Seek Failures Early

“Invert, always invert: Turn a situation or problem upside down. Look at it backwards. What happens if all our plans go wrong? Where don’t we want to go, and how do you get there?

"Instead of looking for success, make a list of how to fail instead–through sloth, envy, resentment, self-pity, entitlement, all the mental habits of self-defeat. Avoid t... See more

The failures and false starts aren't extremely interesting to most people, but having some successes under your belt credibly demonstrates that you're capable of either reproducing them in the future or experimenting your way to new successes in your new environment.

If you are fortunate or unfortunate enough to wonder:

“What should I spend my time working on?”

Then perhaps a better question is:

“Where am I most afraid to fail?”

When we’re avoiding some path because failure would destroy us, that’s often the path we need to go down.

Because if we aren’t afraid of failing, do we really care at all?

Failing is often the best way to learn, and because of that, early failure is a kind of necessary investment.

If you go out and all you do is make the same mistakes that I could have gotten in some other company, then there's no ROI on this investment […] I can buy those mistakes somewhere else. I think that, in some ways, this pursuit of original mistakes is sort what one is doing as a startup founder in a constructive way, right? […] It's a huge red flag... See more