When you keep trying at something and hit a snag, eventually you'd ask this question: should I continue on this track or should I switch strategy?

Essentially the crux of the question comes down to how do you know if you are simply doing it wrong or you are completely on the wrong track?

An easy answer would be to consult a mentor. But that's only applicable if it's a beaten path with an answer. Sometimes there is no answer.

If you were a physicist working on string theory twenty years ago, no mentor is good enough to tell if you're doing it wrong or it's a dead end.

An easier to understand example would be a miner digging for diamond fruitlessly. What if he quits to dig elsewhere, and diamonds are unknowingly inches away?

How should you go about deciding how to go forward? When there is no right answer, I tend to sense of a strong aura of agency in the approaches.

My first instinct says you should go with option that makes you flourish. By playing to your strength (either to carry on or switch), Even if it didn't work out you would at least come out relatively happier.

But it doesn't add up. Switching approach is by definition trying something unknown. How are you supposed to know if it suits you better without jumping in?

Knowing when to quit is a whole category of knowledge in and of itself. Thing is if you get too good at quitting and never commit to anything, the benefits never get a chance to compound and snowball into excellence. Sometimes there's no alternative to digging deep.

There exist two opposing frameworks. The choice is exclusive, it's one or the other but there's no middle ground.

Let's call the first one spray & pray: make a conscious decision to experiment and discard approaches/strategies/methods in rapid succession. Resist the urge the commit and optimize. Pay close attention to how they compare, hopefully something sticks eventually. This pretty much sums up the agile startup approach.

This is easier said than done and not an option when the barrier of entry is high. Like the mining example, digging deep can be non-optional.

Which brings us the second framework: submit to fate & commit. You can stick the current method (keep digging) or switch track. You won't know which is right (even if you don't admit it outwardly) but you must commit and see it through to the end.

The nuance is when dead end becomes obvious. When objective reality is in place it's no longer a matter grappling with unknown-unknowns. In this scenario we have effectively escaped the scope of our consideration here.

The hard part is the submission to fate, of being at peace with whatever the outcome is. It's essentially saying that whichever choice is made here, it's not a wrong choice even if the outcome is failure. Some cultures have might have an easier time dealing submitting to fate, where people assign different sense of personal accountability to outcomes. If you believe in supernatural forces, it's probably much easier to commit to something without attaching to results.

I find this comes easier with age. I haven't had the luxury of believing in the supernatural, but adopting the posture of surprise-maximization helps build outcome-independence. In this frame, if something manages to surprise you, you win no matter what.

That is to say you have to first reach the stage where hardly anything surprises you anymore. There's a sense of nihilistic jadedness but not so intense that it completely stops you in your track. I imagine that's what drives The Dark Knight's Joker and what makes him formidable.