Reconciling Dreams
When the dream you’ve worked toward no longer fits, what do you do next?
I knew from a young age that I was drawn to business. I’d watch my dad build his companies, and I was always curious—how did he do it? Who helped him? What were they trying to achieve? I was fascinated by the whole process. It wasn’t just about commerce—it was about vision, creation, leadership. It felt alive.
By my teenage years, that curiosity turned into something bigger. I remember getting a subscription to Fortune magazine and reading it cover to cover every month. The stories in those pages helped shape a dream. I wanted to build something meaningful. And over time, that dream became even more specific: I wanted to become the CEO of a Fortune 500 company.
That dream stuck with me. At one point, I even printed out a mock cover of Fortune with my face pasted onto it—just something created as a lighthearted, visual reminder of what I was aiming for.
And I worked toward it. Early in my career, I landed at General Electric while Jack Welch was the CEO. It was a masterclass in corporate leadership. From there, I moved into management consulting at PricewaterhouseCoopers, working with some of the most respected businesses in the world. Throughout my 20s and into my 30s, I poured myself into my work. I was gaining experience, growing closer to that dream, and proving—to myself more than anyone—that I could get there.
But life, as it does, started to evolve. I got married in my late 20s and started a family in my early 30s. That introduced something new: a competing dream. I wanted to be a great husband. A present father. A reliable friend. I wasn’t walking away from the dream—I was just feeling a different kind of pull.
Then came a moment I didn’t expect: lunch with the CEO of a Fortune 500 company.
I was working for a large, public company at the time and had the chance to sit down one-on-one with the CEO. We started with business. What it took to get there. What leadership really looks like at that level. I was all ears.
When I asked about his family, he paused for a moment before answering. “I have a son,” he said, then added, “but I’m not married anymore.”
There was a quiet honesty in his tone, and I could tell it wasn’t just a line he had repeated in passing over the years. This part of the story still lived close to the surface.
He told me that one day, after many years of marriage, he came home from work and his wife asked for a divorce. He hadn’t seen it coming. There was no dramatic fight or slow unraveling he could point to. Just a moment—a conversation—that upended everything.
“I was blindsided,” he said quietly.
He looked down for a second, then continued. “She told me, ‘You’re never around. Work is always your priority.’”
Those words stuck with him. You could hear it in the way he said them—not with bitterness, but with the kind of clarity that only comes when you’ve had time to process something you once didn’t understand. He wasn’t just recounting what she said. He was acknowledging it.
I asked how things were with his son. He paused again, then said, “Not great. We’re not close. I wasn’t around much.”
There was no anger in his voice—just honesty. He was clearly reflecting. And then, he gave me a window into the reality of his role.
“This job,” he said, “is always on. 24/7, 365. We operate on multiple continents. When something goes wrong, even at 2 a.m., I get the call. That’s the responsibility—to the team, to the company, to the shareholders.”
He wasn’t complaining. He had chosen that path. But he was also showing me the cost.
As I looked across executive leadership teams at large organizations, I saw a pattern. Lives deeply committed to work, often at the expense of everything else. And to be clear—I’m not judging that. These are people who made a choice. They chose their craft. And many of them are exceptionally good at it.
But I couldn’t ignore what I felt.
That lunch was a pivot point for me. For over 20 years, I had been holding onto this dream. And in that moment, I started to ask—is this still the life I want?
The answer didn’t come quickly. It took time, reflection, and even a little grief. Letting go of a dream—even if it no longer fits—isn’t easy. But as I looked at my family, my friendships, and what truly mattered to me, I realized something important:
Dreams evolve. And that’s okay.
When I first imagined being a CEO, I couldn’t have predicted what it would mean to be married. Or how I’d feel once I had kids. Or how much joy there is in simply being home for dinner. That version of me—the teenager reading Fortune—couldn’t have known. But I know now.
And I don’t see it as abandoning a dream. I see it as refining it.
I still believe I had the DNA to be a great CEO of a large company. The drive. The stamina. The curiosity. But I also had competing values—and that’s where the real challenge lived. Navigating the tension between personal and professional ambition is hard. But being honest about it is freeing.
So, if you’ve ever found yourself revisiting a long-held dream, wondering if it still fits—you’re not alone. It’s not a failure to change course. It’s wisdom. Take stock. Be kind to yourself. Life changes. We change.
And sometimes, letting go of one dream makes space for another.
Which brings me to something that makes me smile. After more than 25 years of subscribing to Fortune magazine, I finally let the subscription go a few years ago. But one of my favorite parts of the magazine—the thing I’d flip to first—was always the last column written under the pen name Stanley Bing. They were funny, sharp, and business-savvy—with a wink.
It’s ironic, really. Because now, here I am writing Rivr Notes—humble little articles with a tone that (maybe?) Stanley Bing helped inspire. Who knows, maybe he was in my head all along.
Funny how dreams evolve—and sometimes come back around in unexpected ways.
See you next week,
Brent, your Rivr Guide
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Thanks Abby!!
Being honest about it is SO freeing. Great piece, Brent.