Last year in December, the day before my 40th birthday, a day in which I was in a particularly introspective mood, thinking about life and the future and what choices I wanted to make, I happened to listen to a podcast that kind of shook me.

It was Megan McCardle and Russ Roberts talking about belonging, home, and national identity. These are all some of my favorite subjects, and maybe I chose to listen to that episode at that moment because some of these things were on my mind. In the episode, they grapple with an idea from author David Goodhart that there are two kinds of people in the world: the Somewheres and the Anywheres.

Goodhart was writing about populism and politics. But the concept applied to everyone, everywhere, and it applied to me. I was an Anywhere who had recently begun to see the virtues of being a Somewhere. And it was the pandemic that accelerated that change in mindset.

Here’s McCardle:

I think the pandemic has illustrated that better than anything could, where all of the people who thought that they were--what one British writer called the 'Somewheres versus the Anywheres.' You know: the people who live in one place and stay there versus the people who are constantly mobile and can go anywhere. Well, the Anywheres found themselves trapped somewhere.

For much of my life, I was that constantly mobile person, the one who could go anywhere. I’d sought to arrange my whole being and existence to make sure I could, and I called these choices optimizing for freedom. I knew not everyone could do the things I’d done, that in some sense I was very lucky to have those choices, but I also knew there are had been key moments in my life, forks in the road, where I’d chosen to take the paths which preserved my options, as opposed to the ones that tied me down.

Then came the pandemic. My partner and I were in Mérida, Mexico, at the time, where we were taking Spanish lessons and eating cheap street tacos and I was writing this newsletter, and we were both on our way to mutual self-actualization.

But the cases were rising and it seemed anything could happen next, so we cut our trip short, flew back to New Hampshire, and there we stayed. I didn’t get on another airplane for more than a year—the longest stretch of not flying in as long as I could remember.

But I didn’t feel trapped, as McCardle said. Rather, I felt lucky, even prosperous. We gardened and baked. We memorized poetry and played music, and went for long walks as a family, even in the cold, wet April mud season. A few of my friends and I continued to climb at the nearby crags, and occasionally we socialized outside around campfires. Everyone was always around, because, well, it was a pandemic.

I wrote about this more extensively in my post from two weeks ago. I called that time of being holed up in Rumney, New Hampshire a Brief, Shining Moment:

I remember being extremely content and satisfied with life around that time, and in the months before and after. Because I was doing the things I loved and spending time with people I loved.

The McCardle conversation gave a different frame to that moment: I had gone from being an Anywhere my whole life to suddenly being a Somewhere. And it felt pretty good.

Optimizing for freedom

Still, my whole life I’ve made choices that mostly optimize for freedom.

A few forks in the road stand out. When I was 22, I applied for and was accepted to American Unversity to do a joint international relations-MBA graduate degree. I knew that down that path possibly lay prestige, money, and a definitive career path. But something about accepting the offer terrified me.

I’d been around D.C. long enough to understand that the city’s many international relations programs—Georgetown, American, George Washington, Johns Hopkins’ SAIS—graduated thousands of similar students each year. And these thousands of students all went onto the same path, looking at the same jobs, heading in the same direction.

Going to AU felt like it would be getting on a very fast-moving train that I would not easily be able to get off. And I didn’t want to get on any train.

Instead, I threw together a hasty application to St. John’s College, where they teach Classical liberal arts via the “Great Books” curriculum. It was a path to nowhere, except to maybe learning how to discover and evaluate new paths.

It also cannot be ignored that it was a path back to Santa Fe, where I’d been born. When I told my dad about the decision to come back, he was happy I’d be so close to him, but also confused and a little nervous that I’d turned down the joint program at AU. He worried for my career.

But of course, I didn’t know what career I wanted, I just knew I wanted to keep my options open.

And, there was another benefit. St. John’s had given me half off tuition. The entire Master’s degree would cost a little over $20k in student debt. Compare that to the combined AU program, which would have run me at least $100k, maybe more.

Of course, the money and debt thing is a big reason why it’s hard to get off fast-moving career trains: because you need the money to pay back the debt you took out to get on the train in the first place. Then, even if you pay off the debt, you get addicted to the money. And once you’re addicted, it narrows the range of paths. Even if you were so inclined to look for another path, it’s hard to conceive of leaving a six-figure job for something that is anything less.

Constraining your choices

Looking back, it’s amazing to see how clever I was at a young age at managing to avoid constraining my choices. I didn’t commit to girls. I didn’t commit to places. I didn’t really commit to jobs. And, I didn’t commit to egregious expenses.

At 24, I was nearly done with grad school and decided the time had come for me to buy a house.

The year was 2006—18 months away from a historic recession caused by irresponsible debt: debt to buy homes, debt packaged into mortgage-backed securities, debt that was triple-A rated by financially- and morally-compromised ratings agencies.

But no one knew that at the time. All we knew was: home prices keep going up, therefore buying property seems wise.

I found a realtor, who found me a mortgage broker to get a pre-qualification. My salary as a local newspaper reporter wasn’t a lot, but it was enough. When I met with the broker at his office in Santa Fe, he slid a print out across the table and pointed to a number: $1,356. That was what I could afford to pay per month in a mortgage payment, he told me. I literally laughed at him. At the time, I was paying $650/month to rent a 1-bedroom apartment walking distance to my office. Now, he wanted me to be on the hook for twice as much.

Millions of people across the country in those years had this exact same conversation with a mortgage broker. Millions shrugged their shoulders and signed up for a payment they couldn’t afford. So what led me to laugh him practically out of the room? I’m not exactly sure. To me, it just seemed imprudent.

Later, during the bailouts, during the political debates in ‘09, ‘10, ‘11, and on about culpability and responsibility and moral hazard, I must admit that I thought all those buyers of homes should have been more circumspect in the debts they chose to take on. They’d had their choices constrained for them. Or, they’d constrained their own choices. However you wanted to look at it.

And me? I was sitting back collecting rent and not really caring at all that the home was severely underwater. I could just wait.

Money and freedom

Of course, money buys you freedom. But only up to a point. Then it constrains your freedom.

Nowhere did I see this better illustrated than in a recent post on Zero Hedge about “F**k You Money.” The proper amount of FU Money isn’t above a certain amount—it’s between a certain amount.

As Nassim Taleb once said in an interview:

Money can’t buy happiness, but the absence of money can cause unhappiness. Money buys freedom: intellectual freedom, freedom to choose who you vote for, to choose what you want to do professionally. But having what I call “f*ck you” money requires a huge amount of discipline. The minute you go a penny over, then you lose your freedom again. If money is the cause of your worry, then you have to restructure your life.

(Also in that interview, Taleb said he’d never once borrowed money: “I follow the Romans’ attitude that debtors are not free people.”)

The reason money can constrain freedom is that to accumulate a lot of money requires you to commit to certain things. Take growing a company: it requires that you constrain yourself in various ways, whether by taking on investors, or making yourself responsible for employees, or God forbid your company goes public, then you are constrained by regulators and the market (one of my marketing clients went public in 2020—everyone got paid, but also everyone became super constrained with the day-to-day stock price of the company).

Again, this is an area I’ve navigated pretty sharply. I’ve accumulated enough wealth to have some FU money, but steered clear before I got to the point where choices were constrained.

Embracing the digital nomad lifestyle

There’s a photo that I often think about when I think about how lovely and free from constraint my life has been:

That was me on a trip to Cabarete in the Dominican Republic a few years back.

I was there with my partner and our kids. They were on Spring break. I was there to kitesurf. You can’t see it in the photo because it’s washed out, but the ocean is right in front of the windows. I was technically “full-time” employed back then, though I’m not sure I ever told anyone I worked with where I’d be at any given time.

I remember at one point I couldn’t access something on the company’s network, because the DR was on the IT Department’s list of “danger” countries. I’d worked remote from the Czech Republic, Greece, and the UK, but this was the first time I’d been blocked from accessing something. I got on the phone with an IT guy. He couldn’t change the settings on the network, he said, but I could download a VPN plugin that would circumvent it.

Such was the lifestyle of a digital nomad: I could go anywhere! Do anything! I once edited, finalized, and sent a company newsletter from the top of a big red double-decker bus in London, grabbing wifi from the tether on my international, Google Fi phone as I was on my way to meet a friend for a beer and a play. Digital nomadism was glorious! And I was damn good at it!

But, there were cracks. I always knew there were.

The most obvious, the one everyone talks about, is the lack of a strong social circle. You leave, but life goes on back home, wherever home is. If you’re alone, you’re really alone. Even if, like me, you have a partner, then you only have you and your partner. Even families that do this—hit the road, travel, worldschool, the whole thing—feel a certain lack of connection. Eventually, what these families want is just another family to hang out with, other kids for the kids to play with.

Everyone knows digital nomadism can be lonely. But I think the problem with digital nomadism actually cuts a little deeper.

Taking the wrong lesson from the pandemic

Today, digital nomadism is having quite a moment.

So many people worked from home during the pandemic, they realized that working from home can be quite wonderful. You can move, live in a cheaper place, even go abroad! You can spend more time with your kids, make your own lunch at home, go for a walk in the middle of the day, have more control.

But I’m afraid we might be taking the wrong lessons from our new-found, post-pandemic remote lifestyles. See, I’ve been living this way for a long while now. I’ve arranged my whole life optimizing for freedom, and for me, the pandemic taught me a kind of opposite lesson. It showed me that being a Somewhere as opposed to an Anywhere is pretty nice. As a Somewhere, I had literally planted seeds in the ground and watched them grow. You can’t do that when you’re an Anywhere.

In the McCardle and Roberts podcast, they talk at some length about Brexit. The Anywheres were arguing that it would be foolish to leave the EU. Didn’t people understand? If you leave, you won’t be able to go to Europe whenever you want! You won’t have freedom of movement. You won’t be able to go work anywhere, go to school anywhere. The anti-leave movement was populated by all these young people who had grown up as Anywheres, like me, with the world at their fingertips, thinking that to remove that freedom would be the height of stupidity.

On the other side of the question were the Somewheres, who heard that argument and replied, in effect: so, what? In fact, the Somewheres believe that when you leave the place you’re from, you diminish it. The Somewheres were saying: All you people who want to go anywhere and do anything? We resent you. We resent you because you decided you don’t want to stay here and contribute to the place you left behind.

McCardle hypothesized that a society full of Anywheres is a society that will begin to disintegrate and fall apart. Freedom is all well and good, but if everyone over-indexes on freedom, you don’t have a community, much less a country.

There’s another exchange in the podcast where they discuss the author Marc Helprin, who dodged the draft during Vietnam, then later wrote an essay about how he’d been wrong to do so. Then, Helprin joins the Merchant Marine:

McArdle: He finds himself on the prow of a ship with a British merchant seaman. And, the guy says, 'Well, why aren't you in Vietnam?' And, he sort of starts explaining it's the wrong war, whatever. And, the guy just looks at him and says, 'But, those are your mates.' Right? It's that kind of very elemental--that is the elemental kind of logic of the Somewheres. And, I actually think it's profoundly, more powerful and actually more important and necessary to human flourishing than the Anywheres want to admit.

Precisely right.

It’s not that you have to choose: Somewhere, or Anywhere. It’s that to arrange everything about your life to be an Anywhere is to miss something important not just to human flourishing, but to your flourishing. You never get a chance to plant seeds.

I’m beginning to understand this more about myself, but also to see it in more places. I know people who don’t want to have kids because they don’t want the constraint. Or they don’t want to buy property, because it would tie them down too much. The swiping apps give people access to anyone, anywhere, so that they resist committing to someone who may be right in front of them. Or, perhaps they want to be a digital nomad so they can roam the world in perpetual travel and have their life be a never-ending stream of learning and new experiences. It sounds lovely.

Except that there is a real opportunity cost to all that freedom. And also, freedom is tough. Having all the choices in the world doesn’t make it easier to choose. But it does make it harder to be satisfied.

Next year, I’m going back to La Ventana to kitesurf. It’s already booked, because I’m not optimizing every decision for freedom anymore. I’m trying to find some balance. Not visit every kitesurfing beach in the world, not arrange my life as a kind of tic list of experiences, but to spend more time in places I love with people I love. I’ve already booked the apartment because I wanted to deliberately constrain my choice. The deposit is down. If I cancel, I lose it, which is kind of the whole point.

Post-Nomad

Over-indexing on freedom