Nine regrets
Published 2025-08-10
Last weekend I was chatted to a neighbor (about Taekwondo) and I said, offhandedly, “I have about nine regrets in life.” I used to have lots of Big Regrets about careers and divorces and investments and so forth. But as I wear into the grooves of my life I realized that if I really could turn back time and skip my freshman year of college to squat in Berlin while the Wall came down, there would be an enormous cascade of consequences spooling off of that, and I wouldn’t have the beautiful life I have now.
So the regrets I have are really curlicues, small ripples in the stream of my life.
- When my oldest started Taekwondo umpteen years ago, I regret that I didn’t start it with him. I also regret that I didn’t get the rest of the family involved too. Our local TKD studio — the whole local TKD “scene,” actually — has such a great community and positive vibe. Inclusive, supportive, big on responsibility, respect and restraint. I miss that community, and that vibe.
- I regret that I bought the first car I did out of college. I wish I had simply ridden my bike to all my archaeology adventures. Yes it would have taken months to crisscross the Great Plains but seriously, what else was I doing in my 20s?
- I wish we hadn’t sold our 2007 Subaru Forester. That car was perfect.
- For my high school graduation my parents bought me a set of luggage, of my choice. I regret that I colored inside the lines and chose luggage when what I should have chosen was a backpack.
- I don’t regret marrying my first wife, or our divorce. I regret that, during its dissolution, I behaved so dishonorably, and inflicted so many humiliations upon us both. I regret that I didn’t behave with more emotional honesty and moral clarity.
- When we remodeled our house, I regret that we didn’t invest much more in planning. I wish we had hired more than one architect, for example, and that we engaged the landscape designer earlier in the process. I regret that we didn’t calculate the ROI of building entirely new vs. remodeling.
- I regret that I have never kept a journal, especially in my 20s. Nothing fancy; I just wish I had kept a regular list of what I was eating, who I was meeting, where I was sleeping, what I was doing for fun. I especially wish I had kept a list of everyone I met, and their contact info. For my life since 2002 or so, I can cobble something like this together from the digital photos, my blog, social media, and so forth. But before then, I seldom took photos and never made a record of my life. I have strong memories of that time but few artifacts to anchor them.
- I wish (not so much regret) that I had spent more time professionallly with maps and mapping. Mapping was adjacent to both my careers, and something I always loved doing. This veers very close to a Big Regret however, because if I had (for example) studied cartography in grad school I might never have gone into web design, which would push my life onto a pretty divergent timeline.
- I wish I hadn‘t sold or given away all my comic books and roleplaying games from the 1990s.