Travel forces us to confront new questions—the kind that jolt us out of our neatly arranged lives. These shakeups are crucial because they compel growth.
I’d argue there are at least two types of “difficult” when it comes to a shakeup like this.
Sometimes, life disrupts us through failures—those painful, external forces that demand immediate adaptation. You lose a job. You face a breakup. You’re forced to act because survival depends on it. The path may be brutal, but it’s often clear.
Then there’s the intentional hard. The kind where, without any external upheaval, you realize: I want to be more like this. No catastrophe, no mandate—just a truth you can’t ignore. Acting on it requires grit, persistence, and a system of small, consistent steps. No one’s forcing your hand. You’re choosing the discomfort. You’re choosing the change.
Both are hard. One isn’t better. They’re just different.
If you’re ready for the intentional hard, here are 5 questions that guided us on a recent Unsettled trip. Now, they’re yours.
It’s easy to ask. Harder to act. But that’s where the wildness is.
Let’s go.
1. What role does play hold in your adulting years?
Have you ever watched sea lions play? Not just swim. Play. Twisting, turning, darting, and flipping with pure, unfiltered joy. They’re not checking their email. They’re not worrying about what’s “productive.” They’re moving because it feels good. Because play is freedom.
Did someone convince you that play was for kids? Or that being productive is more important? Did Play become a dirty word in your world of adulting? When did you decide that joy, exploration, and silliness were luxuries instead of essentials?
Play is power. Play is a survival tool (literally helps those sea lions become better hunters). Play reminds you that life is meant to be lived, not just managed.
Where can you bring more play into your days? Spoiler alert: “I’m too busy” is the wrong answer.
2. In what ways are you stepping out of society’s box?
One of our participants in Unsettled Baja really challenges us on this one. Boxes are easy. Society hands them out like party favors. Here’s your career box, your relationship box, your happiness box — neatly labeled and sometimes, suffocatingly small in its potential.
In Baja, he asked us: “How are you stepping out of the box that society has created for you?” It hit, maybe because we were 10 independent thinkers, well outside of society at this point in our trip.
Staying in the box is safe. But is it you? Or is it someone else’s expectations or vision placed upon you?
Stepping out isn’t always dramatic. Sometimes it’s saying “no” when the world expects a “yes.” Sometimes it’s choosing a path that doesn’t make sense to anyone but you.
Are you in the box or are you breaking free? Even in the smallest ways, or even if you’re already thinking you’re outside of the box, reexamine society’s expectations placed on you and if they’re aligned with your own.
3. What part of yourself is the world asking you to bring forward now?
Life is definitely not static.
There are parts of yourself that are not surfacing — out of fear, out of habit, out of a misguided sense of self-preservation. But maybe now, the world is asking you to bring something different.
A little more courage? A lot more honesty? That wild, weird, raw edge you’ve been holding back?
Listen. The world doesn’t need another muted, half-lived version of you. It needs the part you’re afraid to show. The part that’s been waiting to burst out.
I’ve been following a simple journaling routine that I came up with recently that I call, ‘Opposites.’
I identify a negative mindset, emotion, action, or inaction that I’ve been experiencing lately. I write about the cause and, especially the effect it’s having on my life for 2 minutes. Then I write 3 ways that I can overcome it and how that will affect my life differently.
It’s powerful in that it recognizes and accepts what is blocking me from bringing the “best” part of myself forward, and then it gives me 3 steps in which I can take action.
4. What sparks your wonderment?
On our recent trip in Baja, we hosted an Unsettled Inspirational Happy Hour, where each person (on the beach in this case) shares stories, poems, and quotes that holds meaning for them. I’ve been hosting these Inspirational Happy Hour for a few years now.
On this trip, night fell quickly after the happy hour, and we found ourselves stargazing. Our local guide helped us find a constellation, new to us, shaped like a manta ray — a figure that’s woven into Mexican lore.
In that moment, wonderment wasn’t an abstract idea. It was a full-body experience.
When was the last time you felt that? When wonder didn’t just cross your mind — but it was a feeling, and a good one.
Wonder and curiosity are obvious synonyms, and I think it’s one of the greatest characteristics we can cultivate to discover a new shakeup we may need.
It helps you find the thing that leaves you speechless, which is a strange form of clarity. Then, with that awe, you find you might have to chase more of this thing that left you in wonder. What better way to find an intentional hard than this?
5. When was the last time you were truly still, embraced silence, and listened to the wildness within you?
We talked on our trips about how much screentime we have back home. The shallowness of social. How we always have and look for our phones to remind us that someone is out there. We are constantly connected. Connection is a good and necessary part of the human experience.
But sometimes we use it as a distraction to sitting with ourselves. I sometimes notice the irony on our wilderness trips at Unsettled. We are willing to talk about our habits back home with screens, social media, and work — but often there’s a comfort in avoiding sitting still and alone to embrace the silence and listen to the wildness within us.
Stop running. Stop filling. Be still. Listen. There’s something in you that’s been trying to get your attention. There’s probably also something trying to protect you from being alone, get in touch with that part of you, too.
Because the truth is, the hardest journeys aren’t always the ones you’re forced to take—they’re the ones you choose. When there’s no roadmap, no deadline, no crisis urging you forward. Just you, deciding to disrupt your own life in the best way possible.
Let’s go.
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Growth | Meaning | Adventure
