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Someday. That’s a dangerous word. It’s really just a code for ‘never’,” said Tom Cruise’s character, Roy Miller, in the action movie, “Knight and Day.”
We’ve all dreamed of making a big life change — someday. Perhaps you’ve always wanted to quit your corporate job to spend more time in nature, or you want a career that will help you keep your elite status. Maybe you just can’t stand sitting behind a desk for one more minute, and you want summer Fridays to be, well, every day.
For those of you who study job listings with the same desperate eagerness generally reserved for late-night restaurant menus, we spoke to road warriors from 11 different industries to shed light on how they landed their dream job.
While this list is by no means comprehensive, we hope it inspires you to stop saying “someday” and find a dream job that helps you travel the world while doing work you love.
1. Virtual Teacher
Time on the Road: Varies
Teaching English as a Second Language (TESL) may conjure memories of that post-college gap year you took ages ago, when you traveled to a remote village in South Korea or Japan and taught middle schoolers English for 25 hours a week. But these days, teaching doesn’t necessarily require you to physically be in the same location as your students.
Former Montessori teacher Melissa W. began working for VIPKid, a virtual language-education company, soon after her second child was born. The company’s online scheduling platform allows Melissa, a mother of two young boys, to set up secure one-on-one English language video lessons with children in China, whose parents book tutoring sessions directly through the VIPKid scheduling platform. In turn, Melissa is able to make her own hours and maintain complete control of her income while staying home full-time with her kids. Teachers are paid out monthly via direct deposit, based on the number of classes they taught.
“Making the transition to one-on-one teaching online took a little time, but it wasn’t too bad,” Melissa said. As a result of her career flexibility, Melissa has even been able to bring her toddlers to Taiwan, California, Portland and even Walt Disney World without taking time off.
TPG Tip:If you’re curious about pursuing something similar, sites like My VIPKid Journey offer in-depth information, guidance and even personal coaching for interested candidates.
Time on the Road: Varies
Serial entrepreneur and motivational speaker, Gary Vaynerchuk, once said, “There has never been a better time, in the history of time, than right now to start a business.” Entrepreneurship isn’t exactly a walk in the park, but it does come with the undeniable freedom of making your own hours from anywhere in the world.
Interested in being your own boss, but not sure what exactly you should do? A number of entrepreneurs, including TPG CEO and founder, Brian Kelly, got their start by expanding and formalizing an existing hobby, interest or area of expertise.
Asian Efficiency CEO and speaker, Thanh Pham, built a robust coaching business by simply talking about the year he managed to read 35 books, listen to 21 audiobooks, earn a promotion at his day job and also drop to 14% body fat. “People kept asking me how I did that so I decided to start a blog,” Pham said. This, eventually, morphed into a full-time productivity system, coaching business and speaking engagements.
An Amex Membership Rewards fan, Pham puts all of his business expenses onto his American Express® Business Gold Card, and uses the points to fund personal trips in first class on Singapore Airlines, ANA, Cathay Pacific and other premium airlines. His travels have actually benefited the business in many ways, Pham told TPG.
“The more I travel and see the world, the better storyteller and teacher I become. I’ve noticed I do some of my best and most creative thinking on the plane. My team constantly tells me to keep traveling, because some of our best ideas have come from me being 35,000 feet up in the air.”
Pham isn’t the only one who benefits from being his own boss. His company is 100% remote, and his global team of employees work from wherever they call home: “Anywhere [with] a laptop and an internet connection,” Pham said. “A few months ago, I was in first class on Singapore Airlines on my way to Asia, and I did a company meeting on my laptop while we were up in the air. Never ever did I think I would start a business around my passion for effectiveness, but I’m very fortunate to do what I love while traveling the world.”
TPG Tip: If you’re looking to start your own business, make sure you get your finances straight from the get-go. Learn how to maximize points and miles when starting a business, discover the five steps to building business credit and figure out which business credit cards are right for your company.
3. Hotel Management
Time on the Road: Varies
Hotel employees — yes, even the ones who stand behind the front desk all day — often enjoy significant travel perks as part of their job benefits.
Chris C., a former director for W Hotels, doesn’t hesitate to talk about how he fell in love with Taiwan. “You have the great metropolis [of] Taipei, inspirational landscapes like Taroko Gorge and the flawless beaches like Hualien and Xiao Liu Qiu. And the people are just as beautiful as the land, on the inside and outside.”
Knowing that hospitality was one of his best options for getting paid to move to Taiwan, Chris worked his way through the hotel’s corporate chain to apply for — and land — the coveted position of managing one of Taipei’s most exclusive hotels. And the island’s central location and generally affordable airfares made it very easy for Chris to spend his weekends traveling around Asia.
In fact, working in hospitality landed Chris not just one, but two dream jobs. A couple years after Chris moved to Taiwan with his company, he was offered a senior management position in Hong Kong with one of the world’s most popular technology companies. “Being a hotel manager allowed me to break into many other industries and job opportunities I never otherwise considered,” he said. “Hospitality teaches you the universal language in the current job market: the ability to handle a high-stress environment while remaining a people leader.”
TPG Tip: If you’re itching to move overseas and try the expat life, the credit card game changes a bit. Make sure you read up on the best cards and awards programs for expats, and how taxes work when you live abroad.
4. Information Technology Consulting
Time on the Road: Between 70 and 85% per week during busy times.
One of the best-known career paths for road warriors these days? Consulting. But while many people are familiar with the travel perks of management consulting, information technology (IT) consultants often travel just as much. IT consultants advise corporate clients on how to effectively use technology in a hands-on capacity, and can log hundreds of travel hours per year traveling to their clients.
TPG reader Justin M. earned United 1K status six years in a row from his weekly travels in healthcare IT. “It’s important to be onsite during the project cycle, especially in the early phases,” Justin said. “Most often, it’s at least twice a month, up to every week.” ra
While Justin made it clear that he’s in this career because it’s right for him — not just for the perks — the benefits are sizable. “I book all of my own travel and use my personal credit cards,” he told TPG. “I get the benefit of racking up all the points. I also get to choose the airlines and hotel chains, which is important for the loyalty game, but also for comfort and convenience.”
Justin also gets a weekly per diem, which essentially subsidizes his food expenses for the week. “I only pay for meals when I’m in my home city,” he said. Perhaps best of all, Justin can take as much time off as he wants, as long as it’s OK with the client or if he’s between projects. “Since we’re paid based on the hours we bill, we don’t get paid time off,” he told TPG. “No billable hours means no paycheck, but that’s worth the tradeoff for me. I prefer to take longer trips, and traditional corporate PTO doesn’t often allow for that.”
And no, you don’t necessarily need to be an engineering whiz or computer expert to work in this field. “I studied economics in college,” Justin said, “So no direct use of my degree. I suppose you could say that I use my critical thinking and problem solving skills, but that’s probably just being generous.”
5. Outside Sales Executive
Time on the Road: Between 25 and 70% per week, depending on industry.
You’ve probably heard that people in sales get to travel a lot. But not all sales jobs are created equal, so be sure to do your research before signing an offer on an inside sales job that will keep you tied to a desk cold-calling all day.
“There is no ‘one size fits all’ for how much you travel in a sales role, but if you’re applying for an ‘outside sales’ role, you’re all but guaranteed consistent travel,” said Katie Z., a senior sales executive for a Fortune 500 company. In addition to employee perks such as unlimited vacation, subsidized childcare and six months of maternity leave, Katie’s role also calls for her to fly across the country to wine and dine top-tier clients.
“My company and management believes that spending time face-to-face with our customers is very important, so I can take my customers anywhere I’d like to — steakhouses, concerts, sporting events, wine tastings — any place that can allow me to build good relationships. I also receive a generous per diem amount that I can spend on food and drink, and all of the airline miles and hotel points that I accumulate from my business trips are mine to keep.”
If you’re interested in exploring a career in sales, you’re in luck: successful sales executives come from all types of backgrounds. “It’s the motivation, the drive, the hunger and determination that make a good salesperson,” Katie said. “I’ve worked with extremely successful reps that have a high school degree, and with sales reps that have their MBA from an Ivy League university. If you’re willing to put in the time, face plenty of rejection and wake up and do it all over again, you’ll be great.”
Katie’s employer also offered one additional perk that really helped her ease back into the road warrior workforce after her son was born: “My company pays for Milk Stork, a company that overnights breast milk home in a package with a 72-hour cooler, if I’m on long trips away from home.”
TPG Tip: Many tech companies hire entry-level associates for inside (desk-based) jobs first, only promoting successful employees to outside sales roles after consistent, proven success. But many employers don’t mind inside sales representatives meeting clients face-to-face if they can find the opportunity to do so. So if you’re working in inside sales and have the points and miles to spare, you could make a strong impression by taking the initiative to visit your clients on your own dime (or points stash). Just make sure to clear it with your higher-ups first.
Time on the Road: Varies
TPG staff members Darren Murph, Sarah Silbert and Zach Honig all got their start by pursuing assignments, internships and other opportunities that would help them build their portfolios. Interestingly, all three found that reporting news from various trade shows proved to be a significant stepping stone in their journalism careers.
Meanwhile, TPG’s executive editorial director, Scott Mayerowitz, followed a more traditional route, launching his journalism career as a photographer for his high school, and ultimately running the school paper a few years later. College and internship experience with news later helped him land successive roles in print, TV, online and wire service.
“I’ve always believed that the best way to tell a story is to see it yourself,” Mayerowitz said. “When covering local news, I would drive the extra 45 minutes to talk to somebody instead of calling them up. But I had to earn larger trips. Part of it was working my way up to larger stories that merited travel.”
TPG Tip: If you’re interested in travel opportunities with your company, make it clear to leadership that you’d love to embrace them. “Many people detest travel or have family scenarios that prevent them from traveling, so confessing that you love travel you may fill a huge void for a company,” Murph said. “Proving yourself while on the road is also great for paving the way to a fully remote role, where you’re able to travel and work.”
7: International Education
Time on the Road: Between 25 and 70% per week, depending on industry.
The last time you thought of travel and higher education may have been on your study abroad semester to Prague or Paris. But just because you’re no longer focused on graduating doesn’t mean that college is no longer your ticket to travel. With more than one million international students currently matriculated in higher education in the USSS, universities are competing hard to recruit potential candidates — and their tuition — from overseas.
TPG reader Chris T. serves as the director of international enrollment for a public university, flying across the globe to build relationships with prospective students and alumni, and to represent his employer at education fairs and expos.
“International education is a big focus at many colleges and universities,” Chris told TPG. “By far, the biggest perk of my job is getting to travel so much and to so many interesting parts of the world. My work has taken me to more than 30 different countries so far and has allowed me to meet amazing people, experience different cultures and eat some really delicious food.”
Despite the glamour of traveling to some of the world’s most exciting cities, the job does take its toll. “I have some colleagues at other institutions that travel for more than three months at a time,” Chris said. “My longest trip so far has been five weeks; that was too long for me, and I now try to keep any work travel to two weeks or less.”
TPG Tip: Requirements for these types of positions vary. But as a general rule, most universities look favorably upon candidates with previous international work or travel experience, fluency in at least one additional language, good intercultural communication skills and a relevant master’s degree.
8. Flight Attendant
Time on the Road: Between 30 to 70%, depending on the airline and role.
Being a flight attendant is one of the ultimate careers for scratching that travel itch — and they inspire plenty of wanderlust along the way, too. Linette T., a five-year veteran flight attendant for Emirates, said that her childhood dream was always to be a flight attendant. “A zillion years ago on a family holiday from Singapore to Los Angeles, I looked at the flight attendants and asked my mum if they were all going to LA with us as well. She said yes, and at that time, I thought their lives must have been great getting paid to go on holidays for a living.”
Once Linette landed the coveted position, she found plenty of perks to enjoy. “Staff travel, flexible work schedules, international colleagues, exploring the world while at work, discount tickets for your family and friends — work never gets boring! At one point in my life, I flew home to Singapore from Dubai on my days off so often that I was practically living out of a suitcase, flying back to Dubai only to catch the next work flight out again.”
TPG Tip: Airlines often post open hiring calls for new flight attendants. While the requirements and training programs are rigorous and demanding, a number of resources are available online, including in community groups on Facebook.
9. Tour Operator
Time on the Road: Up to 80 to 100% per week, during the busy season.
After a number of years spent in the corporate grind, Megan “Lundy” Lundquist took the plunge and launched a group travel company with her best friend. “We had both traveled a ton in our lives and studied abroad in different countries, and wanted to share the unique opportunities we had had with everyone we could.”
Their company, Legit Trips, specifically serves young professionals in their 30s whose social circles may have shifted after friends drop out, get married, have children and otherwise stop traveling.
“[It’s] an environment where [tripgoers] don’t have to think of anything,” Lundy told TPG. “We plan every detail of the trip from start to finish, from arrival at the airport, to activities and hotels. The travelers show up, already have a group to hang out with and just enjoy the trip.”
Lundy has even been able to take advantage of her small business expenses by booking every company expense onto various Chase credit cards. “We earn over 20,000 points a month on our prebooking expenses, which we use for our personal travel as well as our work flights for some of the trips we lead.”
TPG Tip: Sign up for a dedicated business card for this type of work, even if you simply need to invest in a better computer or cell phone. A number of the best cards offer purchase protection, baggage insurance, car rental protection and other benefits that can help you protect your investments.
10. Remote Jobs
Time on the Road: Varies
You don’t have to commit to slinging drinks or working a hostel front desk in order to get the lifestyle flexibility you crave. A growing number of companies allow their employees to work where they please, as long as they stay on top of their responsibilities.
Audrey L. was approached with a job offer after a travel company discovered her through her travel blog and product website, and asked her to help develop its Los Angeles community base. Now the full-time head of community marketing for airfare search engine Skyscanner, Audrey has the flexibility to do her job while making her home anywhere in the world.
“My company has offices around the world, and my own team spans several different cities, so there are definitely opportunities to travel for work as well as for personal choice.”
If you, unlike Audrey, don’t already run a successful blog that may lead employers to proactively offer you your dream job, don’t fret. FlexJobs.com offers a database of employment opportunities that are fully remote, while AngelList, a resource for tech startup job listings, offers a filter for employers who are “Remote OK.” If you have a marketable skillset, try bidding on projects via Freelancer.com or Fiverr.
TPG Tip: Since working alone can quickly feel isolating, consider creating a sense of community by utilizing coworking spaces or programs like Remote Year. In fact, if you like WeWork, the Business Platinum® Card from American Express will begin offering complimentary global WeWork access for a year, or “Platinum Global Access,” starting this month.
11. Use Your PTO
Time on the Road: Varies
OK, so maybe you don’t need to quit your day job to travel. Instead, perhaps you should take advantage of a perk you might already have: generous paid time off.
“Most folks I know, even with unlimited vacation, don’t take advantage of the policy,” said Victor Y., a full-time software engineer who travels the world averaging more than six weeks of paid time off each year.
While Victor used to travel to Europe and Asia to collaborate with coworkers from time to time, his current job is headquartered just minutes away from his home. “I do get to travel sometimes for customer visits and conferences, but it doesn’t move the needle too much.” Instead, Victor focuses all of his attention on personal travel these days, taking ample advantage of his tech company’s “open” vacation policy, which Victor says isn’t specifically defined. “You can take time off as long as you get your stuff done, let the team know and have contingency plans.”
TPG Tip: Many companies with unlimited vacation policies are proud to say so directly on their website hiring pages — and if they don’t, make sure it’s one of the first questions you ask human resources.
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