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Minimizing Regret

When I look back on my life, I realize just how much of my life is about minimizing regret and fear. How much I missed out on, because I'm constantly afraid. I can't change the past, but I don't want to lose the future. So I should focus on the present and understand what I'm doing now to cause myself regret and what I should do differently to prevent that form of regret from coming up. I don't understand regret, so maybe writing about it will help disentangle my thoughts.

I think trying to minimize regret at the cost of everything else has led to several suboptimal life trends and practices in my life:

  • My general approach to problems is to take a hammer, and whack continuously at the problem until either the problem breaks or the hammer does. That's why I like simple hammers, because simple hammers in my mind associate to hammers that won't break. In some situations, that might work well. I did end up playing board games with a friend because I'm willing to walk one and a half hours to his house. I am able to read gigantic books that others might not read through all the way.

    However, some problems simply require a scalpel and not a hammer. Some problems require a much more complex understanding, and if you don't appreciate that understanding, you fail really hard when coming up with a solution. You can't just use one tool in order to solve everything.

    For example, you can't program or scale your way into attaining somebody's love and affection. In fact, besides being yourself and not being an arrogant douche and maybe dressing a bit better and going to the gym and having some hobbies (okay yes that's a lot), there's no real way to get somebody to love you.

    There's impostor syndrome too. I don't think you can address impostor syndrome by reading X books a year, or publishing Y posts on a blog, or being the core developer and maintainer for Z popular projects. The solution to impostor syndrome may come from self-acceptance, but it certainly does not come from working harder.

  • I've grown to hate the problems in my life, because of the pain they cause or I think they might cause. What I really want is to absolutely crush the problems I have, to have such an overwhelming superiority that nobody on either “side” has any doubts about who would win. I always imagined it as a D-Day like scenario. I want to have my problems wake up in the morning, look out over the English Channel and see the armada I've built up to deal with them, and go “welp gg” and throw their hands up.

    Problems don't work that way though. At some level, your problems are a part of you. Crushing that part of yourself means you might lose another part that's useful. I used to do art for five years, and I probably have lost a good deal of creativity because I optimized for being methodical. Maybe that part fights back automatically, and then it's less of a D-Day situation than a civil war. What used to be 100% turns into 51% - 49% = 2%. Imagine being 2% of the person you used to be, let alone 110% and growing. That's kind of how I feel about many results. When I fight myself, I'm always the loser.

    Then there's the cost of building up to that solution, which is far more painstaking, problematic, and expensive than building a solution that works “good enough”. What else could you have been doing with your time and energy? That's probably how I found it easier to accept the pain of regret, than to create a “final” solution that can deal with the problem once and never again. That leads to masochism in many respects. I find it easier to go all gopher and start digging my way through the Earth rather than stick my neck up for just a moment. I find it easier to learn Haskell than to accept “bad” code (?).

  • I realize minimizing regret oftentimes leads to a victimhood complex. The notion that I'm trying to steer as far away from what I fear as possible implies that there is something to fear, and a concrete, observable display of that fear, real or not, getting to me and affecting my decision making. In the past, I've often complained about how bad things are, how I wish things were different, most times almost without realizing it. WHen you're preparing for something bad to happen to you, and nothing happens, you almost wish something bad happens to you because then you get to say you were right.

Most of all, when I've minimized regret, I realize every time that the real regret is not embracing the situation. When you build a bunker and live in it, how do you enjoy the sunshine? In short, you don't.

There's this one comic I found on Reddit a few years back. I can't find it now (because there are a lot of comics posted on Reddit and because image search is a hard technical problem), but it goes something like this:

Boy: I want to go outside!

TV: Don't bother going outside! Here's a TV show you can watch!

Boy: OK!

Teen: I want to fall in love!

TV: Don't bother falling in love! Here's some pornography!

Teen: OK!

Man: I want to become fit!

TV: Don't bother becoming fit! Here's some weight loss pills!

Man: OK!

Old Man: I just want to be happy.

TV: Don't listen to yourself! Listen to me!

Old Man: Screw you TV! I'm going outside!

(Goes outside)

Death: It's time to go.

Old Man: But I never got to live my life…

I'm terrified of being that guy. That guy who (still) can't lose ten pounds but can gain fifteen. The guy who's too afraid to say “I love you” to his significant other. The guy who takes the easy way out.


So I have “The Five Regrets of the Dying” as the only post on my blog that I've pinned. I figure that if I have to have a hill that I'm going to die on, I should choose those hills carefully. I choose these five hills. I don't think it's necessarily a mistake to minimize regret. It's about properly identifying the right regrets to minimize.

I think given how I always choose the hard way of doing things, and how I've found success at doing something is doing that something and not failing, seeing how others define “failure” when there's nothing to lose by doing so is highly informative.

I wish I had the courage to live a life true to myself, not the life others expected of me.

I wish I hadn't worked so hard.

I wish I had the courage to express my feelings.

I wish I had stayed in touch with my friends.

I wish that I had let myself be happier.

I think these, more than anything else, should serve as the “master backpressures” to keep in the back of my mind. If there's a pressure to act in a certain way, then I should consider whether not doing it is worth regretting over on my deathbed. Then I should consider whether I'm the guy who takes the easy way out. The guy who would rather spend an extra hour in the office pleasing a boss rather than going home on time to his wife and children. The guy who would rather stay at a shitty job rather than create his own business and take a shot at financial independence that way. The guy who would rather cut corners in making software rather than properly structuring systems to make them complete. The guy who would rather go to bed than stay up and entertain his kids or meet up with friends.

The hard thing about hard things is that most of the times, they're easy. At least for me, I think working 60 hours a week is easy if you're facing marital troubles or if your kids don't like you.

No, the hard thing is to face the cold, bitter truth, and embrace it, and make it warm again. That's what you will wake up to in the morning.