CEO of my Own Itinerary: Owning the World One Solo Trip at a Time
- Torri Ylan
- Sep 4
- 5 min read
If there’s one thing I’ve learned over the years, it’s that life has a way of trying to put you in a box. I’m an unmarried Black woman with no children, and for most of my life, I’ve had a very demanding career and pursued continued education and professional development with everything I had. My days were more often than not filled with deadlines, meetings, late nights, and the constant feeling of having to perform for others. Corporate life can be rewarding, yes, but it can also be draining—always running on someone else’s schedule, always meeting expectations that aren’t your own.
That’s why solo travel became so much more than a vacation for me. It became a lifeline. A way to step outside of those invisible walls and reclaim control over my own time, my own choices, and my own story.
Let’s be real: traveling alone as a Black woman can raise eyebrows. I’ve had people question my safety, my sanity, and sometimes even my purpose. But that only fuels me more. Too often, society tries to define what women—especially single women without children—should or shouldn’t be doing with their lives. I’ve been told to “settle down,” to stop “chasing experiences,” and to think about a future that fits neatly into someone else’s definition of success.
But here’s the thing: my life doesn’t need to look like anyone else’s. Traveling solo allows me to write my own narrative, one passport stamp at a time.
Why Solo, Sister?
When people ask me why I travel alone, my answer is simple: because it’s the purest form of freedom I’ve found. When I board a plane (or train) solo, there’s no one to consult with about where to go, what to eat, or how long to stay. I move at my own pace. I create my own adventures. I wake up and decide if today will be a day of rest on the beach, a 10-mile hike up a mountain, or wandering through streets I can’t pronounce but will never forget.
As a woman who has always been expected to show up for everyone else, traveling solo is my act of rebellion. It’s me saying: I choose me.
Empowerment Through Exploration
Traveling the world alone hasn’t always been easy. There were times I got lost (and I mean really lost). There were language barriers, culture shocks, and moments of doubt. But every challenge became a lesson. Every wrong turn eventually led me to something unforgettable—whether it was stumbling upon a hidden beach with dozens of sea turtles in Kona, Hawaii or getting to be an impromptu co-pilot of a Cessna in Belize.
These moments shaped me. They reminded me that I am capable, resourceful, and resilient. That empowerment stayed with me long after I returned home and logged back into Zoom calls and PowerPoint slides. Solo travel helped me realize that freedom isn’t just about where you are, but about the mindset you carry with you.
Lessons From the Road
Every trip has given me something unique, but here are a few lessons that stand out:
Self-Trust is Everything. When you’re halfway across the world and something goes wrong, you learn to trust your instincts quickly. That same trust has spilled into my professional and personal life. I get more and more courageous with every adventure.
Dubai, 2015 Time is Precious. Corporate life taught me to give my time away freely. Travel taught me to guard it fiercely. I now think more intentionally about how I spend my hours and who I spend them with.
Cancun, 2021 The World is Kinder Than We Think. Despite the news cycle, I’ve met strangers who became friends, shared meals with families who barely spoke my language, and been offered help without asking. Humanity is alive and well if you open yourself to it.
You Can Be Alone Without Being Lonely. There’s a deep difference between solitude
and loneliness. Solo travel helped me embrace solitude as a gift rather than something to fear.
Thankful for Ms. Ross
One of the most validating moments in my journey as a solo traveler came when I saw Tracee Ellis Ross launch her recent show on Roku about her solo travel experiences. Tracee is someone I deeply admire—not just for her career, but for the way she embodies independence, joy, and authenticity. Watching her highlight her own solo adventures felt like she was speaking directly to me. It was a reminder that I am not alone in this journey and there are other women who, despite the whispers of doubt and disdain, embrace the freedom and joy that can come with being at one with exploring the world.
Her openness about choosing solo exploration resonated with me because it put a spotlight on something I’ve been living for years: that there is beauty, strength, and deep fulfillment in carving your own path. Seeing her celebrate that on such a visible platform made me feel seen. It validated the choices I’ve made to embrace freedom through travel and reminded me of the importance of sharing my story, too—because someone else out there might need that same validation.
Choosing Myself, Inspiring Others
When I share my journeys, I do it not just to document pretty photos or check destinations off a list. I do it because I want other women like me—single, career-driven, educated, and sometimes overwhelmed—to know that it’s okay to carve out your own version of freedom. You don’t have to wait for the right partner, the perfect timing, or anyone else’s permission. Your life belongs to you, and you deserve to live it on your terms.
That’s what my blog, The C-Suite Contradiction, is all about—challenging the narrative that success only looks one way. Because success, to me, looks like waking up in a different country, sipping coffee in a café, and smiling at the realization that I built this moment for myself.
For me, solo travel isn’t just about seeing new places—it’s about stepping into my power, again and again. It’s about proving to myself that I am enough. And it’s about inspiring others to realize they are, too.
If you’re reading this and you’ve ever dreamed of packing a bag and going it alone, let me tell you: do it. Take that trip. Book that flight. Trust yourself enough to explore the world on your own terms. It doesn’t matter if it’s across the globe or just a few hours away. What matters is that you choose yourself.
So here’s to owning our itineraries, living boldly, and writing our stories without apology.
Stay tuned for the companion post about the amazing rail systems in Europe and the freedom (and feeling of safety) it gives a solo-traveler like myself.
About the Author
Torri Ylan Smith is a dynamic leader in business, technology, and lifestyle. Throughout her career, she has led exceptional design teams in Engineering and Technology, driving innovation across multiple industries. She holds a Bachelor of Science in Environmental Engineering and an MBA from top-tier universities.
At this stage in her journey, Torri is dedicated to mentoring and sharing her expertise with emerging business and technology professionals. In her free time, she enjoys traveling the world, taking reflective solo walks, exotic beaches, being creative, nurturing her many plants, experimenting with new recipes, and cherishing moments with her chosen family.
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