I used to think freedom looked like a backpack, a one-way ticket, and absolutely no idea where I’d be sleeping three weeks from now.
And for a long time, that was a pretty wonderful definition.
In 2023, I found myself in Essaouira, a coastal town in Morocco, enjoying the particular luxury of having almost nothing on my calendar. I could wake up, wander through the medina, find somewhere to eat, sit beside the Atlantic, or spontaneously decide to head somewhere else.
Nobody needed anything from me. There were no meetings to attend, emails that couldn’t wait, or spreadsheets demanding an explanation.
My biggest professional responsibility was figuring out where to get lunch.
It was glorious.
And after spending years chasing careers, goals, and the usual collection of things we’re told to pursue, I found something unexpectedly satisfying about having no particular place I needed to be.
But as I’ve learned since, freedom has a funny way of changing its appearance depending on the season of life you’re in.
An open calendar and a backpack
I’ve always been fascinated by the different ways people choose to live.
Part of what drew me to traveling in the first place was the opportunity to spend time with people whose lives looked nothing like mine. Different cultures, different priorities, different ideas of success.
I’d meet people who were happiest living close to family, others who had dedicated their lives to building businesses, and plenty who seemed perfectly content doing something the rest of the world might consider completely ordinary.
And then there were people like me, wandering around foreign countries with a backpack, convinced there was something deeply important about catching the next bus.
None of us necessarily had it figured out.
That realization fascinated me.
We spend an extraordinary amount of time absorbing other people’s definitions of a successful life. A respectable career. A certain income. A house. A relationship. The right collection of milestones, preferably achieved in the correct order.
There isn’t anything inherently wrong with wanting those things. I’ve wanted plenty of them myself.
But somewhere along the way, it’s easy to forget that we’re allowed to decide which ones actually matter to us.
Travel gave me the space to question that.
When you’re removed from familiar routines, your usual measures of progress become considerably less relevant. Nobody at a café in Morocco particularly cares about your job title. And if you’re struggling to communicate that you’d like another coffee, your professional accomplishments won’t be much help anyway.
I found that strangely refreshing.
The trouble with having nowhere to be
An open calendar sounds romantic, and often it is. But after enough time traveling, I began noticing something interesting.
Unlimited freedom doesn’t automatically create a meaningful life.
You can wake up anywhere in the world and still feel restless. You can change countries, meet wonderful people, and fill your days with extraordinary experiences without necessarily feeling any closer to understanding what you want.
You also discover that it’s remarkably easy to bring your old habits along with you.
I’d spend an afternoon in some beautiful place, with no deadlines or obligations whatsoever, and still catch myself thinking about whether I was making the most of my time.
Apparently, you can leave the office behind and bring the imaginary performance review in your backpack.
There were moments when I missed having something to work toward. Not because traveling had become less fulfilling, but because I was beginning to understand that freedom and purpose weren’t necessarily competing ideas.
I wanted the ability to explore, certainly. But I also wanted to build things, challenge myself, develop relationships, and feel invested in something beyond my next destination.
At the time, I didn’t have a particularly clear picture of what that might look like.
Which, in hindsight, was probably a good thing.
When life changes the itinerary
A few months before arriving in Morocco, I’d been working in technology sales. I’d recently earned a promotion, was doing well professionally, and had every reason to believe the next chapter would look something like the previous one.
Then I was laid off in late 2022.
It wasn’t a carefully orchestrated departure in pursuit of some grand personal awakening. I lost my job, and with it, a version of the future I’d been expecting.
But the unexpected interruption gave me something I hadn’t anticipated: time.
I decided to return to traveling, something I’d always loved but had gradually made less room for while building my career.
That decision eventually led to a much bigger change than another stamp in my passport.
During that period, an idea began taking shape for a place that combined several things I’d come to value deeply: movement, recovery, meaningful work, and connection.
Eventually, that idea became Gevity.
Espoir and I spent 669 days bringing it to life.
And somewhere between construction problems, financing, permits, hiring, and the endless collection of things nobody mentions when you decide to open a business, I found myself living a life that looked almost nothing like the one I’d been enjoying in Essaouira.
The open calendar was gone.
Very, very gone.
A different kind of freedom
There’s an amusing contradiction to entrepreneurship.
A lot of people start businesses because they want freedom. Freedom over their time, their decisions, their finances, or simply the ability to build something on their own terms.
Then they discover they’ve created a rather demanding job for themselves, complete with responsibilities that occasionally follow them into the shower.
I can certainly appreciate the irony.
Today, I have employees, members, financial obligations, and an entire business that doesn’t simply disappear when I decide I’d rather spend the afternoon exploring a new city.
I can’t exactly throw a backpack over my shoulder and disappear for six weeks without thinking about the consequences.
And yet, in some ways, I feel an entirely different kind of freedom than I did when I was traveling.
There’s something deeply rewarding about putting your energy toward something you believe in, making decisions that reflect your values, and watching an idea slowly become part of other people’s lives.
It’s not the freedom of having no responsibilities.
It’s the freedom of choosing responsibilities that mean something to you.
Of course, there are days when the distinction feels a little theoretical, particularly when something breaks, a problem needs solving, and every item on your calendar seems to have developed three smaller calendars.
But that’s life.
The more interesting part is that I no longer feel compelled to choose between being the person who explores the world and the person who builds a business.
They’re both me.
Different seasons, different definitions
I’ve come to appreciate that life isn’t necessarily supposed to look the same from one decade to the next.
There was a season when I wanted nothing more than to travel with few commitments and as much curiosity as I could carry.
There was another when I wanted to develop my career, learn, and see what I could accomplish professionally.
Now I’m in a season where building something meaningful with my wife occupies a significant part of my time, attention, and energy.
None of those versions feels less authentic than the others.
And I don’t think the goal is to find one permanent definition of freedom and spend the rest of your life protecting it.
What matters to you at twenty-five might not be what matters at thirty-five. And what matters today might change again in ten years.
I’d be more concerned if it didn’t.
I still want to explore unfamiliar places, climb mountains, meet interesting people, and occasionally spend an afternoon doing absolutely nothing productive.
I also want to keep building, creating, and investing in relationships and ideas that require more than a passing commitment.
Sometimes those desires compete for space. More often, I’ve found they make each other more meaningful.
Travel gives me perspective on the life I’m building. Building something gives me a deeper appreciation for the time I spend away from it.
It’s a relationship I’m still figuring out.
Still making room for the unknown
When I think back to that week in Essaouira, I remember how satisfying it felt to wake up with nowhere to be.
I wouldn’t trade those days for anything.
But I also wouldn’t trade the life I’m living now to permanently return to them.
That’s something I couldn’t have imagined back then.
Maybe freedom isn’t about having an empty calendar, living without obligations, or being able to go wherever you want whenever you want.
Maybe it’s having enough awareness to recognize when your priorities have changed, and enough courage to let your life change with them.
Some seasons are for wandering. Others are for putting down roots, building something, or committing to people and things that matter.
And if you’re fortunate, you find ways to make room for a little of everything.
I still have my backpack.
It just takes a bit more planning to use it these days.
