Personal Travel Coaches Are The Hot New Trend. Here’s What They Are And Why You Need One

A lot of people have life coaches and career coaches—but have you ever heard of a travel coach? Dylan Essertier is a travel writer turned travel coach who now works with people looking to reach their goals through travel. “Over the years, I searched long and hard for a travel advisor that would speak to a ‘woman like me’—someone who didn’t just want to escape through travels but use that time away to help me move toward my long-term goals,” says the writer, who also had a side hustle as a life coach.

Since she couldn’t find that person, she created the job for herself. Through her new company, Dylan Grace, Essertier supports people around the world through 1-1 coaching, including road-mapping their trips, keeping them accountable for their goals while they are away and even guiding them through re-entry. Essertier also teaches e-courses and holds retreats to support people interested in making a career out of travel, teaching them ways to grow a meaningful business out of that passion. She founded Dylan Grace with her mother, Toni Essertier, who oversees the booking side of the company.

A travel coach is not exactly a new concept—some people call it the modern-day version of a travel agent, yet one with a laser focus on your goals and mindset. In short, it’s a more holistic approach to travel planning—an intersection of advisory and personal coaching. “It wasn’t until the past decade or so, and even more specifically the past five years, that travel coaching has really taken off,” explains Michael Bennet, co-founder of the Transformational Travel Council. Bennet attributes the new category to the rise of the personal development industry and the growing popularity of experiential adventures. In addition, notes Bennet, many modern travelers are now interested in prioritizing the “why and how” of travel rather than the “what and where.”

“The average age of travelers has been getting younger and younger and these travelers are dealing with existential questions and crises, things like the infamous ‘Quarter Life Crisis’ and ‘Saturn’s Return’ and so forth, where they are facing some of life’s most important questions,” says Bennet. “They also have money for the first time, plus access to immersive and experiential travel experiences more than ever before.”

Essertier says she is noticing a shift in travel psychology, as well: “Many of my clients are less interested in sitting on a beach and forgetting their life back home. Now they want to use their time traveling to reflect, learn, reset and figure out what really matters to them.”

Here, Essertier tells how she reinvented not only her own life through her travels, but how she is helping other women use travel to build better lives through their own travels.

My Career Journey: I started my career working in human resources in training and development. I enjoyed my work and helping employees build confidence, but I became restless. I had always dreamt of traveling the world and becoming a writer so when I got an opportunity to move to the Middle East, I took it. I spent six years working as a culture editor in Dubai, traveling to so many places to report on the latest luxury hospitality trends.

Why I Decided to Do This: When I moved back to New York a few years ago, I continued my travel writing, and some of my friends started asking me to help them plan trips. During our conversations, I wasn’t just asking them if they preferred the beach or snow. Without realizing it at the time, I was trying to discover a more holistic picture: How is work? What’s your dream job? Are there any major changes you’ve faced over the past couple of years? These answers helped us choose a destination and itinerary that felt right, a place where they would get the most out of their time away. Before I knew it, friends of friends were asking me to plan their trips. Some were taking sabbaticals and wanted advice on how to travel alone without feeling lonely, how to make friends while in a new country and how to stay safe. These were all concerns I experienced during my years living as an expat. Since I could relate, we would often stay connected during and after their trips, chatting about all their highs and lows. I didn’t realize I was slowly building a business until I started receiving emails from strangers asking for my travel planning rates.

Trips That Matter: I work with clients going through a job relocation, the end of a relationship, retirement abroad or a career change. I also design shorter trips and host retreats; I especially love planning volunteer vacations. Right now I’m helping plan a one-year anniversary for a couple interested in doing relationship goal-setting during a trip to the Amalfi Coast. This spring, I’ll be hosting a travel writing retreat in the Catskills at the Floating Farmhouse.

Inspirational Journey: I was recently approached by a woman who wanted to spend six months in Bali between finance jobs. When we first connected, she explained to me that she wanted an experience that would include not only fun in the sun, but also “fitness, spirituality, personal interests and cultural immersion.” It was also her first time traveling solo, so we talked a lot about what mindset shifts would happen to reframe her extended time alone from something that might feel nerve-racking and scary into an incredible opportunity to connect with new people and herself. Together we mapped out an itinerary that included yoga, visits to local healers and philanthropy and strategically planned accommodations that would allow her to socialize (ie. hotels with ton of community activities) while still staying accountable for carving out alone time and self-reflection. Before she left, I sent her a poem that touched upon some of the personal things we had talked about, as well as a journal. I encouraged her to write in each night so she could later look back on her moments of bravery and enlightenment.

Getting Creative in the Galapagos: A woman asked me to help her plan a trip dedicated to reconnecting with her creative side. She had been working as a successful entrepreneur for many years, and although she loved it, she wanted to get out of the weeds to make time for big-picture thinking. She was also a nature lover, so we ended up planning a trip to the Galapagos for her around the theme of imagination. Before she left, I prepared a list of questions designed to help her reflect on the evolution of her business. By stepping outside of her day-to-day, she was able to awaken her sense of creativity through new scenery, and also be purposeful about using the trip for internal reflection—a thought process, she said, that led her to develop a new business idea shortly after that trip.

Travel Advice: 3 Easy Ways to Make Your Next Trip More Meaningful

Here, Essertier shares her tips for planning an enriching and fulfilling trip.

• When thinking about your next trip, don’t just ask yourself where you want to go. The better question is: What do I want to feel? Affixing your trip to a conscious emotion will not only serve as a North Star for your itinerary, but it will be something you can return to during every moment of your actual trip.
• Be warned: “I want to feel good” is too flimsy. Try something bold and specific. For example, you could say: “I want to feel unburdened.” This might lead you to plan travel that favors quality time spent in a single destination versus trying to see as many places as possible. It might cause you to pack less, to give yourself permission to not visit popular sights that don’t truly interest you, to turn off your phone and maybe even to sleep more. Understanding your motivations and putting yourself in the right mindset is the key to planning travel that transforms you.
• Bring a journal—and write in it every day. I always send my clients one before they leave and encourage them to record their experiences. At the end of each day, write down your highlights (and lowlights). You’ll enjoy looking back on this later and continue to learn from it.

Where to Go Next: 3 Exciting Experiences for 2020 

Here, Essertier shares three experiences she’s excited about for 2020 that you should also put on your radar.

• Travel Eyes: This incredible organization coordinates group holidays for both blind and sighted travelers. As a sighted traveler, they ask that you share your vision by describing the wonderful world around you. I just love their mission and am really excited about the trips they are putting together.
• Isola del Giglio: Since hearing about Isola del Giglio from Sebastian Schoellgen, the founder of EightyFour Rooms, I’ve had my eye on this tiny unexplored island off the coast of Tuscany. It looks like the perfect place to take a break from the whirlwind of contemporary life, reset, write and eat pasta while listening to the sound of waves crashing against the bay.
• Sailing from Tahiti to Bora Bora: I was recently on assignment in French Polynesia and spent four days sailing from Tahiti to Bora Bora. This incredible experience included snorkeling in secret coves, swimming with humpback whales, and no WiFi. I can’t recommend it enough, and am already planning my next trip back. Flights to Tahiti are fairly inexpensive right now and accommodation is getting much more affordable thanks to a bunch of new family-run guest houses that are opening up in Bora Bora and the surrounding islands.

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