Make Yourself Uncomfortable

In my short time trying to run a web-application startup I’ve noticed something: I am often very comfortable.

I read a lot of stories about other founders and startups going through times of great stress and uncertainty. They wonder if they’ll get funded. Or, if they’re already funded, they don’t know whether their next funding round will go through. If they are bootstrapping, they don’t know whether they’ll have a product that can cover costs early enough to keep going. They worry that users won’t like a new feature. They worry that they can’t develop new features faster than their competitors. The list is long.

Certainly there were times when I was uncertain or uncomfortable. But comparatively I think those times were rare. This is almost certainly due to the fact that my poker winnings have afforded me and continue to afford me the time to pursue ideas at a relatively modest pace. I don’t need any particular idea to succeed. I’m happy just to learn new things every day and work on projects that I love.

But if there’s one thing I took away from Startup School this year it was from Paul Buchheit’s life-story. I’m not sure he actually said it, but I wrote in my notebook “make yourself uncomfortable.” I think this is really important to success and meeting whatever ambitions or expectations you have for yourself.

Because that’s the only way to really grow. That’s the only way to really learn new things. Make yourself uncomfortable. Bite off more than you can chew. If you want your startup to succeed, promise something you might not be able to deliver. Either you’ll come through, or you’ll have learned a ton trying.

If you’re not uncomfortable some of the time in your job, or in your relationships, or in your life in general, then you’re doing it wrong. For me, I’ve been doing it wrong for too long. That stops now.