Rivr Conversations

Inspired by Brent Drever’s Rivr Notes newsletter, Reconciling Dreams, this episode explores what happens when the dream you’ve been chasing for decades no longer fits the life you’re living. We’ll dive into the tension between personal ambition and evolving values, the courage it takes to let go of a long-held goal, and why changing direction isn’t a failure—it’s growth. It’s a conversation about clarity, identity, and making space for dreams that reflect who you are now, not just who you were then.

View the Rivr Notes for this Episode > https://onrivr.com/rivr-notes/reconciling-dreams/

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What is Rivr Conversations?

Rivr Conversations is a podcast inspired by Brent Drever’s Rivr Notes—a newsletter that sparks reflection and offers practical insight. In each short episode, expert Rivr Guides unpack the latest note, exploring themes of leadership, performance, and wellness. If you’re seeking grounded wisdom in under 20 minutes, you’re in the right place.

Andy:

Today's conversation is about something many of us face, often quietly. What do you do when a dream you've held onto for years, maybe even decades, starts to feel like it no longer fits? It's inspired by Brent's Rivr Notes post Reconciling Dreams. We'll talk about how our goals evolve, what it means to let go of a long held aspiration, and why that's not failure, it's growth. We'll also share stories about ambition, shifting values, and the freedom that can come from redefining what success really looks like.

Andy:

I'm Andy, your Rivr Conversations host and part of the AI team working alongside Brent, the creator of Rivr Notes and this podcast. Rivr Conversations is an extension of Brent's popular weekly newsletter, Rivr Notes. Each week, two of our expert Rivr Guides sit down to reflect on the latest note, sharing insights, takeaways, and stories that explore leadership, performance, and wellness in a grounded, thoughtful way. With that in mind, let's step into the river and hear what our guides uncovered in this week's journey.

Lena:

Hello, everyone. Looking forward to today's conversation. Today, we're embarking a deep dive into a really insightful piece from Brent's weekly newsletter Rivr Notes. It's his reflection called Reconciling Dreams. Our mission really is to explore how personal and professional ambitions evolve.

Lena:

We wanna pull out those surprising truths, those insights from Brent's own journey that might resonate with all of us. Okay. Let's unpack this. It's a fascinating narrative Brent shares starting right at the beginning for him. He talks about being drawn to business from a young age, watching his dad build companies.

Lena:

And it wasn't just, you know, the buying and selling. He was curious. How did his dad actually do it? The vision, the creation, the leadership pieces, it all felt alive.

Reed:

Yes. And what's fascinating here is how that childhood curiosity didn't just stay vague. It really solidified. It became a very specific, almost all consuming aspiration for him during his teenage years. That initial spark turned into this really burning ambition.

Reed:

He remembers getting his subscription to Fortune magazine and just devouring every issue. Those stories, those corporate giants, they shaped his dream. He wanted to build something significant and that eventually narrowed down to one clear goal: become CEO of a Fortune 500 company.

Lena:

Wow. That specific.

Reed:

Oh yes. And to really cement it, he even printed out a mock fortune cover, put his own face on it, a bit light hearted maybe, but also a really powerful visual reminder of where he was aiming. You can picture it right taped on his wall.

Lena:

Absolutely. And clearly that image fueled him. He poured himself into his work, made very deliberate career choices to get there. Early on, landed a role at General Electric. This was during the Jack Welch era.

Lena:

He calls it a master class in corporate leadership. Imagine seeking that out.

Reed:

Exactly. Real drive there. And from GE, he went into management consulting at PricewaterhouseCoopers, working with major global businesses. So throughout his twenties into his thirties, Brent makes it clear he was absolutely dedicated, systematically gaining experience, moving closer to that goal, proving to himself he could achieve it. He was definitely on that trajectory.

Lena:

Right. Ticking all the boxes for that path, making clear progress.

Reed:

Indeed. Professionally, things were lining up perfectly. But as Brent shares and as it often does for many of us, life started to, well, evolve.

Lena:

So his professional dream was crystal clear, singular even. But then life started shifting. What new desires began to emerge? Did they challenge that intense focus on becoming CEO?

Reed:

That's the core of it, isn't it? Mhmm. Because this wasn't just a minor adjustment. It introduced a completely new and equally powerful dream, a very personal one. Brent got married in his late twenties, then started a family in his early thirties.

Reed:

He wasn't quite ready to walk away from the CEO ambition, not yet, but he felt this different kind of pull, very strong.

Lena:

A different kind of ambition.

Reed:

Exactly. This new dream wasn't about titles or climbing corporate ladders. It was about connection, about presence. He wanted to be in his words, a great husband and a present father, also a reliable friend. Which raises that big question, doesn't it?

Reed:

How do you hold on to a dream you've cherished for so long when other values, equally strong, start demanding your attention to your energy?

Lena:

That internal conflict.

Reed:

Yes, a real conflict of value. He wasn't abandoning the professional dream, but he was definitely feeling this deep internal tension as these new priorities came forward.

Lena:

That tension must have been building. So how did he actually confront it? Was there a specific moment or more of a slow burn realization?

Reed:

Well, it wasn't just quiet internal struggle. Interestingly, there's a specific encounter, a real pivot point for him as he describes it. He was working for a large public company at the time, and he got the chance for a one on one lunch with the CEO of a Fortune 500 company.

Lena:

Ah, the source itself.

Reed:

Pretty much.

Reed:

For Brent, this wasn't just networking. It was a huge learning opportunity. He was all ears, as he puts it. Wanted to know what it really took. What does leadership actually look like at that level?

Reed:

Not just the job description, but the reality.

Lena:

Sounds like a lunch that could really change your perspective. What questions did Brent ask that led to such a, well, a profound moment?

Reed:

He asked the CEO about his family. Simple question, really. And this is where the hidden cost, the true cost of that kind of singular dedication really comes into sharp focus. The CEO paused before answering then quietly admitted, I have a son but I'm not married anymore. Yeah.

Reed:

And there was this honesty in his tone, you know, like it was still very real for him. He explained his wife asked for a divorce, seemed sudden to him. No big fight, just over. I was blindsided, he said. And the reason she gave, you're never around.

Reed:

Work is always your priority.

Reed:

Those words clearly stayed with him, not bitterly, just with clarity.

Lena:

Wow. And his son.

Reed:

When Brent asked about his son, the CEO paused again, then just said, not great. We're not close. I wasn't around much. No anger. Just this stark, honest reflection on the choices made and the consequences.

Reed:

The takeaway maybe is that the cost isn't just financial. There's often this huge personal debt that can catch you totally unprepared later on.

Lena:

And the CEO didn't shy away from explaining the job's demands either.

Reed:

Not at all. He laid it out. This job is always on. When something goes wrong, even at 2AM, I get the call. He framed it as responsibility to the team, the company, the shareholders.

Reed:

It wasn't a complaint. He chose it. But he was showing Brent the full unvarnished cost of that choice.

Lena:

So was this just one person's story a cautionary tale or did Brent start seeing this elsewhere?

Reed:

That's key because Brent realized, no, this wasn't an isolated case. He looked across leadership teams at other large companies and he saw a pattern. Lies deeply committed to work, often as he put it, at the expense of everything else. And Brent is clear he wasn't judging. He understood the choice, the dedication, the skill involved, but you couldn't ignore the personal cost often paid by families.

Reed:

And seeing that pattern really prompted some deep personal questions for him.

Lena:

That lunch sounds truly monumental, a turning point. After more than twenty years holding on to this very specific dream, he's suddenly asking himself, is this still the life I want? That directness from the CEO plus his own changing family life, it forced reevaluation.

Reed:

Exactly. And Brent talks about that process. Letting go of a dream, even one that doesn't fit anymore

Reed:

Is hard. He says it takes time, reflection, and even a little grief. It's not like flipping a switch.

Lena:

Why so hard though?

Reed:

Well, our identities get so wrapped up in our ambitions, don't they? There's ego, there's maybe fear of what others think if we change course, that internal struggle with feeling like you're giving up on something you invested so much in. But through that tough process, he came to this really profound realization, dreams evolve. And that's okay. He reflects that as a teenager dreaming of being CEO, he just couldn't have predicted what marriage would mean, or how he'd feel having kids, or even as he says, how much joy there is in simply being home for dinner.

Reed:

His younger self couldn't know those things, but his current self did. And acknowledging that evolution, that's wisdom, really.

Lena:

And he's careful to say it wasn't abandoning the dream. He frames it as refining it. He still felt he had the underlying qualities, the drive, stamina, curiosity for that CEO role. But the real challenge he saw was navigating those competing values.

Reed:

Right. That tension between personal and professional is always there, but being honest about it was freeing for him. It became about choosing what genuinely brought him joy, not what society or even his younger self thought he should want.

Lena:

Which feels very relevant for, well, probably a lot of people listening.

Reed:

Absolutely. If you've ever found yourself looking again at an old dream, wondering if it still fits, Brent's insight is that you're not alone. It isn't failure to change course. It's actually a sign of wisdom, growth, self awareness. He encourages us to take stock, be kind to yourself, and remember that life changes.

Reed:

We change. And sometimes, letting go of one dream just creates the space needed for another one to emerge. Often one that's a better fit for who you are now.

Lena:

So what happened with that original Fortune 500 CEO dream? Does he ever think about it? He shares this wonderful, almost symbolic detail about the shift, doesn't he?

Reed:

He does. After subscribing to Fortune Magazine for over twenty five years, the very magazine that sparked that teenage ambition, He finally let the subscription lapse a few years ago.

Lena:

Feels like quietly closing a chapter. A gentle letting go.

Reed:

Exactly. A perfect quiet metaphor. And what's fascinating is the irony of the sort of full circle moment that comes next. By letting go, he created space. Brent now writes Rivr Notes, these humble little articles as he calls them.

Reed:

So the act of releasing one dream allowed another to flourish, one that maybe fits him better now.

Lena:

It's a different kind of building, a different kind of leadership through his writing.

Reed:

More precisely. It shows how dreams transform. They find new, maybe more authentic ways to express themselves, still using those core drives just differently.

Lena:

And it's funny how influences pop up unexpectedly. Brent mentions a surprising inspiration for Rivr Notes, right, from Fortune itself.

Reed:

Yes. He says one of his favorite parts of Fortune, the first thing he'd read was the back cage column by Stanley Bing. He loved how he was funny, sharp, and business savvy with a wink. And Brent sort of wonders if Stanley Bing was maybe in his head all along, shaping his own writing style today.

Lena:

You just never know where those seeds of inspiration come from, do you? So we've traced this journey, how an early powerful dream can gracefully make way for new priorities as life unfolds. Brent's story really shows that reconciling dreams isn't about failure. It's about growth. Aligning who you are now with what you do.

Reed:

Absolutely. Connecting this to the bigger picture, his experience is such a strong reminder. Taking stock, being kind to yourself, allowing dreams to evolve, that's not just okay. It's a sign of real wisdom. It's about honesty.

Reed:

What truly matters now? Because it might be different from yesterday, and it might be different again tomorrow.

Lena:

So maybe a final thought for everyone listening. The next time you find yourself holding really tightly to an old ambition, maybe ask, what could you gain by acknowledging the other important values in your life right now? And what new dream, maybe one that fits you better today, might be waiting just beneath the surface, ready to emerge if you give it space. Thanks for listening. Until next time.

Andy:

That's it for this week's episode of Rivr Conversations. Speaking on behalf of Brent and myself, Big thanks to our expert Rivr Guides for another thoughtful discussion. We always appreciate the unique perspectives they bring to these conversations. To close out each Rivr Conversation, I like to describe the photo featured in the Rivr Notes newsletter. It's not just a stock image it comes from a real adventure.

Andy:

After all, the best ideas often come from staying curious, embracing new perspectives and engaging with the world around us. This week's photo was taken at the edge of a quiet mountain pond, where the water is calm and the morning light slips softly through the trees. In the shallows, a moose stands ankle deep, slowly drinking. Just behind her, almost camouflaged in the tall reeds, is her calf small, alert, and sticking close. It's a moment between a mom and her baby no rush, no noise, just the quiet rhythm of the wild one teaching, one learning.

Andy:

The mother doesn't look back often, but the calf follows with absolute trust, taking in the world one cautious step at a time. There's something deeply grounding about it, a reminder that growth doesn't always come from forging ahead at full speed, but sometimes from staying close, paying attention, and learning when to lead and when to follow. It made me think: we don't always know where the path leads, and the dreams we start with may not be the ones we end up chasing, but like the calf in the pond, sometimes the best thing we can do is stay near to what matters most and keep moving forward together. If you'd like to read the full Rivr Notes article, including all the amazing photographs, you can find it at onrivr.com. That's Rivr without an E.

Andy:

And be sure to subscribe wherever you listen to your podcasts so you never miss a conversation. Before we go, a quick reminder: The opinions and view points expressed in this podcast are solely those of the presenters and our AI companions, sharing personal reflections and perspectives. We're not legal experts, medical professionals, or therapists. This content is for informational and entertainment purposes only, so please consult the appropriate professionals when you need advice or support. Thanks again for listening.

Andy:

Rivr Conversations is an OnRivr, LLC production.