I Ditched Digital Nomad Life, Bought a House, and Next Month, Will Have a Baby

What Millennials Think About Giving Up Their Freedom to “Settle Down”

We just bought our first house.

As a travel nurse and digital entrepreneur, my wife and I traveled to a new city in the United States every three months for two years.

We’re having our first daughter next month.

We used to roam the mountains and valleys of California and Utah, cannon-ball from cliffs into the clear waters of remote oases in the dry Summer heat of Arizona. We picnicked on Half Moon beach, hugged the Redwoods, and played beach volleyball with strangers in San Diego.

It was amazing for our marriage. We camped in Yosemite, mountain biked the Wasatch Mountains, and road-tripped for 55 hours straight in our Honda CRV. We rode everywhere with our two cats from San Francisco to Albany, including through a blinding snowstorm. Let me tell you, love burns truest in the darkest hours.

It might sound like a money pit, but we managed to save an average of 25–35% of our income every month on the road. And we both earned more than ever before working full-time jobs in Washington DC.

I’ll miss that life.

Why “Settling Down” Is a Prison Sentence

Last week, we bought a house in Richmond, Virginia and began building a “nest” for our first daughter who is expected to arrive next month 👐.

That previous sentence is an iron sledgehammer essentially obliterating the possibility of digital nomadism. Homeownership, raising a family, and living in one city add up to what might sound like a prison sentence to an ambitious millennial who wants to remain untethered (so-called “location agnostic”). Some call it “settling down.”

Settling down has always scared me. It carries with it a hint of giving up, perhaps because the word “settling” is in it.

If one’s life were charted on a graph and up and to the right meant positive outcomes such as growth and progress, then settling down, in my mind, would be drawn as a straight horizontal line.

When one settles down, time goes on, but things stay mostly the same. Same house, marriage, family, friends, gym, church, coffee shops, breweries, nature, commute — it all begins to routinize. Of course, there are micro-changes in each of these things. You might encounter someone new at small group. You might order something different at your favorite restaurant. Your son or daughter might learn something new. I’m not saying these changes can’t be absolutely thrilling (more on this below).

But the big things in life hit auto-pilot. House, career, relationships, the week — fall into a “sea of sameness,” which, in the graph of life, is depicted as plateauing.

For a 28-year-old like me, this forms a crux. While some welcome the idea of a mostly predictable life, I see it as rounding off the “up and to the right” graph into a calm, neighborly flat line, desperately hoping the space between the words “flat” and “line” does not close.

The reason I’m afraid of settling down is I crave change. I’m opportunistic. I want to evolve constantly. “Change brings discomfort. Discomfort leads to learning. Learning yields growth. Growth fosters success.” I wrote that when I first decided to quit my job years ago. These are my values.

But these values are exactly what make the word “permanence” so damn terrifying.

Permanence seems to be the elimination of choice. The reduction of many options to one commitment. The absence of the ability to change. The death of freedom.

Why was this not a problem before? My parents and grandparents don’t feel this way. They like their lives how they are and don’t want to change them. At least, they never mention otherwise.

Maybe it’s because instead of wars, economic turbulence, newspapers, cable news, and corporate America, people my age grew up with #instatravel, live streaming, remote work, and Uber Eats.

The Benefits of Settling Down

I polled my Facebook friends with the question: What are the benefits of “settling down”?

Out of 21 answers, a resounding theme emerged:

“Deep community.”

“Stability” was also mentioned a lot. Financially, emotionally, relationally.

Two of my favorite comments:

My parents got married and built a home in ’85. That same year they planted six Pin Oak trees. Today they and I get to enjoy the beauty and shade of those tall trees.


[A] gardening man can’t travel and a traveling man can’t garden.

From this, I acknowledge there are plenty of good reasons for settling down. Everyone has their own idea for their own best life. But I wonder if emerging lifestyles that haven’t been pragmatic or even possible until recent years have remained unconsidered.

For the past few decades, technology has rapidly expanded our opportunities, access to knowledge and people, mobility, and freedoms. Today, we have a much clearer idea of how much there is to gain and how much there is to lose. Because we’re always a tap away from the internet, we know there is a lot more going on in the world outside our own experiences.

And this awareness presents an uncomfortable paradox.

The Strange Persistence of Apathy

In an essay for The Hedgehog Review, Wilfred M. McClay wrote about a paradox in our contemporary culture he called The Strange Persistence of Guilt. It goes like this: As technology improves, so does our global awareness. The more aware we are, the more responsible we feel. McClay explains why we feel guilty because of this:

Science cannot do anything to relieve the guilt weighing down our souls, a weight to which it has added appreciably, precisely by rendering us able to be in control of, and therefore accountable for, more and more elements in our lives — responsibility being the fertile seedbed of guilt. That growing weight seeks opportunities for release, seeks transactional outlets, but finds no obvious or straightforward ones in the secular dispensation.

This paradox about guilt and responsibility works the same with opportunity, as McClay alludes. Just as we feel guilty for not being more responsible with our ever-growing knowledge of the world’s needs, so we also feel guilty for not taking more advantage of the ever-increasing opportunities in the world around us. It could be called The Strange Persistence of Apathy.

So 2019, here we are.

On the verge of “settling down,” one month away from our daughter’s birth, one month into paying a down payment, I’m saddling up for an extended period of permanence.

I’m frippin’ scared.

What Other Digital Nomads Say About Settling Down

TLDR; They’re divided.

Mark Manson, an apex digital nomad, travel blogger, and author, wrote an essay called The Dark Side of the Digital Nomad. He calls people like himself the “New Rich.”

It occurs to me that the New Rich, for all of our impressive values, are just as guilty of materialism as the old rich, it just takes a different form. Instead of an addiction to status and possessions, we are addicted to experience and novelty. And the end result is the same. Our relationships, our connections to what’s real, sometimes suffer. And for the first time in three years of non-stop travel, I quietly wish for a home.

Jessica Festa, a solo travel blogger and millennial digital nomad, wrote on her blog Jessie on a Journey that she’ll never settle down.

No matter how happy I am, how much my blog grows or how many wonderful experiences I have around the world, there are still those who don’t think I could possibly be happy without a ring on my finger, a mortgage and baby bump before 30.
This couldn’t be farther from the truth.

Dan Moore just published a story I Feel Like a Bad Person for Not Wanting Kids and described a vivid personal clash with this paradox. He wrote:

Whatever the reason, my apprehension fills me with guilt. I feel — logic be damned — like not wanting kids is wrong. I don’t want to, but I do. And a feeling so born in the gut is difficult to rebuke.

From these stories, others, and conversations with friends, family, and most importantly, my wife, I have arrived at three conclusions that will hopefully carry us through the years of “permanence” to come.

Happiness is an internal configuration, not an external curation.

When I worked for an employer, I thought “If only I had the freedom to do my own thing.” Or, “If only I could pursue my passion projects full-time, then I could become an entrepreneur and finally be happy.”

That was two years ago. Five cities later, I’ve come to find a big problem with being happy. It’s not about circumstances, people, or things. It’s an internal perspective. A choice to risk losing it. I wrote poem in a journal entry when I realized this.

Let the grass be greener on yonder hill, 
Let greatness tempt with brightness still, 
Let life and its clock be a grinding mill.
I’m free from it all and care just nil
For I hold life’s paper, ink, and quill.

My brother’s head football coach teaches his players four-second phrases. They’re short and easy to remember.

One of them is:

“Content, but not complacent.”

It’s possible to be still, located in one place, swimming in the sea of sameness, and be content. Permanence doesn’t have to mean complacency. I haven’t experienced this yet, but I know it’s true. It has to be. At least, that’s what I’m clinging to.

You love what you sacrifice for.

Do you have a dog?

Do you wake up and take the dog out in the bitter cold morning so it shits?

Do you have to arrange for a dog sitter every time you fly out of state?

Does the dog ever chew up furniture?

Have you had to clean up the dog’s nervous pee or vomit on the carpet?

Does the dog ever not get along with other dogs or people?

All this pain, and yet it’s 100 percent worth it. Because people love their dogs.

Dogs are optional.

Kids are optional.

Kids are like dogs but many times more meaningful.

And meaningfulness grants us deeper, less fleeting happiness.

This is why people have kids. This is why we’re having a kid.

Maturity — delayed self-gratification — doesn’t feel like happiness in the moment, but it sure as hell feels good looking back.

I gave up alcohol for #DryJanuary.

Last night, on the 19th of January, I was burning for a beer. I had had a bad day — low motivation, tired, and nothing got done. I just really wanted to forget the day and fall into the bottom of a cold pint.

I drank two La Croix cans and hot tea instead. Today, the next day, I look back on yesterday I am proud of myself, just a little. My self-esteem is a hair higher. My willpower seems a tad stronger. In the grand scheme of things, it might not have mattered that much. But, looking back, I’m proud of my decision and it feels good to be proud.

I’m imagining that owning a house and raising a kid will feel the same only on a much larger scale.

The fear I have isn’t going away. My wife and I still catch ourselves dreaming of traveling to Nashville and Austin later this year. Then we remember we’ll have our baby girl and how it will be harder to travel with her. There is sadness. There is nervousness. There are questions. “Are we sure we really wanted this?”

I’m not going to end this with a pretty pink bow on top, saying something like, “But then we’ll see our daughter’s eyes and we’ll look at each other and it will all be worth it.”

The truth is, I don’t know. Circle back with me in six months. We’ll see how it’s going. For now, I’ll leave you with where I’m at now:

  • Happiness is an internal configuration, not an external curation.
  • You love what you sacrifice for.
  • Maturity — delayed self-gratification — doesn’t feel like happiness in the moment, but it sure as hell feels good looking back.