Put Yourself In A Position Where You Can Fail

I want to put myself in a position where I can fail. While this might not sound very appetizing, I’ll make a case that it is.

I could wait two years until someone decides I’m ready for the next level, or I can decide that I’m ready–experience be damned. At a certain point, more book learning or current level learning isn’t helpful.

I could talk myself out of taking the next opportunity, or I can just do it and try my very best.

I could whisper to myself that once I learn X, then I’ll finally be able to do that thing that fascinates me. (Hint: X usually changes to Y once you know X. Or you say that you don’t know X well enough yet. And repeat.) I’d rather try using what I know and learning just-in-time and take a chance that I won’t figure it out in time.

Whether adventures are deemed a success or failure, I learn more about myself and gain more skills than had I taken the more known route. What’s more, I gain experience in the skill of advancing by my own will.

One problem with coasting is the opportunity cost of not doing something more interesting or valuable. The best are continually improving, so by standing still you are going backward by comparison. If you are in the top 1% of the world at something, there are still sixty million people to compete with.

When you can’t really fail, there is no downside. However, this means there’s probably little potential upside. Exposing yourself to risk is the key to getting disproportionately higher upsides.

Financial advisors say to take risks with your 401k when you’re young because you can make more money and there is still time to recover from setbacks. I say to be risky with your career when you’re young, because you have a lot of time to use what you learn, and that on average you’ll make more impact (and money) in the long run.

I think most risks are far overstated. Using the analogy above, always taking the safe route is actually more risky in the long run.

Therefore, I propose a life heuristic: if there is little to no chance of failure in what you are currently doing, you are missing out on something.

The actionable advice of this is: actively seek to put yourself in a position where you can fail.

If I am wrong about my abilities or the amount of actual risk, I want to know this as soon as possible so that I can course-correct. Putting myself in positions where I can fail lets me fight my way out of problems. I’ll learn by having the chance to mess up, and then succeed.

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