An Exercise: Facing Past Choices

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A while ago I caught myself reflecting on my life choices, and my wish to have done things differently. Sure we all do that, but I found myself going over what could be, and it was distracting. There’s a point where done is done, and going over things yields no useful lessons and wastes time.

I also wanted to get this non-productive overthinking out of my system, both to stop doing it but also to see what I could learn. I quickly came up with an exercise that I want to recommend to people – because I’m sure many of you go into “what if” phases as I did.

Set aside at least an hour of your time and go to some place where you can have a nice non-distracted walk or sit (a park, a large mall, etc.). Take your phone, but during your time there don’t use it – it can be a distraction.

Now while you walk (or sit) do the following:

  • Take your most recent “life choice you may have done differently” and ask what would have happened if you had really made another choice. Keep it to two or three possibilities like “if I’d done X then probably Y and Z,” and make sure the answer “feels” right to you.
  • Once you finish with that item, move to the next, earliest “choice point” in your history and do the same, working through your life backward.
  • It’s OK to say the answer to any of your questions is “I don’t know.” That’s fine and healthy.
  • Go back as far as you need to, though I found for we older folks 18 is more than enough.
  • Don’t rush this, just don’t dwell on anything so deeply that you go down a mental rabbit hole.
  • When done take a break.

I found this an incredibly cleansing exercise. It got me over some things I kept obsessing over. It gave me an excellent retrospective. It definitely shortened this phase of “what if I had done things differently.”

I guess it got a lot out of my system.

I also had a few insights I want to share that may help you make sense of your own choices if you do this exercise:

  • Saying “if I did X then I don’t know” was liberating – as was the effort to see if I really could guess at what changes my choices would bring.
  • I found some interesting divergence points in my life where I could have become radically different in ways I could visualize. I didn’t always like those mes.
  • I was able to recognize people and groups and occurrences that helped keep me grounded in my life, and that may explain some of my behavior and what things keep my attention.
  • Significant trends in my career became apparent – as in there are three locations I kept thinking of moving career-wise to since my teens to 30’s. I live in one of those locations now.
  • A lot of my childhood interests are still part of my life. I wanted to work in tech, in science, and be a writer. I’m more or less doing those things, just in different ways.
  • I had a much better sense of what I wanted mattered to me.

Feeling reflective to the level it’s like being in a hall of mirrors? Try this exercise and see what you find.

Steven Savage