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Biggest regret?

It is a strange sensation to go through a moment that you are certain you will regret later. But lucky for me my regret detector is broken.

Last year, I decided not to attend a Web development bootcamp (it’s called Dev Bootcamp) that I had been preparing for and building up to for months. I spent at least 90 minutes writing an email at my red Ikea desk, asking to be withdrawn from the program, then felt enormous anxiety as I waited for the response and wondered if I had given in too easily to my struggles with the material and the super-extroverted structure (paired/collaborative videoconferences…yuck). I was outside my comfort zone, [string of other cliches], etc. Plus, wasn’t I leaving money on the table? If I made it through, I would probably have made much more money than at my current position.

The program admin emailed me back after three agonizing days (in which I contemplated sending a “disregard my other email” follow-up) and by the end of that week I was done with the program. Each time I struggled at something in the months following that, I remembered that withdrawal and had not only something like regret, but an even worse feeling, what many call “fear of missing out” (FOMO). The alternate world I sketched out in my head of what things would be like if I had gone to the bootcamp seemed so much better than the one I was occupying.

Now though, it’s not regret I feel, but nostalgia – for the months leading up to when the camp was supposed to start. I had been accepted in June 2013 and slated to attend in June 2014. I was excited about the prospect of going, and I fondly remember the weird looking-forward of that year, if not so much the actual moment of preparation and program initiation, when it finally came. I didn’t like the work, really, but that felt secondary – there was, I felt, certain change ahead, and that was exciting, especially considering the tumultuous professional track I had been on from 2009-2013.

After I stepped out of my office and onto Clinton St. in Chicago on the last day of April 2014, the instant regret of three days prior was gone, replaced by relief, even if what I’ve come to regard as pseudo-regret/stupid-FOMO encroached upon it for a while thereafter. This was my hint that Dev Bootcamp had really just been a vehicle for me – a thing-to-look-forward to that lived its life, got me through a hard transitional phase in life (the summer after the startup I worked for predictably hit headwinds, and the same summer in which I got married, weirdly enough) and then expired like an old, almost empty carton of milk.

The biggest regret wasn’t not attending; it’s that I had to “trick” myself into feeling good during the program run-up, by putting in place something that I didn’t even like (a software development bootcamp) rather than just being happy because I was alive, healthy, etc. It really was a case of regretting what I had done, rather than what I had not done. I’m glad I didn’t do the program, but sometimes regretful that I put myself through a sort of induced happiness coma by inventing (maybe “latching onto” is more accurate) things to look forward to. It made me realize that I could have been happy and could have survived without needing the external validation of having been admitted.

I think the old adage about “I do not regret the things I do, but those I did not do” isn’t the incredible wisdom it presents itself as. Not-doing has its place and is essential to remaining sane and not being overwhelmed by obligations. For me, regret doesn’t spring from the sense that I “missed out” on something (a completely intractable problem if one allows it, since there are just too many options out there now thanks to smartphones), but from the sense that I wasn’t allowing myself to feel genuinely happy or make others feel happy, too.

The Duke of Wellington, who defeated Napoleon at Waterloo, had perhaps my favorite answer ever to what he would have done differently if he could have lived his life over. He didn’t say “climb Mt. Everest,” “become more technical,” “make more money,” “bet a different lottery number,” no – he said only that he wished for an opportunity to “give more praise.” He wanted a redo on being able to make others feel good about themselves – what a quaint and rare idea!

Plus, giving praise is often its own reward – it feels so much better than giving criticism, at least once the act is complete (knocking someone down a peg always seems more thrilling in theory, but becomes less satisfying with time). Perhaps he realized that reasons to feel good are often in short supply or simply inaccessible (for reasons of disposition or background) to so many of us, and that he could help. It sure beats wanting to go back in time to do prom all over again or ensure that Ruby nd Python were learned at an early age.

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