The monkeywrench moments chain.
That’s the thing I’ve been thinking about lately. Not the Monkeywrench Moments themselves — I’ve written about those — but how each one made the next one conceivable. The Philippines venture depended on having already done the nomadic RV life. The RV life grew directly out of the AT thru-hike.
I don’t go from 0 to 100. I take one leap — and that leap changes what’s conceivable next.
We get about eighty-five years on earth (though I’ve promised Inday I’ll live to 100). The world is enormous. I’m never going to see or live or experience most of it.
So I try to live as much as I can.
But not as much as I can in the bucket-list sense. I’m not trying to collect experiences. I’m trying not to waste time.
That’s the driver under the Monkeywrench Moments, if there is one. Not a bigger life. A less wasted one, by my own measure.
When a turn shows up, my head doesn’t run a drama. It runs something closer to this: This is a thing I want to do. How do I make it happen? What do I do if I fail? Can I survive that?
Practical questions. Recovery questions. That loop has been running for decades now, and I trust it more than I fear my fear.
Looking back, my adult life doesn’t read as one long arc. It reads as a series of lives, with transitions in between.
Or maybe those are just chapters, and I’m dressing them up. I don’t know. People talk about chapters in their lives all the time. Am I inventing a grander vocabulary so I look bigger to myself? There are certainly people who live much bigger lives than I do.
I’m going to keep using “lives” and “transitions” anyway, because from the inside the breaks feel real — not page turns in one continuous book, but a change of operating system. If that’s self-mythology, fine. It’s the mythology that matches how the time has felt.
There was a first settled life: job, marriage, car payment, house, child, pets. The life you’re supposed to want. And I did. I wanted it. I loved that life.
Then divorce, and single parenting. I’m still not sure whether that was a life of its own or a transition — the fumbling stretch where you know something has to change but you don’t yet know what.
There was a second marriage. A move to Boston. Condo life. No debt. Travel.
Then a Monkeywrench Moment I can name cleanly: I resigned from a job to thru-hike the Appalachian Trail. I didn’t go back to the corporate world. I started a video business with Jodi. We met people. We grew the business. It was a new world. A good life, right up until the question showed up: we’ve built this — now what?
Another divorce. I drove away from that life in a motorhome and spent nearly five years on the road. That was a life! I wouldn’t trade that experience for anything, as lonely as it eventually became.
Was Johnson City apartment life a life, or another transition? It didn’t suit me. Sometimes that’s how you know you’re still fumbling: you can feel the misfit before you can name the next turn.
Then the Philippines. Inday. The farm. The leap that scared me the most — and the one that made the whole chain make sense.
And ahead of me — and already under my feet — this bi-hemispheric life: America and the Philippines, one existence spanning both.
And it’s not just the geography. It’s the juxtaposition. West and East, side by side in an ordinary day. Carabao and Starlink.
I’m not going to try to explain people who live one life all the way through. I don’t know their insides. I only know mine.
Here’s what I’ve noticed about the transitions.
Sometimes you know a change is needed, but not what the change is. You fumble around for a while until it makes itself clear.
That’s okay. You still wake up every morning and eat breakfast.
The fog isn’t failure. It’s the in-between.
And here’s what I’ve noticed about the leaps themselves.
In the moment, these turns don’t feel “larger.” That word is a rearview word. At the time they’re fitting. The right size. The size of change that’s acceptable in your life, because you’ve made changes before and change is part of your operating system now.
Only looking back do they line up as incrementally bigger: trail, then road, then another country, and now this bi-hemispheric life.
That’s what distance does. I wrote about it in the Distance post — how stepping away from the Philippines finally let me see it clearly. It works the same way with time. You can’t see the chain while you’re inside it. I couldn’t see the Filipino operating system while I was living under it, either. Step back far enough — an ocean, a few years, a couple of lives — and the shape appears.
Limitations, for me, are mostly mental.
I posted a Facebook memory of my dad not long ago. My brother commented on how long ago that was — eight years! And I thought: That was only eight years ago? My God, I’ve lived three lives since then.
That’s what this feels like from the inside. Not one long career narrative. Stacked lives. Dense time. The density is the point.
When I was first exploring moving overseas, I struggled deeply with it. It scared me. Was this too big? Was I too old? If it was a mistake, could I recover?
I even paid an online therapist for an hour just to talk it through. (Worth every penny, by the way. Sometimes you have to say the scary thing out loud to a stranger to hear what it really sounds like.)
The questions were still the same practical loop: How do I make this happen? What if I fail? Can I survive that?
I made the leap anyway. Because it was a thing I wanted to do, and I could see a path, and I believed I could survive being wrong.
So where does that leave the Monkeywrench Theory, years after that first post?
Still the idea that sometimes you throw a wrench into the works, blow up a life, and start over.
Still the choice to lean toward the itch instead of talking yourself out of it with “I have a life; I can’t quit now.”
Still not a claim that my life is big. Only that I keep trying not to waste the stretch of years I’ve got.
As my brother once said to me: “Your life isn’t boring!”
No. It isn’t. One fitting leap at a time, breakfast in the fumbling, and a chain that somehow got me to Inday, the farm, and a bi-hemispheric life I couldn’t have pictured from the first settled chapter.
