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.
The exercise in question is a fun one (go read the rest of it and try it). One of the difficulties I experienced with the exercise was that at any one of the juncture points I visited in my past, I was tempted to default to "I don't know" and be done with it. Not because I couldn't make up my mind, but because I've long had a terrible tendency to oversubscribe to the idea that I can't possibly know all the decisions that could be viable at any given point.
At the end of it, I realized I'd performed versions of this exercise many times in the past. One common "what if I had done this?" nexus was if I had decided to self-consciously seek a career as a literary author in the vein of some of my original idols — Pynchon, Harry Mathews, etc. I strongly suspect if I had tried to do that, I would have ended up playing to my weaknesses as a creator and not my strengths. One of the worst-case scenarios was not failure, but success — success of the kind that goes swiftly to the head, especially a young head, and leaves it swollen for life.
The other thing about such a choice is that it might well have left me unemployable. If the literary career burned out, I wouldn't have had a plan B. Right now, my day job provides me with a good solid foundation to work on my creative projects at night, and it's given me a skillset that's broad enough to retool into any number of other related careers. I was somehow lucky enough to not kid myself into thinking that I was actually a hedgehog that knows one big thing (see: Isaiah Berlin), instead of merely a one-trick pony.
I come back often to the Patrick Farley webcomic The Guy I Almost Was, which plays like a version of this exercise in the form of fiction. It's hard to look back on our lives and find the unquestioned assumptions that led us to the present moment. In that story, the narrator realizes, belatedly, that his dead-end, borderline-starvation life is in no small part due to him expecting to live in a gleaming OMNI Magazine cover future by the time he turned thirty. All he had to do, or so he thought, was survive long enough to inhabit a techno-pagan paradise whose encroachment seemed inevitable.
But once he realizes how fatalistic and silly the whole thing is, he is presented with another temptation — the possibility of constructing his life as if it were an artifact of an alternate time. He will buy a manual typewriter; he will dress unfashionably; he will not ingest any culture produced after 1964 or so; he will drop out of participating in a techno-hipster future that he can't afford to live in and that gaslights him every time he tries to engage with it anyway.
However, before he can execute his plan, he's summoned for a temp job in Cupertino right as the Internet is about to go mainstream. He never does follow through on his plan, but he does wonder: if that other me and this me were to meet, would I envy him, or he me? The door of what-if can swing both ways.
I ended up thinking the same way about all the other possible paths I could have taken. Would the serious-novelist-me look at what I have now and feel like he had been cheated out of something? That me might well have looked at all the "childish things" I like now and flipped up his nose at them — not because he actually hated them, but because it didn't fit the model. He would have been more interested in being right than in being curious. He would have been, in a word, a bore.
And there isn't a day that goes by when I realize that I still have, inside me, all of the tendencies that would have allowed me to turn into him. What makes me what I am now is not any one choice I made, but the fact that I keep choosing to be that way — that life is not about the choice made at some fork in the road but about how one tacks against or with some particular wind. Mary Oliver's line, "what is it you plan to do/With your one wild and precious life?" is in the present tense for a reason.
New York City
Other Lives Of The Mind