You should regret decisions that you reasonably should have made differently with the information you had at the time. Pound a fifth of vodka and run grandma over with your car? You should regret something like that because it's immediately obvious it's stupid.
If you're regretting decisions which are exclusively unwise with the benefit of perfect hindsight, you're commiting the sin of pride. Pride that you believe you could possibly be all-knowing, which you are not. Such as "Why didnt I buy BTC at $5" when you had never heard of it and didnt live in the cryptographic niche culture to have done so so early.
I have precious few regrets because my errors in judgement were rarely foreseeable, and the probability of much worse outcomes if I chose differently very high.
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