Giving Yourself a Chance to Fail

I’ve been on my startup journey for over a year and a half now. This is no doubt the most emotionally and mentally challenging thing I’ve ever done. I guarantee that unless you’ve been through it yourself as an early stage founder, you simply have no idea what it’s like. I’ve been told that sometimes people need pep talks in accelerators, or people freaking out, and people giving up under too much stress. None of that surprises me because even for me it’s a series of decisions to not give up. It’s a series of decisions to pick yourself back up.

Most things in life don’t offer you the chance to fail. For one you can never fail in school. I don’t mean fail in the sense of you didn’t pass a course. I mean a chance to fail as in there is real uncertainty whether what you’re doing is even possible to begin with. Most jobs are like that too. When I worked at Microsoft or Well.ca, there was basically no way for me to fail. At those companies I don’t go home worrying about the very existence of the company or the viability of the business.

In Paul Graham’s Do Things That Don’t Scale essay, he talked about:

Almost all startups are fragile initially. And that’s one of the biggest things inexperienced founders and investors (and reporters and know-it-alls on forums) get wrong about them. They unconsciously judge larval startups by the standards of established ones. They’re like someone looking at a newborn baby and concluding “there’s no way this tiny creature could ever accomplish anything.”

I think that’s a symptom of people never being in that fragile situation. They’ve never had the chance to fail and their entire perspective is built out of something already built for them. A plant grows out from a tiny seed, so don’t judge the seed that way. It’s also a great thing to keep in mind because you must not judge your own startup that way. Have the belief that you’ll figure things out and prove your hypothesis one small step at a time.

Giving yourself a chance to fail is hard and unconventional, but if one wants to change the world there’s no way around it.

When it ultimately gets hard though, I collect motivational articles such as this one on lifehack to replenish my will power. Persistence and determination are two things I value a ton. It’s the kind of superhero power I want. So when faced with a real chance to fail, there is no giving up until absolutely all possibilities have been exhausted.