The Perfectionist’s Trap: 3 Deadly Enemies of Getting Things Done
Episode 13 confronts the barriers to finishing a project and provides tactics for getting from 80% or 90% to "done"
I remember being 22, in Paris for the first time after graduating from college, standing in front of Ebih-Il of Mari in the Louvre. His bright blue eyes shone out from the alabaster the rest of him was carved from, and I was transfixed. I’m sad to say that I’ve forgotten most of the amazing art that I saw there, but Ebih-Il sticks with me.
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 is a bestseller, your software is the next billion-dollar unicorn, and your research paper is 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:
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.
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.
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!
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.