Do You Really Choose Your Own Adventure?

(Cross-Posted on Clearing out the Clutter)

It’s August 2, 2016, and I’m staring at the garden of the Northern Estate, having finished watering all of the house plants, and I’m wondering about destiny. Does it really exist? If it does, is that reassuring or frightening? Great that there’s some master plan, or terrifying that your fate isn’t really in your hands to decide? Maybe a little bit of both? On the other hand, the same holds true if it doesn’t exist. Great that you’re in charge of your future, and terrifying that there’s really no overall order to this world? Where you stand on this spectrum probably says worlds about you.

I just finished reading Neil Gaiman’s amazing Sandman anthology, and I can’t recommend it enough. It’s the tale of the Sandman (a.k.a. “The Lord of Dreams”) and includes his siblings Death, Delirium, Despair, Destruction, Desire, and Destiny. As you might have guessed, Destiny walks around with a big book explaining what the future brings. It never matters what his opinion is, because he knows what is to come.

I’m also thinking about a friend that I recently reached out to for the first time in almost 20 years. His story isn’t mine to tell, but I’m sure his life hasn’t played out as he would have expected the last time we saw each other, and I’d probably say the same about mine (though in hindsight, I’m not entirely sure that’s true.) Mind you, there’s a lot about my life that I appreciate. I’m not saying I wish I had a total do-over. Just a few bits here and there that perhaps could have been handled differently. That leads me to think about where I could have made different choices, and whether or not that would have led me down a different path.

It’s like those old Choose Your Own Adventure books that were around when we were kids. “You’re an astronaut flying towards the moon. You have two flashing buttons on your console. Turn to page 84 if you pressed the green one. Yay! It’s a booster rocket that gets you to the moon faster. You’re now the king of outer space! Turn to page 90 if you pressed the red button. Oh, sorry, that was the self-destruct button. You die alone in the great void.” (Note: Some of those books were remarkably dark.)

There’s also a famous Doctor Who episode called “Turn Left,” where the Doctor’s companion Donna Noble is at an intersection and when she turns right, it basically leads to the end of the world, and when she has a chance to redo it and go left, everything works out just fine. Who knew a traffic stop could be so high-stakes?

So for kicks, I start reviewing the last 20 years or so, and try to figure out if there were any specific moments in my life, where in hindsight, a different decision might have led me to another destination. There are really only a handful of past choices that come to mind (which strikes me as interesting), so let’s see what happens when we play them out:


I was hired by a New Hampshire political campaign shortly after graduating college, and I quit the job two or three days later when a different campaign offered me a much more significant role. The first candidate won, and mine lost, so would I have stayed in New Hampshire to work for that person, if I had been offered a job? My sense is that I probably would have for at least a few years, but I still would have wanted to give Boston a shot since most of my college friends were there at the time, and of course, it would be easier to get to more Red Sox games.

The specific places I worked in Boston might have been different, but I still likely would have been lobbying with a specific interest in non-profit work. So this choice that might have been a detour on the path, but it still probably would have led in the same direction.


One could make an argument that I should have taken many more chances in my personal life as a general rule, but putting that aside, three women come to mind in this exercise. (They shall all remain nameless in order to avoid the embarrassment of being linked to me.)

The first was someone I met in the 1990’s who was just a fascinating person. We had a number of political friends in common, and there was a stretch where I thought there was some chemistry. However, she suddenly disappeared, and I always wondered if it was because I was too slow to move. In the world where I act much faster, my guess is we might have dated for three to six months, and then it would have fallen apart, because I remember her being much more adventurous than I was, so that probably wouldn’t have changed my path that much.

The second was a long-standing crush who made my head spin every time I was in her presence. Seriously, I could feel my brain short-circuit when I was around her. She drunkenly made a move on me one night, and as much as I was pleased by the interest, being stone sober at the time, I felt like I couldn’t in all good conscience reciprocate. If you were anywhere near me as I walked home that night, you would have heard my internal voice screaming, “That was the single dumbest thing you have done to this point in your life so far!” (Which may possibly still be true.)

After that, the moment passed. If I’m in the mood to beat myself up, I’ll tell myself that this would obviously have been the start of a life-changing adventure, but let’s be honest. The odds were pretty good that it would have been over 24 hours later, so that doesn’t really take me too far off the path either.

Finally, there was a time in my life where I was interested in two women at once and made a conscious decision to go after one in particular. Long story short, my choice didn’t work out, so there’s a temptation to wonder what would have happened if I’d chosen differently, but a) there was no guarantee that the other woman would have returned my interest, and b) my guess is we might have dated about six months, and then decided we wanted different things, so that doesn’t really change the path.

I guess there’s one more item that should be included in this exercise. My mom’s death was probably my single biggest worry over this time period. I couldn’t have predicted the exact date or anything, but it played out pretty much exactly how I feared it would, so if anything, that part of the path feels more predetermined than anything else we’ve been talking about here.

Final verdict

I’m not prepared to prepared to declare a complete belief in destiny (though he’s one bad-ass character in the Sandman stories). To do so feels like it would be an abdication of responsibility over my own life, and that doesn’t work for me. At the same time, looking back over this story, it does sort of feel like no matter what decisions I made, the odds were always pretty good that come August 2, 2016, I’d be staring at the garden of the Northern Estate, having finished watering all of the house plants, and wondering about the path that brought me here.