Do big dreams die slowly?
It’s midnight. I’m sitting here thinking about pulling the plug on something I’ve given 20 years of my life to. And it doesn’t feel dramatic. It feels quiet. It feels sad, if not resolute. And that’s how I know it’s time.
This isn’t a story about failure. It’s a story about honesty.
It Started With a Spark
Twenty years ago, I read about two guys dreaming of electric cars zipping around Silicon Valley. I thought they were crazy. Then I drove one. Then another. And just like that, I was hooked.
I started writing about electric vehicles before most people knew what they were. I wasn’t a polished writer. My editors weren’t happy. But I was enthusiastic, and I learned fast. I shot videos. I built an audience. I thought I’d found my calling.
Then I made the jump to electric air mobility — aircraft that don’t burn jet fuel, that move people quietly and cleanly through the sky. I was welcomed into the industry. I traveled the world. I spoke at events, chaired sessions, and moderated panels. I have a drawer full of lanyards to prove it.
Three Big Breaks That Broke
I got three real shots at making this my career.
The first was a communications role with a well-known startup. I walked in with everything I had. Three months later, I was out the door — no warning, no real explanation. Just gone.
The second was a position with one of the biggest nonprofits in the space. Six months in, my biggest ally became my biggest problem. I was let me go at an airport, four hours before my flight. The parting words were: “It’s business, not personal.” That didn’t help.
The third put me in a Chief Strategy Officer role. Big title. Not much substance. No one was listening to the strategy. A young leader stepped in, things fell apart, and I walked out on my own this time. Eight months later, the company folded.
When Loyalty Becomes a Trap
Here’s the thing nobody tells you: passion can become a prison.
You hear it all the time — dream big, keep going, believe. And yes, there’s truth in that. But dreaming big was always meant to travel alongside reason. At some point, you have to ask the hard questions: When do you call it quits? When is enough, enough? When do you draw the line?
I kept going because someone once told me I never stuck with anything. And instead of brushing it off, I believed them. I felt small. I thought they saw something in me I couldn’t see myself. So I held on — not out of strength, but out of a quiet fear that they were right and I was wrong.
They weren’t. Life had been presenting me with real moments of magic all along — and when they came, I recognized them, I took them, and I did well with them. The mistake wasn’t in following those sparks. It was in staying too long after the flame went out.
But there’s a difference between perseverance and punishment. Perseverance is pushing through temporary difficulty. Punishment is what happens when you keep going just to justify what you’ve already spent. Twenty years without sustainable income is a clear sign something isn’t working.
The other website has been up for three years. The other podcast in its second season. One sponsor in over a year. The phone doesn’t ring much.
At some point, the numbers tell you what the heart doesn’t want to hear.
This next chapter is a little bit of both: magic, because something new is already taking shape, and wisdom, because this time I know the difference.
So When Do You Actually Walk Away?
I’ve been thinking about this a lot. Here’s what I’ve landed on.
You walk away when the effort is no longer teaching you anything new. You walk away when the sacrifice is hurting people around you, not just yourself. You walk away when you’ve honestly tried — not just once, but many times, with real adjustments — and the door stays closed. You walk away when the elevator doesn’t come back.
You don’t walk away because it got hard. You walk away because staying has stopped making sense.
The One Question I Never Asked
Sixty years of jumping in. Languages, computers, networks, real estate, electric cars, aircraft. From the south of France to Japan to New York to Los Angeles to Savannah. One leap after another, most of the time without knowing how I got on the plane, let alone where it was going.
And in all of that, I never once stopped and asked the most important question. Not to the industry. Not to the market. Not to a mentor or an editor or a boss.
I never asked myself. The human. The one underneath all the doing.
We talk a lot about being spiritual beings having a human experience. Or we go the other way — purely practical, driven by goals and grit, no room for feelings. But the truth is somewhere in the middle and both. There is a spirit, yes. And there is also a human being. One who gets tired. One who carries resentment without naming it. One who has wins and flaws and a full emotional cocktail that nobody checks in on.
That night, sitting in the dark, watching shadows from the trees slowly across my window, I finally asked.
How are you feeling?
The answer came quietly. Tired. Worn out. A little angry. Sad. And mostly — surprised. Surprised that it took 60 years for me to ask.
I gave the human in me something I had never given it before: space. I didn’t rush it toward a solution. I didn’t reframe it into an opportunity. I just let it be. Let it feel. Let it arrive at its own conclusion, on its own time, in its own way.
And something I didn’t expect happened. I felt whole.
Not fixed. Not launched into the next great thing. Just whole. Complete. Quiet. Tired. Serene. I didn’t feel the pressure to perform for anyone — not an industry, not an audience, not even myself.
That’s what I want to leave you with more than anything else in this article. Not the timeline. Not the three jobs that didn’t work out. This:
How often do you talk to the human in you? How often do you stop — really stop — and ask how it feels about the life it’s been living? How often to you give the space and honor it?
It doesn’t need a big answer. It just needs to be asked.
What Comes Next
My wife and I are going to buy a business. Something real. Something local. Something where the work shows up on people’s faces in a tangible way.
Maybe that sounds like trading in a dream for a spreadsheet. But I think there’s more wisdom in serving people close to you than in chasing a vision that was never quite within reach.
Ancient traditions understood this. There is no shame in redirecting your energy. The shame would be in staying out of stubbornness while life waits quietly on the other side of the door.
The light’s going off. And for the first time in a long time, I feel okay about that.
Perhaps big dreams die slowly.
Have you ever walked away from something you loved? What helped you know it was time? Share in the comments.