Photo by Sonja Guina

Do What Scares You

When faced with a choice, do the one that scares you more

Kevin Cheng
kev/null/writing
Published in
2 min readDec 1, 2011

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I was on the phone in the parking lot of Yahoo’s San Francisco incubator, Brickhouse. My job was fantastic. I had just months prior designed Pipes, dubbed, “a milestone in the history of the internet,” by Tim O’Reilly.

We had an incredible office, incredible location, great people, extremely flexible hours, the flexibility to work on what projects we wanted to, and the healthy pay that came with being a part of Yahoo.

On the phone with me was my younger brother, Jamie, who had started his own game company up in Vancouver. We were discussing whether I should take an offer to join a startup as an early, pre-Series A employee. A lot of pros and cons were thrown around: the commute, the risk, the industry, the economy, etc. Then he asked me:

“Which job would you learn more from?”

And it became immediately clear which choice was right. While Brickhouse was enjoyable and fulfilling, I knew that I was not learning much with each subsequent project. The growth had become incremental. So I took the leap and joined the startup.

In the past few years, I’ve been approached more for career advice. The problem with career advice is that everyone’s goals, personalities, risk profiles, and priorities are very different. But, assuming you’re looking to build a career which involves professional growth (as opposed to having it only as a means to an end), then my one piece of advice is always the same:

“Do what scares you.”

Some might call it, “getting out of the comfort zone,” but that term is almost a euphemism. It doesn’t convey the base emotion you should feel.

When you’re scared, it’s because you care a lot about the consequences. If you care, it’s probably the right thing to be doing. You’re scared because you don’t know exactly how to do it — which means you’ll probably learn a lot no matter the outcome.

When you think about the next thing you’re going to work on, you should feel that nervous, excited energy you get when you know you’re about to do something crazy, and you might royally fuck it up. But if you put everything into it, you will always have the lessons and the growth.

Take that leap.

Doing something that scared me.

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Product and design leader. Formerly Indeed, founded Incredible Labs, led product for #newTwitter. Wrote “See What I Mean”. Drew OK/Cancel webcomic. I also DJ.