7 successful freelancers, entrepreneurs, and employees share how they managed to travel the world without quitting their jobs

7 successful freelancers, entrepreneurs, and employees share how they managed to travel the world without quitting their jobs

woman travel passport suitcase

Charday Penn/Getty Images

Being a digital nomad isn't the only way to build travel into your life and career.

  • The idea of long-term travel is appealing to a lot of people. But how do you do it when you have a full-time job and bills to pay?
  • We're sharing the stories of professionals - from marketing consultants to tech employees to hairstylists - who've made travel fit into their lives and their careers.
  • Some of them became freelancers, some asked for transfers, and others took a sabbatical or leveraged their travel to advance their careers.
  • "You are in control of the life you want to live, and if travel is a priority for you, than plan ahead and take advantage of the opportunity to do so," said Myam Yusuf, a Seattle-based hairstylist at Antonio Salonwho builds sabbaticals into her schedule every January.
  • Click here for more BI Prime stories.

The idea of long-term travel is appealing to a lot of people. But if you didn't take a gap year or backpack around Southeast Asia after college graduation, it's easy to feel like you've missed the boat. Unless you work in a field that lends itself to the digital nomad life and want to live out of a suitcase for the rest of your life, you're stuck with two weeks of vacation a year until retirement. Right?

Not necessarily.


There are, in fact, plenty of options somewhere in between. I know firsthand from my own life; last year, I took a year-long career "pause" to travel. And to further illustrate, I'm sharing the stories of other professionals - from marketing consultants to tech employees to hairstylists - who've also made travel fit into their lives and their careers. Some work for themselves, some are freelancers, and some are full-time employees who've found creative ways to swing multi-month trips.

If they can do it, couldn't you? Here are a few ideas to ponder.

Shape Up Your Future 16th & 17th September 2021
  • 15+ Knowledge Sessions
  • 30+ Industry leaders
Watch Live
Meet Our Speakers
Nikhil Malhotra
Nikhil Malhotra
Dan Schawbel
Dan Schawbel
Ronnie Screwvala
Ronnie Screwvala
Dr. KV Subramanian
Dr. KV Subramanian
Benjamin Pring
Benjamin Pring
Sanjeev Bikhchandani
Sanjeev Bikhchandani

1. Ask for a transfer to another location

Ana Cristina had spent her career in San Francisco and New York but always dreamed of living abroad. So, in what she describes as a "now or never" moment, she started browsing her company's job board for international roles.


"I kept myself open to a broad range of jobs and locations," she explained, ultimately landing a new job with her employer, a major tech company, as an advertising video specialist in Dublin, Ireland.

Ana Cristina exploring Prague, Czech Republic

Ana Cristina

Ana Cristina exploring Prague, Czech Republic.

She's loved living in the European city, and the move has allowed her to travel much more than she was able to in the States. "Being part of a global company, I have the flexibility to work from remote offices and tag on a few extra days to explore," she said. In the past two years, she's been to 30 new countries and checked off bucket-list items like running the Berlin marathon.


Of course, living far from home hasn't come without tradeoffs. "I sacrificed a comfortable lifestyle and being near family and friends, and I took a considerable pay cut," she admitted. "But in return, I've met people from all over the world, learned the importance of independence, and consider myself so much more adaptable, curious, and open-minded."

If you're employed by a large, global corporation, chances are there are similar opportunities. Or, if you're not ready to completely uproot your life, look for shorter-term stints - like covering someone's parental leave or filling in during a busy time.

Nicholas Granzella skiing in Sun Valley, Idaho

Nicholas Granzella

Nicholas Granzella skiing in Sun Valley, Idaho.


When Nicholas Granzella, a Washington-based emergency medicine physician (and my brother), worked for a previous employer, he was able to arrange a one-month remote assignment in Sun Valley, Idaho to help out during ski season. "It was a win-win - it helped fill a needed role and it allowed me to explore (and ski in!) an amazing new destination," he shared. "It was a life-changing trip."

2. Take a sabbatical

Creative UX Writer Karina Portuondo also wanted to live abroad and had arranged an international transfer with her employer, a technology company. But a few months before she was set to leave, her team reorganized and asked her to stay in her role in San Francisco.

"By then, I had already had my heart set on a life change and I had given up my lease," she explained. So, she negotiated with her managers to let her take a three-month sabbatical instead.


Portuondo used the experience to explore Tanzania, Morocco, Spain, the Netherlands, Belgium, Italy, Luxembourg, Hungary, and the Czech Republic. The sabbatical was unpaid, but the break was worth it. "I did have to leave everything buttoned up before I left, with documented plans and contacts for all my projects," she said, but once she left she wasn't expected to check in with the office at all.

While the company doesn't typically offer these types of leaves, it does make exceptions in certain circumstances. Portuondo was glad she made the request and encouraged others to do the same, even if it's not common practice. "If I hadn't have asked, I wouldn't have gotten it," she said. "So my advice is to wait for when the timing seems right and put it out there."

Myam Yusuf in Nusa Penida, Indonesia

Myam Yusuf

Myam Yusuf in Nusa Penida, Indonesia.


Myam Yusuf, a Seattle-based hairstylist at Antonio Salon, builds sabbaticals into her schedule every January - she's traveled to Zanzibar, Tanzania, and Bali in the past three years. In an industry that's completely dependent upon client interaction, many people in her shoes feel like they can't break away, but she's been able to make it work by choosing a time of year that tends to be less busy, after the holiday rush.

"Now, my clients know to expect me to be gone around this time of year and can plan accordingly," she said. "I explain to my clients that I need to take some self-care time to rest and reboot so I can come back with a fresh set of eyes. This also gives them something to look forward to hearing about when I see them again in the new year."

Her boss has been supportive, too. "He is an advocate for taking time off to explore, so it's been easy as long as I gave enough notice," she shared.


3. Freelance to create your own flexible schedule

One of the most common ways to have a travel-friendly schedule is to take on freelance or consulting projects, where you have the flexibility to work wherever you'd like, instead of going to the same office every day.

Peter Brooks made this shift a few years ago, leaving his full-time role to found 28th & Foster, a growth marketing consulting firm for early-stage startups. He meets with his clients in person when he needs to, but otherwise has the freedom to do his job remotely. And he takes advantage of that as much as he can to jet to new destinations. "Normally, I am away from home at least a week every month, and sometimes longer," he shared.

Peter Brooks at a Buddhist temple in Cambodia

Peter Brooks

Peter Brooks at a Buddhist temple in Cambodia.


Lest you think that means he's relaxing on a beach somewhere, Brooks is quick to admit that he puts in about 60 hours each week. "I generally work 100% of the time while I am abroad, whether it's stopping in a client's local office or working remotely," he said. Overall, as long as he has his laptop and a stable internet connection, he's good to go, though he added that the time difference can be challenging.

"A lot of my clients are in California, New York, and Western Europe, so it can become difficult working and being available for their core business hours," he said.

Still, to him, it's worth it. "I love meeting new people, seeing new cultures, exploring new sites, and expanding," he said. "I have never gotten so much enjoyment for any other activity quite like traveling."


4. Use travel to advance your work

Alden Wicker, an NYC-based journalist, sustainable fashion expert, and founder of ethical fashion and travel website EcoCult.com, didn't just want to travel for the sake of travel - she wanted to deepen her understanding of her work by learning more about how clothing is made around the world.

So she spent a year abroad, visiting factories and workshops and writing about her experiences, which inform her career even now that she's back.

"I'm still working on stories based on my research. I now have contacts and friends all over the world, too, for future stories," she said. "I have a new perspective that incorporates my conversations with factory owners and managers, garment workers, artisans, entrepreneurs, and designers, almost all from the Global South."


When she set off on the trip, she wasn't sure if she'd return to New York, but she quickly realized that full-time nomading wasn't the path for her.

Alden Wicker and her husband in Jaipur, India

Alden Wicker

Alden Wicker and her husband in Jaipur, India.

"In a lot of ways, for me and my husband, this year of traveling was an experiment," she explained. "A lot of travel and digital nomad influencers talk a big game on social media about what you could accomplish if you just take the leap, but we learned what was possible and practical, and came back to New York with a renewed focus, having sliced away all the 'what ifs.'"


Sometimes, she added, "it's only when you go all in can you be satisfied that you tried it, and it didn't work, so you move on with excitement for the next chapter."

Her advice for those who plan to combine a job with travel: Pick a few destinations and stay a while. While she typically spent a week or two in each place, she recommended that "a month or more is probably better and less expensive. You can't really do deep work when you're moving between places."

5. Do a remote year - or quarter

On that note, if you want to take your job or freelance gig abroad, but aren't ready for all the ups and downs that travel can bring, programs like Remote Year and Hacker Paradise are designed to simplify things. The idea is that the company provides the itinerary (typically one city per month over the course of two to 12 months), and handles all the logistics, from booking flights and lodging to hosting coworking spaces and travel experiences.


For writer and editor Laura Brothers, this was the perfect option. "I wanted to get out of my comfort zone and do something totally different," she said. "But, I had never traveled long term before, and especially not while I was working, so having a company take care of the nitty-gritty details was great."

Laura Brothers working in Cape Town, South Africa

Laura Brothers

Laura Brothers working in Cape Town, South Africa.

She asked her company to work remotely while embarking upon a four-month program through Remote Year - and they agreed. She spent a month each in Croatia, Portugal, Spain, and South Africa, clocking a full-time schedule in each place.


"Everyone was very receptive and we worked out an arrangement where I would work US hours Tuesday through Thursday. I was available those days for meetings and client calls, and then Monday and Friday I was free to work the hours that suited me," she said.

She loved the experience so much that she continued traveling after the program ended (and switched to freelancing, so that she has a more flexible schedule). "I wasn't ready to stop (and I'm still not!) seeing new places and cultures and experiencing new things," she said.

Of course, not all of these options will work for everyone. But I hope the takeaway is this: There are options. And if traveling is important to you, it's worth getting a little creative to see how you can fit it into your life. As Myam Yusuf put it, "You are in control of the life you want to live, and if travel is a priority for you, than plan ahead and take advantage of the opportunity to do so."