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Small airports hold a peculiar magic—they exist in the present moment while preserving a vision from long ago. For decades, I watched small aircraft come and go from these little strips, until at 49, that pull became a question I couldn’t ignore: what was I missing by staying on the ground? What relationships—what dialogue—awaited me in the sky?
The early hours of flight training in spring 2021 were humbling, even terrifying.
I remember my mother saw my reading and writing at age six was voracious, and I had run out of books. She went to her bookshelf and handed me Martin Buber’s I and Thou, saying, “You’ll understand this someday.” The book spoke of how humans approach the world in two fundamental ways: I-It, where we analyze, use, and experience things objectively, and I-Thou, where we enter into genuine relationships with them. “All real living is meeting,” Buber wrote. Though I wasn’t ready for its truth at six years old, those words would echo through my journey to come.
The early hours of flight training in spring 2021 were humbling, even terrifying. Every landing was a lesson in humility. “The world of It is set in the context of space and time,” Buber wrote in I and Thou. “The world of Thou is not set in the context of either of these.” I was drowning in technical knowledge—V-speeds, emergency procedures, regulations—while the essence of flight remained elusive. But slowly, something shifted. The checklist transformed from mere procedure into a ritual of relationship, a dialogue between pilot and machine.
Those first lessons took place in the forgiving Cessna 172—with its vinyl seats worn smooth by countless students before me—which became both classroom and confessional.
Expanding Horizons
By late 2023, the journey led to more ambitious horizons—marathon Texas cross-countries that tested both technical skill and spiritual resolve. Threading between thunderstorms over San Angelo, watching lightning arc through distant clouds, or navigating tricky approaches into Marfa, every decision became a dialogue between capability and conditions. Flying through Big Bend country, watching sunset paint the desert in impossible colors, I finally understood what Buber meant when he wrote, “All real living is meeting.” The high desert has a way of making you feel incredibly small and surprisingly capable all at once.
On long cross-countries from Fort Smith to Marfa, I watched the land transform—from arid desert to fertile plains to the green sweep of the Mississippi Delta. The aircraft became more than a machine; it became a partner in exploration. “The world is not comprehensible, but it is embraceable: through the embracing of one of its beings,” Buber wrote, and mine led not just to mastery of flight, but to a continuous dialogue with the sky itself. Each flight added new layers of understanding—the way morning fog clings to river valleys, how afternoon thermals dance over mountains, the particular way crosswinds speak to the wings.
The logbook’s precise columns document the quantifiable journey—hundreds of landings across dozens of states, from grass strips to major airports. But they can’t capture the real transformation—the gradual shift from seeing flying as a technical challenge to experiencing it as an ongoing dialogue. They don’t show the magic of sharing first flights with friends and family, like that perfect summer evening city tour in August 2023, watching faces light up as Nashville’s skyline glowed below. As Buber noted, “When two people relate to each other authentically and humanly, God is the electricity that surges between them.”
Those logbook entries—dates, aircraft tail numbers, airports visited, hours logged—form a skeletal record of experiences whose true essence exists in memory and sensation.
Each passenger’s first flight with me became what Buber described as a direct relation where “no system of ideas, no foreknowledge, and no fancy intervene between I and Thou”—shared moments of genuine encounter. BBQ runs to Muscle Shoals turned into philosophical discussions at altitude. Weather diversions became opportunities for deeper understanding, chances to share not just the technical aspects of flight but its profound impact on the soul.
Finding the Eternal
Some of the most profound moments have been the simplest—those late-night patterns under the stars, the quiet early morning departures when it feels like you and the airplane are the only things awake in the world.
The numbers tell one story—600 hours, many hundreds of landings, countless destinations. But the true measure lies in the moments between: the smooth landings at distant fields, the dance with crosswinds on mountain approaches, the quiet communion with sunset at cruise altitude.
Now I understand what Buber meant when he wrote, “All real living is meeting.” In these moments, the boundary between I-It and I-Thou dissolves. The sky ceases to be merely airspace to navigate and becomes instead a presence to encounter. Through every hour logged, every challenge met, every moment shared with others seeking their own conversation with the infinite, I’ve learned what Buber knew: that true flight, like true life, is not about mastery or control, but about entering into a genuine relationship with the world above. “In the beginning is relation,” he wrote, and in the end, that’s what these 600 hours have taught me—that flying is not just about moving through the air, but about entering into dialogue with the sky itself.
- What the Sky Taught Me - May 19, 2025
Brian,
Thanks for sharing.
Thanks Dean!
Love your YouTube channel! Great article! Thanks!
Thanks Greg!
Great article Brian! Love the podcast and the community!
This article reminded me of the days past when I was flying my Cessna 337 Skymaster back and forth from Saginaw MI to the home base of Grand Rapids MI often – many times late at night when ATC communications were sparse and the lights both on the ground and in the sky were twinkling. I had accomplished a number of significant maintenance items over the few years of ownership myself thanks to a partner owner who had his A&P license and could sign off. Thus my relationship with this plane extended to more than just piloting. As I was flying along at 3AM one night, the thought suddenly came to me that this airplane was more than just a machine to own and operate. It was a real friend – and it had a soul that touched me in that respect weird as that may sound. Other humans had invested honorable time to design, build it, and make it available for my use. Their souls were invested and I was sensing them as well. I began to feel that this machine could be trusted to let me know if it had any aches and pains that would need my attention. After arrival at my hangar, I got out and patted the front cowling on the way to the hangar door. It was my pal!
So true, unlike a car that can malfunction but that alone would rarely cost you your life caring for an aircraft like a friend or loved one is fitting IMO.
Great story thanks for sharing!
I didn’t even notice the author’s name as I started reading this story, but as I neared the end, I thought, “Gosh, this sure sounds like something Brian Siskind would say.” Sure enough! Well said, Brian. You perfectly put into words what flying is for me. Marcus Tyrrell, aka Fiftyx60.
Small world! So awesome I really appreciate it.
Great piece Brian! So well written and lyrical. I might steal your line about a checklist being a dialogue between the pilot and the airplane. Also, I want to hear more about your mom and her bookshelf! Wow.
You are an inspiration sir!
Brian, so inspirational! Your personal reflection reminded me of a book I read many years ago titled “The Flying Mystique”
by Bauer. Because of your writing, I purchased ‘I and Thou’ and look forward to reading it. Thank you for your story.
That’s great to hear. I have enjoyed revisiting it!