Gratitude, New Beginnings, and What’s Next

Where to even start? In June, I made one of the hardest decisions of my professional life—I left Valerie Wilson Travel and Chase Travel Group. Walking away from something you helped build, from a brand you poured your heart into, from people who became family? That takes courage. And some days, it still feels like a leap without a clear landing spot.

But I knew in my heart it was the right move. I’m incredibly proud of what we built together—Valerie, Jennifer, Brian, and the entire VWT team created something special. My life has been rich with adventure, global travel, intellectual growth, challenges that deepened our commitment to building a company with integrity. I am forever grateful to Valerie for giving me a chance when she hired me in 1995. This precious brand is in fantastic hands with Chase Travel Group. But it was time for me to spread my wings and try something new. Time to wonder why things are done the way they’ve always been done. Time to ask different questions.

So I took the summer off. Not to escape, but to breathe. To think. To wonder.

And then in the fall, something remarkable happened.

I soft-launched Keep Wondering Why (yes, a playful nod to my initials: KWW) at ILTM North America’s Proud Experiences event, speaking about trans and non-binary travel trends. Standing on that stage, I channeled Ash’s courage with every word. But here’s what made it a real launch: it wasn’t just that I stood on a stage—it’s that I spoke with complete intention, in full alignment with every part of who I am. A mother. An LGBTQ+ advocate. A luxury travel expert. A thought leader who believes transformation begins with curiosity.

For the first time in a long time, all of me showed up. Not the compartmentalized version. Not the ‘professional hat’ or the ‘mom hat’ or the ‘advocate hat.’ All of it. At once. Fully integrated.

That’s what Keep Wondering Why is really about.

November has always been a month of gratitude for me. The changing leaves (though I’m a summer girl at heart), the vibrant colors, the gentle hibernation before winter gives way to spring’s rebirth—it all invites reflection. And this year, more than most, I felt called to pause and say thank you.

If you’re reading this, I’m grateful for you. Whether you’re family or friend, a business colleague, or someone who helped me through a difficult moment—you’re part of my story. You’re part of why I’m here today, doing this work, asking these questions. So this message is for you: thank you for being a part of my life.

This also felt like the perfect moment to share what’s next.

I’m building something I deeply believe in—a company where I can continue making a difference, not just in travel, but in family businesses, family offices, the luxury mindset, and of course, the LGBTQ+ community. I’m excited to speak on main stages and in boardrooms, to facilitate workshops and conversations that don’t rush leaders toward easy answers, but instead invite them to embrace curiosity and ask why.

Because the best transformations don’t come from having all the answers. They come from asking better questions.

As we head into Thanksgiving week here in North America (and I recognize not all of you celebrate this holiday), I want to offer this: it’s a beautiful opportunity to pause. To reflect on the lives we’re privileged to live. To appreciate the choices we get to make. To honor the people we choose to surround ourselves with—the ones who bring smiles to our faces, the ones who challenge us to grow, the ones who make us feel less alone.

So, happy Thanksgiving. Happy gratitude season. Happy pause-and-wonder season.

As we enter the holiday season, please know: I’m grateful for each of you. And if you’d like to learn more about Keep Wondering Why, or if you think I might be able to serve you or someone you know—whether through speaking, consulting, or simply continuing a conversation—it would be my absolute privilege.

With love, gratitude, and endless curiosity,