The single biggest mistake I’ve made in my creative life is to fall for the trap of perfectionism.

In hindsight it’s obvious, but the overachiever in me was set up to fall hard for the illusion of perfection. Today I’ll step through some of the areas in my life where I fell for the trap and what the outcome was.


My first attempt to publish content on the web was in 2007. I tried to self host WordPress, I tried Posterous, Tumblr, Blogger, Squarespace, Medium and eventually

The problem was perfection. I saw some amazing blogs, and I wanted mine to look just like those. I could never get the page layout to look the way I wanted, I spent too much time worrying about the purpose behind the blog or the topics I wanted to write about. The net effect was that I didn’t write and I never published. I missed out on years of practice and learning because I was trying to get the perfect platform first.

As of late 2023 I found a combination that I love; Ghost as the publishing platform, and Ulysses as the Mac writing app. These two amazing pieces of software finally have me writing with some consistency… but the delay was ultimately not worth it.

Task Management

Basically I fell for perfection on day one. Getting Things Done ( a task organization methodology) was an elegant process that offered the illusion of total control. After years of fidgeting with planning methodologies and learning different pieces of software, I had basically delayed getting anything done.

I delayed learning how I think about tasks, how I process work, how I prioritize, how I schedule work.. and I did this in exchange for what I thought was going to be the perfect task system with the perfect task application. Yet again, the delay was not worth it, I would have been better off using an imperfect system. I would have learned a lot more, and I’d be more productive today.


I bought my first camera in 2003, a Pentax Optio S. After that, a Canon PowerShot, Canon Rebel, Panasonic G1 , and then the Olympus OM-D E-M5.

I spent years trying to get the perfect camera setup before ever really focusing on photography and the subject of my photography. I obsessed over cameras, I obsessed over lights, I obsessed over lenses. Basically it’s called G.A.S.

Sure, I tried some interesting tests along the way.. I photographed a friends wedding, I did portraits, I shot some product photography. But I lost more time trying to figure out the gear, and should have spent more time taking photos and discovering what subjects I love to shoot. Yet again, years of creative progress were lost.

Videography / YouTube

Around 2015 I realized that video was more dynamic than photos, and would likely be a more exciting path. Perfectionism struck again. I couldn’t decide what types of videos to make, and I couldn’t get comfortable publishing those videos on the web. In my “shame” I made personal travel edits for me and my family, and only ever published those behind a password on my Smugmug page.

The end result? You guessed it. Years of progress lost. Nothing compares to the learning and feedback you get from putting your work out in the wild. The more you shelter your work, the more you slow down the pace of feedback and the rate of learning.


Perfectionism delayed the development of my skills in each and every example. Perfectionism was the excuse for imposing impossible constraints, and never actually getting anything done. So what do I actually recommend?

Just do it, just get started immediately. You only learn by doing. Pick a “good enough” starting point, and just get after it. Don’t even think until you’ve done that thing 50 or 100 times, set yourself a goal of how many times you’ll do something before starting to perfect it. Try out different varieties, learn what you like and don’t like. Most importantly make mistakes, you’ll never forget those lessons.

Perfection is the enemy of progress