Valentine’s Day 2020 was a curious day. I wasn’t sure what my motivation was but that day, I bought this then-obscure cryptocurrency called Dogecoin. It was quite a significant amount.

I sold them all the next day at a similar price when I bought them. I changed my mind.

Fast forward a year later, Doge rallied alongside other cryptos — and pumped by Elon Musk — to 20x its price from when I bought it. I’ve forgotten that I’ve bought Doge, and ultimately sold it, until I saw my transaction history.

Imagine the regret.

I’m sure many of you can relate to my experience above. The one that got away. An opportunity missed. Be it in stocks, crypto, or other types of assets, there was one time that we almost get a grip on a great investment return, but for some reason, it slipped from our hands.
A measurable kind of failure

Dealing with investment regret s****. It’s more common than you think and it happens to many investors out there. But this realization still doesn’t make everything easier.

I think the part of the regret comes from the fact that we can quantify our failure. We know how much the amount of money we should have gained with the investment. Our brain can digest such failure easily than failures related to a career move or dating someone, which there’s no exact way we can quantify those in some type of metrics.

We can’t grief on things we can’t quantify how much exactly we miss. In investment, those missed dollars would haunt you longer than you’d like them to.
Famous people’s famous misses

If it makes you any better, famous investors celebrated for their wisdom and insights are not immune to some big misses in their career.

A prime example would be Warren Buffet. He is famous to have missed great opportunities investing in technology and internet companies. He got into Apple, which now comprises the large part of Berkshire Hathaway holding, pretty late in 2016, more than two decades after the company went public.

He missed out on big names like Amazon and Google. Warren Buffet admitted he made a miss, admitting that he should have bought it long ago.

I don’t have a good answer. Obviously, I should’ve bought it — long ago because I admired it long ago, but I didn’t understand the power of the model — as I went along. And the price always seemed to more than reflect the power of the model at that time. So it’