The Regret Criteria

“Let’s go streak the ocean guys!” Nate said excitedly.

I love how enthusiastic Nate gets for just about everything, but this sounded a bit ridiculous. “I’m sorry what?” I said, laughing.

“Let’s streak the ocean!” Nate repeated, just as excitedly.

Having regretted many things earlier in life, nowadays I try to live my life without regrets as much as possible. Because I tend to be risk-averse, my regrets are usually centered around NOT doing something versus doing something. That is, I’m pretty good at avoiding stupid things, but perhaps too cautious when it comes to making life choices, big or small.

I never thought that NOT “streaking the ocean” would be something I would regret, but there I was, fully clothed, staring off into the ocean and pondering that very question as my friends frolicked in the waves.

“Will you regret this?” is usually the first question I ask myself whenever I’m faced with a decision with regret-potential. Sometimes the stakes are high (should I take that job offer?), and sometimes they’re low (should I eat a second dinner?).

A few years ago I was presented with an exciting job opportunity that also sounded incredibly demanding. Having just been through a super tough work season I wasn’t super pumped about that, but I also knew that if I passed on the job I’d definitely regret it. So, I took the job, learned a ton, and got some great experience doing something new and interesting.

The second question I typically ask myself is, “How important is this?” Most of the time it’s not, but even then those regrettable decisions can still stick with me. I will always remember that one time in Paris when my friend proposed having a second duck confit dinner after an amazing first duck confit dinner (different restaurants, of course). I considered it but ultimately said no.

In hindsight, I kind of wish I agreed just so I could say I did it. Seems kind of silly, I know, but it was also exactly what I was thinking back on the beach, while starting to regret my initial decision of NOT streaking the ocean. The risk was low enough: it was dark and we stayed just a short walk from the beach. I just didn’t want to deal with having to shower again, and using your clothes as a towel didn’t sound that fun.

So I came up with another question to help nudge me in the right direction whenever I’m facing a similar dilemma in the future: “When’s the next time you have the opportunity to do this?” Part of the magic of that particular moment was the serendipity of it all. It was the first time I was traveling together with these particular friends, and the way it came together was pretty awesome. As much as I’d want to travel with these friends again I’m not sure when it might happen next. And the chances of being at the beach again, with Nate egging us on to streak the ocean?

Shoot, is it too late to jump in now…?

…

What are your regrets?