Since Joe and I started traveling full-time while working remotely, we’ve gotten the same question again and again: How do you pick where to go?
I wish the answer was as simple as “Wherever we want!” How much fun would it be to close your eyes, point to a map, and head to that destination for a month?
Actually… probably not that fun. At least for us. We need to feel grounded as we travel to a new ‘home’ each month. Otherwise, this life wouldn’t feel sustainable in the longer-term. Knowing where we expect to live is part of feeling grounded.
Plus, deciding on each destination involves a ton of moving parts — many more than I’d expected. Find the right neighborhood. Book trains or flights. Lock in our Airbnb, adjust our closet, lock in dates… We need time to get everything in order.
In the course of our first year traveling, Joe and I have figured out how we plan out our next destinations.
We split up our sessions.
Before leaving Brooklyn, Joe and I dedicated two full weekends to brainstorming, deciding, and booking our first six months on the road. When planning for Europe, we spent an hour here, an hour there over six months. To plan the second half of 2018 — a month in Brooklyn, the rest of the year in Montreal! — we broke it up into three chunks:
- Brainstorming (the fun one)
- Deciding (the fun, difficult one)
- Booking travel and apartments (the tedious one)
This has worked the best for us by far.
We get out of the house.
Deciding where to travel next should be exciting! All too often, it can feel stressful — especially when we’re into the nitty gritty of the neighborhoods to live in, the AirBNB to choose, the exact dates we’ll travel there…
So we make most planning sessions an outing. We’ve decided the next steps of our lives at Dizzy’s in Brooklyn, Bud Rips in NOLA, the Pancake Pantry in Nashville, KHP Coffee House in London. Doing so reduces stress and keeps us excited for our next adventure.
We tackle six-month stretches.
Joe and I planned our six months in Europe in rolling two-month increments. We slowly nailed down the details: Split, Croatia and Bologna, Italy. Then, Berlin, Germany and some time in France. Finally, London and Edinburgh in the UK.
We began talking about Europe in early October over pancakes in Nashville. We booked our Edinburgh apartment (where I’m writing from now!) in late March. The planning was hung over our heads the entire time.
We’ve since settled on tackling bigger stretches of time in one go.
We take turns deciding.
Because deciding is the best part! I chose Montreal, Split, and Edinburgh. Joe chose Portland, Maine; Bologna; and London.
We set criteria.
Having the world to choose from is overwhelming. Brainstorming with some parameters in place helps us focus. Otherwise, how could we ever pick?
To narrow our options, we focus on areas that are compatible enough with Eastern Standard Time and will have excellent WiFi. Joe’s company BeerMenus is located on the East Coast (although they’re a remote company). I work primarily with clients based in New York City. We wanted at least some of our day to overlap with the people we work with. This eliminates Asia and Australia. for now We’ll get there someday.
We also prefer medium to large cities that are either walkable or have great public transportation — or both!
We’re both planners. Traveling this year has been a lesson in letting go of the details a bit. Ironically, these parameters have lightened the load of planning each destination. So we can spend more time exploring our new homes, and less time picking our next ones.
PS — I’d love your help! I’m always thinking on the stories and learnings that will be most fun to write, and most interesting to you. Did you like this post? What other parts of this full-time traveling process are you most interested about?