Basics:
- Have a job that supports it. Do not try to figure out your income stream once you’re already on the road. Even better: travel with a friend or partner who also has an income stream, so if one of you struggles you’re not totally SOL.
- Move slowly, especially at first. This is not vacation, even if it is travel. We spend 4-6 weeks in each place, which honestly feels rushed sometimes. You’ll really have your weekends on “vacation” and some evenings, but you need to make sure you’re not so overcome with FOMO that work becomes too stressful.
- Figure out your connectivity in advance, and have backup plans: research cellphone coverage and internet in the places you’ll go. Have backup plans, like cellular-network-based hotspots for mobile internet or two different cellphone providers if traveling with a partner or friend.
- Don’t overpack. It can be tempting to prepare for literally every situation when you’re traveling for months, but you will hate yourself if you’re lugging tons of bags around. Of course, we like climbing everywhere we go, so we have an extra bag that’s just ropes and quickdraws, but that just means we have to be even more careful with our other packing.
- Don’t underpack. There’s nothing worse than feeling sick and having no meds, showing up in a beautiful place and not having a raincoat when it pours, or sweating like crazy because you only brought one pair of shorts. Sometimes, it really pays to be prepared.
- Think about insurance. Check whether your medical insurance covers you where you’re going. Consider global rescue/evacuation plans. Look at what kinds of protection your credit cards provide for your flights and rental cars. Make sure you understand exactly what is covered and what isn’t.
More advanced:
- Bring a few comforts of home. Maybe this means a candle you love or your favorite tea — something small that makes a new place feel familiar.
- Prioritize rest. I developed a little “sleep kit” for myself with good earplugs, an eye mask, and moisturizer, and it helps immensely. You never know how loud or bright a new room might be until you get there, no matter how much research you do.
- Plan your weekends, but be flexible. I try to show up to a new place with half the weekends planned and a few potential evening activities. This way we’re not wasting our first few days blindly looking for something to do and can get oriented quickly, but we are also able to respond to the weather or cool suggestions that come up.
- Integrate your life. I don’t try for work-life balance, I just make sure I get my work done. This might mean tons of hours one week and a light week the next, or working from the ferry and passenger seat of the car on a travel day. It might mean working through a week of rainstorms so when it’s sunny I can take a Wednesday off to hike. Be reactive.
- Scratch that social itch. It’s hard to not be able to make longterm friends, so assume you’ll be coming back. Seek out other frequent travelers. Visit existing friends and acquaintances. Find a social hobby (for us this is climbing) and meet people. Invite friends along on your travels.
- Recharge sometimes. We periodically stop over at my parents’ house or my partners’ parents’ house for a week or two. This is crucial for going to the dentist, but also for taking a breather and resetting.
- Keep yourself safe. This is true no matter where you live, of course, but travel is riskier because you’re often far from a support network and in unfamiliar places. We also do a lot of hiking and climbing, which are inherently risky activities. Always pay attention to weather forecasts, local news, and the vibes you get about an area. Have printed versions of your flight information as well as digital. Carry money in several places and have multiple credit/debit cards. Basically, do anything that you might do in a normal travel situation, but be extra careful about it — if your phone gets stolen and you’re not just going back to a city with an Apple Store next week, it becomes much harder to replace it.
Niche:
- Bring your favorite foods. I cannot live without peanut butter (I’ve tried). I make sure I always have some with me when I travel so if we can’t make it to a grocery store, I’m okay.
- Keep your routine going. We obviously adjust to the time zone we’re in, but we try to sleep from 11pm-8am or so everywhere we go, and spend an hour before bed hanging out in the hotel/Airbnb/cabin/whatever. At times this isn’t possible, but having this plan makes life feel more stable. We also cook most of our own meals rather than eating out, which also helps regular days feel like regular days.
- Always have something to look forward to. Counterintuitively, constantly going to amazing places can be kind of dispiriting, because you’re so busy and also so far from people you love but madly trying to cram as much exciting stuff into every day that you feel guilty if you’re not having an amazing time. It helps me a lot to get hyped about the next place we’ll go (or my next visit to see my parents) while I’m still immersed in the previous place.
- Plan an actual vacation. It can feel weird to take a vacation when you’re constantly traveling, but vacations aren’t just about travel; they’re also about decompressing. It’s still important to take breaks. Maybe this means taking a few extra days off somewhere you really love, going somewhere totally different for a week in between digital nomad spots, or lounging on your parents’ couch for a week doing absolutely nothing, make sure you find time for it.
- Have other goals. You’d think work and travel would be enough for me to be satisfied, and it almost is. But it’s super important psychologically to be making progress toward something, which is the role hobbies play in many people’s lives. And if you’re just working and then experiencing cool places, you’re not necessarily actually progressing. I find having a hobby that I can work on and improve upon overtime, even while traveling, super important to my well-being.
- Call home. When traveling, you’ll realize who your real friends are. Who do you actually miss when you don’t run into them? Whose conversations can you pick right back up again after not seeing them for months? Call these people. Make sure they know you love them.