A guide to working remotely

I spent 12 months as a Program and Community Leader for Remote Year, leading a group of digital nomads across a full year of destinations, on top of my own 8+ years of working remotely. Here’s what I actually tell people who ask how to make this work.

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1. Why do I actually want to work remotely?

Working remotely from abroad isn’t a permanent vacation, it’s a regular job with better scenery and worse wifi some days. The real first step is deciding whether you want constant movement, a few home bases, or one slow-travel location, since building a plan around the wrong version of this life is the most common early mistake people make.

  • Working remotely from abroad is your regular job, just with better scenery (and worse wifi some days).
  • Decide upfront whether you want constant movement, a few home bases, or one slow-travel location.
  • Build your plan around the right version of this life, not a generic one.

2. How do I choose where to go as a remote worker?

Wifi reliability, time zone overlap with your team, cost of living relative to your income, and how long you’re allowed to stay on a tourist visa matter more than how photogenic a destination looks. Time zone overlap especially trips up people whose jobs require live collaboration. Visa length is the detail most people research last, even though it causes the most last-minute problems.

  • Wifi reliability, which you can check through nomad community reports or by asking in local Facebook groups before committing.
  • Time zone overlap, since a destination 12 hours off from your team is a real problem if your job needs live overlap.
  • Cost of living relative to your income, because a place can be beautiful and still quietly wreck your budget.
  • How long you’re actually allowed to stay on a tourist visa, which trips people up more than any of the above.

3. How do I set up a workspace while traveling?

A repeatable setup matters more than a permanent desk: a coworking space, a hotel with a real desk, or a café you trust for a full day all work, as long as you use the same type of setup consistently. Consistency in routine matters more than the specific location you choose to work from each day.

  • You don’t need a permanent desk, but you do need a repeatable setup.
  • A coworking space, a hotel with a real desk, or a café you trust for a full day (not just a coffee run) all work.
  • Consistency matters more than the specific location.

4. How do I stay connected while working remotely?

An eSIM used as backup to whatever wifi you’re relying on solves most connectivity failures before they become a missed meeting. Always having a plan B for connectivity on anything time-sensitive is the single habit that prevents the most stressful moments of remote work travel.

  • An eSIM as backup to whatever wifi you’re relying on has saved more of my work calls than I can count.
  • Always have a plan B for connectivity on anything time-sensitive.

5. What insurance and safety steps do remote workers need?

Real travel medical insurance built for long-term nomads, not a one-off trip policy, plus registration with your embassy’s travel program for longer stays, cover the two essential safety steps for remote workers abroad. A subscription-based nomad insurance like SafetyWing renews automatically as you keep moving between countries.

  • Get real travel medical insurance built for long-term nomads, not a one-off trip policy.
  • I use SafetyWing (details on the Helpful Websites page).
  • Register with your embassy’s travel program for longer stays.

6. How do I avoid loneliness as a remote worker?

Structured programs like WiFi Tribe and Noma Collective solve loneliness by design, since working remotely alone city after city gets isolating fast. Solo travelers can get the same benefit by seeking out local nomad meetups, coworking spaces, or booking a short structured trip specifically for the built-in community it provides.

  • Structured programs like WiFi Tribe and Noma Collective.
  • If you’re going solo, seek out local nomad meetups or coworking spaces.
  • Or book a short structured trip just for the built-in community.

7. How do I manage money while moving constantly?

One main bank account, a multi-currency tool like Wise for conversions, and a backup card stored separately from your primary one form a simple money system that survives constant movement. Simplicity matters more than sophistication here, since a complicated system is the first thing to break down while jet-lagged.

  • One main account.
  • A multi-currency tool like Wise for conversions.
  • A backup card stored separately from your primary one.
  • Simplicity beats a complicated system you won’t maintain while jet-lagged.

8. What mistakes do remote workers commonly make?

Over-scheduling sightseeing on top of a full work week, skipping real insurance to save money, choosing destinations based on photos instead of wifi and time zone reality, and skipping routine entirely are the most common mistakes remote workers make. Each one looks harmless early on but compounds into burnout or a real problem within a few months.

  • Over-scheduling sightseeing on top of a full work week and burning out by month two.
  • Skipping real insurance to save a small amount of money.
  • Picking a destination based on photos instead of wifi and time zone reality.
  • Not building in any routine at all, which sounds freeing and becomes exhausting fast.

Remote work travel is one of the best ways I’ve found to see the world. It’s also, some days, just a job with a slightly better view than an office park.