How to travel intentionally
15 questions that will completely change how you travel
I’ve dedicated this year of my life to learning how to live more intentionally and in line with my core values. I realize this can sound woo-woo to some, until you realize how much of your life you’re actually living on autopilot.
We all say yes to things we don’t actually want to do, and we all pursue goals and jobs because we think we’re supposed to follow a linear path! We tend to make decisions based on what looks good rather than what feels good. We’re so busy performing our lives that sometimes, we forget to actually live life. And I’ve realized nowhere is this more obvious than in how we travel.
I’ve noticed that people tend to book trips to a certain place because everyone else is going there—think about how many people you know that have traveled to the Amalfi Coast or Dubrovnik in the past year. We follow itineraries designed for someone else’s values, or designed without values in mind. We race through cities checking boxes, collecting photos, performing the experience instead of having it. We come home exhausted, vaguely unsatisfied, and can’t quite articulate exactly why we’re feeling that way after spending $10k on a vacation. Sometimes, friends describe their trips to me after returning, and they sound more like an episode of The Amazing Race than a restorative vacation.
Living intentionally means constantly asking: Does this align with who I am and who I’m trying to become? It means filtering decisions through your actual values, not the values you think you should have. Values-based decision making means being honest about what you need in life, what you’re running from, and what you’re running toward.
And when you start looking at travel planning through that lens, everything starts to change, for the better.
Our honeymoon was a two-week trip through South Africa, Zimbabwe, and Mozambique. On paper, it was our dream trip—a few nights in Cape Town, a city we’d been dying to get a taste of, wine country, plenty of safari time off the beaten path in nature, Victoria Falls, and one of the most gorgeous beaches in the world in Mozambique.
In reality, most of our time was spent transferring from one place to another, with internal flights every few days, airport transfers, and being shuttled around in more vans than we could count. We traveled over 18,744.45 miles in two weeks. We were surrounded by guides at every turn, unable to enjoy more than a few minutes alone on any given day, because everything had been planned down to the very minute.
It fell flat for many reasons, but the biggest reason is that we leapt to that destination decision without thinking about the bigger “why” behind the trip.
Distracted with wedding planning, we didn’t make time to set trip intentions. I was busy and overwhelmed planning our wedding and outsourced the honeymoon planning to a popular travel agency that didn’t even ask us what our favorite things about travel were. I should’ve known that the trip was going to be chaotic when they fought back on making itinerary changes I asked for, and I later learned that many people we knew took that exact honeymoon, booked through the exact reputable agency we used, and did the same things, down to certain meals. There was no differentiation between the trips, despite us all being completely different people. The agency also discouraged us from planning a honeymoon to Japan—something we had dreamed of for years, but ultimately we decided against it because the agency said it would be too hot and humid for us to enjoy ourselves.
In the end, the issue was that the trip wasn’t curated especially for us. It wasn’t our trip, and there was zero intentionality behind it. The whole process felt like borrowing a pair of gorgeous shoes from a friend that almost fit but were slightly too small. We came home feeling defeated and blistered, rubbed the wrong way.
It wasn’t all bad, though. I was grateful for the moments of joy we shared, but I walked away knowing that there had to be a different lens to see and plan travel through, a lens that would prevent this from happening again. It was a huge learning moment for me and helped me shape Mindholiday into what it is today!
Most of us book trips on autopilot. We see a deal, or a recommendation, or a trending destination, and we jump. We don’t pause to ask if this trip actually serves us—if it aligns with what we need right now, who we’re trying to become, or what actually matters to us.
So before you book your next trip, I want you to sit with these 15 questions. Not all of them will be relevant for every trip, but I promise that the act of asking them will change how you travel.
Questions to ask about your “why”
1. What am I running toward vs. what am I running from?
This is the big question—are you booking this trip because you’re genuinely curious about a place. or because you’re burned out and desperate to escape your life for a bit? There’s zero shame in needing a break. We’ve all been there. But if you’re running from something (your job, your relationship, your life in general), a week in Greece isn’t going to fix your underlying life problems.
Here’s a better question to ask yourself: What do I actually need right now—adventure, rest, perspective, connection? Can this trip give me that, or am I expecting it to solve something only I can solve?
2. How do I want to feel when I come home?
Close your eyes for a minute and imagine yourself a week after you return from your adventure. How do you want to feel? Rested? Inspired? Connected? Transformed? Now work backwards. What kind of trip would actually create that feeling for you?
If you want to feel rested, maybe you don’t need the 10-day solo backpacking whirlwind tour of Europe. If you want to feel connected to others, maybe you don’t need the silent meditation retreat. Let the desired feeling guide the trip, not the other way around.
Here are some travel intention examples to get your thinking jump started. These aren’t supposed to be limiting (I encourage you to think beyond these), but I’m providing these in the hope that they might spark your own special travel intention!
I want to return home feeling recharged and not needing a vacation from my vacation.
I want to have at least three meaningful conversations with locals.
I want to prove to myself that I can navigate a place where I don’t speak the local language.
I want to understand how a culture’s history influenced how they are today.
I want to feel small in a way that reminds me that there’s so much more to the world than my own personal problems!
I want to practice presence, living in the moment, and being where I am, rather than thinking about the next thing.
I want to do new things that make me feel alive! And a little bit scared!
I want space away from my regular life to process what I’ve been going through.
I want to strengthen my relationship with my partner by being fully present together.
I want to gather inspiration for work by experiencing new places, colors, textures, and perspectives.
I want to become more comfortable with uncertainty and not always having a concrete plan.
I want to learn how to make one dish really well from a local, by taking a cooking class.
I want to turn home with a heightened sense of gratitude for what I already have.
I want to be better about noticing small details I normally miss, like the way light hits buildings, or the rhythm of a certain place.
I want to celebrate and mark a life milestone in a way that feels significant.
I want to remember who I am outside of this difficult season of life!
I want to create memories that honor what I’ve accomplished or survived.
I want to return home from my trip with stories that remind me I’m not playing it safe.
I want to see a different way of living that challenges my assumptions about what’s “normal”.
I want to understand what daily life actually looks like here, not just the tourist experience that most people see.
3. Will I remember this in five years?
Not every trip needs to be extremely memorable and transformative. Sometimes you need a long weekend at the beach. But if you’re planning on investing significant time, money, and energy into planning a trip, ask yourself: will this one matter? Or will it blue into the background of a dozen other trips you took because you were supposed to?
The trips I remember aren’t always the most exotic or expensive. They’re the ones where something shifted within me—where I learned something about myself, or connected deeply with someone I didn’t expect to connect with, or saw the world differently.
What makes a trip memorable isn’t where you go. It’s who you are when you’re there.
Questions about impact
4. Who actually benefits from my presence here?
This is an uncomfortable question, which is exactly why it’s worth asking. If you know me, you know I hate tourism that is more extractive than it is additive. Travel should expand your world without exploiting the world!
Tourism can drain local resources, inflate local prices, displace locals, and commoditize culture. Before you book, ask yourself: Who actually benefits from you being there? Is your money going to locally owned businesses or international corporations? Are you taking more than you’re giving?
Of course, I’m not saying don’t travel—I’m saying travel responsibly! Always choose local guides. Eat at family-owned restaurants. Take the food tours that bring you to local stalls. Stay in neighborhoods where your money supports the community.
Also, I completely understand that sometimes you’re going to stay at a big hotel chain. Sometimes, that’s what makes the most sense for your trip budget, the comfort level you’re looking for, or your specific needs. Just be aware and acknowledge that your money is going to a corporation instead of a local business owner, and then maybe balance it out by changing other behaviors—such as eating at neighborhood restaurants, booking local guides, or shopping at artisan markets instead of touristy shops.
At the end of the day, intentional travel isn’t about being perfect, it’s about being aware and making small behavioral tweaks and changes.
5. Am I prepared for some discomfort?
Real travel (I’m referring to the kind that changes you) requires some discomfort. It means not understanding the language! Eating things you can’t identify! Navigating transportation you don’t recognize! Being the outsider!
If your answer is “No! I want everything to be easy and familiar!” that’s fine, but call it what it is: a vacation, not an exploration. There’s literally nothing wrong with vacations, we all need and love them, and I’ve taken many myself. But if you are seeking transformation on your trip, you have to be willing to be uncomfortable, and willing to not have all of the answers.
6. How does this trip align with my values?
I’ve started to filter every travel decision through my values: connection, compassion, curiosity, creativity, community. If a trip doesn’t serve at least one of those, I rethink why I’m drawn to it in the first place.
Ask yourself: What do you actually value? (If you haven’t identified your values, start here.) And does this trip reflect that?
If you value sustainability, are you flying across the world for a three-day weekend? If you value connection, are you booking a trip where you’ll never interact with locals or new people? If you value learning, are you going somewhere you’re genuinely curious about, or somewhere you think you’re supposed to visit?
Your trip should reflect your values, not someone else’s.
Questions about yourself
7. What am I curious about right now?
When you’re thinking through this, I want you to think about what genuinely interests you in the moment, not what you think you should be curious about, and not what sounds impressive.
Maybe you’re really into food or architecture (if so, boy, do I have a Mexico City itinerary for you). Maybe you want to have a better understanding of how people in other cultures approach work-life balance (consider Copenhagen or Amsterdam). Maybe you want to go to a place where you can feel confidently and unabashedly yourself (hi, Brazil). Let that curiosity guide where you go and what you do when you’re there.
Curiosity is the difference between seeing a place and actually understanding it.
8. What do I need to learn right now?
Travel is fantastic because it has the ability to teach us lessons we can’t necessarily learn in the comfort of our own home—patience, flexibility, how to navigate alone, how to ask for help, and how to sit with discomfort.
What’s the lesson you’re avoiding? Travel can be your teacher and spirit guide, if you surrender and let it be.