learning to fail

There are many books written about “how to succeed.” There are far fewer books written about “how to fail.”

More specifically, I am interested in the question of when is the right time to give up on things. You are faced with this question all of the time — and yet there seems to be no great set of guides as to when you should throw in the towle and quit.

I think I know why. I mean it’s an uncomfortable topic broadly. People like talking about winning. They do not really like talking about losing and failing. But one could argue that life is full of both ups and downs. And guides to the downs. Helping know how to better fall. Well that seems like it would be a useful thing to know and get good at.

This prompt at nearly all levels of abstraction. How to fail.

  • When should you give up on a project you have been working on?
  • When should you give up on a person you have been supporting?
  • When should you call it a night at work because you want to go home and sleep?
  • Etc.

In lifting weights, there is a concept called training to failure. This basically just means continuing to do a set of a certain movement until your muscles fail, or are really just about to fail.

Training to failure is challenging, especially for more beginner weightlifters, because it is hard to know if and when to give up on something.

Most people give up way too early on most things. That’s at least what I can see. They could be lifting heavier and running faster. They could be working more hours. They could be bringing more intensity to whatever it is they are doing.

But there are times…there are times where people are digging in the wrong direction and yet, they do not stop. They do not know when to stop. They are going beyond failure, and they are just digging themselves a bigger hole. This is dangerous, too. As in the case with weightlifting but also beyond.

People spend their lives working on projects that are not only never going to but also never were going to work. And so this awareness – this asking the right questions and informing your failure mode and your path to giving up…this seems like an important thing to care about.

I do not want to waste my life and time on the wrong things. Now, what is right and what is wrong is surely upstream of this. But why should the default state be doing?

I think the default becomes engrained in people earlier than they think. Their biases and problem solving habits do not really evolve much unless they materially change their environments and conditioning. And so they work the same job or roughly the same job for decades. And so they settle. And so, so they perhaps should have given up sooner.

My message is not that more people should give up more quickly. I am not sure of that. I mean potentially it’d be better. I tend to think a min max approach to investing is a good one. In other words, be prepared to go all in and then when you feel conviction in something – actually do that, with lots of intensity. Do things with intensity, even if scary, because you, no matter what, will maximize your learning curve.

There’s an adjacent topic to the above which is this notion of learning to fall – like literally fall – gracefully. It’s not something I remember learning myself but I definitely know in Karate they teach it. The roll out of things.

I remember one time I published a resume of failures. Like I wrote out all the times I have failed and then used that resume to apply to jobs.

That’s my roll.


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