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I don’t know if this is just me, but my biggest regret in markets isn’t losses.
It’s the money I kept sitting on the sidelines.
I’ve taken losses before. Bought things that dropped 20 to 30 percent. Held through red months. That stuff hurts for a bit, but you recover mentally faster than you think.
What stays in your head longer is the cash you didn’t deploy.
There were so many times I waited for the “perfect entry.” Especially during crashes. I’d tell myself it’ll fall more, I’ll buy later.
Later never came.
2020 crash was one. I had funds ready but fear was louder than logic. Same again during the 2022 drawdowns when sentiment was horrible. In hindsight those were solid accumulation zones, but at that time everything felt like it would go lower.
Losses feel real, but they’re temporary.
Missed opportunities feel worse because you keep replaying them. You start calculating what would’ve happened if you just stayed consistent instead of trying to time bottoms.
Over time I’ve realised being completely out of the market during major recoveries hurts way more than being wrong inside it.
At least when you’re invested, you participate in the upside eventually.
Sitting in cash feels safe in the moment, but years later it feels like you paused your own compounding.
Curious how others here see it.
What stings more for you personally, money you lost… or money you never invested?