My Biggest Regret

Almost twenty years ago I was a professional gambler and I ended up getting a little bit sloppy with my procedures, which resulted in casinos catching me and confiscating all of my money. I only paid taxes when I removed money from casinos, so I kept most of it in them, which meant that my net worth dropped by over 90% in one day.

Should I regret my actions which caused that?

I remember the day. I remember waking up, where I was sitting when I looked at my computer and realized what had happened, and even where I went for dinner, who was there, and what I ate. I also remember not being upset by it, and in some ways feeling relieved. I had had enough gambling and was ready to move on anyway.

I’d certainly take the money back if someone offered it to me, but maybe my life would be different now in a way that I wouldn’t want. I’m 100% happy with my life now, so I can’t really say that I regret it, because maybe that small change would have a ripple effect and make my life worse today.

I can think of a few small things I would change, mostly times that I took some action through ignorance that ended up negatively affecting someone else. One time I got the day wrong on a flight, didn’t realize it, and got a text from my then-long-distance-girlfriend asking where I was while she waited for me at the airport. That small thing wouldn’t have changed our relationship, and I wouldn’t want it to have been any different anyway, but I regret making a mistake that inconvenienced her and maybe changed her idea of how I thought about her.

Whenever people ask me what my biggest regret was, though, one thing always springs to mind.

One day, when I was either in college or freshly dropped out but still living there, I checked my daily deals sites and saw something amazing. For $1000 I could buy a ticket on the Concorde, the only supersonic passenger jet. I would fly from Austin to New York in coach, fly the Concorde to London, and then come back in coach a day later.

A thousand dollars was a lot of money to me a the time, but I could have afforded it, and I understood what a big deal the Concorde was. I emailed friends to see if anyone wanted to do it, but they all said no.

I started to book my ticket but hesitated at the final checkout stage. Maybe I should sleep on it.

The next morning I woke up and was fully confident that it would be worth it. I went to go book the ticket, and the deal was gone. A few years later Concordes were gone too. I missed my chance to ever ride the first passenger SST.

This is, of course, a very stupid biggest regret and it reveals what an easy life I’ve had. My life is so good and I’ve faced so little serious hardship that there’s nothing I would choose to reverse other than the chance to do one more really cool thing.

On the other hand, there are lessons to be learned. I’m not sure I ever missed anything due to hesitation after that. The only reason I got to be the one to live in LA and be written about in The Game was because I was the first to say yes. The reason I live in my favorite city in the US is because I bought a condo there sight unseen as soon as I realized what a good deal it was. I may not be married if I hadn’t pushed to meet up with my wife the same day we matched on Tinder, before she went back home.

Acting with no hesitation is a skill than anyone can easily build, and it’s primarily a function of trusting oneself. It sure would have been nice if I had that skill back in 2001.


Photo is a nice sunset on the island

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