The two questions I get the most often

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Almost five years into my life as a digital nomad, I still encounter people for whom this lifestyle is novel and unprecedented. I am happy to serve as an ambassador, educating others about the freedom, joy, and possibilities of working remotely without a permanent home.

But there are two questions that I get more than any others — and their honest answers often leave my audience surprised or disappointed.

“What is your favorite place that you’ve visited?”

If you were to peruse any of the Facebook or reddit groups of digital nomads, you’d hear journeys of self-employed entrepreneurs exploring exotic, foreign locales: Thailand! Istanbul! Athens! One recent post asked where to go in Italy for the best food: Bari, Palermo, Bologna, Napoli, Rome, or Cagliari? In another post, a nomad wrote: hey, I saw the city Cochabamba on a map, so I bought a ticket and went there, for no other reason than I liked the name. (It’s in Bolivia!)

Surely my adventures achieve these heights, and asking what my favorite place was will unveil some extraordinary, colorful tales of which the listener can only imagine??

Not exactly. My nomadic journey began five months before the pandemic; for the next three years, my travels were solely domestic as I drove around the United States in my Prius. Even now that COVID is unlikely to be life-threatening to the vaccinated, my destinations are still somewhat limited. My employer requires that I not be out of the country for more than three months, lest my status change from “employee” to “contractor” and I lose my healthcare benefits. And even without that imposition, being in a foreign country means I need to leave behind many of the things that I regularly depend on: my car for mobility; my spice rack for cooking; my bicycle for stress relief. I have had stints outside the USA — a month each in Costa Rica and Budapest, a few weeks each in Barcelona and Munich, a whirlwind tour of Australia and New Zealand — but those are the exceptions, not the norm.

So when someone asks, “What’s your favorite place?”, what they’re not expecting is the mundane truth: Bend, Oregon, has some of the most diverse outdoor activities I’ve found anywhere — hiking, cycling, kayaking, and snowshoeing, all within a thirty-minute radius. And it’s home to the world’s last Blockbuster Video!

Tied with Bend is Missoula, Montana. It’s a diverse, welcoming city, which makes it exceptional in its state; the river flowing through the middle makes for great walking, kayaking, and tubing; the restaurants are wonderful and accommodating of diverse diets; and it’s home to some of my best friends and their dogs.

Those are my favorite places — and I’ve been asked about them often enough that my answers are now rote. For some original responses, here are different angles one could try:

1. What place surprised you the most?
2. What’s a place you’d go back to? Or wouldn’t go back to?
3. Have you been somewhere that was hard to get to, or hard to leave?
4. What city has the best food?
5. Where were people the friendliest?
6. What place affected you the most?
7. Was there anywhere that was easier or harder to work from?
8. What’s the most expensive place you’ve stayed?
9. What’s the best accommodation/Airbnb you’ve had?
10. Where did you feel most at home, or most isolated?

I’d welcome the opportunity to ponder those questions! Much more so than the next most common question I get:

“How long are you going to keep doing this?”

I’ve been a nomad for almost five years — even longer than the friend who inspired me to adopt this lifestyle. Many people assume that this pace is unsustainable, and that I will eventually settle down, either because I’m exhausted or because I want the things that can only come from being anchored in one place.

Neither assumption is correct. This lifestyle engenders not exhaustion, but momentum. Halting that momentum would be as difficult as becoming a nomad in the first place: it would be the reverse of putting everything into storage, selling my possessions, finding new insurance policies, and more, while losing the incredible cost savings and freedom to travel that comes with a nomad. All that effort and sacrifice to transition to being rooted in one place would be far more difficult than simply finding my next Airbnb. To suggest someone should abandon any lifestyle and adopt another dismisses how incredibly emotionally and financially taxing such a task would be. (Imagine asking someone, without provocation, when they’re going to sell their house — what a strange and presumptuous question!)

More fundamentally, the question itself is a loaded one. I’ve tried to underscore this flaw by turning the question around on the asker. When one person asked me, “When are you going to stop being a nomad?”, I responded, “Why aren’t you also asking me when I’m going to stop being vegetarian?” He seemed offended that I’d suggest he would ever disrespect my value-driven diet. Yet both questions have the same implications: I live an aberrant lifestyle, and I’m expected to conform to a societal norm.

Yet it’s not so abnormal! According to a Forbes article from August 2023, the number of digital nomads who claim US residency is 17 million, or 11% of the country’s workforce. And nomads tend to be happier in their careers than their anchored counterparts:

80% of digital nomads say they are highly satisfied with their work, versus 59% of people who aren’t digital nomads. Digital nomads also tend to be happy with their income levels, with 82% of digital nomads say they are satisfied or very satisfied with their income. Among workers who aren’t digital nomads, 69% report the same satisfaction levels.

Elaine Pofeldt, “Digital Nomadism Continues To Grow, Despite The ‘Back To The Office’ Trend“

With that in mind, I tried a different approach with another friend who asked me when I’m going to stop: I deflected by asking, “What’s your favorite hobby?” The answer was archery. I asked why they enjoy it, and they provided a raft of positive reasons, from physical fitness to the mental health benefit of being good at something, maybe even competitively.

“That’s wonderful!” I beamed. “I’m so glad you found something that makes you happy. Archery is such an unusual pastime, and it makes you so interesting; I don’t know anyone else who does this.”

As they basked in this, I added: “When are you going to stop?”

I could see the confusion in their face: Why would someone give up something that makes them happy, interesting, unique, and rich, both emotionally and potentially even financially?

Now that is a good question.

(Featured image by Mohamed Hassan from Pixabay)