Perfectionism and pragmatism for new founders

Former perfectionist founder here. I run Mini Exhibitions and Art in Res with my cofounder. Sharing some advice I learned the hard way:

There's a meme about job interviews that goes like this: The interviewer will ask you, "What's your biggest weakness?" And you respond, "Probably that I'm a perfectionist."

I've never been asked this question in an actual job interview, nor have I asked it. But, I do think there is some wisdom in there. Perfectionist tendencies can make you a great fit for some jobs, and an awful fit for others.

My own career so far has basically been two jobs.

Career path 1, investing on Wall Street, is a great fit for a perfectionist.

• The stakes are very high ($10-100M+ might be riding on a single investment).
• A slight edge can be hugely profitable.
• A slight disadvantage can be hugely punitive.
• You can focus your attention on a particular area where you can outperform others (and you're typically encouraged to).
• You can ignore things that aren't relevant to your investments and prospective investments.

Career path 2, tech founder, is a terrible fit for a perfectionist.

• You will have a huge list of important to-do's that feel important, and no choice but to triage.
• Most mistakes can be fixed.
• Most advantages last only as long as you keep investing in them.
• In the early days, you and your cofounders need to wear all the hats (tech, sales, marketing, accounting, legal, HR, management, etc). And in the beginning, you'll suck at almost all of them.
• In most cases, quickly shipping and iterating beats trying to ship something flawless.

Is there something generalizable in here? I think so.

If you're thinking about a job where small mistakes are particularly costly (civil engineer, aerospace engineer, surgeon) or small advantages are particularly well-rewarded (lawyer, investor), these will play to your perfectionist tendencies.

Or, are you interested in a job where you can iterate quickly (software engineer, marketer, writer) or your ability to ship is more important than avoiding mistakes (artist, entrepreneur)? Pragmatists will outperform.

As a first-time founder, it took time to unlearn the perfectionism tendencies I picked up as an investor. And despite all the reading and all of the good advice I consumed, I still made a lot of classic newbie founder mistakes as a result: I shipped too slowly. I expected too much from version one. I didn't course-correct fast enough. I was too married to my original vision.

New job seekers and career-changers, I hope you can introspect on your own perfectionist or pragmatist tendencies and find the right career fit for you. And to the perfectionist founders reading this, take it easy on yourself.

PS: The original post is up at my blog here.