Welcome to Fly With Ian. This is my story – and it starts with a dream that refused to die.
Life is not linear.
It has a beginning, and an end. But, ultimately, it’s a choose your own adventure story.
Someone I looked up to in college told me that once, and it’s shaped how I see everything since. Including how I ended up here, at 35, finally chasing the dream that’s been with me since I was a kid.
The Broken Beginning
Picture this: early teens, and I’m handed an old, broken, incomplete radio control airplane. Most people would see junk. I saw possibility.
For years – my entire teenage years, actually – that plane never successfully flew for more than a few seconds. But I kept trying. I kept believing that somehow, someway, I’d figure it out.
It’s funny how the universe works. That “failure” led me to discover the Titusville airport, where they had a grass runway that somehow – and I still don’t know how they allowed this – let us fly our RC planes.
Finding My People
That’s where I met them. The older pilots who became my unexpected mentors and friends. Dick Saxton stands out among them. He had just jumped into the hobby himself, but his passion was infectious. While I shared my technical knowledge with him, he shared something more valuable – the pure joy of flight.
Those afternoons at Titusville changed everything. Being around real aircraft, hearing the stories, watching planes take off and land… it sparked something deeper. A desire to learn to fly real aircraft.
But life, as it tends to do, had other plans.
The Winding Path
Fast forward through undergrad, grad school, divorce, and restarting life as an intern at Disney. Life became a rollercoaster – and not the fun kind.
The financial reality was harsh. There were weeks when squeezing money together for groceries was a challenge, let alone pursuing something as expensive as flight training. When you’re counting every dollar just to make it through the week, a $15,000+ pilot’s license feels like an impossible dream.
I’d see planes overhead and feel that familiar tug, that longing. But then I’d look at my bank account and reality would crash back in. Flight training wasn’t just expensive – it was a luxury I couldn’t even begin to consider.
So I put the dream on the shelf. Not abandoned, just… waiting. Waiting for life to stabilize, for finances to improve, for the right moment when I could finally afford to chase what I’d always wanted.
Dreams, it turns out, are patient. They wait.
During those Disney years, I learned about magical moments – those fleeting instances that most people see as inconsequential but that can change everything if you’re paying attention. I was always looking for those moments, writing about them, trying to capture what made them special.
I just didn’t realize my biggest magical moment was still coming.
The Gift That Changed Everything
Christmas 2022. My fiancée (now wife) surprised me with a discovery flight out of BVY.
I can’t adequately describe what it felt like to finally be in the left seat of a real airplane. That broken RC plane from my teens, those afternoons at Titusville, all those years of dreaming – it all came rushing back. But this time, it was real.
Then, Christmas 2023. Another surprise. A Bose A20 headset.
But here’s the thing – it wasn’t just the gifts. It was what they represented. For the first time in my life, I had someone who wasn’t just tolerating my dreams but actively pushing me toward them. Someone who saw that this wasn’t just a hobby or a whim – it was part of who I am.
She believed in this dream even when I couldn’t afford to believe in it myself.
She’s been enabling my goals even when they’re difficult, expensive, and inconvenient. Something I’ve never really been afforded before. And more importantly, she’s been patient while I worked to get to a place where we could finally make this happen financially.
Why I’m Sharing This Journey
So here we are. I’m 35, I’ve started ground school with The Finer Points app, and I’m working through my knowledge test before beginning flight training.
I’m sharing this journey because I believe in the power of authentic stories. Not the highlight reel, but the real stuff – the struggles, the setbacks, the small victories that might seem inconsequential to others but mean everything to the person living them.
I want to document the magical moments I find in ground school (yes, they exist), the anxiety of first flights, the frustration of difficult landings, and hopefully, eventually, the joy of earning my wings.
But mostly, I want to show that dreams don’t have expiration dates. That life isn’t linear. That sometimes the path to your destination is longer and more winding than you expected – but that doesn’t make it any less worth taking.
What’s Next
I’ll be sharing my ground school progress, the resources I’m using, the concepts I’m struggling with, and the moments that make it all worth it. When I start flight training, you’ll be there with me – for the good flights and the not-so-good ones.
This is my choose your own adventure story. And I’m finally ready to turn the page.
Welcome to Fly With Ian.
What’s your aviation story? Have you always dreamed of flying, or did you discover it later in life? I’d love to hear from you in the comments below.
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