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Freedompreneurship

How to create your dream travel job, from 7 people who did.

Being a professional traveler is the ultimate dream for so many. Here at Discovery Sessions, our mission is all about giving you the tools to design your ideal non-auto pilot life around sweet freedom and take on a career that makes you feel alive. If you are reassessing your work and visualizing a future where you can create your dream travel job that you wish existed, here are some inspiring tips from seven people who built theirs.

In the pursuit of exploration and job satisfaction, these individuals created their own dream travel jobs infused with their desired ingredients — warm weather, community, adventure, walking, and even foreign languages. Here is what they had to say.

7 CREATORS OF THEIR DREAM TRAVEL JOBS

Luke Charny: Food Tour Designer

The backstory: I’ve worked in the travel industry for over 15 years and the thing that has always attracted me to a destination is the food. There is nothing that gets me as excited as a colorful, neon-lit Asian street food market or perching at a Mexican taco stand with a cold beer. So, four years ago I made that my job. Now I get to travel and eat for a living designing food adventures around the world.

In 2016, I became disillusioned with working for someone else in the travel industry. It’s ironic that many people who work in the travel industry don’t get to travel nearly as much as people think.

I quit my job, flew to Bangkok (a city I knew well), and created our first food tour along with a Bangkok chef. I named the business A Chef’s Tour. Today, we have had over 15,000 guests join our portfolio of 15 food tour destinations from Hong Kong to Bogota. 

Tips to create your dream travel job: If there’s something that gets you fired up and doesn’t exist as a job, think about how you can build a business around it. There’s always an angle. It might be a slog to begin with, but when it starts to get traction, build teams around you to remove the parts that don’t involve your dream work but are necessary for the business (like accounts or customer service). Try to do this without investment because as soon as you owe someone, you risk holding onto that dream job as priorities change. 

Debbie Arcangeles: Remote Podcaster and Content Writer 

The backstory: On my podcast, The Offbeat Life, I share meaningful advice from experts and expats on how to become location-independent. 

I felt unfulfilled in my 9-5 and decided to interview remote workers and digital nomads. It began as a passion project in 2017 and became a real job when I was able to get sponsors for my show. A year and a half after starting, I was able to do it full time, and I have since included a dedicated website that provides resources for others who wish to be location-independent. I love inspiring people to go out there, take risks, and create more freedom in their lives. 

dream travel jobs - debbie from the offbeat life

Tips to create your dream travel job: Find something that will combine purpose, passion, and profit. One without the others won’t work. In the beginning, you won’t see a lot of progress, and it takes a while to build something good, so the profit won’t be there. Passion and purpose are so crucial because sometimes they are the only things that will keep you going. However, without profit, you can’t put food on your table so if you can combine all three, then you have found real magic. 

Donna Hudgeon: Coordinator of Fun at Bonaire Landsailing Adventures

The backstory: I always knew I wanted to create something fun for other people. Too many of us are out of balance, and life can get pretty heavy. My motivation was to facilitate something inclusive, active, healthy, eco-friendly, and unique, and Blokart landsailing ticked all the boxes.

dream travel jobs - bonaire landsailing

Blokarting was one of our family activities in New Zealand for about 15 years and my husband, Andrew, races them at events all around the world. Landsailing requires a few critical components, though, namely consistent wind, a flat area, and access to active people. To find a home for the business, we made a shortlist of potential places and set out on a reconnaissance trip. Bonaire was our second stop, and we canceled the rest of our journey because from the minute we landed, we knew we had come home. Bonaire Landsailing has now been going strong for about four years.

I need variety in my work, and thankfully, my job gives me that. My favorite days are in the fresh air and sunshine at the landsailing track, and I get to talk to guests about how amazing it is on Bonaire and watch them have the most fun they will ever have on three wheels.

Tips to create your dream travel job: Imagine your perfect day at work. Where are you? What are you doing and who are you doing it with? Then dissect that and break it out into categories. What skills do you need that you don’t already have? Who do you have to bring into your inner circle to instigate your plans? Talk about it (a lot) until you start believing it is a possibility. Most importantly, take action and keep iterating until your dream becomes a reality.

Travis Levius: Travel Journalist and Content Creator

The backstory: I had no real idea that freelance travel writing was a thing when I quit my Atlanta-based assistant teacher job and moved to London with little money and a hunch that said “move to London by the summer” and “start writing”.

Based on that “start writing” hunch upon arrival in London, I asked my friends for writing leads and eventually got my first paid gig writing content for a photography tech company. That then turned into an unpaid gig as an editor covering London’s food and drink scene for an American website. It wasn’t until months later that I realized the same website had a travel section, and that kickstarted my career. 

dream travel jobs - travel journalist travis levius in a luxury suite in the maldives

Eventually, I’d branch out from writing travel for the website and learned the art of pitching to other outlets and publications, and that’s when I evolved into a professional freelance travel writer.

I have now been doing this for seven years, and I specialize in luxury travel, so I experience high-end hotels, yachts, and the like to create features for several media titles.

Tips to create your dream travel job: Establish career goals, but allow your intuition to lead you. Sometimes what you think is your dream job could be the second-best (or even worst-case) scenario, and I believe you’ll only know what’s truly meant for you when you begin following your gut. 

Bronson Soares: Latin America and Brazil Travel Marketer

The backstory: Being from Hawaii, a destination that depends on tourism, I observed where many companies fail in their marketing campaigns in terms of being aware of how to appropriately depict the local culture, which is critically important to the local community in Hawaii.

I am the CEO of LUXE LATAM, and my job is the perfect confluence of two topics that I am strongly passionate about both personally and professionally — Latin America and travel. I develop compelling, country-specific strategies and marketing campaigns for luxury hotels and resorts, destinations, and cruises seeking to engage Spanish and Portuguese-speaking consumers, and my goal is to always promote the particular business in a way that respects the destination’s culture.

There are certainly benefits to having a more structured job position, but with my own business, I can dictate my company’s growth, set my own schedule, and have a more balanced way of living.

Tips to create your dream travel job: Be honest with yourself about what your personal and professional goals are and where travel fits into that. Also, find and carve out a niche and become an expert at something. In an increasingly complex travel environment as a result of the COVID-19 pandemic, expert advisors are more important than ever.

Beth Santos: Founder of Wanderful

The backstory: I’m the founder of Wanderful, a women’s travel community, and the creator of Wanderfest, the world’s first-ever outdoor travel festival for women. Back in 2009, I found myself living in São Tomé and Príncipe, a small two-island nation off the coast of Gabon in West Africa. I was 23 years old and had an art history degree during our great recession — suffice to say, I didn’t have many job prospects. I met the former director of the Peace Corps in São Tomé at a picnic. He started a non-profit after the Peace Corps pulled out in the ’90s and he could offer free room and board to volunteers. As a Portuguese-American, I already spoke Portuguese (which is also what they speak in São Tomé), so I figured, why not? I literally moved to a small country site unseen.

And what an experience it was. I was completely solo, and wow, did it affect me. It was one of the first times I really experienced living hyper-locally in a place where there was very little formal tourism. I also came to understand that reality as a woman, and the simple fact that women’s experiences abroad are quite different from what the media portrays (which is either that solo travel for women is a big fashion-induced self-fulfillment fest or that it’s prohibitively dangerous), and different country to country. I didn’t have a space to share my very real questions, musings, thoughts, and concerns, so I started to write about them.

That blog was the beginning idea of what is now a global membership community of women travelers. Our mission is to make travel better for all women — that means creating a trusted and supportive network of women worldwide that can help each other through an online member portal, chapters in 50+ cities worldwide, an international global hosting network, and more. It also means disrupting the travel industry, encouraging industry marketers to be more thoughtful and inclusive, and helping women-owned businesses thrive. We are the creators of the WITS Travel Creator + Brand Summit, a major influencer event that’s been running since 2014, as well as the annual Bessie Awards, named after Bessie Coleman.
 
Our business started with a dedicated community of women worldwide, and that’s how it grows and develops today, constantly challenging the way we talk about travel, who it’s for, and who it affects on the other side.

Tips to create your dream travel job: There are a lot of messages out there that glorify diving into a new idea with no hesitation and giving up everything to pursue your dream. But the reality is that not everyone has the luxury of risking everything. That in itself is something that only a certain set of people have the security to do. But it also doesn’t mean that your dream needs to take a backseat.

If you’re sitting on something that you want to do, start with small steps. Work on it for a few hours in the morning. Take a night class to build your skills. Maybe you quit your full-time job but work for someone else part-time to pay the bills until you can afford to support yourself with your dream job. There are so many different ways you can achieve this, and there’s a right recipe out there for you and your needs. Don’t try to fit yourself into an unrealistic expectation of founders today. Find your own founder story that’s right for you.

Serkan Toso: Co-founder and COO at Byfood.com.

The backstory: When I first came to Japan seven years ago, I studied at a university surrounded by rice fields and not much else. Since I couldn’t speak any Japanese, I couldn’t reserve restaurants or read menus. I was always depending on my Japanese friends because 90% of the restaurants in Japan didn’t have an online reservation system. After a challenging experience in rural Japan, I decided to launch byfood.com to solve these problems.

In the beginning, it was quite challenging. First, I did part-time jobs and worked on my business simultaneously. Later, I found my co-founder and decided to work together. Now we have 70 team members, and I was selected for Forbes’ 30-under-30 Asia list.

The most exciting part of my job is that I travel all around Japan to join food experiences and give feedback to the hosts to improve their experiences. I also work with the Japanese government to create food experiences in remote parts of the country. Via my job, I eat the most delicious, authentic, and local food Japan can provide.

Tips to create your dream travel job: Most of us are scared of the unknown nature of entrepreneurship; we like our safe jobs. However, when you take the first step to start your own company, the rest comes easily. Taking that first step is crucial. When you have an idea, don’t think about all the negative things; just take action and start it. I am from Turkey, and I started a business in Japan. Just believe in yourself.

TRAVEL RESOURCES

What is the best travel insurance for frequent travelers?

Safety Wing is the ultimate made-for-nomads-by-nomads travel insurance provider. Protect yourself anywhere in the world with their flexible nomad insurance.

How can I find accommodation around the world?

There are great deals to be found for short and longer stays (of up to 30 days) anywhere in the world on Agoda, Trip.com, Expedia US, or Booking.com, where you can search for accommodations and filter according to criteria like desks, air conditioning, private bathrooms, and complimentary Wi-Fi.

How can I get an international SIM card when I’m traveling?

It’s quick and painless to get an eSIM (or digital SIM card) and data plan from Airalo that covers practically any country in the world before you get there, so you never have to bother going into a phone shop. With the Airalo app, you can keep track of your data usage and top up easily.

Where can I find useful travel resources for travelers and digital nomads?

You can find all our nomad-friendly resources right here on this page. These will help you out with everything from the best flight search tools to digital SIM cards. 

If you’d like ongoing reflections, frameworks, and interviews on navigating change, you can also subscribe to the Discovery Sessions newsletter on LinkedIn.