Key Takeaways
- When I started traveling the world on my first RTW trip, I planned out everything. Where I was going to stay, what I was going to do. “First I’d visit
- Not only was it fun to plan, but I genuinely thought all of my well-laid plans would guide me along as I traveled the world solo.
- It was only a few days into my trip when I realized that, while planning is important, those plans will quickly fly out the window.
Updated: 08/04/2019 (Originally posted 8/17/11)
When I started traveling the world on my first round-the-world trip, I planned everything meticulously—where I’d stay, what I’d do, and how I’d get from place to place. “First I’d visit X, then take the train to Y, then bus to Z.”
Planning was exciting—and I truly believed those carefully crafted itineraries would steer my journey.
But within days, I realized that while planning has value, real travel rarely follows the script.
Because you’ll meet locals or fellow travelers who urge you to detour to an off-the-map village.
Because you’ll arrive somewhere and fall in love with it—extending your stay without hesitation.
Or conversely, you’ll feel disconnected and leave earlier than intended.
Though planning is useful, what makes solo travel transformative is the profound sense of freedom it offers.
I’ve always leaned toward indecision—weighing options, shifting priorities, pivoting on impulse. And long-term travel doesn’t penalize that; it celebrates it.
When you’re on the road for weeks or months, rigidity fades in favor of adaptability. You make space for spontaneity—the kind that leads to unexpected friendships, unplanned festivals, or quiet moments that reshape your perspective.
That openness changed everything for me on Ko Lipe—a destination I hadn’t even considered before arriving. To this day, it remains one of the most meaningful stretches of my entire journey.
By allowing myself to revise plans, test new ideas, and follow curiosity, I’ve experienced things no itinerary could have predicted. Planning helps you begin—but freedom helps you truly live.
As a child, I dreamed of being “captain of my own ship”: working because it fulfilled me—not just paid bills; traveling whenever inspiration struck; designing a life rooted in flexibility, time, and choice.
Yet adulthood often steers us elsewhere—student debt, career pressure, societal milestones—until suddenly, we’re entrenched in routines that feel less like choices and more like obligations.
One day, you pause and ask: “How did I get here? And why does this feel so small?”
That question led me to step away from conventional paths—and into travel.
The hardest part was leaping. Everything after? Surprisingly simple. What hooked me wasn’t the passport stamps—it was the liberty to wake up and decide, “I’m heading to Ukraine tomorrow.”
Or launch that bakery idea.
Or relocate to Thailand to teach yoga, English, or simply learn to surf.
This reflection surfaced recently as I looked back over a decade of movement and meaning—how easily we absorb external definitions of success, only to realize they don’t align with our inner compass.
Society prescribes a linear path: degree, job, marriage, home, children, retirement. But what if you wake up at 30—or 40—or 50—and realize you’ve deferred joy, passion, and discovery for decades?
Perhaps that’s why midlife shifts happen—why someone picks up motorcycling again, buys a dream car, or switches careers entirely.
For many, travel becomes the first act of reclamation.
Yes, seeing the world matters—but what resonates deepest with most long-term travelers is the liberation: the open horizon of possibility, the absence of fixed timelines, the quiet thrill of owning your time.
That’s also why returning to structured life can feel jarring. Once you’ve lived outside the box, fitting back in feels less like settling—and more like surrender.
I travel to explore cultures and landscapes—but I live this way because each morning, I know I hold the power to walk out the door and choose *anything*.
Right now, that choice expresses itself through travel. In a few years, it may look different.
But whatever form it takes, one thing remains non-negotiable: I won’t trade my freedom—the ability to pursue what lights me up, on my own terms, whenever I choose.
