Act As If

Entrepreneurial Life Advice from Conan O’Brien

People suffering from and trying to overcome Impostor Syndrome (the feeling that even though you are doing good work and have made some big accomplishments that you’re really an “impostor” at your job and people are going find out) are somewhat endemic to startup and tech circles.

I think most of this is brought on by the rapidly changing toolsets, frameworks and technologies that you need to grapple with to put out a modern web app.

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So, it was pretty surprising that the best advice that I’ve heard on the subject comes from Conan O’Brien.

“In improvisational acting there is this great rule that I’ve used in my life: ‘Act As If’. Act as if this is completely normal. Of course I’m supposed to be interviewing Barack Obama. Of course I’m supposed to be playing guitar with Bruce Springsteen and of course there’s a big part of me inside that’s saying: ‘What are you talking about?’”

From “Conan O’Brien Can’t Stop” — 21:00

The best entrepreneurs that I’ve worked with have (without naming it) exhibited this same pattern.

1. Recognize privately and intellectually that some big crazy thing is about to happen: a key investor meeting, a sales call to a big new client or interview with a major publication.

2. Do the hard work of preparing and making sure their product and facts are all in line.

3. Execute through their fears and anxieties by “acting as if” in public.

Nothing is a cure all, but it is surprising how much even a simple phrase repeated to yourself can help.

Case in point: “Of course I should be writing a blog post about Impostor Syndrome.”


Michael Buckbee @mbuckbee — runs ExpeditedSSL — an add-on for Heroku that makes SSL fast and easy to get going.