Regret is a terrible emotion. Especially as an investor. Investors (more like speculators) in the Dot-com bubble lost money not because of greed. I believe they feared missing out on the next big thing. It is what is called FOMO (Fear of Missing Out).
Every investor knows this feeling. That feeling of regret when a stock that he/she passes becomes a multi-bagger. That does hurt. In hindsight, everything seems to make sense. But that is just hindsight bias.
One thing I have learned which is absolutely pivotal to me. It is not about catching great opportunities but It’s about letting go of some potentially great opportunities which are not in your investible universe. These are the stocks you are not comfortable to buy. Being happy to miss out on certain rallies and having no regrets is an underrated trait. Regret is a dangerous emotion, especially in markets. More than mental peace, it ruins investing behaviour. It takes many years to form an investment strategy fitting your personal discipline. But it takes a few moments of regret to change it.
You cannot catch every multi-bagger. One has to learn to be peaceful and amused even if the opportunity you passed on becomes a 100x. One needs to swing only if something falls near the strike zone. Opportunities will come. One just needs to keep some faith.
Multiple multi-baggers are waiting in the market for the next 10 years. To be successful, one only needs to catch a few. It’s better to wait for an opportunity that is in the circle of competence. Buy a mispriced gamble when you see it.
It is more important to miss out on good money if it helps to cultivate a good investing attitude. Former might make money for the short term but it will definitely ruin you for the long term. While the latter will almost certainly not bring you pain and help you survive to the least. You can be lucky once or twice. Maybe thrice if you are blessed. But even god can’t make you lucky every time. Rationality trumps emotions every time, especially in markets.