Dear ones,
The bad news is we're all falling. The good news? There is no ground.
When I first heard this Zen koan, it felt obscure. Soon after, the ground disappeared beneath me. After fifteen years building and leading an organization that felt like the whole of my identity and life's work, I found myself (suddenly, shockingly) untethered…and reeling. The uncertainty was dizzying, but forced me to make a choice: I could scramble for solid ground, or embrace the expanse of an open sky.
For decades, I'd championed stepping off life's well-trodden paths. Now it was time to practice what I'd preached.
My husband Joel and I pulled our young boys out of school, packed our house into the attic and our gear into a few carry-ons. We left home to spend a school year on the wild edge of possibility: learning in new contexts, living in new ways, looking out from as many perspectives as possible. We had few plans, and even those we held loosely. My hope was to heal, reflect, and prepare to begin….again.
Along the way, something surprising happened to my relationship with writing, too. I found myself waking before dawn, smiling at the same cursor I used to curse. "You can't pretend you hate writing when you get up early and no one's watching," Joel observed after months of this routine. He had a point 😉
After a professional heartbreak that had nearly swallowed me whole, I was writing from a new place – from love, from hunger, from delight. The impact was profound: it taught me to trust again, breathe again, be again. The process showed me the way back to myself and, eventually, a more expansive vision: reimagining what's possible when we dare to learn – and lead – on purpose.
That’s why, in 2024, alongside my brilliant cofounder Chalon Bridges, I launched The Flight School – a rebellious rite of passage for our next generation dreamers and do-ers. In a world dazzled by artificial intelligence, we're reinventing the transition after high school to unlock what makes us authentically human: our capacity for wisdom, courage, and freedom to fly.
It's the opportunity I wish I'd had at 18 when I finished high school with a sinking sense that school had taught me many things, but not the subject that mattered most: myself. I'd played the game well, and won the golden prize – Stanford! But standing at the finish line the achievement felt hollow. In all that striving, something essential had been lost. I couldn't shake a nagging question: Whose race was I running?
The world has changed dramatically since then – but our approach to school hasn't. High school is still a high-stakes race to college. We still teach to tests that AI can now pass in seconds. We still expect students to choose majors before they've found their missions.
We created The Flight School to break this cycle. Our campus is in the cloud, our curriculum is real life, our re-imagined faculty are the world's most inspired and impactful leaders. And importantly, our students don’t graduate with a piece of paper — they take flight, with a compass in hand.
While The Flight School focuses on the magical moment between high school and what comes next, the art of turning transitions into transformations spans every age and stage.
As word spread, something unexpected and beautiful happened: parents, educators and leaders from around the world began reaching out to ask: "Can I join, too?!"
Their question felt familiar. Aren't we all searching for an education higher than higher ed? A way to discover what breaks our hearts and lights us up? A path to become more alive, calm, grounded and free?
This community is my answer.
We're never too old to learn to fly – not as an escape from reality, but as a portal into it – and I'm convinced it's the most essential and regenerative skill we'll ever need.
I'm creating this space to gather those of us who sprinted from the classroom to the boardroom without pausing to ask which race we were running. For the achievers who feel overwhelmed and underwhelmed at the same time. And for those wondering if it's too late to hit CTRL-ALT-DEL and reboot our lives.
It's not.
Whether you're navigating a disorienting transition, or simply sensing that there’s more to life than the endless hustle - you’re in the right place. These are your people. We are your people.
Courageous tricksters who will call it when the emperor has no clothes.
Impatient optimists ready to re-define success on our own terms.
Dreamers and do-ers determined to envision a more hopeful and humane world — and to get to work building it.
Each month, I'll share field notes from building while flying – insights from wise teachers, ideas that light me up, practices that stretch and sustain me.
Because the world has never changed this fast, but will never change this slowly again.
We’re taught to follow the leader, but we were born to fly.
Will you join me?
Abby
This community is LITERALLY both an answered prayer and dream come true. 🫨🤓😎
Thank you, Abby. 🙏🏾🙏🏾
I’m ready to fly. 🫡🚀
💫
Hope there’s room for an Elder on this spaceship♥️