Ah yes, preach! I have been on the road for 4+ years and it’s been wonderful (personally and professionally) but challenging.

There’s a constant tension between misconceptions and reality:

• I’m on vacation (nope, rarely — other than major holidays, I think I’ve only taken a total of 10 days off in 4 years)
• I’m supported by a fairy godmother (no, I am earning income to support myself — although I obviously am privileged in many ways)
• Everything is so easy! (my lifestyle and freelancing career both require work, time, and effort)

Even with everything in the media about remote work and freelancing, it can still feel like an uphill battle to have to constantly explain how I work and that my priorities and deadlines are as real as anyone else’s.

My family and close friends are starting to finally understand (and maybe respect) the realities of my lifestyle — that I am not always (or ever) on vacation, that I do actually work, but also that my priority is NOT to work 30+ billable hours a week.

My goal is to have a productive professional career and make a reasonable income, but I also need time to enjoy this special lifestyle of traveling full-time & see the places I’m in.

In my non-work time, I am usually very active in exploring a city, learning about culture and history. Although I sometimes choose places that have a more relaxing vibe, I want to optimize this lifestyle opportunity to really learn about the world firsthand. So I pick different destinations and spend my time “off” in a different way than the standard, relaxing vacation.

There’s also the complexity of juggling freelance clients – in a standard job, there is a manager that identifies priorities and assign projects to team members to balance everyone’s bandwidth.

But as a freelancer, when 3 different clients suddenly have demanding needs at the same time, none of them care about the other & all (understandably) want our time focused on their project. And it’s hard to say no to clients when you’re slammed — it’s important to keep them happy and returning, or you won’t have a business and income.

Plus! the planning of travel. Most people plan for a vacation once in a while (or a business trip with clear parameters), and they spend their downtime at work and home excitedly planning their special trip. But in a lifestyle of traveling full-time, figuring out where you will live next is a necessity that requires time – and competes with client work & enjoying the current location.

Depending on how quickly I am moving around (daily, weekly, monthly), the planning time required varies, but it can easily be 3–10 hours each week. So it’s a non-billable, non-client task that ultimately as important as work to me because if it doesn’t happen, then I’m likely to have visa, housing, or transport problems (which would be very costly financially or legally).

So… phew. Yes, I feel you :)