The worst mistakes are not made by being dumb (or maybe just ignorant), the worst mistakes are made by being dumb or ignorant and proud of it. Mistakes don’t cause failure, but being proud of those mistakes certainly does.

Even your most ignorant decisions can be at least partially corrected, sometimes painfully, when you realize you’ve made a mistake. But those same ignorant decisions can quickly turn catastrophic if your pride causes you to ignore the warnings and persist in your stupid decision again and again and again.
Look around, you’ll see abundant examples of both of these obstacles. I know the popular advice these days is to fail often, fail quickly. But I disagree – failure is never good, that’s why we call it failure. So it’s not ok to fail, but it is essential to be able to fail.

Lots of people say “nobody’s perfect,” which is true, but they say it almost preemptively – like they expect failure. Some even go so far as to teach that we should fail because that’s how we learn and each “no” is one step closer to a “yes.” Utter nonsense. Failure is not what anyone wants for themselves, their friends, or their family. Failure should only be something we observe after the fact, not something we plan for.

If you think you’re going to fail (or worse, you’ve convinced yourself that there’s something noble about expecting failure), then you need to stop what you’re doing right now. You’re caught in the pride-fear trap of perpetuating a mistake – you are not able to fail, you are only able to persist until catastrophe forces failure upon you.

Even worse is actually planning to fail, which is more common than it seems it would be. Somehow justify it by saying it’s a learning experience or that the more failures we rack up the closer we are to success or some other such nonsense and totally stupid. Instead play to win.

Do not expect failure. Rechart your course again and again until you have no expectation of failure. If you notice failure upon you, rechart your course again. That’s being able to fail. You played to win, you lost, you upped your game, and you played again. Failure may have been what you observed after the fact, but it’s not what you planned for. And that’s what makes all the difference – each time you rechart your course, it’s not because you want to find the next failure as soon as possible, it’s because you expect to win.