The Thai Teacher
And a new Vision Quest session!
Before you read on, I want to acknowledge the injustice, cruelty, and outright brutality unfolding in America right now. I am not minimizing any of it by sharing a personal story here. And at the same time, I’m choosing—just for this moment—not to bring that collective heaviness into this space, so we can separate the outer world from the inner one and allow a little room to breathe. Consider this a small respite for your soul, if that feels right for you.
Back to reality.
Not all of me is back quite yet - it does take a while for the soul to catch up with the body after traveling through multiple time zones.
But I am back enough to answer some of your questions about our recent trip to my homeland. You want to hear about the adventures, the peaceful Thai temples and beautiful southern beaches. Plus,
How was the food?! How did the kids experience their other cultural half—one that is mostly foreign to them?! How are the fake monks doing?
I’ve answered those questions honestly, for the most part.
What I haven’t shared until now is that, personally, the best part of the trip was not the food, or the beaches. It wasn’t even the incredible Thai massages or the precious family time. Those were all stupendous, but the best part of the trip?
It was Lily.
Lily was one of our guides on the day at sea in Krabi. Downy was the lead guide; Lily was her assistant trainee. With a speed boat, they took us to several islands, hidden beaches, and coves with the clearest waters for snorkeling.
We couldn’t have done the long day without the guides.
Even though I’ve dipped in and out of Thailand over the 38 years since I left, I can recognize a ladyboy right away—and Lily is one.
Ladyboys are people who were assigned male at birth but live as women. The stereotype is that these individuals thrive in the entertainment industry. But in reality, most of them live completely ordinary lives, holding everyday jobs—like becoming a tour guide, which is exactly what Lily was doing.
I don’t know much about Lily’s personal life. If I had to guess, I’d say she’s in her mid-twenties. Lily grew up in Songkhla province (the same one as my father), but now lives in Krabi, where there are more reliable jobs in tourism.
She has long black hair that she kept pulled back in a ponytail—boat rides are brutal on hair. She wore a tour-guide uniform, but her face was exquisitely done: eyelash extensions, beautifully shaped brows, and that perfect red lipstick. She was perfectly put together for a day at sea!
For eight hours, Lily supported Downy through every part of the tour. But her true gift was in photography and videography. She made sure every shot she took of us exuded joy. She searched for the best backdrops and the right light, fixed our hair when needed, and modeled the poses she thought were “cute.” She did it all with such genuine delight that you couldn’t help but laugh, smile, and play along.
“Let’s make Lily happy!” we would yell before each snap.
Never mind the limestone cliffs and turquoise water—Lily was the real spotlight of the day. She was fully herself. Fun. Funny. Unabashed. Unapologetic.
It made me wonder who she might have been if she hadn’t been allowed to become herself. What would Lily’s life have looked like if ladyboys weren’t socially accepted—if she had been forced to stay inside a male body and role, performing a version of boyhood and manhood that never fit?
Instead, Lily broke through that wall, opened all the doors, and chose freedom. She chose to be herself.
Selfishly, her choice gave us one of the most fun and beautiful days of the entire trip!
Can we all feel free enough to do what Lily does?
To live from the inside out?
To break the molds and boxes we were put in, physically and societally, so we can find joy for ourselves in ways that naturally spill into other people’s lives?
Midlife is a beautiful time for this. I don’t just think it. I know it.
Some of us need to debunk the assigned gender.
Some of us need to debunk the assigned paradigms, systems and beliefs.
Some of us need to debunk all the things.
It doesn’t have to happen overnight, of course.
But it does have to happen over time, if we want to experience our authentic selves—and the life with more joy that is still possible for each of us.
If Lily could light up our entire day just by being herself, imagine what you could do for your life, and for everyone you touch, by showing up as the truest version of you.
I hope 2026 is treating you well so far!
With love and gratitude,
xoxo
Kit
P.S. Willow and I are thrilled to open up an additional session for the Chinese New Year Vision Quest!
If you wanted to join, there are still a few spots left for the second session on February 8, at 2pm. Early bird registration for it is open and there are a few spots left!
Join us for a Woo-Way to Welcome Year of the Fire Horse!