Hack My Personality

My oldest friends (and fiancée) are the only ones who'd label me these days as an introvert. But even those opinions are based more on history than present. Somehow, I've convinced the people I spend all day with, my co-founders at Zapier, that I'm not.

Even they wouldn't go so far as to call me an extrovert but I've managed to escape the introvert label. Read on to learn how I did it.

Early Introversion

My family bought it's first computer when I was in elementary school. I remember spending nights and weekends playing Graal Online, writing assembly games for the TI-83+, and learning web development by coding profiles for AIM – instead of playing outside, much to the detriment of my parents. In that world, it's so easy to hide and deflect.

Sometime early in high school, I became very cognizant of myself acting more and more introverted and wanted to change my behavior. So I put plans into motion to fix this by literally forcing myself into uncomfortable situations.


In high school I started to perform magic (ie. a “magician”). Out of all the things I've done, this ranks as one of the hardest. I can still viscerally remember the gaze of 20-30 fellow students watching me perform during passing periods.

The performance metric I tracked was how much my hands shook. In the beginning, I was so nervous that I couldn't even perform tricks properly. That passed slowly with time but never fully went away. Even today my hands still shake if I perform.

This culminated in me asking a girl (successfully) to our high school prom using a magic trick. I haven't performed nearly as much since.

The skills I learned weren't wasted though! These were important first steps to get comfortable in unknown situations.

Mechanical Engineering

Towards the end of high school I had to make some decisions about my college major. Given my predisposition to computers, computer science was the obvious way to go, right? That's what everyone told me at least.

But I decided not to. I didn't want to go the comfortable route. The same motivation that got me into magic is the same that drove me to choose Mechanical Engineering.

I was partially concerned that computer science might encourage more introverted behavior but even more driven to try a major outside my comfort zone.

While I ended up back in technology post-college, I am really glad I did something different for my major.

At worst, it kept me growing during my four years of college instead of stalling. At best, it kept me from burning out on tech which allowed to me to get into…


At some point in college, you realize you need to start worrying about what's going to happen after you graduate. For me, that my junior-year summer when I went looking for engineering internships and came up empty.

Three years into college, I wasn't hurting for cash that summer but I was getting that itch to grow again. I had been playing around by creating some Facebook applications on the side and was writing developer-focused articles for Inside Facebook.

I grew a presence in the Facebook developer community and started receiving inbound leads for consulting and development work. Soon after I started saying “yes”. I only ended up making $5k from all the work, but it was enough to pay for a new laptop. I was hooked.

I kept this up in my spare time and actually intended to take it full-time post college. But as chance would have it, freelancing ended up being my segue into…


October 2011 was the first Startup Weekend in Columbia Mo. I originally didn't have a strong drive to attend since there was a steep admision fee.

I recall messaging my now co-founder Bryan Helmig to see if he was going. I thought maybe if I knew someone it would be worth it. Bryan had decided to buy tickets – so I followed along.

You can read the rest of that story here.

I can confidently say I've grown more in the past two years building Zapier than any other period of my life. The amount of experiences and new situations I've been in are astounding.

If there is one thing you could do to guarantee you'll be thrown outside of your comfort zone, it would be to start a startup.

Personality = sum(Experiences)

I think of my personality as nothing more than a sum of my experiences.

Although I only came across this recently, an excerpt from Ryan Hoover's “Knowing When It's Time to Move On” summarizes my general strategy these days.

When you look back at yourself six months from today and don’t feel embarrassed by your naiveté, there’s a problem. That means you’re not learning, growing.

Eight years after the decision to break my introverted mold, I still continually force myself into new situations and experiences. This has had the single greatest positive effect on my personality.

You don't have to accept the personality label you've been given. Keep doing new things and keep being uncomfortable.

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