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Minimizing Regret

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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:

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.


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