Do you think it's harder to hold a losing position or to sell a winning one?
Personally, I definitely find selling a winning position more difficult, because I'm never sure it's the right time and I keep thinking I might hold a little longer since the uptrend may not be over. Paradoxically, a losing position bothers me less, because if the fundamentals haven't changed, I see it as a buying opportunity and expect to keep the shares in my portfolio for a long time.
From my experience, it's sometimes better to be a bit greedy and take profits rather than wait for a stock's peak and sell only when it feels fair. Because then it falls and you keep wondering whether you should have sold or waited. You just have to make the decision yourself—nobody will do it for you. As they say: a bird in the hand is worth two in the bush.
I agree. With a losing position I often just wait and hope, because there isn’t much I can do and it’s mostly a matter of time, whereas with a significantly profitable—often already overvalued—position it’s much harder. The risk is that I either miss the peak or sell too early and miss out on further big gains (which hurts).