For the love of travel: Olegana Travel Boutique’s origin story
Guest blog post from Felicity Leo
When I first met Anna, Olegana Travel Boutique hadn’t yet been born as a business. But even then, I was lucky enough to experience the same enthusiasm, professionalism, and zest for life that she now pours into every trip she curates.
In Episode 17 of the Sign Your Own Permission Slip podcast, inspiringly titled “Permission to Travel and Take That Vacation,” host Anna Fishman, founder of Olegana Travel Boutique, engaged in a powerful conversation with business coach Sarah Walton about the transformative power of travel for women.
Anna shared her deep passion for making meaningful travel experiences more accessible—especially for women craving a break from the everyday routine.
“Travel. It’s always been travel. I travel to forget, I travel to celebrate. I just travel.”
— Anna Fishman
That sense of purpose truly lit the path to what would eventually become Olegana Travel Boutique. After a thriving career in tech advertising and compliance, Anna boldly and courageously stepped away from the corporate world to pursue her true calling: travel!
With the unwavering support of her husband, Oleg, she planted the seeds for what would grow into a flourishing and impactful travel company—one that emphasizes custom travel planning and curated group trips for women.
Anna’s story is a powerful reminder of what can happen when you trust your intuition, embrace change, and give yourself full permission to explore the world on your own terms.
From wanderlust to a thriving business: creating a travel company for women and solo travelers
Writing about it now, it might come across like one of those easy-breezy start-up success stories we’ve seen glorified all over the media lately. But while Anna’s story is definitely inspiring, her path—from passion to purpose, and eventually to successful business owner—was anything but effortless. Building something meaningful from the ground up, especially in such a grassroots way, takes guts. It’s not for the faint of heart.
I still remember when we both worked at a recently IPO’d tech company—one known for its innovation and all the perks of a scrappy startup culture. It was a fast-paced world powered by creative, out-of-the-box thinking, quick decision-making, and the reality of everyone wearing multiple hats. I truly believe that environment helped further spark Anna’s drive to forge her own path and launch the incredible business she runs today.
After earning her MBA and juggling the roles of wife and new mom, Anna began seriously thinking about how to start something of her own. She half-jokingly credits Google’s search engine with helping steer her in the right direction. In those early days of 2016–2017, she realized that building her own business would also give her the gift of time—time to be fully present as a new mother. Once she pushed past those initial hurdles, what followed was a journey of growth and personal transformation.
But why travel?
What can you say about a girl who bravely came to a new world—and then made it her own? She grew up to build a life full of rich travel experiences and meaningful connections.
In a recent podcast, Anna reflects on her journey immigrating from Ukraine to the United States as a child, alongside her parents and grandparents, 25 years ago. She beautifully emphasizes the power of owning your story — and the strength and empowerment that come from sharing it.
With honesty and heart, she opens up about the challenges they faced and the personal growth that followed — the self-discovery, transformation, and inner resilience that shaped who she is today.
That same warmth, entrepreneurial spirit, and relatability now shine through her fun, thriving company, Olegana Travel Boutique.
Give yourself permission to explore.
Whether it’s your first solo adventure or your next unforgettable getaway, Anna and her team will guide you every step of the way — with expert planning, stunning destinations, and deeply personal touches that make your journey feel uniquely yours.
You’re not just booking a vacation — you’re unlocking a new chapter of your life, filled with discovery and unforgettable moments.