My Top 5 Worries as a Digital Nomad (And What I Actually Do About Them)
People see the photos. Laptop, coffee, some view that makes your cousin back home jealous. What they don't see is the running list of worries that never really shuts off.
I'm a freelancer, who's had stints of slow madding and those where the travel is fast a furious (with limits, I prefer to make somewhere a home base for at least a few months). that said, these are a few things that hold space in my head constantly. I wonder how many other nomads consider these things all of the time too.
1. Continuing to Make Money While Traveling
I'm a freelancer, and that can sometimes lead to boom and bust cycles with clients. One month you're turning work down, the next you're refreshing your inbox wondering if anyone still knows you exist.
So my main worry is keeping a healthy client list: keeping current clients happy, having regular clients, and never getting complacent after completing a big project. That last one is the trap. The invoice clears, you coast a few weeks, then you look up and nothing's lined up.
What I do: I keep prospecting even when I'm busy, because that's when you pitch best. I chase retainers over one-offs, and I try not to let any single client become most of my income. And I over-communicate. Clients don't care that you're in Japan. They care that the work shows up.
Just watch the burnout. In a 2023 survey of about 950 U.S. nomads, 77% said they'd burned out at least once.
2. Maintaining Visas
Whether I'm living in Thailand and reporting every 90 days, figuring out which visa I'll do next, or in Japan figuring out how much time the visa allows, there's always a calendar in my mind.
And the rules move. Thailand's 60-day visa exemption ended September 15, 2026. Now nationals of 60 countries, including the U.S., UK, Canada and Australia, get 30 days visa-free, and it's tourism only. If you were living on border runs, that math just got a lot worse.
For anyone who wants to stay longer than a few months at a time, I'd recommend a proper (emphasis on PROPER) education visa or the DTV, but remember, you'll have to go back home to apply for it now.
Japan is getting pricier to leave too. The departure tax tripled to ¥3,000, and JESTA, an ESTA-style pre-travel authorization, is due in fiscal 2028. But, honestly, the Yen is at such a favorable rate, that it kinda makes it worth it.
What I do: track every entry date, screenshot every stamp, and set reminders way early (working on an app for this!). Honestly, this headache is a big part of why I started building Stamped Nomad.
3. Workspaces
This may not be a huge worry for people who like working at their place. But I'm a vampire. I need places open at weird times, with outlets and big tables.
One hack I've found works in like 75% of places: 24/7 McDonald's. Many have the absolute best workspaces around. AC, cheap coffee, usually wifi, big tables, and nobody hassles you at 3am. Outlets are hit or miss, and buy something every couple hours so you're not that guy.
Other options:
Local coffee chains. Often cheaper, sometimes with better hours.
International chains (i.e. Starbucks). Predictable anywhere, which counts when you just landed.
Hotel lobbies. Underrated. Buy a drink, get comfy seats and solid wifi.
Co-working spaces. Great setup, though I'm not really a fan of going to the same office every day. Day passes are the move.
Always carry a power bank, a small multi-plug, and hotspot data for when the wifi dies mid-deadline.
4. Comfortability
I'm a traveler, and part of that is getting used to being uncomfortable. However, at this age, I greatly prefer a comfortable Airbnb (including a comfy bed), easy-ish transportation, good food, and fast internet. If I'm traveling and not working, I can stand a bit less comfort. But after a long day of work, I'm not trying to deal with more pain than we've already signed up for.
What I do: search Airbnb reviews for "bed" and "wifi," ask hosts about internet speeds (if the experience is different, it'll make it easier to cancel and get a refund), and stay longer. Also, I ONLY book with Super Hosts. I used to be an AirBnB host in LA, and I know what it takes to maintain that status. Thus, trust me... Stick with the Super Hosts. They have a lot to lose if you leave a bad review. Slow travel is cheaper and less exhausting, and many nomads now average 5.7 weeks per location.
5. Staying in Contact with Family and Friends
This includes family and friends back home, plus the ones I've met on the road. Time is a super limited resource. But if you don't invest time into the people you find important, that relationship will eventually deteriorate to a point of no return.
As a traveler, nomad, expat, whatever you want to call it, I've slowly learned that much of the reaching out is on us. You're the one who left. You're the one who has to call. Research on nomad loneliness points the same way: a lot of it comes down to social support and staying somewhere long enough to build a network.
So I'm very intentional about connecting. I'm also very intentional about cutting loose those I honestly don't have the time or desire to connect with. A few good friends will always beat a gaggle of half-wayers.
Honorable Mentions
Taxes. Americans can exclude up to $132,900 of foreign earned income in 2026, but it doesn't cover self-employment tax.
Schengen tracking. The EES has logged your 90/180 days digitally since April 10, 2026. ETIAS still has no official date.
Health insurance. Food poisoning, alone, on deadline. Have coverage that works where you are.
Frozen cards. Carry two cards from different banks, stored separately.
Passport validity. Many countries, Thailand included, want six months left and a blank page.
Never switching off. 83% of nomads feel guilty disconnecting from work. Guilty as charged.
Air quality. Chiang Mai's burning season, usually late winter into spring, is worth dodging.
The Bottom Line
None of these worries go away. You just get better at managing them. Keep the pipeline full, keep the calendar in your head, find your 24/7 McDonald's, and do the reaching out. It's on us.
Got a worry I missed? Hit reply. I'm probably awake.
