Choose the Failure You’ll Regret Least

If you’re really going for it in life, you’re going to fail.

The more responsibility you take on and the more aggressive you are in pursuing a goal, the more risk of failure you’ll have to take on to yourself. And you’re going to fail so often, it’s going to seem like most of your choices are just choices among which failures to accept.

Here’s a tip for making the best of that: choose the failures you’ll regret least.

It’s never going to be easy to face failure when it comes. But much of the angst in failure comes in wondering how we could have done better.

And on this count, failure after trying is far less painful than failure from a failure to try. 

Failure from a failure to even try? It’s far easier in a moment of risk and doubt to wait and see, to analyze, and to hold back.

It’s quite easy to choose this option in the moment. The only problem is that overanalyzing will stay with you long after the moment of opportunity passes. You’ll always wonder what would have happened if you had acted. And you might never know the answer.

Fail because you tried instead.

Take on the challenge in front of you with as much intelligence and courage and hard work as you can muster. Fail if you must. By trying, you test your limits and the limits of reality. By trying, you gain concrete data about the problem you were trying to solve and the reasons for your failure.

And you will regret it far less. You can live with failure after an attempt, because you have succeeded at least in having the courage to act.

James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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