Some time in my mid-‘30s I started allowing myself to harbor serious regrets about things. Prior to that time I think I was mostly a “no-regrets” kind of guy.

After hearing someone reject the idea of taking a time machine back in time to reverse regrettable decisions, I had to reconsider my position: Yes, I would definitely take that time machine back if offered:

• I’d be much more open-minded
• I’d not reply to certain critical letters or emails from family members (you know the sort…my dad, for one, could write the most withering letters-of-criticism)
• I’d consider the amazing job opportunity without grumping out about it
• I’d spend more time relaxing, playing, and so on…

So yes, regrets for sure. Not even just a few. A lot.

A really cool thing about regrets

So after I started thinking through my regrets, I had another big realization: I can’t go back in time, but I can start applying this information forward right now.

• I can crank my mind way open, try things, experience them, and then evaluate.
• I have the option of not only not replying to the occasional crazy-mail, but I can be proactive in lots of ways, and e.g. let people know when they do something that makes me proud of them.
• I can deeply analyze new opportunities and talk to people with relevant experience
• I can set aside time for fun and play, and actively evaluate the type of play that makes me happy.

It’s a sad fact that by not regretting things, you can say I was allowing unlearned lessons to damage my future prospects. I was also restricting my excitement for my future; it turns out that reducing the likelihood of crappy things happening in the future even a little bit really makes you feel better inside.

So yeah—I’ve definitely got regrets. I hope to recognize and analyze even more regrets in the future.

Filed in: Productivity /119/ | Energy /120/ | Careers /39/ | Therapeutic Practice /144/ | Openness /49/ | Planning /17/ | Goals /52/ | Control /110/ | Thinking /70/