Awesome post. I've never been good at poker, but I've been investing small amounts of money for over a decade, and I've learned to listen to my gut but to not always follow it. When my gut tells me something, I use that as a cue to assess my original strategy. Has something changed fundamentally about the investment that I didn't know about when I bought? If not, hold. If yes, sell and cut my losses.
Honestly, I've always had a harder time selling than holding for whatever reason. But during my crypto investing days it's been awful difficult to not sell. I have some rather lofty long term price targets for the cryptos I'm invested in, so when I double or triple my money it's almost intolerable continuing to hold. It goes against everything I've learned about investing, but with this one it works.
Thanks for the excellent comment.
Yes, an important thing to remember about crypto is, this is a market where you can get in at the very beginning of a project. Many times, even before they have a working product, before anybody even has a tangible reason to believe in it. If the product comes then naturally the coin is worth much much more than it was in the beginning. Previously it was only very rich people who had the opportunity to get in so early. So it's weird compared to common stocks, but no so weird when it's put into perspective.
Of course, there's nothing wrong with taking some profits or rolling them into another project, even if you think your first speculation will go much higher.