May 21, 2026 May 21, 2026 2026-05-21

In March 2010 I wrote a primer on being a digital nomad — what it meant, where you work, how you manage relationships when you have no office to point to. I was two years into the lifestyle, working out of coffee shops in Romania, and the word “digital nomad” was barely two years old itself. I was describing something so new it didn’t have proper infrastructure yet. The audience for that post was small because the audience for that lifestyle was small.

Sixteen years later this topic has a visa category (countries creating special digital nomad visas), a real estate industry (on purpose building and planning for digital nomads), and a Reddit community with 2.5 million members.

What Was True in the Primer

The philosophical approach — work around your life instead of living around your work — is still very much true. It’s still the right way to look at your life. Most of hands on advice in that post must be updated, but that underlying orientation turned out to be durable in a way I couldn’t fully understand when I wrote it.

The six workspace types are still roughly accurate but the composition of each has changed. Coffee shops got worse and better simultaneously: worse because every city now has the same three chains optimized for throughput rather than for the slow, uninterrupted hours that produce real work; better because WiFi finally became universally reliable. Libraries improved dramatically — quieter, better infrastructure, and now genuinely comfortable to spend a full day in. Co-working spaces became a real estate category, which made them more available and more generic in equal measure. The airport sketching is still real. So is working from the backyard, though I’ve upgraded the backyard a few times since 2010.

What COVID Did to this

COVID ran the experiment involuntarily for roughly 300 million people who hadn’t asked to be remote workers and discovered in the process that they hated some parts of it and loved others. What mass adoption did to the infrastructure was unambiguously good — better tools, better connectivity, better social acceptance. What it did to the experience was more complicated.

Before 2020, explaining to someone that you worked from a coffee shop in a different country required a conversation. After 2020, it required nothing. The social friction of the lifestyle nearly disappeared overnight, which I’d expected to feel like a relief. It did, mostly. But it also removed something that I hadn’t noticed was shaping the experience: the choice was visible. Working this way before it was normal was a declaration of something. After normalization, it became just a configuration option among many. It is what it is.

The people who chose this lifestyle before 2020 had a clear reason why. That reason — I want to work from interesting places while building something on my own terms — turns out to matter more than the logistics. Without it, remote work is just a commute-free version of the same job you had before, which is fine but isn’t the same thing at all.

What AI Changed – Spoiler: a Lot

The original post was written by one person producing written content: blog posts, occasional ebooks, some consulting. The ceiling on one-person output was whatever you could write and manage in a day. AI didn’t just change the tools — it changed the ceiling.

I’ve built eight apps in the App Store over the last few months, most of them with significant AI assistance. Not because I became a better programmer — I did in a way, but that’s not the point. I could build those apps because now I just describe precisely what I want and have “something” translate that into working code. The product loop that used to require a small team now runs in a laptop (sometimes even in in iPad). For a digital nomad in 2010, “one-person operation” meant writing and consulting. In 2026 it can mean software products, AI-assisted workflows, and small content operations that cover multiple formats simultaneously. The leverage available to a single person has expanded logarithmically, and most of it happened in the last one year.

Working Around Your Life — Within some Limits

The inversion held in principle and got more complex in practice, for two reasons I didn’t see coming.

The first: “your life” isn’t static. In 2010, my life was relatively lightweight — a bag, a running practice, a blog, a preference for interesting cities. In 2026, my life includes a one-and-a-half-year-old with strong opinions about everything and no interest in my schedule. Working around your life when your life includes a small child is a categorically different problem from the 2010 version. The flexibility is still there, and more necessary than ever — but what it’s protecting, and what it has to accommodate, looks completely different.

The second: after years of continuous movement, I’ve settled into splitting time between two fixed locations — one in Asia, one in Europe — rather than moving constantly. This wasn’t scaling down, although sometimes I fell that need, it was merely an update to what “working around your life” means when your life has accumulated enough that constant novelty is no longer what you’re optimizing for. My lifestyle matured and I matured with it. The mobility is still there when it’s needed; it’s just no longer the main point.

What the Primer Actually Missed

Predicting the future is optimistic by nature, and the 2010 post was no exception. It described the rewards without accounting for the costs that accumulate over years. The cost of being everywhere, lived long enough, is eventually being from nowhere in a way that requires active management. Roots have to be built, or accounted for, when they’re not given to you by circumstance. That’s doable — I’ve done it — but the primer didn’t mention it.

The other thing it couldn’t have predicted: the lifestyle became a product. There are now entire businesses built around selling the digital nomad dream — courses, visa services, curated communities, retreats, influencer accounts photographed in front of the right laptops in the right cafes. Some of it is genuinely useful. A lot of it is selling the 2010 version of the lifestyle, preserved in amber, to people who’d be better served by something more honest.

Sixteen Years After

The thing that still holds from the original post isn’t any specific workspace advice or tactical observation. It’s the underlying orientation: you are responsible for designing how your work fits into your life, and that design is worth doing deliberately. That was true in 2010 when almost nobody was doing it. It’s true now when millions of people are doing some version of it. The tools changed, the infrastructure changed, the cultural moment changed — but the fundamental choice, which is a choice about attention and sovereignty over your own time, remains the same.

The primer described the mechanics of a lifestyle. What it was really pointing at was something simpler: the decision to treat your work as something you arrange, rather than something that arranges you. That part aged very well.