Learning From Your Past
This week’s Rivr Notes is about making hard decisions by learning from your past—and choosing what matters most.
Several years ago, I co-founded a private equity firm. At the same time, I had just launched a micro-school for middle schoolers in my community, was leading a successful online education company, and, of course, trying to be present for my family. It was an exciting time—full of vision, momentum, and… chaos.
Shortly after announcing the launch of the new company, a good friend of mine sent me a message that still echoes in my mind to this day. Her note was warm, supportive, and also incredibly perceptive. It read:
“Just wanted to check in and see how the PE world is treating you so far… and the school, and the online education company, and the family... wait, is there anything you aren't doing right now?”
That message landed with unexpected weight. Not in a bad way—but in that “hold up a mirror” kind of way.
At the time, I laughed it off. I was genuinely excited about everything I was building. I had energy, purpose, and ambition. But beneath the surface, I was stretched too thin. I was juggling so many responsibilities that I didn’t have time to breathe. And while it may have looked impressive from the outside, it was taking a toll.
The truth is, when work becomes my primary mode of operation, something—or someone—usually pays the price. For me, it was a mix: my health, my sleep, and the relationships I cared about most. I didn’t want anything to drop, so I tried to hold it all up. But you can only do that for so long.
That message from my friend became a checkpoint in my memory. A quiet reminder. A whisper that said, “Hey… remember what happened last time?”
Fast forward to this past year—and there it was again. A familiar juggling act.
I had launched Exit Pathways, a business that helps founders and business owners successfully sell their companies—work I genuinely enjoy and have real expertise in. A few months prior, I launched OnRivr, which included Rivr Notes, my weekly newsletter focused on Leadership, Refined. That quickly expanded into Rivr Conversations, a companion podcast to Rivr Notes. And there’s another venture I’m working on behind the scenes (more on that in the months ahead).
Then I looked at my plate.
It looked… familiar. Too familiar.
Once again, I found myself in a version of the same dilemma: too many things requiring too much of me.
So I asked the question I hadn’t really paused to ask years ago: Have I learned anything?
Thankfully, the answer was yes.
A few months ago, I reached out to that same friend and told her just how much her message had stuck with me. We laughed, but I also shared how it had quietly shaped the way I make decisions. Because this time, I’m choosing differently.
I’ve decided to sunset Exit Pathways.
It was a difficult decision. I’ve loved the work. I’ve invested meaningful time and resources into building the company. And I know I could continue helping people in that space. But I’ve learned that if I don’t make these hard calls, even good things can become unsustainable.
And I’m not willing to let that happen.
I don’t want to sacrifice time with my family. I don’t want my health to take a backseat. I don’t want to half-show up in too many places instead of fully showing up in a few.
So, I’m lightening the load.
OnRivr—with Rivr Notes and Rivr Conversations—continues to be a space where I’m investing deeply. It’s energizing, it’s rewarding, and most importantly, it’s sustainable. Why? Because I’ve created the margin for it to thrive.
Stepping back from Exit Pathways isn’t about failure or regret. It’s about alignment. It’s about learning from the past and choosing a path that’s grounded, healthy, and intentional.
I share this because I think many leaders—maybe even you, reading this—have faced, or will face, a similar moment. A moment where everything looks good on paper, but feels unsustainable in practice. A moment where you have to ask: What is this really costing me?
Saying yes to too many things comes with a hidden price tag. Sometimes that price is your peace. Sometimes it’s your presence. Sometimes it’s your health, your creativity, or your relationships. For me, it’s been a bit of all of the above at one point or another.
But here’s the upside: you can learn from your past.
You can choose to pause. To reflect. To pivot.
And when you do, you create space—not just to do more, but to be more present, more intentional, and more whole.
That’s what I’m aiming for now. Fewer things, done with more purpose. Less noise, more clarity.
So here’s to learning from the past—not with regret, but with gratitude. Because those seasons of overload? They taught me what balance feels like—by contrast.
And this time, I’m choosing balance.
See you next week,
Brent, your Rivr Guide
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🎧 Bonus: If this sparked something for you, you might enjoy the companion podcast episode of Rivr Conversations. It builds on the ideas in this Rivr Note—offering a new angle, deeper reflection, and practical ways to carry the story forward.
🎙️ Subscribe to Rivr Conversations and listen wherever you get your podcasts—just search for “Rivr Conversations” on your favorite platform.
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