original work requires a significant mental effort to recall where you were and what you were doing next.

• Self-Interruptions are far less disruptive. This is when you consciously decide to switch tasks, like finishing a paragraph and then choosing to check your email. When we self-interrupt, we naturally do it at a logical stopping point. We also subconsciously “save our state” by making a mental note of what to do when we return.

The takeaway is clear: taking control of how and when you’re interrupted is crucial for protecting your focus.

Tip of the Week: Go Bimodal

To thrive in today’s work environment, the best approach is to adopt a bimodal schedule. Instead of being completely asynchronous or constantly available, you strategically separate your time into two distinct modes.

• Mode 1: On and Responsive (During Work Hours). During your core work hours, aim to be more responsive. Check your email and chat more frequently. Don’t turn on all your notifications—that invites a constant stream of external interruptions, which are still costly. Instead, practice disciplined self-interruption by choosing when to check in. This allows you to stay in sync with your team and feel connected without sacrificing control of your focus. It’s also important to set explicit team expectations around responsiveness during these hours.

• Mode 2: Off and Unreachable (After Hours). To prevent burnout and all the other awful effects of constantly being on, it’s important to be truly off sometimes too. Protect your personal time. Use tools like our Inbox Pause feature to schedule your email to stop arriving after a certain time (say, 6 PM) and resume the next morning. It may take a few days for your brain to unwire its compulsive need to check for new messages, but breaking the habit creates a clear separation between work and life.

By being intentionally responsive when you’re on and intentionally disconnected when you’re off, you get the best of both worlds: strong team cohesion and the protected downtime you need to recharge.

To learn more, listen to the full podcast episode.

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The "post-vacation blues" is a common experience. Research shows that while only about 12% of us hate our jobs, 87% of us dread coming back from a holiday. And for good reason! Between the pile of catchup work and biological responses to all the rapid changes you’ve been through recently, getting back into your normal routine is a legitimate challenge.

We have some good news, though. With a little preparation before you leave and a smart strategy for your return, you can significantly soften the landing and get back into your groove without losing that vacation glow.

The Science Behind the Post-Vacation Slump

So, why does returning to normal life feel so jarring? It comes down to a cocktail of brain chemistry and psychology.

When you're on vacation, your brain is firing on all cylinders. New experiences trigger a release of dopamine, your brain's "this is cool and new!" chemical. Even less glamorous experiences like navigating a foreign train system produce dopamine as long as they’re new, and especially exciting experiences produce even more of it.

This constant stimulation creates a feeling of excitement and engagement. At the same time, navigating unfamiliar environments puts your body in a low-grade "fight or flight" mode, producing a steady stream of adrenaline. The adrenaline levels are low, so you may not feel anxious, but it’s enough to keep you alert, engaged, and learning.

When you come home, that flood of dopamine and adrenaline suddenly stops. Your body has to recalibrate to its baseline levels, which can feel like a chemical letdown.

On top of that, you’re dealing with a massive context switch. Studies show that even just switching between apps on your computer can create trouble for your brain. So it’s no wonder that switching from a world of exploration or relaxation back to a world of emails and deadlines is a jolt to the system.

The Art of Coming Back

Once you’re back at your desk, three calendar appointments are the key to quickly regaining your productivity momentum. Be proactive and schedule three key things for your first week back:

First, create a dedicated catch-up block. Block off a couple of hours on your calendar explicitly for reading and responding to emails, chats, and reviewing meeting minutes from while you were away. This treats the process of getting up to speed as a significant and important task. It helps anchor your mind and stops you from feeling like catching up will be a never-ending upstream swim. It also sets expectations for your colleagues.

Second, schedule a coworker coffee chat. Schedule a brief, informal 15-30 minute chat with a trusted teammate who you enjoy spending time with. Reading through chats and emails and meeting minutes can tell you what happened, but a person can tell you how it happened. Plus, this early social reconnection helps you recapture the team's spirit and allows for a back-and-forth dialogue to fill in any gaps.

Finally, and most importantly, schedule something to look forward to in your personal calendar. The dopamine dropoff from vacation is one of the biggest factors in the post-vacation slump, so counteract it by planning a personal activity you'll enjoy. Some people go ahead and start planning their next vacation, but it doesn’t have to be something big. Whether it's brunch with friends, a trip to a museum, or even just a calendar block to sit at home and read a book, having something you are excited about on the horizon makes the return to routine much more palatable.

From a more mechanical point of view, 2025 is a fantastic year to be coming back from a vacation because AI tools have finally reached the point where they can really help. Even as recently as a couple years ago, some of the best advice was to sort your Inbox by sender or subject line rather than by date to find important messages.

Today, technology offers a far better solution. Modern AI tools built into platforms like Gmail, Outlook, and chat tools like Slack and Teams are incredibly effective at summarizing what you missed.

When I came back from our most recent trip, I opened Gemini inside my Gmail window and prompted it to "Show me the fifteen most urgent emails that came in since {the day my vacation started}.” It was spot-on, and it caught an email with a next-day deadline that I otherwise probably wouldn’t have caught in time. Copilot in Outlook offers similar functionality, and Slack’s features for summarizing all of the unread messages in a channel were adequate, if not perfect.

If you haven’t tried the AI tools in the last 3-4 months, you’re in for a big, positive surprise. They’ve gotten a lot better recently.

Finally, if you’re traveling across time zones and suffering from jet lag, there are a few ways to minimize the impact. First, try low-dose melatonin (1mg) about an hour before your new target bedtime for 1-3 nights after you arrive in the new time zone. Second, make sure you get sunlight from directly overhead early in the morning the first few days. Finally, eat a large breakfast at your new breakfast time the first day, even if you’re not normally a breakfast person.

Pre-Vacation Strategies

A little bit of preparation before you head out on vacation can make your return to the office feel less like a chaotic scramble.

First, tackle the Zeigarnik effect, the psychological tendency to remember incomplete tasks better than completed ones. On your last day at work, take a few minutes to write down all your "open loops." These are the unfinished projects, lingering questions, and nagging to-do items floating around in your head. Getting them onto a document clears your mind, allowing you to relax more fully on vacation. It also serves as a helpful transition document for any colleagues who might be covering for you.

Next, do your future self a favor and clean your physical and digital workspace. Coming back to a tidy desk is far more calming than returning to a mountain of papers. Similarly, use email management tools to your advantage. If you use a tool like Boomerang, you can schedule important emails to return to your inbox after you’re back. A word of caution: don't have them all arrive on your first morning back! Stagger them over your first few days to create a more manageable flow rather than a digital tidal wave.

Finally, think about your travel schedule. Flying out on a Saturday and back on a Sunday gives you the most travel days while using the least amount of vacation time. But returning mid-week (on a Wednesday or Thursday) can make your catchup period smoother. This gives you a shorter work week to ease back in, catch up, and re-acclimate before the weekend provides another short break.

A Fresh Start for Your Habits

Returning from a vacation has one big productivity upside as well! Coming back from a trip is what researchers call a "temporal landmark"—a point in time that mentally separates the past from the present, like a birthday or New Year's Day. This creates what's known as the "fresh start effect," providing a powerful psychological boost to build new habits or break old ones.

Because your routine has been completely disrupted, it’s a perfect clean slate. If you’ve been meaning to start a new morning routine, read more, or start an exercise routine, the first day back from vacation is a surprisingly effective time to start. The data shows that we are more likely to succeed with goals we initiate after a fresh start.

However, the flip side is also true: vacations can easily break the good habits you’ve already established. Maybe you lost your workout rhythm or forgot about your weekly review. Be mindful that restarting an old habit can sometimes feel even harder than starting a new one. Acknowledge this potential resistance and make a conscious effort to jump back into the positive routines you don't want to lose.

Why It Was All Worth It

When you're buried under a pile of work, sometimes you might wonder if the vacation was even worth the hassle. The answer, from a productivity standpoint, is a resounding yes.

Research from Ernst & Young found a direct link between vacation time and job performance. For every 10 hours of vacation an employee took, their year-end performance reviews were, on average, 8% higher. Taking time off is a powerful antidote to burnout, which is a total productivity killer. It boosts creativity by exposing you to new ideas and environments, and it gives your mind the space it needs to solve complex problems in the background.

The highest-performing employees also tended to be the ones who took the most vacation. That said, we’re not sure which direction the causality runs, so if you’re underperforming, don’t book a long vacation and tell your boss we said so! But as far as we can tell, vacation is not just a benefit. It’s a smart investment for your employer, leading to higher engagement, lower absenteeism, and better work.

Tip of the Week

Before your next trip, set a reminder for yourself a week before you leave. When it goes off, open your calendar for the week you return and schedule three things:

1. A block of protected time just for catching up on emails and projects.

2. A brief, casual meeting with a coworker to get the human summary of what you missed.

3. A personal activity you can look forward to, like a nice dinner out or a weekend outing.

Taking these simple steps will transform your return from a stressful ordeal into a smooth, controlled transition, helping you hold onto that relaxed vacation feeling for just a little bit longer.

To learn more, listen to the full podcast episode.

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Although real-time chat apps and virtual meetings present new issues, managing the email flood remains one of the biggest productivity challenges we face. While there’s no single magic bullet, understanding some core principles of email management and developing a personal system can transform your inbox from a source of stress into a… source of slightly less stress.

The Origins of Email Management

Email is now 54 years old, but the main systems that shaped modern thinking around managing significant amounts of it appeared about half that long ago. The conversation often begins with David Allen’s groundbreaking productivity method, Getting Things Done (GTD). Published in the early 2000s, GTD wasn’t only about email, but its central idea was revolutionary for knowledge workers: your brain is for having ideas, not holding them. The goal is to get tasks, reminders, and obligations out of your head and into a trusted external system. If you listened to Episode 1 of the podcast, this idea probably sounds plenty familiar!

As email became a primary channel for work, these principles were adapted to the inbox. The popular movement known as Inbox Zero, coined by Merlin Mann, grew from this philosophy. The core idea is that every email in your inbox represents an open loop or an unfinished task cluttering your mind. By processing each one, you clear both your digital and your mental workspace.

The GTD framework for processing items in your inbox is built around a simple but powerful decision-making process, often called the "three D's":

1. Do it. If a task takes two or three minutes or less, do it immediately. It will take you longer to file it, track it, and come back to it than to simply get it done.

2. Delegate it. If the task is not for you, forward it to the right person.

3. Defer it. If you can’t do it now, you need a system to remind you to handle it later.

This "defer" category has always been the trickiest. In the early days, people created complex manual systems to manage deferred emails. One famous method was the 43 Folders system, a physical filing technique adapted for the digital world. You would create 43 separate email folders: one for each of the next 31 days and one for each of the 12 months. If you needed to see an email again on July 15th, you’d drag it into the "July" folder. Then, on July 1st, you’d move it from the "July" folder into the "15" folder. On the 15th, you’d finally move it to your "Today" folder. It was a logistical nightmare.

This is why the invention of email snoozing (something very close to our hearts!) was a game-changer. Instead of manually moving an email through a labyrinth of folders, you can now simply tell it when you want it to reappear at the top of your inbox.

To File or To Search? No Longer a Debate

Another major shift in email strategy came about 15 years ago as email search technology incorporated techniques from web search and became significantly more powerful. Now meticulous filing is (or at least should be) mostly a thing of the past.. Creating a complex tree of folders for projects, clients, and receipts used to be standard practice. However, research has turned this idea on its head.

Studies have found that searching for an email is about 3.4 times faster than trying to find it in a folder. This doesn’t even account for the time you spend organizing and filing in the first place. The problem with folders is that they require perfection. An email about a flight receipt could go in the "Travel" folder, the "Receipts" folder, or a project-specific folder. When you need to find it later, you have to remember the exact logic you used months ago. With powerful search functions built into modern email clients, it's far more efficient to archive everything and trust that a quick keyword search will pull up what you need.

This leads to a related debate: should you delete emails or just archive them? With free accounts offering 15 GB or more of storage, the need to delete for space is less of an issue. The mental energy spent deciding whether to keep or delete an email is often not worth the minuscule amount of space you save. Unless it's obvious junk, simply archiving is the path of least resistance.

A Cautionary Tale: Always Check Your Spam

Even with sophisticated filters, email systems aren’t perfect. Important messages can and do get lost.

At our 20th year MIT class reunion (how did that happen so fast?!), astronaut and former space station commander Jasmin Moghbeli was the featured speaker. A highly accomplished MIT graduate and military helicopter pilot, she was a top candidate for NASA's astronaut program. After applying, she waited for NASA to contact her references. The day came and went, and she heard nothing, assuming she hadn't made the cut.

At the last minute, she decided to check her spam folder and found the NASA emails buried there. She frantically called her references, urging them to check their spam folders as well. They found the requests, submitted their recommendations just in time, and the rest is history. A similar story involves a restaurant that almost missed its invitation to receive a Michelin star because the email landed in their junk folder. The lesson is clear: if you’re expecting something important, always check your spam.

A Toolkit of Strategies for Taming Your Inbox

Developing a personal email system is about picking the strategies that fit your work style and challenges. Rather than following one rigid method, you can combine several powerful techniques to build a workflow that brings you clarity and control.

Technique 1: Triage Before You Process

Just as an ER doctor triages patients, a good first step in managing your inbox is to quickly sort and clear out what isn’t urgent. This prevents you from getting bogged down in low-value messages.

• Perform a Bulk Deletion: Before you read a single email, scan your inbox and use the multi-select feature to check off all the obvious junk, sales pitches, and notifications you don't need. Delete them all in one go. Clearing out 10-20 emails in seconds provides immediate momentum.

• Use a "Promotional" Email Address: A powerful long-term strategy is to pre-filter emails at the source. Create a separate, free email account (like an Outlook.com or another Gmail address) that you use exclusively for online shopping, newsletters, and loyalty programs. This keeps the vast majority of promotional emails from ever hitting your primary inbox, but makes them accessible when you need them.

Technique 2: Move Through Your Inbox with a System

Once the clutter is gone, process what's left in a systematic way. This avoids the common trap of randomly clicking on messages, which drains focus and energy.

• Enable Auto-Advance: In your email client's settings, turn on the feature that automatically opens the next message after you archive or delete the one you're on. This creates a focused, sequential flow and prevents you from getting distracted by returning to the full inbox view.

• Apply the Two-Minute Rule: For any email that contains a task you can complete in two minutes or less, do it immediately. Approving an expense, answering a quick question, or confirming a time is faster to do on the spot than to track and return to later.

• Move Big Tasks to a To-Do List: Your inbox is not a project management tool. If an email represents a significant task, your goal should be to move that task to your dedicated to-do list. Use an integration that can create a task directly from an email, including a link back to the original message for context. Attaching this context automatically is key: emails, or email threads, will often contain much of the information you need to complete the task, and linking it to your to-do automatically will save you time-consuming admin work (or, god forbid, trying to remember the details in your brain!). Once the task is created, archive the email. It's now tracked in the right place, and your inbox is clear. Both Gmail and Outlook come with simple to do lists, but if you need a more powerful option, GQueues is a good to-do list app that we happen to build!

Technique 3: Master the Art of the Deferral

Many emails can't be actioned immediately. The key is to get them out of your sight and trust that they will reappear at the right time.

• Snooze for Later: Use the snooze feature for time-sensitive but not immediate items. If you get a flight confirmation for a trip next month, snooze it to the week of the trip. If you get an agenda for a meeting in three days, snooze it to the morning of the meeting. Gmail and Outlook now provide free options for this, but if you’re a power user or need to snooze messages and have them only return if someone doesn’t get back to you, check out Boomerang for Gmail or Boomerang for Outlook, the products that first brought the concept to life and have continued to improve the features since.

• Batch Your Brainpower: Some emails require deep thought and a lengthy response. Instead of letting them linger in your inbox, creating a persistent, low-level stress, set them aside and use a dedicated work block to power through them en masse. You can create a "Requires Response" label or snooze them all to a specific time, like 3:00 PM. This allows you to tackle these demanding messages with fresh energy, rather than squeezing them between other tasks.

Technique 4: Manage Your Emotional Responses

Finally, some emails are challenging not because of the work they require, but because of the emotions they provoke. Having a strategy for this is crucial.

• The "Cool-Down" Draft: When you receive an email that makes you angry or frustrated, resist the urge to fire back an immediate reply. Instead, open a reply draft, but immediately delete the recipient from the "To" field so you can't accidentally send it. Write out everything you want to say, no matter how harsh. Then, snooze that draft until the next morning. When you revisit it 24 hours later with a cooler head, you can edit it into a professional, productive response that serves your goals.

Tip of the Week

Ready to build a better email habit? Try this simple, week-long experiment to train your brain to process your inbox more systematically.

1. Set Up Auto-Advance: First, go into your Gmail settings and turn on the "auto-advance" feature. This will automatically move you to the next email after you archive, delete, or mute a conversation.

2. Use the Flowchart: Print this simple flowchart that walks you through the decision-making process for each email (e.g., Is it actionable? Can it be done in <2 minutes? Do, Delegate, or Defer?). Tape it to your monitor so it’s always visible.

3. Run a 20-Minute Drill: Set a timer for 20 minutes. Start with your newest email and work your way down. For each message, use the flowchart to make an explicit decision. The goal isn't necessarily to reach inbox zero, but to practice the habit of making a quick, definitive choice for every single email.

Repeating this drill daily will help make the workflow feel automatic, turning a cluttered inbox into a manageable part of your day.

To learn more, listen to the full podcast episode.

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Understanding Your Chronotype

Your chronotype is mostly determined by age and genetics. While you can adapt slightly with lifestyle changes, your innate preference is mostly fixed. As we age, though, our chronotypes shift. As most parents know, young children naturally wake up early, then as we enter our teenage years, our natural wakeup time shifts about two hours later. From there, we slowly shift to earlier and earlier chronotypes, about 15-20 minutes per decade, explaining why seniors, like toddlers, frequently wake up at dawn.

For working age adults, researchers have identified three core chronotype categories: morning larks, night owls, and those balanced in between.

Around 40% of working-age people are natural morning larks. They wake up early, often without alarms, and experience peak productivity between 10 AM and noon. They're energized by morning routines and fade by early evening.

On the flip side, about 30% of working age adults are night owls. They prefer waking later and hit their peak productivity between 2 PM and 4 PM, often experiencing a creative second wind around 7 or 8 PM.

The remaining 30% fall somewhere in the middle, enjoying flexibility without strong preferences for morning or evening hours.

Society's schedule often reflects the preferences of those in charge, who are typically older and wake up earlier. So night owls, though a significant portion of the population, can struggle with societal expectations built around early schedules.

The mismatch between personal chronotypes and societal expectations can lead to chronic sleep deprivation, negatively affecting mood, health, and productivity. Studies, including the groundbreaking chronotype survey conducted in Munich in 1976, have shown clear biological roots for these preferences. Turns out there’s a biological reason senior managers are always complaining about young employees being lazy and wanting to sleep in!

Optimizing Your Productivity Based on Your Chronotype

Once you identify your chronotype, regardless of which one it is, strategically organizing your tasks around your natural energy cycles can significantly boost productivity.

As you’d expect, you generally want to work on projects that require analytical thinking or long stretches of deep, focused work during your peak energy hours. If you’re going to be making major decisions, whether on your own or in a meeting, you’ll generally be better at it when your energy levels are high rather than when they begin to flag.

Interestingly though, recent research from the National University of Singapore suggests that creative work might be best done outside of your peak energy times. Their working theory is that reduced executive function during lower-energy times of day also reduces self-criticism and self-censoring. So your mind spends more time considering high variance ideas, which can lead to breakthroughs.

That means morning larks should reserve intensive analytical work for late morning, around 10 AM to noon, with creative or administrative tasks scheduled for the afternoon.

Night owls, on the other hand, should save deep analytical tasks for their natural peak hours in the mid-afternoon, roughly between 2 PM and 4 PM. Creative or routine tasks are best tackled during your second energy peak, later in the evening, or during the groggy early morning hours.

Practical Tips for Better Sleep and Productivity

To support your chronotype, you’ll want to follow sleep best practices, nothing crazy, just the kind of boring advice basically every credible medical resource provides. From an energy-levels standpoint, the single most important element of that is maintaining a consistent wake-up time, even on weekends. Consistent means “within an hour or two” rather than a rigid tiny window - it’s okay to sleep a little late some days.

More irregular sleep than that schedule create "social jet lag," making you feel continually tired, much like real jet lag. To minimize this, if you have a really late night, consider opting for a short afternoon nap instead of oversleeping. Naps are underrated: Einstein was known for napping daily, and NASA performed research that showed a 20 minute nap (set your alarm for 30 minutes) can make an enormous improvement in long-haul pilot capabilities.

There are a couple more high-impact, low-effort sleep tips: limiting screen time two hours before bed, especially blue-light-emitting devices like smartphones and tablets, significantly improves sleep quality. If screen time can't be avoided, enable warmer, yellow-toned night modes. Choose a distant TV over a closer tablet for your late night binge watching.

Finally, morning sunlight exposure, especially in the receptors located at the bottom of your eyes, also plays a vital role. That morning light helps reset your circadian rhythm. So consider a morning walk.

Supporting Your Team

In workplaces, optimal scheduling means balancing individual chronotypes with team needs. One optimization is from establishing a reduced set of core hours when all team members must be available. That leaves the rest of the schedule flexible so employees can choose to work at the peaks of their individual productivity, like early in the mornings or late in the afternoons.

Ideally, create a weekly schedule for your team that includes a stretch of 2-3 meeting-free hours during one or two mornings and one or two afternoons per week. That way, both night owls and morning larks can find time to get into flow state for their deepest work.

Finally, if you have a mission-critical meeting, 3pm is the absolute best time to schedule it. Night owls are at their peak energy levels, and morning larks typically hit a second wind after a 1-2:30 lull.

Tip of the Week

If you don’t already know whether you’re a morning person or a night owl, take the "Five-Item Ultra-Short Munich Chronotype Questionnaire (MCTQ)," a simple tool to determine your natural sleep and wake preferences. Once you know your chronotype, spend a week tracking your energy levels throughout the day, identifying peak productivity and creativity windows. Adjust your schedule accordingly, and you'll likely see a noticeable improvement in your efficiency and overall wellbeing.

To learn more, listen to the full podcast episode.

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• We lose track of time

• We stop paying attention to the outside world and our own worries

• We’re completely engrossed in the project we’re working on

• At the end, our energy levels were as high or higher than when we started

• We got our absolute best work done

Psychologist Mihaly Csikszentmihalyi, the pioneer of positive psychology, coined the term "flow" after discovering that people often felt happiest not while lounging on a beach, but while fully engaged in a challenging activity. In his book Flow: The Psychology of Optimal Experience, he writes about his experience studying artists, athletes, CEOs, and more. He found a common thread: during their best moments of performance and fulfillment, time faded, self-consciousness vanished, and everything just... flowed.

Why Flow State Matters

Getting into flow isn't just about feeling good. Research from McKinsey found that executives reported being up to 500% more productive when they're in flow. People who regularly spend time in flow state also report lower levels of burnout and higher job satisfaction.

Consider Frank Lloyd Wright, the legendary architect. He famously designed Fallingwater, one of his most iconic works, in a single two-hour session. After mulling it over in his mind for some time, he finally sprang into action when his client called to say he was on the way. That burst of focus, a flow state, produced a world class masterpiece.

Archimedes offers another fascinating example. Legend has it he was so engrossed in solving a geometry problem that he didn’t notice the Roman army had captured his city. When Roman soldiers entered his home, he confronted them, yelling his last words - "Do not disturb my circles!" They scuffled, and Archimedes was killed.

Archimedes was famously distraction-resistant, and that intense focus contributed to his many groundbreaking discoveries in mathematics, physics, and engineering, like his principle of buoyancy, early work on levers and pulleys, and ingenious war machines. Archimedes is a testament to how deep concentration can unlock world-changing ideas.

Fallingwater and Archimedes’ Principle may require genius, but flow doesn’t. Flow can be a child building a complex LEGO set, oblivious to the world. Or a software engineer debugging code for hours, only to look up and realize the day is almost over. Or even a gardener planting a row of carrots under the warm sun.

When you're in flow, your brain activity changes. The parts responsible for self-awareness and worry quiet down. Meanwhile, areas linked to reward and motivation light up. It’s not just an anecdotal experience—it's a neurochemical one that you can see with brain imaging.

In fact, flow might be one of the keys to thriving at work and in life. So what does it take to get into flow?

The Flow Formula

Unfortunately, I have bad news. Short of some very spooky experiments involving wires in the brain, nobody has quite figured how to summon flow on demand.

All we can do is put ourselves in an environment that allows it, and hope that it comes. To increase your chances of entering flow state, there are a few conditions that you can try to meet:

• A balance of challenge and skill: The task should be tough enough to demand your full attention, but not so hard that it feels impossible.

• Continuous feeling of progress: It helps to get feedback as you’re working that you’re accomplishing something as you go.

• A sense of control: Flow isn’t about going where the universe takes you. You want to feel in command while you’re in flow.

• Uninterrupted time: Distractions are the ultimate enemy of flow. Even a single ping can knock you out. And getting into flow takes time, so if you don’t have at least an hour, you probably won’t achieve it.

Meditation can help, too. People who regularly meditate are more likely to get into flow, thanks to their ability to calm their minds and focus attention. And increasing skill levels in an area can also help bring on flow state - Csikszentmihalyi’s research showed that the higher the skill level a practitioner had in their profession, the more likely they were to regularly experience flow.

Interruptions: The Flow Killer

Unfortunately, modern work life isn’t designed for flow, and as best we can tell, people are spending less time in flow state than ever. Microsoft research shows that the average knowledge worker experiences 259 interruptions a day. Emails, Slack and Teams messages, phone calls, and meetings constantly pull us out of focus.

And the cost? According to UC Irvine researcher Gloria Mark, it takes 23 minutes to fully resume working on a task after an off-topic interruption. Multiply that by the number of pings and pop-ups you face each day, and you're losing an estimated 2.1 hours daily—nearly five weeks of work per year to interruptions.

How we engineer flow prone state for our team

To combat interruptions and increase flow, we implemented a company-wide "maker time" at Boomerang. Everyone paused their inboxes, turned off Slack, and blocked off an entire afternoon free from meetings, once per week for deep, uninterrupted work. Because everyone had the same interruption-free schedule, there was no expectation to be responsive during that time. So people had the opportunity to create those blocks of time, and the encouragement to pick tasks that would be well suited for flow state and deep work.

We also try to batch as many meetings as possible into one day a week. That way, most of the team has enough schedule flexibility to create a lot of flow state opportunities. Meeting Thursday is always pretty tough, but Flow Friday often makes up for it.

Finally, one way our team taps into flow is through company hackathons. For the past several years, we've organized dedicated retreats designed specifically to foster deep focus and creative thinking.

We clear all our calendars from typical meetings and provide meals, a place to work, and a place to stay for everyone. We deliberately choose to work on projects that are a little bit more “weird” and creative than we’d normally get to in our every day work. By pairing those projects with long stretches of empty time, people consistently achieve remarkable breakthroughs and leave feeling energized and inspired.

Tip of the Week

If you don’t already have dedicated flow time in your schedule, carve out at least one uninterrupted two-hour block this week. Silence notifications, pause your inbox, and let your team know you’re focusing. Consider pairing this with a ritual to cue your brain—a specific playlist, a cup of tea, or a breathing exercise. And if you lead a team, set the example. Let others know when you're entering flow, and respect their focus blocks, too.

To learn more, listen to the full podcast episode.

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Checklists aren't flashy or complicated, but their impact can be profound. But why is something as straightforward as "checking a box" so valuable?

The answer is because checklists prevent failures of execution, not failures of knowledge. Failures of knowledge can be remedied by training and education. But failures of execution reflect a fundamental limitation of the human brain. Most people can only keep 7 things in working memory, but most processes are longer than that! Checklists are the lightest-weight tool available to fill that gap.

So how can you and your team best put these incredibly simple project management tools to work to prevent errors and keep everyone on track?

How a Disaster Gave Birth to the Checklist

Checklists first emerged from tragedy. In 1935, Boeing’s innovative new airplane, the B-17, crashed during a demonstration flight. The cause? Pilot error. The crew forgot a basic step: disengaging a lock. Realizing humans can only hold so many tasks in memory, Boeing developed the first pre-flight checklist. This simple 19-step list quickly became aviation standard practice, ensuring pilots didn't overlook critical steps.

NASA adopted this powerful tool for the Apollo missions. Astronauts walking on the moon relied heavily on cuff checklists to manage their complex tasks in the unfamiliar lunar environment. Even highly-trained people like the astronauts need the assistance of documentation when operating in the high-stress environment of outer space.

One humorous and secret addition even appeared during Apollo 12—a playful prank by ground crew who included NSFW Playboy centerfold images tucked discreetly into the astronaut's cuff lists.

Checklists Save Lives in Operating Rooms

The aviation industry's success with checklists inspired Dr. Atul Gawande, who wondered if they could also help in operating rooms. He observed highly trained surgeons making preventable mistakes, like leaving sponges inside patients or even operating on the wrong limb.

Gawande's groundbreaking research revealed that a simple surgical checklist—just 19 items—reduced surgery-related complications by 36% and surgical deaths by a staggering 47%. The World Health Organization now officially recommends surgical checklists worldwide, validating how critical a structured, simple reminder can be, even among highly trained experts. Gawande wrote a book about the experience, The Checklist Manifesto that has become a favorite read of many on the Boomerang team.

Bringing the Checklist to the World of Knowledge Work

While not life-or-death, checklists also offer enormous benefits to teams doing complex knowledge work—like launching software, onboarding new hires, or running marketing experiments.

At Boomerang, we learned firsthand how powerful checklists could be after repeatedly encountering preventable mistakes during product launches. After launching (and, sadly, discontinuing) Boomerang for Yahoo! Mail, we realized we needed a reliable, repeatable process to prevent oversights.

Our product launch checklist was developed after missteps like forgetting to do something that we had identified as important from a previous launch. This has become a vital part of our workflow, refined over more than a decade. It includes everything from analytics setups to pricing grid checks—avoiding costly errors and saving countless hours.

Our marketing and in-product experiment checklist has also been a lifesaver for our team. In 2024, our “year of experiments,” we conducted 52 different experiments across product and marketing. At first, we’d inevitably forget something important - like making sure we could reassemble who was in which cohort for analytics, or that we needed to make all the variants accessible for QA purposes. But by the end, our experiment checklist had solved that problem, and as long as we remembered to use it, our experiments usually ran without a hitch.

Another place checklists are critical for Boomerang's team is employee onboarding. At Google, they discovered that simply giving new hires a short onboarding checklist increased productivity by 25%, and was equivalent to onboarding employees a full month faster. Now, things like administrative to-dos, key training, and more is documented in a checklist that we plan ahead of time and share with new team members on their first day.

Creating Checklists That Actually Work

Not all checklists are created equal. To be effective, they need to follow three key rules:

1. Make Items Decidable and Deterministic: Each step must clearly define what “done” looks like. Avoid vague instructions like "Check analytics." Instead, say something concrete: "Confirm Google Analytics is capturing event X."

2. Balance Specificity and Generalization: Checklists should be specific enough to be actionable, yet general enough to apply broadly. They become most powerful when refined over multiple uses, building on collective learning.

3. Ensure Team Ownership and Buy-In: Checklists can't simply be imposed from above. Teams must be involved in their creation and improvement, understanding why each item matters, removing ones that become irrelevant, and adding new ones when helpful additions are identified. Without buy-in, checklists risk becoming mere paperwork rather than useful tools.

These principles are laid out nicely in academic research on secure software development done at Vanderbilt University. But we’ve independently learned these lessons through trial and error as well. We’ve found a dramatic uptick in launch checklist adherence since we started updating it as a team before a project starts and after a postmortem meeting. That also gives us a focused, dedicated time to set up instance-specific items before the process begins.

Our experiment checklist has become more deterministic and more decideable as we’ve improved it. Originally, the checklist contained items like “set up analytics,” which were not specific enough to confirm. Now, it’s expected that an engineer setting up an experiment will trigger the event behavior, then go into the analytics platform and confirm that the event shows up from testing. Reliability has increased significantly.

Another important distinction is between "do-confirm" checklists, for workflows that can be verified after all the items are done, and "read-do" checklists, for instructions that need to be followed in a specific order. Our product launch checklist is a series of “do-confirm” lists, where different people can work on different items in parallel, making sure they’re all done before launch day. Our payroll checklist is a “read-do” checklist, because it’s very important that we change deductions before we try to pay taxes!

Tip of the Week: Identify Your Own Checklist Opportunity

Here’s your tip for this week: Look at your workflow or team operations. Identify at least one task or event you regularly handle that has at least 5-7 steps. Could a checklist reduce mistakes, save time, or help onboard new team members more smoothly? If so, build your first checklist.

Whether you're running payroll, preparing a product launch, or even organizing your next team offsite, investing the time to create and refine a checklist is an investment in future efficiency and sanity.

And remember, checklists aren't about compensating for ignorance or lack of skill—they protect you from human error when your mind is busy juggling too many details.

To learn more, listen to the full podcast episode.

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There’s a reason for this: productivity strategies aren’t one-size-fits-all, nor are they timeless and eternal. What works today may falter tomorrow because your role, your responsibilities, or even your energy levels change. But here’s the good news: that doesn’t mean you're failing.

The Myth of the Perfect System

Productivity methods, much like trendy diets, are appealing precisely because they seem like silver bullets—easy solutions for complex problems. But just as no single diet works universally, there's no one productivity approach that suits everyone. For example, studies on dieting repeatedly demonstrate huge variability: some participants lose significant weight, while others actually gain weight—on the very same diet! Identical twins given the same meals even showed different results.

Those studies on dieting offer a helpful mental model for productivity techniques. A 5 a.m. morning routine might energize someone who went viral on social media, yet leave you feeling exhausted and frustrated. Bullet journaling may provide clarity and control for a season, then suddenly feel cumbersome. These shifts aren’t failures—they're signals that something has changed, and it's time to adjust.

Productivity is a Journey, Not a Destination

We often imagine productivity as a destination—a perfect state of accomplishment and clarity. But productivity is much more like a river, constantly flowing and changing. Life is dynamic, and so are your workflows and strategies. Accepting this truth helps reduce stress and guilt when your favorite method stops working.

Instead of chasing perfection, think of productivity as building a "toolbox" filled with tactics that you can pick and choose from based on your circumstances. If waking up early boosted your productivity for three months and then left you feeling under-rested, that's still a win, even if it’s no longer sustainable. The value comes in having multiple strategies ready, knowing when to switch between them, and understanding that a temporary strategy isn't a failure—it's a resource.

Recognize When It’s Time for a Change

To effectively adjust your productivity tactics, you need awareness. One powerful way to do this is through regular weekly reviews. Take stock of your progress: Are tasks consistently slipping through the cracks? Has your role or your daily routine changed, and your usual methods aren’t keeping up?

A weekly review acts as an early-warning system. If you notice you're repeatedly missing key goals or deadlines, it might not be due to your abilities or discipline, but rather an outdated approach. Whether it's a new team dynamic, different project management tools, or a shift in personal circumstances, recognizing that it's time to adapt is crucial.

Leverage the Fresh Start Effect

Once you recognize it's time for a change, another valuable productivity tactic is using the "fresh start effect." Psychologists have found that we’re more likely to commit to change at the start of new periods, such as New Year's Day. But January 1 isn't the only date you can try turning over a new leaf: a birthday, a new job, or even after returning from vacation can all be helpful milestones for you to kick off a new habit or routine. While many people abandon New Year’s resolutions after a few weeks, a significant number successfully make lasting improvements by capitalizing on these symbolic fresh starts.

Short-term Wins Count, Too

Don't dismiss short-lived commitments, like New Year's resolutions that didn't make it all 365 days, as failures. Instead, view them as valuable bursts of motivation that can help establish new habits or reset your routines. Even short-lived productivity wins are valuable. Maybe you did a daily seven-minute workout routine consistently for four months before stopping. Rather than viewing that as a failure, recognize that during that period, you achieved something meaningful.

At Boomerang, we have tried to instill this philosophy as part of our team’s culture. The guiding principles document that we review with all new hires includes the phrase “better is good,” a deceptively simple mindset. Our former president reflected on this exact attitude in an inspiring speech. Short-term wins are still wins, and they add up and contribute significantly to your overall growth and success. And if you look for an upcoming milestone to kick off a new fresh start, you can compound your wins no matter how long they last. Celebrate these achievements rather than dismissing them simply because they weren’t permanent.

Embracing Change (Like a Buddhist)

The Buddhist principle that "change is constant" can greatly benefit our productivity mindset. Change is inevitable, and our resistance to it often increases our own stress. Instead, approaching productivity with openness and flexibility can alleviate frustration. If your circumstances shift—perhaps a new commute alters your morning routine or a promotion changes your workload—acknowledge the change and adapt rather than clinging to outdated practices.

Tip of the Week: Build Your Productivity Toolbox

The key takeaway from this episode is straightforward: start building a toolbox of diverse productivity tactics that you can turn to as your situation changes. Consider strategies that have worked in the past and ones that might work under different circumstances. When one tool becomes less effective, it isn’t a failure. See it as an opportunity to try something new from your toolbox.

Keep experimenting, stay flexible, and remember that productivity isn’t about finding a perfect silver bullet—it’s about continuously refining and adapting as you find what works and your situation changes.

To learn more, listen to the full podcast episode.

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Why Accountability Matters—Especially When You’re The Boss

When you're an entrepreneur, freelancer, or someone forging your own path, there's often nobody around to enforce deadlines. Coming straight from environments like college or traditional jobs, where deadlines, grades, and expectations are clear, can make this shift challenging. Without clear consequences or timelines, it's easy to let tasks drift.

That's why successful entrepreneurs and self-starters build their own systems for accountability. It can be the difference between launching a successful product and running out of money before you ever launch.

Four Proven Ways to Create Accountability

Research suggests that simply thinking about your goals isn't enough. If you want to achieve meaningful progress, here are four strategies that can significantly increase your odds of success:

1. Write It Down:
   Studies show writing down your goals increases your chance of success from 43% to 61%. Simply committing to paper can make your goals more concrete.

2. Set Action Commitments:
   Adding clear steps and "trigger” statements boosts your chances further. For example, "On Monday morning, after I get coffee, I will write my weekly report." Anchoring the task to immediately follow something you already do anyway helps with follow-through.

3. Tell a Friend:
   Sharing your goals with someone else jumps your success rate to 76% (the source on this statistic is highly questionable!). This method introduces social accountability without the need for authority or power dynamics.

4. Regular Check-Ins:
   Regularly updating someone—whether a friend, coach, or accountability partner—can significantly increase your consistency and success. This explains the effectiveness of executive coaching, where simply knowing you'll report progress to someone helps keep you on track, even though the coach technically does not have any authority.

Accountability Tools: Flow Club and Body Doubling

Sometimes the mere presence of others—even strangers—can dramatically improve your productivity. Platforms like Flow Club and Focusmate leverage this by letting you work virtually alongside others for set periods. You announce your goal, work silently for a fixed period, and then report back.

This strategy, known as "body doubling," is especially popular in ADHD communities. Surprisingly, even having strangers silently working alongside you on Zoom can create a powerful accountability effect. You're essentially adopting an identity as someone who follows through.

Pair Work Sessions: Boost Productivity and Accountability

Working alongside someone else—even on different tasks—can provide similar accountability. Many find "work sessions" or pair programming highly effective because:

• You stay focused, knowing someone else is present.

• You benefit from immediate feedback and support.

• Your productivity and sense of satisfaction often increase.

Instead of filling your day with meetings, consider scheduling more paired work sessions. It keeps you accountable and makes daunting tasks feel manageable.

Raising the Stakes: Commitment Devices

For some tasks, you may need to increase stakes further. Websites like StickK.com use financial and social stakes to drive accountability:

• Financial stakes: You put money on the line. If you don’t meet your goal, you lose money.

• Anti-charity option: Money goes to a cause you dislike if you fail, dramatically boosting effectiveness.

While not for everyone, these "commitment devices" often deliver strong results by adding real consequences to missed goals.

What About Habit Tracking and "Don’t Break the Chain"?

Another method—"Don't Break the Chain"—involves marking each day you complete a task, building a streak. However, its strict daily nature isn't practical for everyone. Instead, it’s best suited for forming new habits, not necessarily for flexible task management.

Tip of the Week: Find Your Accountability Style

If you're struggling with accountability, experiment with one of these methods:

• Flow Club or Focusmate: Ideal for immediate accountability.

• Set Personal Deadlines: If you respond well to internal commitments.

• Pair Work Sessions: Great for collaborative and team tasks.

• Commitment Devices: For high-stakes goals that need extra motivation.

Identifying which style resonates most can help clear tasks that linger on your to-do list, turning your "leftovers" into accomplishments.

To learn more, listen to the full podcast episode.

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Understanding Task Avoidance

Why do we avoid certain tasks? Often, it's personal. What's simple and enjoyable for one person might be daunting for another. For instance, one team member might eagerly dive into analyzing dozens of spreadsheets but dread reaching out to new contacts, while another might experience the exact opposite.

At its core, task avoidance usually stems from discomfort, uncertainty, or overwhelm. Recognizing what triggers your avoidance is the first step toward overcoming it.

Change Your Environment to Get a Fresh Start

One of the simplest yet most effective methods for tackling unwanted tasks is changing your environment. Surprisingly, small adjustments can significantly boost your productivity.

Research shows that our physical space influences how effectively we perform different types of work. For instance, rooms with high ceilings (eight feet or higher) are conducive to creativity and problem-solving, often referred to as the "cathedral effect." In contrast, spaces with lower ceilings enhance focus and analytical tasks. So if you're writing creatively, an open, airy space—or even outdoors—might help. Conversely, analytical tasks, like crunching numbers, are best done in smaller, quieter, enclosed spaces.

Temperature also matters. A study from Lawrence Berkeley National Laboratory found the optimal office temperature for productivity is around 69 to 71 degrees Fahrenheit. Performance noticeably declines if the temperature rises much higher.

But even beyond science-backed strategies, simply switching locations—from your regular workspace to a coffee shop or another room—can shake things up enough to break your procrastination cycle. Changing your lighting, working while standing, or even putting on a particular soundtrack can also cue your brain to engage with the task at hand.

Moah even has a dedicated soundtrack (from The Gilded Age) she plays to get her to tackle her inbox.

Make Friends with the Rats

A Dutch Zen master named Paul Loomans once described procrastinated tasks as "gnawing rats"—things that silently nag at the edges of your mind. Instead of trying to kill the rats, try sitting with them.

That means opening the doc you’ve been avoiding and just staring at it. Sit in the closet you need to clean. You don’t have to act immediately. But once you’re there, your brain can’t help but begin solving the problem. A task that once seemed daunting can become intuitive all of a sudden once you’ve put yourself in a position to begin engaging with it.

Making Tasks Easier and Less Intimidating

Another effective approach is to simplify or break down tasks, making them feel less overwhelming. Often, the hardest part is starting, so creating smaller, more manageable steps can ease you into action. Instead of "writing a report," set the goal to "write 150 words” or even “write just one paragraph.” These smaller goals significantly lower the barrier to starting and help build momentum.

Setup for Success: The Pre-Work Strategy

One highly practical tip to overcome inertia is preparing your workspace in advance. Before you head out for lunch or take a short break, set everything up for your next task. Open necessary documents, arrange your notes, open the right browser tabs, and create a clear, inviting space. When you return, the easiest path forward becomes diving straight into work, significantly reducing the resistance to getting started.

Time-Based Goals: The Pomodoro Technique

If task output feels overwhelming, shifting to a time-based goal can be liberating. The Pomodoro Technique—working for 25-minute intervals followed by a five-minute break—can be particularly effective for repetitive tasks. While it might not work for everyone, for certain tasks, setting short, manageable periods can make intimidating work feel more approachable.

Tailoring Tasks to Your Strengths

Sometimes, changing the format of your task helps make it more approachable. If creating a presentation feels overwhelming, begin by writing bullet points or a long-form outline instead. Once your ideas flow, translating them into the required format is far easier. Leveraging AI tools can also simplify this transformation, turning rough ideas into polished final products effortlessly.

Tip of the Week: Prepare Your Workspace

This week's actionable tip is straightforward yet powerful: Set up your workspace before stepping away for a break or lunch. Open the necessary files, arrange your materials, and position everything exactly as you need it. When you return, your environment will naturally guide you into productive action, turning intimidating tasks into achievable ones.

Remember, conquering task avoidance isn't about eliminating discomfort entirely but about developing strategies that make tasks feel approachable, manageable, and ultimately doable.

To learn more, listen to the full podcast episode.

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How to Prioritize Like a Pro

When your tasks pile up, it can feel overwhelming. One way to break the cycle is by using proven methods like the Eisenhower Matrix and the Ivy Lee method, both surprisingly effective tools developed nearly a century ago.

The Eisenhower Matrix helps categorize tasks into four clear quadrants based on two dimensions, their urgency and importance:

• Important and Urgent: These tasks naturally take priority and typically include critical deadlines and crises.

• Important but Not Urgent: Often neglected but essential for long-term success, such as strategic planning or customer research.

• Urgent but Not Important: Tasks that feel pressing but don’t significantly impact your goals, like minor administrative tasks or meetings without clear outcomes.

• Neither Urgent nor Important: Tasks that can be ignored or deleted altogether.

Identifying tasks with the Eisenhower Matrix way helps ensure you're not wasting precious hours on minor details, like spending excessive time debating office snack choices (we've all been there!), but instead investing in tasks that drive real value.

Prioritize Your Day the Ivy Lee Way

Charles Schwab, the magnate of Bethlehem Steel, which was one of the world’s largest heavy manufacturers, wanted to improve management of his massive operation. In 1918, he asked Ivy Lee, a productivity consultant, for help. Lee agreed, and requested time with each of Schwab’s executives. Schwab, being a businessman, wanted to know what it would cost — and Lee said nothing, unless it works; then, after three months, you can send me a check for whatever it’s worth to you.

Lee transformed the productivity of the company’s executives with a straightforward strategy:

1. At the end of each day, write down no more than six tasks to accomplish the next day.

2. Prioritize these tasks in order of importance.

3. When you start your day, tackle tasks in that specific order—no skipping around.

This method, surprisingly effective, forces clarity about what's genuinely important and prevents endless procrastination. But don’t take our word for it — Schwab was so pleased, he paid Ivy Lee a hefty consulting fee, equivalent to half a million dollars today!

When to Say No: The MoSCoW Method

Prioritization isn’t just about what you do—it's also about clearly deciding what not to do. The MoSCoW method helps teams align by sorting tasks into four categories:

• Must Do: Non-negotiable tasks.

• Should Do: Important but negotiable.

• Could Do: Nice-to-haves, optional based on time and resources.

• Won’t Do: Explicitly ruled out tasks.

Being explicit about your "won’t do" tasks frees mental space and allows you to fully commit to tasks that truly matter.

Flexible Time Blocking: The Real-World Solution

Rigid scheduling can backfire in unpredictable work environments. Instead, try flexible time blocking, especially for tasks that are important but not urgent—like strategic thinking, content creation, or customer research.

Alex has tried dedicating time to specific tasks throughout his day, but finds that if something comes up (something actually urgent and important) that interrupts this schedule, the whole system is ruined.

Rather than scheduling every minute of your day, set aside large, flexible blocks of time (e.g., at least two to three hours) dedicated to strategic priorities. If an unexpected event arises, simply shift this block elsewhere within your week. This method keeps your commitments manageable while ensuring essential work doesn't slip through the cracks.

For example, if you want to dedicate five hours weekly to customer research, allocate two blocks of two hours and three hours on Monday and Tuesday. If something urgent interrupts your scheduled time, you move this block to a day later in the week rather than losing it entirely. It's about flexibility and planning for turbulence, much like keeping a coffee cup at 80% capacity on a turbulent plane ride—by planning for flexibility, you won't spill everything at the first sign of trouble.

Motivation Matters: Choosing Tasks That Match Your Energy

Another often overlooked aspect of prioritization is matching your tasks to your energy levels and motivation. Tasks that excite you will naturally feel easier and more satisfying. But the real challenge lies in tackling tasks that aren’t as appealing—something we'll take a closer look at in the next episode.

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Tip of the Week: Flexible Time Blocking

If prioritization feels overwhelming, start with flexible time blocking. Dedicate specific, moveable blocks in your week to the crucial but not urgent tasks that typically get neglected. This helps ensure you make consistent progress without feeling boxed in by rigid scheduling.

First, identify which important tasks have been slipping. Next, allocate weekly blocks of time to these priorities without overfilling your calendar—allowing for adjustments as life inevitably gets messy. Remember, progress is always better than perfection.

To learn more, listen to the full podcast episode.

Understanding the Zeigarnik Effect

In the 1920s, psychologist Bluma Zeigarnik noticed something curious. Waiters at a café could perfectly remember customers' orders—until the bill was settled. Once paid, their memory of the order disappeared. Inspired by this observation, Zeigarnik conducted research that revealed our brains hold onto unfinished tasks, creating mental "open loops." This is why your mind insists on reminding you about incomplete tasks, often at inconvenient times like bedtime or during a relaxing weekend.

These open loops create cognitive stress and drain mental energy, reducing productivity and increasing anxiety. The key to reducing this stress, and improving productivity, is deceptively simple: you must manage your open loops effectively.

Finding Your System

Everyone manages their tasks differently. Some use digital tools from the straightforward and flexible, like GQueues, to the complex, like IBM Rational; others swear by pen and paper or even simple Google Docs. There's no universal solution—what works for one person might feel chaotic to another. Research backs this up: a survey by Atlassian showed that over half of people with a productivity system feel their approach would make no sense to anyone else. Yet, what's important isn't the complexity or elegance of your system. It's having a reliable place to put your tasks so your brain can let them go.

Alex has tasks scattered across multiple platforms—from Slack to email to physical reminders like a check tucked away in a backpack. Despite feeling overwhelmed, his system is almost effective, with very few tasks slipping through the cracks. However, the stress of juggling multiple locations still linger.

Moah is more structured, using a Mise-en-place kanban template after moving on from bullet journaling. She modified the template to have a simple 5-column layout for organizing tasks based on whether they are still awaiting prioritization, or if they need action today, this week, or in the indeterminate future. That way, it’s easy for her to always know what she needs to be working on, without any juggling needed.

Even simpler systems—like a daily checklist in a Google Doc—can also provide mental clarity by reducing the number of places you need to look for your tasks. The simplicity of knowing exactly where tasks reside helps in relieving the cognitive burden.

Productivity’s Hidden Benefit: Better Sleep

The act of capturing and writing down tasks has another surprising benefit—improved sleep. In a 2018 study by Baylor University, researchers divided participants into two groups: one wrote down tasks they had completed, while the other noted tasks yet to be done. Those who listed unfinished tasks fell asleep faster and experienced better sleep quality. By writing down these open loops, they effectively offloaded mental stress, quieting their minds.

So, contrary to popular wisdom, ending your day by reflecting on completed tasks isn't nearly as restful as noting the ones you still need to do.

Productivity Tips to Manage Your Open Loops

Here are a few actionable strategies to tame your open loops:

• Establish a Single Source of Truth: Choose one primary place—digital or physical—to store your tasks. This reduces confusion and the mental burden of remembering where everything is.

• Set a Daily Routine: At the end of each workday, spend 5-10 minutes updating your task list. Setting a daily alarm or reminder can help establish this habit quickly.

• Try Bullet Journaling or a Simple List: For beginners or those overwhelmed by complex systems, a notebook with daily to-do lists or bullet journaling can provide clarity and control.

• Automate with Caution: Automation tools, such as Slack integrations or AI-driven task capturing, can help organize tasks effortlessly. However, automation alone might not deliver the same psychological relief as manually writing tasks down, as the action itself can be therapeutic.

Team Productivity: Why Organization Matters

Organization isn't just a personal productivity issue—it's crucial for teams, too. According to Atlassian’s research, 80% of workers prefer taking on extra work rather than collaborating with a disorganized teammate. Leaders should actively help their teams adopt clear productivity systems to reduce collective anxiety and boost overall efficiency.

Tips of the Week

• If you don’t have any system for tracking your tasks, try something simple—bullet journaling, a paper to-do list, or tools like GQueues, Trello, or Google Tasks.

• Set an alarm on your phone 30 minutes before the end of your workday to remind you to update your to-do list. This helps you consistently maintain your system.

• If you already have a system, challenge yourself to use it more by adding at least one extra task this week that you ordinarily wouldn't write down.

Take Action Today

Remember, productivity isn't just about doing more—it's about freeing your mind to focus on the right things. Capture those open loops, quiet your mental chatter, and enjoy the peace of mind that comes with clarity.

To learn more, listen to the full podcast episode.