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
Usually I come to this page with an idea of something to write about. Not today. This will probably be one of those random posts with little bits of everything in it. Have you ever noticed that my first paragraph is always long enough to make that drop cap thing on the left look right? Often I'll want to start off with a single sentence, but I write some fluff to make it look right.
I just gave my fish some medicine. They still have fin rot. It's really scary because huge chunks of their fins just dissolve into the water, so they look really pitiful. I've bought tons of different kinds of medicine for them, but none have fixed them yet. Each time they seem better, but then after the treatment the symptoms start showing up again. Of course I'm trying to treat the root problem, too, although I don't really know what it is. I change the water and feed them less. Almost everyone feeds their fish too much.
I really love my fish. I think they're the best pet ever. I can go out of town and not have to worry about them, but whenever I have a spare moment I sit and watch them swim around. Now I don't like watching them as much because they're sick so it makes me feel bad. It's amazing that they can just swim around and not die of boredom. I couldn't.
Last night I was in the Las Vegas airport, waiting for boarding to start on my flight. I went there an hour early because I didn't have time to play poker, so I figured I could get on wifi and get some work done. I knocked out a couple small SETT bugs, and then remembered about getgoing.com, the YC-backed discount flight site. The way it works is you pick two deeply discounted flights that you'd be willing to take, put in your credit card, and getgoing picks one for you. You don't know where you're going until after you've paid. When I first got invited to the site I mucked around with it and found some really great fares to both Beijing and Shanghai.
Maybe I should go to China, I thought. Twenty minutes later my flight to Shanghai was booked.
I like making impulsive decisions like this. My past is filled with them, and none that I can think of have ended in regret. Actually, if I were asked what I thought my biggest strength is, I would probably say that it is making good decisions very quickly.
I wasn't always good at making quick decisions. Twelve years ago I had the opportunity to fly on the Concorde for $1000. It was usually over $10,000 round trip. I really wanted to do it, so I called a few friends to see if anyone else was interested. There was some hemming and hawing, but no one was ready to commit. Well, I thought, I'll wait until tomorrow and buy a ticket then if I still want to go. The next day came and the deal was gone. Now the Concorde is decommissioned and I'll never have the chance to ride it. Strange is it sounds, this is probably one of the bigger regrets in my life. I really wish I got to ride the Concorde before it folded.