What I Learned From 6 Months On The Road

I recently drove across the country and back, living in a bunch of cities. Here are my meta-learnings:

Traveling this way is surprisingly easy.

  • Road trips are hard. Or at least, they’re supposed to be. I think most of that is the pain of boredom – staring out at the world as it blurs by, a sea of sameness for hour upon hour.
  • That was not at all my experience. Our trips, even long ones – 20 hours of driving in 3 days, etc. – were relatively painless.
  • We barely even turned on podcasts. We just talked about the next stage of the trip, the phase that had just passed, and our post-trip plans.

I didn’t miss New York that much

  • It’s my first (and to date, only) city love, but it’s kind of emptied out as a place for me specifically:
    • I don’t drink anymore
    • I don’t usually love restaurants, much less crowded and loud ones
    • My closest friends left
    • I don’t work in finance anymore, nor do I need to be plugged into it
  • It’s still the one pool where I’d happily drown. But I don’t think I need it to be happy, and it might hinder my happiness in the long run.

We want a mixture of history and density that is hard to get outside the East Coast

  • History (at least, history that lasts more than 150 years) is hard to come by in most of the US.
  • My partner and I both need a bit more than that – a place that needs to be here, that means something to the world, that offers a tiny rush of being a part of something bigger than yourself. I want somewhere that originates culture rather than borrowing ideas from others.
  • Livability is also important, but means something different than we thought at the outset
    • Good, accessible and uncrowded nature. Likely not world-class, as those things are too crowded and distant from the nearest cities
    • Walkable for most stuff, easy to drive and park in for all the other stuff
    • Lots of people and things around, but not to the point that everything is rammed and booked weeks in advance
    • Some beautiful scenery in the immediate area, preferably green space or water
  • History and density are brutal filters. Effectively, you’ve ruled out all but the northeast with those two; we may just be East Coast people, after all.
  • This was more of a surprise to my partner than me, but it wasn’t a wholly expected thing for me either, despite my myth-making about feeling out of place in California because of my East Coast roots.

I was really bad at predicting what I’d actually like

  • I was wrong about nearly every stop on our trip. I liked San Francisco much more than I thought I would. I was impressed by Portland. I was deeply unimpressed by Vancouver. Seattle seemed like a cool place. I predicted none of this beforehand.
  • Why was I so bad at predicting things? Some ideas:
    • I didn’t know what I was talking about when I made my predictions (operating on limited information about places I’d never been)
    • Filling in and leaving out tricks (I underestimated how lovely it was to have people in San Francisco, for example)
    • I focused on the perceived coolness of the thing rather than the experience of the thing itself. My area near DC isn’t cool, for example. But it’s beautiful, historic, and next door to some cool city stuff. Which means I wildly underrated how good it feels to be here.
    • I underrated my self-knowledge.
      • I am genuinely a fan of the East Coast of the US.
      • I dislike being disconnected from work people and my family back east.
      • Ease of travel (shorter/direct flights, etc.) matters to me, and I prefer being close to Europe to being close to Asia.

Changing your mind isn’t that bad

  • Both my partner and I were wrong at every turn on this trip.
  • But we were open with each other about it, and it turned out fine! Nobody got skewered for being an idiot or flip-flopping, and thus we were free to speak openly with each other.
  • If you make it OK to change your mind in any social dynamic, people will do so.

Over-calendaring is painful but unavoidable.

  • A scenario that happens reasonably often: We’re booked for a normal amount of stuff, then something happens that we didn’t anticipate. A friend comes to town at the last minute. A work trip crops up. Somebody dies.
  • Our initial balance is thrown off. Now we’re in a crunch.
  • You can’t plan for a thing like this to happen and operate at 70% capacity all the time. But inevitably, if you’re at 85%, some demon is sneaking up behind you to throw another 25% on your plate and laugh as you struggle under the weight.
  • The hard thing is that operating at 85%+ capacity is a good thing most of the time. It’s a policy that works for us. We can handle little stuff that comes up without getting overly busy, and we’re not bored. But it’s prone to major disruptions, and there’s no getting around that one.

Quick hits

  • Having (some of) your own stuff with you makes travel feel less transient.
  • All the travel and exploration didn’t cut down on my reading time all that much.
  • I found healthy eating harder than I expected – it kind of feels like I’m on vacation and using vacation rules all the time.
  • Same with exercise. I probably missed more workouts in the back half of the year than the front. I could have benefited from a more regimented schedule.
  • Being in a car-based place makes me feel caged – I need to walk but don’t want to walk when surrounded by major roads.
  • I didn’t feel overly reliant on my partner for social stuff. We saw some friends along the way and were fine to spend a bit of time solo.

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