Being a professional traveler is the ultimate dream for so many. Here at Discovery Sessions, our mission is to give 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 six individuals created their own dream travel jobs infused with their desired ingredients — warm weather, community, adventure, creativity, and even foreign languages. Here is what they had to say.

 

THE CREATORS OF THEIR DREAM TRAVEL JOBS

 

Cynthia Morris: Creativity Guide 

The backstory: I’ve been a coach for writers and artists since 1999. In 2004, I was taking a leadership training when I got the idea to host a creativity workshop in France. I teamed up with a friend of mine and we designed a program in Arles. It was called Journey of the Senses. We explored Provence with our sketchbooks in hand, using drawing, painting, writing, and cooking as a way to remember and savor the experience.

 

My company is called Original Impulse. Through workshops and books, I help people bring their creative ideas to life. One way I do this is by leading creativity and writing retreats in Paris and elsewhere. Using the environment as both classroom and inspiration, we’re able to experience the world and ourselves in new, transformative ways. The emotions we feel when traveling are heightened, and I engage the senses to facilitate fun experiences that change us forever. My Capture the Wow and Write Your Heart Out retreats give people a new way to think about their creativity, plus new approaches to travel. 

 

 

As a young person dreaming about living in France, I couldn’t have known that I would be able to travel there regularly and share my love for the country with others. 

 

How people can create their own dreamy travel jobs: Give your idea a go. Do a test run and see what works and what doesn’t. If you want to lead groups in other countries, lead one at home. Run through the entire experience. You’ll see which parts are tough, which parts are fun, and whether you like the job outside of the idea of it. We live in a time where so much is possible. The dreamers who become doers get to craft a life that involves things they love, including travel.

 

 

Olly Gaspar: Professional Travel Photographer

The backstory: While working a comfortable desk job in Brisbane, Australia, I felt unfulfilled simply because my job was just that – a means to an end. It did not allow me to practice or develop skills related to my true passions of travel, adventure, and outdoor photography. I eventually left my desk job with some measly savings and flew, with my partner Haylea, to Southeast Asia. Initially, I worked for free with local hotels and tour companies in order to build up a reputable portfolio. 

 

 

 

How people can create their own dreamy travel jobs: The absolute best advice that I can give anyone looking to pursue their dream travel job is to start today. If I didn’t take the plunge and leave that comfortable desk job, chances are I’d still be there, and I’d still be feeling unfulfilled. It’s cliche, but the truth is that the barriers to starting out are often self-built out of doubt, rather than tangible issues. 

 

What I’d ask anybody is to question whether this is something that they really want to do. If the answer to that question is a resounding yes, then there isn’t a barrier strong enough to prevent you from starting right now. That doesn’t mean it’s going to be easy. In fact, I’d say the opposite is true and that anything really worth doing rarely is. 

 

 

Kimberly Pong: Travel and Lifestyle Coach

The backstory: I have been traveling since 2011 and throughout my entire travel journey, I would always get messages from people asking about how I quit my job and how they wanted to do it too. One day, I got a message from someone saying that she quit her job to travel, and it was all because of what I said to her. I gave her tips, inspiration, motivation, and the right words to know that she could also successfully do it. When I read that message, I jumped up and down with excitement and was so happy that I was able to help her achieve her dream.

 

At that exact moment, I had an epiphany that I wanted to create a job helping others quit their jobs to travel. The Universe sent me that epiphany and I instantly knew that I wanted to create this dream job of mine. Nothing makes me happier than helping others pursue travel and their dreams of seeing the world. 

 

 

As a travel and lifestyle coach and creator of digital products, I teach my community how to ditch their 9-to-5’s so that they can explore their wanderlust desires. Since going off the conventional life path, I have explored over 53 countries and now share the travel hacks that I have learned along the way. My focus is to equip others with practical planning, overcoming limiting beliefs, traveling the world on a budget, and making money to continue their journeys around the world.

 

How people can create their own dreamy travel jobs: There are so many ways to make money and travel. Trust yourself and know that you can always pivot. Another piece of advice is to find a community of people who are also pursuing their dream jobs. It can get lonely and hard sometimes, but having a community that “gets you” is a game-changer. 

 

 

Joli Moniz: Founder of A Vontade Tours in Cape Verde

The backstory: I was raised in Connecticut by loving second-generation Cape Verdean-American parents who instilled in me a love of my culture. My first trip to Cape Verde at age 15 sealed my connection with the country of my ancestors and my passion for travel. For decades I’d say that one day I would spend a few months here to learn the language of my ancestors and be enveloped in my culture, but life always got in the way.

 

In 2012, I was itching for a change. I had been in a career for 10 years (I was director of admissions at a private girls’ school in Westchester, NY) and was engaged to marry a guy I had been with for nine years. I thought the change I craved would soon come in the form of marriage, a new home in the ‘burbs, and kids – the American dream. But as my wedding day approached, I realized that, as much as I loved my fiancé, I was about to sign up for a life that wasn’t for me, and one that left not much space for travel or creation. Within two days, I called off my wedding, gave my employer three months’ notice, and told my family I was moving to Cape Verde for “a year or so.” 

 

 

A few months in, I realized I couldn’t imagine leaving. I had never felt so alive. After living in several states in the US, for the first time, I truly felt at home. I founded the boutique travel company A Vontade Tours in the Spring of 2013. The goal of A Vontade, which means “feel at home,” is to encourage people to visit Cape Verde and several other countries of the African diaspora, and to experience them in a culturally authentic way while contributing to their local economies. It was slow at first, but news spread by word of mouth. Eventually, I was able to let go of side gigs and focus on it full-time. Now my team and I can barely keep up with the demand, which is such a blessing.

 

How people can create their own dreamy travel jobs: Just jump. Life is both too short and too long to spend so much of it in jobs or careers that do not fulfill you. In the beginning, you may need to juggle your dream job with side work just to pay the bills, but if you pour consistent energy and love into it you will be successful and most of all happy.

 

 

Jeremy Clement and Rob Keen: Co-founders at Project Expedition

The backstory: Jeremy and Rob met back in 2009 in Mumbai while on a work assignment for Bloomberg, and from that point on, the two became great friends who shared a passion for travel. Maybe it was over pints in London, sushi in Tokyo, or late-night pizza in New York City, but at some point, the two friends realized they also shared a passion for entrepreneurship. So they decided to set out to try and bring cohesion, quality, and reliability to the fragmented tours and activities segment of the travel industry. 

 

After quitting their jobs in finance, Jeremy and Rob initially had to travel to Costa Rica, Belize, and Panama to convince their first tour operator partners to give them a shot. Now their company, Project Expedition, partners with nearly 2,000 tour operators and provides travelers with access to more than 25,000 tours and excursions across 150 countries and territories around the world – including everything from Eiffel Tower tours in Paris to helicopter tours in Hawaii, wine tasting in Tuscany, and more.

 

 

Entrepreneurship is one of the most difficult and richly rewarding endeavors that someone can pursue, and that couldn’t be more true than in the travel industry. We operate in one of the most intensely competitive markets out there, but the challenges are worth it because we have the unique privilege of connecting people with different experiences, cultures, and activities that often end up being the highlight of their trip, and can even leave a lasting impression on their lives. Being in a position to make a living while sharing this passion with others is the ultimate dream job.

 

How people can create their own dreamy travel jobs: My advice for someone who would like to create their dream job is to dream big, but start small. It can be too easy to be overwhelmed by the distance and obstacles between you and your goal, but if you adjust your focus to each step on the journey, you will eventually look back and see how far you have come.

 

Practical advice? Focus on acquiring your first paying customer who is a complete stranger. Realizing that someone you have no connection to is willing to pay for the simplest version of your product or service purely because they are interested in it is an incredibly validating milestone.

 

 

Kristin Tellis Quaye: Co-founder of Certified Africa

The backstory: I always knew that the traditional lawyer or corporate 9-to-5 lifestyle wasn’t for me. I dreamed of traveling full-time with my family and being able to work remotely from anywhere. It never made sense that I would spend the majority of my time with co-workers and not the people I loved. But there literally was no blueprint or map for the type of life I wanted.

 

Without a clear-cut plan on how to make everything happen, I sucked it up and decided to just find a job that had nice people, good vacation time, and the ability for me to help people with my legal degree. The work-related stress took a toll on my health. My hair started falling out, I gained weight, and I started having panic attacks. I felt trapped. I traveled to Ghana because it had been a lifetime dream of mine. It absolutely changed the trajectory of my life. I found my purpose in connecting the African Diaspora to the Continent, and while I was in Ghana, I met my husband. We are now the founders of Certified Africa together.

 

 

Certified Africa is the leading source to book all-in-one private and group travel experiences to the African continent, authentically learn about Africa, and explore cultural heritage, lifestyle, and business/investment opportunities in Africa.

 

How people can create their own dreamy travel jobs: It’s tough to think about creating something new, but we must not allow fear to control our lives. There were so many people who tried to convince me not to take my initial trip to Africa, and not to leave my job as an attorney to start Certified Africa, even though I wasn’t happy. I know from experience how fear and the projection of fear from people in your life can cause you to go down a path that may lead to regret. You could wake up five or ten years from now and not recognize who you have become and wonder why you didn’t live life for yourself.

 

 

Alissa Musto: Luxury Cruise Ship Entertainer

The backstory: I started performing on cruise ships as a piano bar entertainer. Then my agent offered me a unique opportunity to write my own show and perform that on the ships. I have been playing the piano since I was four years old, and I have spent my entire life performing. I have also always loved traveling since I studied abroad in Spain in high school. Being a cruise ship guest entertainer is truly my dream job because it combines both of those passions: performing music and seeing the world. While I loved performing in the fun piano bar atmosphere, I prefer performing the show that I wrote because I am able to truly showcase who I am and my original music, and tell my story.

 

As a guest entertainer, I perform for cruise ship audiences a few nights per week in the theatre, which gives me almost full flexibility during the day to discover the ports and enjoy the itineraries. To date, I’ve been to around 50 countries.

 

 

I have written two shows that I produced and perform for cruise lines. The first, 10,000 Keys, features both original songs and covers by some of my greatest inspirations, such as Carole King and Bruce Springsteen. I also tell anecdotes from my life and share stories about my travels. The second, Piano Ma’am, is a Billy Joel tribute. When I join a ship, I bring my sheet music on board and rehearse the show with the live band. In addition to performing and practicing, sometimes I’ll have meet and greets onboard, sell CDs, or participate in other entertainment activities.

 

How people can create their own dreamy travel jobs: My advice for performers or creatives looking to create their own travel dream job is to first test out your show and techniques locally to see what works and what doesn’t. Cruise audiences are not always forgiving, and the industry is very competitive. When pitching or presenting your show, project, or business, you want it to be polished and well-tested.

 

This is part 2 of our “Create your dream travel job” series. Click here to see more dream travel jobs in part 1.