One of my friends has been unhappy at his job for a while and is contemplating a switch. But he’s worried that he’s making the wrong decision. “What if it’s worse than my current job? What if the hours turn out to be bad? What if I don’t make the right decision?”.

Here are the issues with overthinking and obsessing over making the “right” decision:

1. The world is noisy. It’s often impossible to know if you’re really making the “right decision”. A better approach is to focus on whether your decision-making framework, or policy, is correct, rather than the specific choice you made (which could be correct in one randomly seeded version of the world, and wrong in another).
2. Making right decisions doesn’t help you build strong convictions

Strong internal convictions are born out of real-world experiences, and the strongest internal convictions often come from mistakes or mis-steps. “A win doesn’t feel as good as a loss feels bad, and the good feeling doesn’t last as long as the bad. Not even close.”

As much as we can try to internalize learnings without undergoing failure ourselves (like reading about others’ mistakes), first-hand experiences are fundamental to our growth and learning. We’re not perfectly rational machines.

I’m not saying you should go do something irreparably reckless. There are times when you’re more free to make mis-steps, like when:

1. The cost of attempting again or switching paths is low.
2. The difference in outcomes between the right and wrong decision is minor.

In my friend’s case, he’s already discontent with his current job – so it’s unlikely a new one would be much worse, and he has backup job options if things don’t work out. If things work out, great, and if not, he’ll at least develop a better sense of sense of self – of what he likes and doesn’t like.