10 Paths to…Traveling More Often

So, here’s a question: what’s holding you back?

From traveling more often. From changing careers. From writing that book, creating that art, recording that song you wrote. From doing whatever it is you’ve been longing to do.

The longer I travel, the longer I’m self-employed, the longer I live an unusual life, the more I wonder about this. About what it is that holds us back.

I think one of the answers is black and white, all-or-nothing thinking. 

When we think about digital nomads, for instance, we tend think in all-or-nothing terms. You either quit your job, get rid of everything you own, and travel the world. Or you stay in your 9 to 5, keep the house, and take two weeks of vacation every year.

But really that’s not how life works.

In between those two extremes are a thousand other options. I know a couple who retired early and now travel full-time…sort of. But they still keep a home base in a town they love near people they love and in between two- to six-month travel adventures, they return to that home to rest, connect, and plan their next adventures.

I know another couple who travel farther and faster than I do, but who still maintain a home in Utah, renting it out on Airbnb when they’re not in town. They’ve also got mini home bases in several places in the world and they return to those places every year to nurture community and stay connected to those they love.

Another friend of mine owns a business that she has to be there in person to run. But because traveling the world matters deeply to her, she chooses to work half-time (two weeks on, two weeks off) so that she has the time for extensive adventures.

That all-or-nothing mindset is one I fall into far too often. And it’s one I try to challenge myself on just as frequently.

And since it’s something I watch other people struggle with often too, I thought I’d start a new blog series to jolt us out of seeing the world as sets of just two options and start seeing the thousand pathways in between.

I’m calling it “10 Paths to” and today I’d like to try and offer 10 different paths to making more time in your life for travel. Not every path is an option for every person. Not every path will appeal to every person. Some of them take a lot of time and commitment before you get to the end reward. Others are quick. But the point at the end of the day is that most of us have more options than we think.

So, without further ado, 10 Paths to Traveling More Often:

1. Get a job that both requires and pays for travel.

Sales jobs. Translation. Diplomacy.

Pilots. Flight attendants. Travel Magazine Editors. Tour Guides. Bus Guides. Travel Agents. Archaeologists. Recruiters. Au Pairs. Business Consultants. Photographers. Cruise Line Workers. Event Planners. Diving Instructors.

There are about a hundred jobs that not only allow you to travel, but require it. If you feel a burning desire to see the world, maybe it’s time to find a job that sends you around it.

2. Get your ESL certificate.

There are English teaching jobs all over the world. Want to live in Asia for a year or two? How about spend a summer in France? Teaching English is one way to do that, often at no expense to yourself and with the opportunity to save a little along the way.

3. Go freelance.

While it certainly takes time to build up a freelance business, once you’re established, you have the power to set your own schedule, which can mean the freedom to travel more.

It took a few years to get here, but these days I try to take a month off every single year. The fact that I’m a full-time freelancer is a big part of what makes that possible.

4. Change your schedule.

Speaking of schedules, what if you could change yours? More and more people are asking employers for a four-day workweek (longer hours, less days), which means a constant supply of three-day weekends (and while a three-day weekend might not be enough to get you safariing in Africa, it’s most definitely enough for more nearby explorations). Others negotiate more vacation time (my second year in my agency job, I asked for senior-level vacation time instead of a raise–and got it).

5. Work part time.

Not every part-time job can support a person full-time. But some can. Especially if you’re in a highly skilled profession. So, here’s the question: could you cut your hours by 25% or even 50% and still support your lifestyle? (Or could you shift your lifestyle so that it’s easier to support?)

It’s taken years to get here, of course, but now I work less than 25 hours a week and always take a three-day weekend. And I know a few other people who do similar things. One friend—an orthodontist—chooses to work one week on, one week off. Another friend—a flight attendant—works the maximum allowed hours for a month or two or three in a row, then takes the maximum allowed time off before coming back into a long-hour work schedule.

6. Learn travel hacking.

Okay, so maybe it’s not your schedule standing in the way. Maybe it’s money. Which is where something like travel hacking can come in. A friend of mine has been taking flights for $11 a pop lately because she finally sat down and taught herself how to travel hack. Others claim they fly for free. Like anything else, travel hacking is a skill. And as a skill, it can be learned and used to your advantage.

7. Give yourself time between jobs.

Back when I was starting out in my career and I didn’t have as much flexibility (or the clout to ask for that flexibility), I had to get more creative. I only had two weeks off per year in my jobs, but when it was time to take a new job, I always gave myself buffer time in between.

What if, instead of going straight from Job A to Job B, you gave two weeks notice at Job A but told Job B you couldn’t start for four weeks? Now you’ve given yourself two extra weeks to travel.

8. Microadventure.

Travel is a priority for my orthodontist friend, so in addition to the couple international trips she takes each year (which she has started funding through travel hacking), she also makes time for adventures nearer to home. A night in a bivvy bag in the mountains, a hiking weekend at your nearest national or state park, an impromptu weekend with friends across the country because you just found a crazy low sale fare on Southwest…all of this travel can happen in between workweeks.

9. Become location independent.

When I first started my business, I worked all the time. It took a good four years or so to get to the point where I was senior enough, established enough, and connected enough to charge higher rates and work part time.

For some, it happens faster. For me, it was a journey.

But I wasn’t going to let hard work stop me from seeing the world.

Which is where full-time travel comes in.

Because I could do my work (copywriting, content strategy, web consulting) from my little ranch house in Denver, I realized I could also do that work from a guesthouse in Scotland or a balcony in the Swiss Alps. And even if I was working crazy hours, when I did have a few moments to myself, I was already in a cool new place to explore. Even if I only took one day off a week or only had an hour for lunch each day, there’s a lot of exploring that could be done in that time. And so even a crazy chaotic schedule was one I could squeeze travel adventures into.

10. Choose a job with more time off.

Working at a school often means long breaks in summer and winter and short (but still long enough to travel) breaks in the spring and fall. And don’t forget that it isn’t just teachers who work in schools. School librarians, counselors, management, etc. also benefit from school schedules.

Seasonal workers can also take long swaths of time off without fearing losing their jobs and highly skilled workers like nurses, dental hygienists, and therapists often have a range of options that include both high and low workloads.

Growing up, I remember being in awe of the woman who cleaned my teeth because every time I came in, she had some new international adventure to tell me about. She had worked out a schedule with her employer that gave her several weeks off several times a year and she took advantage of her flexibility to travel.

So, remember: the point isn’t that you should do all or any of these things. The point is that with almost every desire in life (to travel, to create art, to change careers, etc. etc.), there’s more than one set of options. It’s not just A vs. B. It’s a hundred mixed up paths in between.

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So, any other ideas? How else can people make more time for travel? Drop your thoughts in the comments.