I've experienced both before. I bought glove stock at the beginning of covid in 2020 and it dropped slightly so I sold it at loss. Then the glove sector strated to rally ten folds which I missed the boat.
For me buying in downtrend is kinda worse. I bought bitcoin at a high price around $50000, when it dropped I was happily averaging down because the market was so optimistic with the bright future of crypto at that time, the current price is now $18000. Multiple crypto platform collapsed whereby I was trapped in one of them, it causes mental stress.
I think buying in bear market is ok, just have to do analysis and confident that the fundamental of the company is still good and able to recover.
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