Ground Control to Major Dream: Damien's Leap

The Work Dreams We Don’t Outgrow

Damien and some of his pictures from up above.

You make trade-offs to build a work life you love. You pour your whole heart into it. You take risks.

My father was obsessed with flight. Late in life, he got his license, splurged on a small Piper hobby plane, and bought cheap land in Paraguay to fly there and back and — in the in-between, become a farmer. His passion-filled bet didn’t pay off, so he sold the farm and the plane.

Damien Roemer, a colleague who had left Google a few years before I did, brought my dad crashing into my mind last year when I came across a post (to the tune of La Vie de Rêve) he’d shared: stunning photographs taken from a commercial pilot’s point of view.

Like my father, he was obsessed with flight. Unlike my father, he turned it into a life.

I Always Wanted To…

I reached out to Damien. As far as he could remember, "pilot” was how he’d answered the "what-do-you-want-to-be-when-you-grow-up" question. No hesitation.

As it happens, life got in the way.

"The dream began to blur, to seem too complicated, too out of reach, not meant for someone who didn’t know anyone in the industry. On top of that, flight school was expensive. It’s not for me, he told himself.

He found another way to succeed. He graduated from business school, traveled the world, worked as an intern at the French Embassy in Washington, D.C., and later settled in Paris as a communications specialist. Eventually, Damien joined Google's comms team. He started to build a family.

Then, he turned 30.

He thought: now or never. And he decided to start again.

Flight, Freedom, and Fear

Flight and freedom have been "metaphorically” connected since Icarus donned wings of wax. Peter Pan, Jonathan Livingston Seagull, E.T., and Mary Poppins all use flight to tell stories about eternal youth, escape, personal growth, breaking with the constraints of the adult world, and magical escapism.

Erica Jong's "Fear of Flying" is a metaphor for sexual liberation, tinged with the terrifying notion of letting go and surrendering. Its evil twin is the “fear of failing.”

Flying, falling, and failing all stir similar gut-deep feelings. They flirt with freedom, risk, and the dizzying pull of letting go. To fly is to defy fear and the limits that keep us grounded.

My father may have been flying away. Damien was flying towards something.

Wonder, with a Side of Guilt

“Google is an incredible company to work for,” Damien told me. The colleagues are brilliant, the pace is exhilarating, the resources vast, and the compensation generous.

But, as he put it, there’s a cost: “It’s hard to leave.”

That’s a common thread among those who’ve left, whatever their reason. You don’t just walk away from a job; you walk away from community, identity, and momentum.

And sometimes, you walk straight into guilt.

For Damien, it came from choosing a path that, as he climbed up the ranks in the beginning, took him away from his young children for long stretches. Piloting, he said, can be a selfish job. It took time to come to terms with that. His first job with Ryanair in London meant being away five days a week.

I couldn't justify it as something I was doing for them—I was doing it for myself," he said.

He hung in there and today flies for Air France, piloting across ever-changing landscapes—from the Alps to the Pyramids to the deserts of North Africa. He hasn’t lost any of the wonder that pulled him in to start with. Good for Damien.

Pursuing a work life you love is about finding what you want to do, actually doing it, risking failure, and feeling the guilt of choosing for yourself.

Resist the blah-blah that you only need courage and hard work to succeed. So many other variables shape career outcomes: timing, network, luck, and, when risk-taking ends in failure, whether or not you have a cushion to fall on.

As I think about Damien and my dad, I've asked if I had a dream.

For a while, I wanted to be a diplomat so that I could travel the world and solve "world peace." I also wanted to be an astronomer — so I could travel the universe, I guess? I ended up in journalism and communications because my dad nudged me in that direction when I couldn't decide what I wanted.

Only now, twice Damien's age, I am restarting as a writer.

I love it, but I would be lying if I told you I write without concern about who my words are reaching. There are weeks when I post an essay, and all I hear is crickets: no comments, no dopamine-inducing "likes," zero new subscribers to this Substack.

Last week, a dear friend told me she reads every essay of mine. Then, my heart cracked a little when she asked, "Does AI write them?"

If there's a lesson to be had from Damien's story, it's not only how he dared the fates and took a leap to pursue a dream — paid the tolls and succeeded — but also how he had a dream he never let go of.