6 questions to ask yourself before booking that ‘Eat Pray Love’ trip, according to a travel coach


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In a perfect world, solo travel is an indescribably empowering experience of a lifetime. You embark on this exotic adventure filled with architectural beauty, decadent meals, and Javier Bardem. Yes, the idea of a solo trip glorifies leaving your life behind, only to return once enriched by a kind, wonderful world. Don’t overthink it! Be bold! Buy the damn ticket!

Cut to: you halfway across the world with a pack of feral dogs standing between you and an outhouse.

The secret to solo travel is that it isn’t necessarily something that you should do alone—or at least not something that should make you feel alone. But it totally can—trust me. According to Dylan Grace Essertier, a travel coach who focuses on guiding clients through their emotional, spiritual, and literal journeys, solo travel has a way of deeply changing us. But it requires some soul-searching that goes beyond asking yourself “Where do I want to go?”

“If approached with the right mindset, this type of travel can be more than just time spent away from ‘real life’ but an incredible opportunity to reconnect with who you are, what you want, and create shifts that make way for new career paths and possibilities once you return home,” says Essertier.

What to ask yourself before you embark upon solo travel

1. “What’s great in my life right now?”

“I don’t believe in travel as a way of ‘escaping’ since as I’ve learned through my own experience as an ex-pat, ‘wherever you go, there you are,'” Essertier says.

When she first moved abroad, Essertier thought the same fresh start things we all think: that she would start working out, start working on that book, start to become best version of herself. The reality involved stress-eating junk food, not putting enough pen to paper, and getting through the agonizing process of adjusting to a new locale sans friends and family.

I get it, I get it, we travel because we want newness and novelty. The more realistic expectation, though, is working to elevate and enhance the things in your world that you already love.

“Focusing in on what’s working in your life right now—and how traveling could make it even better— will help you move toward creating an empowering experience versus seeking an unrealistic escape from your problems,” she says.

2. “Is my financial situation in order?”

In Frances Ha, one of my forever rewatch movies, the titular character books a spontaneous weekend solo trip to Paris using a credit card. It is a bad decision from every angle, culminating in credit card debt that has her living as a (27-year-old!) summer resident at her alma mater. Basically, don’t do that.

“I can’t emphasize this enough: You don’t want financial stress to disrupt your time of deep thinking and exploration,” says Essertier.

Finances have to sometimes take priority over experiences, so really keep an eye to your budget before you swipe that card. Good news, though: there’s a really great way to motivate yourself if you want to put aside a travel budget, and it involves an on-the-go vision board.

“If you crunch the numbers and you’re not in a position to pack your bags quite yet, one great tip passed on to me by financial expert Kristen Euretig is to cut out a picture of the place you want to visit and tape it to the front of your debit card,” she says. “This visual reminder can be extremely powerful in helping you reach your travel savings goal faster.”

3. “Am I looking for quality or quantity?”

Are you backpacking across Europe or do you want an immersive week in Tokyo? There’s no right or wrong answer, but you do want to take a minute to analyze how many places you want to see… and if loading up your itinerary will ruin the overall experience.

“Part of the joy of travel is discovery, and it’s hard to discover new things if you’re trying to hit too many destinations and not allowing yourself room to explore,” Essertier says.

4. “How available do I want to be while I’m away?”

Basically, is this a moment for a digital detox, or are you literally going to be posting to Instagram every day? Look, we all deserve at least one millennial pink brunch spot picture per solo trip, but Essertier urges you find some time to pocket your phone.

“Social media can be an amazing tool to stay connected with friends and family back home, but I encourage my clients to be thoughtful about carving out some designated time to both unplug and socialize with the new friends they make on the road,” says Essertier. “In-person connection is key to mental well-being when you’re traveling alone for extended periods of time.”

5. “Who am I envious of?”

Huh? This one might sound weird, but it’s all about the core of what we want, whether it’s happiness, fulfillment, or a change of pace. Ideally, you want at least two of those things; figuring out what it is specifically often comes from looking at what other people have.

“Making a list of 10 people we’re envious of is a great exercise in understanding our deepest hopes for ourselves,” Essertier says. “Plus, what’s better than turning useless envy into action? For example, jealous of that friend who runs her own company? Think about what skills she might have that led her to create that reality. Perhaps it’s leadership, a thick skin, the ability to take more chances.”

6. “Who will hold me accountable?”

Solo travel is a great opportunity to strengthen your independence, but dude… be safe. Make sure that other people back home have your back during this journey. According to Essertier, any major travel decision can be a source of both joy and stress, so on an emotional and logistical level you still need people, you know?

“Bring other people you trust and care for into your plan and have them support you before, during, and after your trip,” Essertier says. “Also, I always encourage my clients to share an outline of their itinerary with friends and family as well as register with the local state department so they can be alerted of any important updates.”

Remember, solo travel is about finding yourself, not feeling lost.

Excited to explore, but don’t know where to start? Here are 6 dreamy travel locales you should put on your wish list. And here’s what you should know before booking that vacation rental.

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