Extremely concise guide where I say some opinions that I wish I knew when I started life as a digital nomad a year ago.

Should you do it?

Most guides would give you a bunch of questions to ask yourself and then tell you to think about it. I’ll skip that step and say that you should. If it’s logistically possible (e.g. no dog, wife, etc.) and it even slightly appeals to you (appeals enough that you’re reading this) then go. It’s easy to stop once you’ve started but it’s impossible to do it without starting.

Where to go?

There are some things I worried about when I was picking where to go, that you shouldn’t worry about. Safety, whether or not people speak English, and how easy it is to get a Visa are all really unimportant. Instead, worry about how you’re going to meet people. Here are the three best ways to meet people, and you should pick the majority of your locations based on your ability to execute one of these three strategies (fine to sometimes go to a cool place where you won’t be able to meet people).

Knowing Locals

This is the best way to meet people because they can also show you their town and they know a bunch of tricks.

Go With a Travel Group

I like Hacker Paradise for this, although Remote Year also exists. This is the best way to meet people but it’s expensive and not flexible. I recommend doing it on and off, though. I met a bunch of friends through HP who I now travel with all the time.

Go To A Hub

Chiang Mai, Bali, Da Nang, Playa Del Carmen, Bansko, Lisbon, Medellin, Florianopolis… These cities are known among Digital Nomads (and expats) and it’s very easy to meet fellow travelers. There are other cities that work the same way, research it on nomadlist or elsewhere.

How to Plan

To start, I recommend picking a region and booking at most 2 months of accomodation (one month per location). Then you can go to the first location and feel out the lifestyle, only booking your third month when you’re done with the first. Keeping a short time horizon like that, where you only book a few weeks out, is optimal. That’s because you’re going to learn an immense amount in that first month about what you like and don’t like (also in the 2nd-3rd months). You don’t want to get tied down, but you also want to have enough certainty in your future that you can be productive during the day.

How to Pack

The classic advice is to pack less than you think you need. If you won’t certainly need it during your first week of travel, and you can buy it at many stores, then don’t pack it. Also, if it’s something you don’t need that often (e.g. formal clothes, hiking boots) then don’t pack it. I fit everything I own into a 40 liter backpack, which is small enough that I can carry it onto airplanes and it weighs 10 Kg (25 lbs). In there I have a 5lb computer and 17 pairs of underwear and 17 t-shirts. I like to splurge on bringing a ton of clothes because it means I have to do laundry less, and I fucking hate doing laundry. I used to dedicate more space to productivity stuff, but I found that a keyboard, laptop stand, and external monitor aren’t requirements for me and they take up more space than I’d like. I use packing cubes to “organize” my clothes, and I recommend them. I also recommend buying a lot of 1 gallon ziploc bags to have around (and other sizes). That way if you suddenly acquire a deoderant or soap or something that you didn’t have before, you’ll have a place to put it. I keep all my toiletries in 1 gallon ziploc’s because I find the toiletry cases sold in stores are far too bulky.