Some nomads want to travel and move around as much as possible, others want to find a place and settle in for a few months or longer (summers in the north, winters in the south), and still others will use their digital nomad base to give them the freedom to live permanently in a location of their choice (at the beach, in the mountains, in a small town with a cheap cost of living or in a major city).
First, you will want to determine what your ideal location is (don't worry, you can always change this later if your ideal location doesn't turn out to be so ideal). Then you will need to look at issues such as lodging (hotels would obviously be on the high range of the scale, house sitting on the low range, short-term rentals would be somewhere in between), internet access (a major issue if you work online), cost of living (for food, utilities, services, etc), and the general surroundings (some people like daily access to the beach, others like a lot of museums and cultural opportunities).
Next, and this is the hard part, you will need to go. Here are a bunch of tips from when we were nomading about for a couple of years:
- Our first stop was at a friend's house for a month. It was a slow entry into being a nomad (read homeless) and in a different part of the country (during which we decided that the southeast in spring with tornado warnings every day was not the spot for us). Note that we did a lot of fix it work around their house, made dinner every night, and generally made ourselves useful guests so we wouldn't wear out our welcome.
- No matter where you are it pays to have some sort of schedule. If you act like you are on vacation every day you will not be successful in your work because you will be too busy having fun. My schedule was to exercise every morning, work for four or five hours straight, then spend the rest of the day doing whatever (being a tourist, hanging out with friends, etc).
- Internet is pretty easy to find in most places. Even the smallest of third world country villages usually has some sort of internet service. Note that when you do use public internet and not the internet at a friend or family member's house, you will want to use a VPN service for privacy and security.
- Depending on how long we would be at one location we would determine if we needed a local SIM and calling/data plan for our cell phones. If you will only be in a country for a few days you can probably go without a phone (or use international roaming if it is free from your US provider), if you will be in one location for a while, a local SIM and plan is a good idea. Skype is a very good option for hours' long client meetings.
- When we got to a new city/country we would usually stay in a hotel for the first few days until we could check out the area, determine the neighborhood we wanted to stay in, then chatted up some locals who usually had better ideas about what properties were for let than standard places where these were advertised.
- For a "vacation" from our vacation or when internet access wasn't crucial, re-positioning cruises were both inexpensive and enjoyable.
- Cheap lodgings can be found: house sitting, with friends, with relatives, via Couchsurfing, via WWOOF, via AirBnB (sometimes), via Servas, camping or backpacking, as a camp host in national and state parks, in your van (van dwelling), renting a room from a local, in a hostel or pensione, etc.
- Local transportation is generally easy. The poorer the country, the more public transportation options there are. Also, most developed countries (ie: Europe and Japan) have exceptional public transit option.
- You should keep your car insurance in place is you plan on driving other people's cars (this covers you in the event of a wreck).
- When we hit the road we had very few bills--a storage unit, car insurance, health insurance, cell phone bill, and some web hosting services. All of these were either paid annually (insurance) or on auto-pay through a credit card (everything else). Most everything else was paid in cash (groceries, rent, etc).
- Major transportation (ie: traveling around the US or overseas) was a mix of just about everything from Greyhound (not recommended) to Megabus (highly recommended), to trains (Amtrak was meh, Japanese trains were amazing), to local Southeast Asian Airlines that no one has every heard of (cheap but scary) to military SpaceA flights (meh sometimes the wait times were way too long, like weeks, but you can't beat the price), to churning (using credit cards to receives tons of air miles which were used for free flights). The only thing we didn't try was hitch hiking or Craigslisting free rides.
- The stuff you need to bring with you really isn't that much. One medium-sized backpack carried literally everything I needed. Food and toiletries were always bought local. One laptop died so we had to stay in one place a few extra days waiting for a delivery from on online store.
- Laundry was simple. For a couple of bucks you can have a couple loads washed, dried, ironed and folded in Southeast Asia. Laundromats were plentiful in pretty much every city or town we visited. And hand washing really isn't that hard.
- Food ranged all over the board. We preferred to cook whenever possible, got thoroughly tired of eating out when there were no cooking facilities, and generally haunted street food stalls and hole-in-the-wall restaurants.
- Work was...interesting. There could be long stretches of time to really dive into a project. Fast, non-glitchy internet was a joyous experience. Getting up for noon meetings in the states when it was 2am where we were at was a pain. Signing off from a meeting because a tornado was on the way drew some amazement from the other meeting attendees. Brown outs were a thing in some places (thank goodness for battery back-up).
- Traveling with the seasons is always a good idea. It's always summer somewhere and waking up to sunshine every day sure beats being stuck in a snowstorm or lugging boots and heavy coats everywhere we went.
- Major shopping is much cheaper in the states (duty, tax, import fees, and shipping is quite expensive if you are buying something expensive in the states and having it shipped overseas).
- The currency exchange rate may also make a difference in your travels. Obviously you want to be paid in US dollars or Euros and hopefully stay in a place with a favorable exchange rate.
- Always make sure your (document) ducks are in a row. Make sure your passport won't expire anytime soon. If the country you are in requires a visa, know the process to get one and don't let it expire while you are still in-country (visa runs are a thing). Keep extra passport pictures with you as you will never know when you will need one. Be aware of credit card, driver's license, and other important document expiration dates.
- Finally, remember that you can always change things up. Some people get tired of traveling (we did) then find a new place to setting down/buy a house/etc. Some people get tired of the self employed grind and go back to the employee grind. Do what works for you.