Took some Melatonin last night (naitch) and read this New Yorker article on “unled lives,” which is largely tied to this book. You probably understand the concept, but it’s basically lives you could have led but didn’t — other schools, other partners, other biz opportunities, other industries, other cities, etc.

First place my mind went is that, in summer 2001, I was 20 (about to be 21) and living in DC for the summer with some good friends. We had a little crew that we called “Superb Six,” and it sometimes extended to a 7th person. Out of those 7, we now have:

  • Two are married to each other (nice)

Anyway, that summer we were young bucks, and we had been drinking like fishes, and at one point I think we were 39 nights straight of at least one beer. PS I’ve done that in my 30s, which might explain my general lack of success. But before I bash myself against rocks, basically we hit 39 nights, and it’s a Sunday, and a bunch of us decide to watch Sliding Doors, which is a Paltrow movie about just this: unled lives. If you miss a subway, could your entire life change? Perhaps, if your future spouse was on that specific train. It’s similar in ethos to “the butterfly effect.”

Because we were young and living in DC, we invited some ladies from Michigan over to watch this movie. They were “interning on the Hill.” It was all very fancy. Now, remember, we promised to not drink. I’d say about 45 minutes into this movie, our friend gets up — dude is an eye doctor now — and disappears. Seconds later, you hear a blender whirring in the kitchen.

“Who wants margaritas?”

So yea, sliding doors. Unled lives. Sunday night margaritas. Etc, etc.

How applicable is this concept?

Massively. I’ll give you a few of my own:

  • My junior year of college, I wanted to be a coordinator of “New Student Orientation” for the next year. I didn’t get that. So, I applied to be Senior Class Committee Chair. I ended up getting that. As I was waiting for my interview for that, I was across the room from an Indian girl who I kinda knew and seemed like a bitch at the time. This is maybe April 2002. I made pleasantries with her, then we both made the Board (I was Chair, she was Secretary). So, we became friends. She dated my roommate senior year, and I married one of her friends from high school. At this point we don’t talk anymore, but if I hadn’t gotten rejected from that new students gig, I never would have applied to this other thing, never met her, etc.

Basically, if any of these things goes even one iota differently, my whole life is probably different. And that’s true for you too. Heck, I got a full ride to Syracuse University. Imagine if I went there? Some of my closest friends currently I’d never have known. Now, maybe I’d have other close friends (you’d hope), but would I have doubled down on journalism? Would I have the №1 sports podcast on iTunes right now? You just don’t know. You get one life (best we know) and you gotta take the best crack at it possible.

Should you pine for other possibilities?

I would argue no, but add “you can learn from mistakes” and “you can always improve the inputs of your decision-making.”

What is life, even?

I don’t think anyone truly knows or understands, and most of us are fumbling around at some intersection of connection, purpose, “success,” monetary achievement, kids, dogs, houses, family, friends, and whatever else. I think each individual path is different, and colored/guided by so many elements and minute moments, we really have a possibility of about 1,000,000,000 lives lived … all divided by how, why, when, and where we do certain things. It’s interesting to consider, but I wouldn’t pine for it, no.

Careers are largely the same way. A lot of “thought leadership” wants to tell you that careers are something you build and develop and nurture and all that, and in some ways and for some people, yes. For many of us, at some point we hit layoffs or need to move or whatever, and we’re chasing a check based on what skill sets we have. There is a “path” and a “ladder,” sure, but that path has been changing for a minute. A lot of us are just doing what we can to get by, find that partner, find that purpose, find that meaning. Some of us are intentional with career choices, sure. More than half? Doubtful.

What is your “unled lives” moment?

Blogging, largely about work and how to improve it. How I make (some) money:

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