I’ve been relatively stationary in Pittsburgh for the first half of 2023 but I’ve got a couple of trips coming up in the next few months. My first trip of the year starts in a week, and it’s a new one for me: a visit to a national park (Yosemite) followed by a cross-country Amtrak excursion back to Pittsburgh.

I’ve done long road trips in the past, but typically the destinations have been urban areas—places I thought I could count on getting easy access to things like power and Wi-Fi. I didn’t always plan ahead properly, and as a result I learned:

• Outlets can be a hot commodity when you’re working out of coffee shops or other public spaces
• Just because a place offers free Wi-Fi doesn’t mean it works
• Long-distance Amtrak routes don’t have Wi-Fi, and Greyhound Wi-Fi is spotty

These things are annoyances for typical travelers, but can be huge sources of stress for working writers who have clients waiting for responses and assignments that need to be completed by a deadline. Being prepared for potential snags can save you a lot of headaches and wasted time, letting you actually enjoy your travels and keep up with your work at the same time.

I’ve traveled a lot in the past, but mostly under the usual vacation format: taking time off work and dedicating all my time to exploring a new place. Early in my freelancing career I took a working road trip, a multi-stop ramble from Pittsburgh to LA and back in a mix of Greyhound busses and a friend’s converted van, and I quickly learned what lots of folks reading this probably already know: traveling is hard work. On that first trip I’d only had a part-time workload, with fewer clients and longer deadlines than I have currently, and it had still been tricky to squeeze it all in between getting from place to place—and actually enjoying myself once we got there. The trip was fun but exhausting, and I came back completely spent and with a pile of work to catch up on.

For my most recent attempt at a the much-touted digital nomad life, I decided to take a different approach: slow traveling. I booked my entire one-month stay in Mérida, Mexico, kept my full client load, and set out to test whether it was really possible to enjoy traveling while I worked, or if this was all just some big scheme orchestrated by travel agents and Instagram influencers.