Ten missed calls in two minutes.

Text: “We need to talk Steven.  Don’t leave yet.”

I was at the airport, about to board a plane for a new city.  The messages came from a woman who I had dated but not actually slept with, my chances dimmed when she shared that she was married.

Now she was behaving as though we would never see each other again, but I would be only five hours away.

How did I get into this mess?

This past year has been unstable for me in terms of romantic relationships.  Well, to be honest, probably the past ten years or so.  Lucky for you, I may have stumbled on a necessary feature of relationships that no one discusses.


What is freedom?  My freshman year in university I took a class that asked this question.  Unfortunately it was a philosophy class so we never actually answered it.

Freedom here derives heavily from Harry Browne’s “How I Found Freedom in an Unfree World”.  In the book, Browne focuses actually on the traps that prevent freedom, rather than the yearning for freedom.

Why would a book about freedom focus on its opposite?

The nature of freedom, it seems, is actually difficult to see.  We go through life in a prison of sorts, where we can’t actually identify the shackles that bind us.  If we look carefully, we often can see the shackles on others, but never our own.

One of the charms of children is their willingness to verbalize the shackles that chain those around them, as in the story of The Emperor Wears No Clothes, where everyone subconsciously accepts the Emperor’s shackles around their opinion but a child who immediately sees the world for what it is.

At some point most of us lose the freedom of that child to say what we see, probably when we verbalized an adult’s shackles and they responded by placing more shackles on us.

So we grow up, and we can’t really see the shackles that bind us, except for when they first bind us, and when others point them out.  And most people are courteous enough not to point them out, so we can get on for quite some time without noticing any of our shackles.

This problem is so vicious, that I can write about it yet still not see my own shackles.

So I won’t talk today about my psychological shackles.  Instead I’ll focus on the more superficial shackles that I’ve seen in others, and hope they don’t hate me for pointing them out.

The first freedom I’ve found is location.  As Americans, we have an extraordinary freedom of location: our passport can basically get us anywhere in the world not run by a dictator.

I remember the feeling of getting my passport in 2007 and choosing where to go.  It was scary and exciting and thrilling.  It felt like I was letting go of very large shackles.

As of 2014, only 46% of Americans actually have passports, and a smaller set actively use them.  For many Americans, location is not a freedom, but a shackle they’ve placed on themselves.

Recently I dated a woman who adamantly wanted to buy a house.  The challenge with home ownership is it places a shackle on your location freedom.  Sure, you can leave your house behind and travel, but most people don’t.

Buying a house, incidentally, is an issue that brings our freedoms and shackles to forefront.  If your location is already a shackle, then buying a house makes complete sense.  If your location is free, however, buying a house can feel risky.

I wouldn’t realize most of this, except in traveling I discovered people for whom the location shackles are more visible and real.  As an American, I can fly to a dozen countries and start teaching English tomorrow, making more money than 90% of the population there.  I can actually fly there with no money and a forged roundtrip ticket.  The location shackles for me are negligible.

As a citizen in Vietnam, or the Philippines, however, moving to a new continent carries a high burden of evidence that you can take care of yourself and you won’t try to stay in the new country.

The cost can easily approach a year’s salary.

When I travel between countries, then, I’m flaunting my freedom in front of those who don’t have the same.

Its humbling to realize how privileged I am to travel.  Its inspiring to see those who overcome this hurdle in SE Asia to travel anyways.  And its frustrating to then meet Americans for whom travel is “not possible right now.”

The second freedom I’ve found is time, the ability to (mostly) choose when I do work.

As a child I spent summers helping my grandfather deliver newspapers before sunrise.  Often we’d start at midnight and deliver until 5am.

Later, I started working 6am shifts at McDonald’s, every possible time of the day at Denny’s, and the entire day at Domino’s.

My first real attempt at starting a company was a delivery service from 10pm to 2am.

Growing up, I didn’t know anyone who was happy working a 9-5 schedule, but I found I enjoyed these different schedules and jobs.  Getting to work and seeing the sunrise is kinda cool.  Working through the tempos of dinnertime and bars closing gives you a cross section view of society.  At 3am, everyone at Denny’s is eating the same food.

From this experience, I discovered that work is an action, not a time and place.  Most people think work is their office, but really work is what you do.

If you don’t get this, you won’t have a place to go to work for much longer.

There are hundreds of articles online emphasizing that high achievers are also early risers.  If you want to get ahead, they whisper, you need to wake up earlier.  If you can’t, its because you’re not good enough, they imply.

Except thats not true.

Increasingly, work is something we can do at any time of the day.  This is equally true if you work retail, drive an Uber, or freelance in knowledge.  Its not true for those in middle class office jobs, but hey thats your choice.

The third freedom I’ve found is freedom of Tempo.

Last week I found myself in a conversation with three successful guys from a tech startup.  For ten minutes, all they could talk about was who in the office would get the best desks with a slightly better view of the bay.

I’m competitive, and in an alternate universe I would already have a house with a white fence and a two car garage.  I would obsess over what school my kids will attend and grimace when my neighbor buys a boat.  I would compare the color of my business card with that of Paul Allen.

The desire to keep up with the Joneses is real.  The US culture created these milestones for getting ahead in life, and Facebook perpetuates them when everyone you know posts the best parts of their life in all of its filtered glory.

But a funny thing happened on my way to the Joneses shackle factory.

I started traveling, and realized most of it is arbitrary.

Living in Asia, my status suddenly became impossible to measure.

I’m a white male who isn’t an English teacher, so its somewhat measurable.

But there was no one to actually compare myself against.

When I returned to the U.S., I noticed many people placed my status based on their own disposition.  East Asians would look at me with skepticism, concluding that I’m a bit young for a sexpat.  White Americans would project their own unrequited wanderlust on me and conclude that I’m living the dream.  No one would conclude that I’m in roughly the same circumstances, trying to get ahead in life and making compromises along the way.

Back to the office conversation.  Having spent so much time out of the rat race, I can’t even run against other rats anymore.  I quickly excused myself and found some engineers to interrogate.

Then I remembered an important lesson from Doc Wong, a chiropractor who runs motorcycle clinics in the peninsula.

One weekend I showed up at the ride in the rain.  There were only three other riders (normally over 60) and each had more years of riding experience than I had years total.

On the wet ride through the mountains, with over 1,081 turns, they would disappear ahead of me for minutes at a time, only to wait at the next big intersection until I caught up.

Later I asked why they did this, Doc Wong explained “I didn’t want you to be tempted to keep up.  Its important to run your own race.”

Choose your own tempo.

The final freedom I discovered is freedom of ritual.

Tithing is the act of paying a percentage of your earnings to the church.  Its a useful metaphor to explain a lot of the obligations we face in society.

Most of us grow up with some collection of rituals, obligations, and rules we have to follow to keep our membership in a tribe.

I grew up in a holiday Christian family, meaning we’d show up to church for major holidays only.  My grandparents wanted me to learn to give to the church, so they would give me money that I would put into the plate myself.  That didn’t work as intended: I never made the connection that this was my money going into the plate.  I was always just handing their money over.

I resisted a lot of obligations growing up.  Homework seemed unnecessary, chores were never adequately explained, church was a place you visited once in awhile.

Thinking I was not religious, I looked forward to moving to Vietnam, where I assumed religion would be less common.  Instead I found a collection of cultural beliefs without the religion figurehead to easily dismiss it all.

Turns out, its easy for me to lampoon Scientology or Mormonism, but its difficult to explain why believing in ghosts is ridiculous.

The tithing and the church look slightly different for everyone, but its generally a shackle we accept when we’re young.

For some its the obligation to take care of their parents when they’re old.  For others its the obligation to stay in an unhappy marriage for the sake of their children.

I am religious, but my religion is a collection of hard-won truths and rituals I’ve adopted on my own, not a manual handed to me by others.  Its a religion of one.

What does this all mean for relationships?

If you’re a digital nomad, it means everything.

These freedoms of location, time, tempo, and ritual are relatively new to our society, and finding someone with matching freedoms might be necessary for a happy, stable relationship.

Location: if you are location independent, dating someone who is location shackled creates a clear challenge the minute you start to travel.

Two relationship types for me stand in contrast.  In one, I date a woman who has never left her country.  When I travel, she will have a small meltdown about it, assuming the worst.  I didn’t leave her country, I left her.

Remarkably, this occurs whether the relationship is with a woman who actually cannot leave her country, or just one who has mental shackles around the idea.

In the other relationship type, I date someone who lives outside of her home culture.  She sees travel as a temporary thing, and an expression of a freedom she has as well.  When I travel, the relationship moves online.  I didn’t leave her, I just checked in someplace else.

This second one can come with its own set of issues (what woman is crazy enough to travel like I do?) but overall its far more stable.  Or, you can stop traveling and learn to love one location.

Time: I’ve found my lifestyle matches best with students, because they can still choose when they study.  And workaholics, because they work too much to notice my freedom.

But the 9-5 types don’t stay around for long.  They have a pattern to their life, which includes a case of the Mondays, Hump Wednesdays, and daydreams about Fridays.  They want their weekend to mean something because their M-F does not.

When work is what you do, its difficult to explain to someone for whom work is where you are.

Freedom of time means choice of time, which can be difficult for someone to accept when they have obligation of time.

I became acutely aware of this freedom while dating another freelancer.  At first it seemed like an easy match: she could work any hours of the day, from anywhere.  Her work was an action.

On closer inspection I discovered the shackles: she didn’t actually want that life, she wanted the 9-5 job.

This one might solve itself with children, since the fantasy of a 40 hour workweek quickly disappears.  I’d be interested to hear how others handle this.

Tempo: the lack of direct competition in my life hasn’t become a problem yet, but I suspect it will.

From my observations, most women, even those who take a detour to China, will settle and want to find their own Joneses to keep up with.  Thanks to Facebook, its easier than ever to take the detour and still have the same Joneses when you return.

Its easy to run my own race when I’m running alone.  Running with someone else is a series of compromises on where you’re going to run and how fast you’ll run to get there.

If you’re committed to running your own race, the best hope seems to be to find someone for whom your race is so far ahead of theirs that just being with you is a win.  This makes marrying from another country easier.

Other choices might be artists, entrepreneurs, other nomads, and the trust fund children.

The best way to avoid competition is to play in different leagues.

Ritual: this might be the most difficult of freedoms for a digital nomad.

Some of you have a strong religious background and can ignore this section.

But for those who shun religion, value exploration, and lack an Asian tiger mom, matching your rituals with others can be difficult.

One of the hidden reasons marriage occurs earlier in life for the religious is the value of intersecting rituals.

When you can walk into a cathedral and know everyone there roughly shares the same rituals, its far easier to choose a mate.

A square peg fits into a square hole.

When your rituals are a journey rather than a starting point, they can deform into something that doesn’t fit with the rituals of others.

The solution here, if you’re lucky, is to find someone who’s rituals match or at least are compatible with your own.  As you age and diverge this seems less likely.  The alternative again is to jump leagues.  Or start your own religion.  But that has its own problems.

That text message, I haven’t spoken to her in the many years since.  No hard feelings, just different shackles.

On Freedom and Relationships