I often get questions from young readers who are still trying to decide what they want to do for their career, and they’ll often ask if I have any tips in terms of what lines of work they could pursue that involve a lot of travel.
It’s a fair question, and understandably, travel is a passion for many people. So the idea of getting paid to travel sounds awesome. However, I think there’s a more fundamental consideration.
Before I share my take, let me acknowledge that I’m perhaps the wrong person to be giving any sort of career advice, as I’ve taken an unconventional path (I’ve been a full time blogger for over 17 years), and I’m lucky everything worked out the way it did. However, as a kid, I certainly also asked myself the question of what job is best for travel (which I guess I sort of ended up getting… inadvertently?).
There are lots of careers that involve frequent travel
If you’re starting your career and one of the main goals is to travel a lot, obviously there are some jobs that immediately come to mind. Management consulting, international sales, IT, etc., can all involve a lot of travel. Heck, being a flight attendant or pilot also involves a lot of travel.
I think perhaps the bigger question is what aspect of travel you find most appealing:
- Is the goal to just be on the road for as many days per year as possible?
- Is the goal to see as many places as you can, and actually have free time on the ground?
- Is the goal to get another party to simply fund your travel, and your pursuit of miles & points or elite status?
One other thing worth acknowledging for those pursuing careers that involve a lot of travel is that over the years, preferences change. If you’re young, maybe the thought of traveling sounds fun, and you think you’d never bore of that.
But being on the road can get exhausting. Life circumstances change. You might get married, might have kids, might have family members you want to care for, etc. What once seemed like a dream can very quickly become a challenge.

Business travel isn’t all it’s cracked up to be
I have a good friend who has the best travel policy imaginable, and is always allowed to fly in the top cabin (including first class) and stay at very nice hotels. In theory that sounds pretty amazing, right? Well, what’s his travel actually like?
During a recent month, he took three business trips — two were day trips to Kansas City on a regional jet. One was an international trip in first class, where he was gone from home for 24 hours — he flew from New York to Frankfurt, had a meeting, flew from Frankfurt to London, had a meeting, and flew from London back to New York on the evening flight. While someone else paid for his $12,000 ticket, that’s not a trip I’m jealous of!

I think this really gets at the gist of the reality of business travel. If you’re really into travel, it sounds amazing to travel on someone else’s dime, but you’re not going to be spending endless hours strolling around Paris or Tokyo.
Instead, you may end up in a situation where you’re primarily flying economy domestically, staying in hotels in business parks off interstates, and spending all day in conference rooms. Or the “glamorous” travel people think of (international first and business class to fun destinations) typically involves getting in and out as quickly as possible.
When it comes to summing up the reality of business travel, I think nothing does that better than the 2009 movie “Up in the Air.” It perfectly captures the (theoretical) allure, plus the reality of what this kind of travel is like.
Focus on jobs that give you flexibility and choice
As much as it’s easy to romanticize business travel (I did for years — after all, who doesn’t like someone else paying for their travel?), I think it’s much more fun to pursue leisure travel on your own terms, and to focus on finding a job that you find fulfilling, and that gives you time and flexibility (at least in the long run).
When I was much younger, I thought I should become a consultant, because it would allow me to travel the most. And then I realized what drew me to that wasn’t a passion for what I’d actually be spending 50+ hours per week doing, but rather the corporate hotels in small towns that I’d likely end up in, along with the possible weekly domestic flights.
So if my life hadn’t worked out the way it did, I don’t think I could have followed through on that. I think I would have done something completely different, even if it involved no travel. And then I would have dedicated my resources (time and finances) toward traveling in a way that I enjoyed.
I do believe that if you’re passionate about something and can add value, that’s where you’ll find the best setup in the long run. And honestly, as the years go by, we see fewer and fewer people with typical desk jobs. It’s no longer considered completely crazy to take an unconventional path.
For example, rather than picking a job simply because it requires a lot of travel, I’d much rather get a remote job where I can work from anywhere, and have the ability to travel the way I want to. Even if you go a more traditional path, there’s something to be said for jobs where you can “bank” vacation time, either by working longer shifts, working on individual projects that you can take breaks between, etc.

Bottom line
I’m by no means a career counsellor, so by all means take my advice with a grain of salt. However, I tend to think that pursuing a career simply because it requires a lot of travel is a bad idea.
I think a much better strategy is to try to find a job that involves something you’re passionate about (regardless of the travel implications), so that you can actually spend your days doing something you enjoy. On top of that, find a job that gives you flexibility and/or lets you work remotely, because odds are that this will let you do a lot more travel on your own terms.
What’s your take on the concept of seeking out a job that requires lots of travel?













