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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.
Today's conversation is about something many of us wrestle with, how to recognize when we're repeating patterns that no longer serve us. It's inspired by Brent's Rivr Notes post, learning from your past. We'll explore what it looks like to make hard decisions not just in the moment, but in light of lessons from years before. This episode is about reflection, self awareness, and how choosing what to let go of can be just as powerful as choosing what to build. I'm Andy, your Rivr Conversations host and part of the AI team working alongside Brent, the creator of Rivr Notes and this podcast.
Andy: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.
Reed:Have you ever felt like you're just stuck in this loop? You know, your calendar is completely jammed, the to do list just keeps getting longer not shorter And well, from the outside, people think you're absolutely killing it.
Lena:Right. Like you're doing everything.
Reed:Exactly. But inside, there's that little voice, that kind of unsettling feeling that, yeah, you're doing everything but maybe maybe not doing anything really well.
Lena:It's real paradox, isn't it?
Reed:It really is. That feeling of just having too many good things on your plate, too many opportunities, too many commitments, and you're just desperately trying to juggle it all.
Lena:It's that allure of saying yes, I think. You know, every chance seems like a step up, like growth.
Lena:But add them all up, and suddenly you're drowning. It creates this this invisible barrier almost to actually doing things well. It's just chronic overwhelm.
Reed:Precisely. And that exact feeling, that personal dilemma, that's what we're getting into today. We're drawing from a really, really compelling story Brent shared in his Rivr Notes newsletter. It was titled Learning From Your Past.
Lena:Yeah. And what's really powerful about Brent's piece isn't just that he learned something from being before, but how he actually used that awareness.
Lena:So our goal here for you is to unpack how even really good projects, things you want to do can somehow lead to this state of chaos, of unsustainability. We wanna look at how, you know, paying attention to yourself, reflecting, making deliberate choices, how those are the keys to finding a healthier balance, and hopefully offer some things you can use in your own life maybe before you hit that wall.
Reed:Okay. So let's dig in. Brent starts his story talking about a time several years back. He mentions cofounding a private equity firm. I mean, just that alone.
Reed:Yeah. That world is intense. Right? High stakes, long hours.
Lena:Oh, yeah. Absolutely. Eighty hour weeks aren't uncommon there.
Reed:Right. So picture that. But then at the same time, he just launched a microschool for middle schoolers. You know, something needing not just money, but real hands on community work. Very personal.
Lena:Okay. Wow. That's a completely different kind of demand.
Reed:And on top of that, he was still running a successful online education company.
Lena:Good grief.
Reed:And, you know, trying to actually be there for his family through all of this. He calls it, an exciting time full of vision, momentum, and chaos.
Lena:That phrase, vision, momentum, and chaos, it really captures it. What strikes me is the sheer mental load. Yeah. Private equity, a school, an online biz they're not just tasks. They're whole ecosystems.
Lena:Ecosystems. Different skills, different pressures, different emotional energy for each one.
Reed:Totally different.
Lena:So the excitement, the momentum, sure. That's real. But the chaos, that feels almost inevitable when you're trying to operate at that level across so many different fronts plus family.
Reed:It's like fighting a war on too many fronts against your own capacity.
Lena:Exactly. It's how ambition, even positive ambition, can accidentally overload the system.
Reed:And then comes this, this external perspective. Shortly after he launched the PE firm, a good friend messages him and Brent says it landed with, quote, unexpected wait. The friend basically said, just wanted to check-in. How's the PE world and the school and the online company and family? Wait.
Reed:Is there anything you aren't doing right now?
Lena:Oof. That's direct. But perceptive.
Reed:Very. What does it actually take though to really hear that kind of feedback when you're so deep in the hustle and that ambition? Bubble?
Lena:That is a great question. Because often when you're right in it, you're running on purpose, maybe on adrenaline. You get tunnel vision.
Reed:Yeah. You justify it.
Lena:You totally justify it. The hours, the split focus, the constant push. So a message like that, it's not really judging. It's just holding up a mirror.
Reed:Right.
Lena:And to actually see that reflection, it takes a moment of, well, vulnerability. You have to let that outside view pierce through the story you're telling yourself about how busy and productive you are.
Reed:It's a gift, maybe, but a tough one to open.
Lena:Definitely. Very uncomfortable sometimes.
Reed:And Brent admits, back then, he just laughed it off. Yeah. You know, he was genuinely fired up, full of energy and purpose, go mode.
Reed:But underneath it all, as he realized later, he was just stretched too thin, juggling so much he didn't have time to breathe. He says, you know, it might have looked great from the outside, but it was taking a toll. And he names the costs, his health, his sleep, his key relationships.
Lena:Yeah. Those are usually the first things to fray.
Reed:He tried to keep it all going, didn't wanna drop any ball, but admits, you know, you can only sustain that for so long.
Lena:That's such a critical point, and so many people learn it the hard way that hidden toll isn't always some dramatic collapse. Often it's slower like erosion.
Reed:Right.
Lena:Maybe your sleep gets worse bit by bit or you're just edgier with people you care about or that creative spark you had just feels gone.
Reed:Yeah. I can relate to that.
Lena:I remember early in my career, my schedule looked like this badge of achievement, but honestly, I was barely sleeping. You get trapped because the external validation, the looking busy feels good until the internal cost just becomes too obvious to ignore. Bren's point about trying to hold it all up, it's a sprint strategy, not a marathon one. We're just not built for that kind of constant strain indefinitely. The sacrifice is happening even if no one else sees it.
Reed:And that friend's message really stuck with him. He calls it a checkpoint in my memory, a quiet reminder, a whisper that said, Hey, remember what happened last time?
Lena:I like that phrase, Checkpoint in my memory.
Reed:Yeah, it really resonates. It suggests this reference point he could always go back to. Like a lesson learned, almost baked into his awareness, an internal alarm bell.
Lena:It really speaks to wisdom gained from, well, living it. These checkpoints aren't always big lightning bolts. Sometimes they're just a quiet comment from someone or an internal nudge.
Lena:They're like early warning signals helping you spark the pattern before it completely takes over again. That ability to remember and check-in with yourself, that's how you break those cycles.
Reed:It's the difference between knowing fire is hot because someone told you and knowing it because you touched the stove.
Lena:Exactly. You develop an instinct. You feel the heat starting, and you pull back faster next time.
Reed:Okay. So he has this internal checkpoint, this lesson learned, but you know, life likes to test us on these things. So what happens when Brent finds himself facing a really similar situation more recently, Fast forward to this past year, he's back in what he calls a familiar juggling act. He'd launched Exit Pathways, helping founders sell their businesses. Work he liked was good at, but again, demanding strategic client facing.
Lena:Requires a lot of focus.
Reed:Then just a few months before writing this, he launches OnRivr. That includes Rivr Notes, the Newsletter, which is a real commitment. Right? Consistent content.
Lena:Oh, yeah. Weekly is a grind.
Reed:And that quickly grew into Rivr Conversations, the podcast. Yeah. Another layer of production engagement.
Reed:Plus, he mentions there's another venture he's got going behind the scenes.
Lena:Wow. Okay. So the pattern repeats. But what's striking is how easily it happens even when you know the risks.
Lena:These new ventures sounded great. Things he was passionate about, skilled at. It's not like he failed. It just shows how sneaky that pull towards more can be, especially when it's disguised as passion or good opportunity. It reminds you that self awareness isn't a one and done deal.
Lena:It's constant practice.
Reed:You have to keep checking in.
Lena:Exactly. Yeah. The world keeps offering shiny objects, and our internal too much filter can get clogged again.
Reed:Right. And Brent describes that moment of realization. He says he looked at my plate. He was back in a version of the same dilemma. Too many things requiring too much of me.
Reed:That whisper from his friend years ago now is probably more like a shout inside his own head.
Lena:Which must have been, yeah, powerful, but maybe uncomfortable too, recognizing that feeling again. Circumstances changed, new companies. But that internal sense of being stretched thin, it was back. Yeah. And that repetition forces the big question he asked, have I learned anything?
Lena:That's a tough moment of self reflection. A lot of us just push through instead of asking that.
Reed:It takes guts to really face it.
Lena:It does. Especially because the answer might mean making some really hard choices.
Reed:Well, thankfully for him, the answer was yes. He actually shared that he reached out to that same friend, one who sent the original message.
Lena:Oh, interesting.
Reed:Told her how much that message had meant, how it stuck with him. They apparently laughed about it, but he also told her this time he was choosing differently.
Lena:Okay. So that's the key step, isn't it? Moving from just knowing to actually doing something different. Yes. And choosing differently takes serious courage, especially when it means letting go of something that's actually good.
Lena:By objective standards, it's working.
Reed:That's the hard part.
Lena:Yeah. Cutting things that are obviously failing is easy. Walking away from something successful, something you like because it's subtly draining your core capacity, that's real wisdom in action.
Reed:And he backed it up. He made the tough call, decided to sunset Exit Pathways. Wow. And he's clear. This wasn't easy.
Reed:He loved the work. He put meaningful time and resources into it. He knew he could keep helping people there.
Lena:Right. So it wasn't failing. It wasn't something he hated.
Reed:No. Not at all. It was purely about realizing it didn't fit into his larger picture of a sustainable life.
Lena:That really drives home his lesson. If I don't make these hard calls, even good things can become unsustainable. It cuts against that cultural narrative of more is always better, doesn't it? Totally. Or that idea that our value is tied to how much we can handle.
Lena:Sometimes, real success, real sustainability means deliberately choosing less.
Reed:Focusing.
Lena:Yeah. Understanding that your energy, your focus, it's finite. You have to allocate it carefully, which means saying no sometimes. That sunk cost fallacy too. It's hard to walk away when you've invested so much even if it's not serving you anymore.
Reed:And he's really clear now about what he not willing to sacrifice again. He says, I don't wanna sacrifice time with my family. I don't want my health to take a back seat. I don't wanna half show up in too many places instead of fully showing up in a few.
Lena:That distinction half show up versus fully showing up. That's huge.
Reed:It really is. It's about quality, isn't it? Yeah. Presence. Being truly there.
Lena:It connects to redefining success for yourself, doesn't it? For Brent, it seems like it shifted from just external benchmarks to more internal ones, well-being, real connection, deep work in select areas. He's actively guarding those core values, family, health, presence, and understanding that creating that sustainable space or margin as he calls it, it's not optional. It's essential for things to actually thrive.
Reed:Right. It's not a luxury.
Lena:Not at all. So he's focusing on OnRivr, the newsletter, the conversations because, as he says, it's energizing, it's rewarding, and most importantly, it's sustainable. Why? Because he made space for it.
Reed:He chose deep over broad.
Lena:Precisely.
Reed:And for Brent, letting go of Exit Pathways isn't failure. He doesn't see it as regret. He calls it alignment. He says it's about learning from the past and choosing a path that's grounded, healthy, and intentional. That reframing is so powerful.
Reed:It's not defeat. It's a strategic move towards something better.
Lena:That shift in perspective is absolutely key. It turns what could feel like a loss into a conscious empowered decision. It's recognizing growth isn't always about adding more. Sometimes it's about refining, focusing.
Reed:Getting clearer.
Lena:Yeah. True alignment is when your actions really match your deep values and what you want your life to feel like, not just what opportunities pop up. It's saying no to the good so you have capacity for the best.
Reed:And he really feels this isn't just his story. He thinks it's a universal thing for leaders, saying
Reed:Many leaders, maybe even you, have faced or will face a similar moment.
Reed:A moment where everything looks good on paper but feels unsustainable in practice.
Reed:Which brings us all back to that really critical question. What is this really costing me?
Lena:That's the core of it, isn't it? And it goes deeper than just time or money. That hidden price tag for saying yes too much, it's paid in currencies like peace, presence, health, creativity, relationships, often, like he says, a bit of all of the above. It's this quiet drain that wears you down sometimes before you even notice it happening.
Reed:It steals the joy.
Lena:Exactly. It dims the joy, makes connections feel superficial, clouds your thinking. These invaluable things get on the altar of busy.
Reed:But the positive message here, the really empowering part of Brent's story, is that you can learn. You're not doomed to repeat the pattern.
Lena:Absolutely.
Reed:He points to specific actions. You can choose to pause, to reflect, to pivot. These are active choices. It's a blueprint for change.
Lena:And what's great is the simplicity of those actions yet how profound they are. Pausing creates the space to ask, what is this costing me? Reflecting clarifies what truly matters, maybe by contrasting how you feel now with how you want to feel. Right. And pivoting.
Lena:That's the courage to act on those insights even if it means saying goodbye to something good. When you do that, you create space.
Reed:Yeah. Space to be more, not just do more.
Lena:Exactly. More present, more intentional, more whole. It's about shifting from frantic activity to deliberate living, improving the quality of your life, not just the quantity of your output.
Reed:His new philosophy really nails it. Fewer things, done with more purpose, less noise, more clarity. That's a powerful guiding principle for anyone feeling swamped.
Lena:It really is. And it leads to this sense of gratitude he expresses for those past seasons of overload. He doesn't regret them. He sees them as teachers.
Reed:Right. They taught him something crucial.
Lena:They taught me what balance feels like by contrast. It's like, you don't appreciate breathing until you've struggled for air. That past pain, that discomfort, it forged the clarity he has now.
Reed:So he's using those lessons.
Lena:Using them as guides, not burdens. This time, he's actively, consciously choosing balance.
Reed:So wrapping this up, what's the big takeaway for you listening? I think the core idea from Brent's experience is just how valuable it is to learn from those times you felt overwhelmed. To use that knowledge to make deliberate choices now for a life that feels more balanced, more sustainable. And sometimes that means letting go of things that seem objectively good. It's not really sacrifice, it's strategy.
Reed:It's about investing your limited energy where it counts most in the things that genuinely align with your purpose and well-being.
Lena:It really is a powerful invitation to look inward, which leaves us with a thought for you to consider. How can you start to identify your own hidden price tags? What are your current commitments really costing you beyond the obvious? Is it peace? Presence?
Lena:Your health? That creative spark?
Reed:And maybe, taking inspiration from Brent's courage, what good things in your own life might need to be released or at least reprioritized so you can create that essential space. Space for what truly brings you that sense of peace, presence, and purpose you're looking for.
Andy:That's it for this week's episode. 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. After all, the best ideas often come from staying curious, embracing new perspectives and engaging with the world around us. This week's photo captures one of those rare, breathtaking moments where nature seems to whisper something just for you.
Andy:It was taken just after a summer rain, in the golden hour where the light turns soft and everything feels more vivid. Stretching across the sky is a stunning double rainbow bold, full and perfectly arched framing the high desert landscape like a quiet promise. The inner rainbow is rich and vibrant, while the outer one, fainter but still visible, feels like a shadow of the first, like a
Andy:memory echoing in the sky. Below, the land is a mix of soft sagebrush, rocky paths, and a grove of evergreens standing tall and still. The light casts a warm glow across the hills and trees as if the earth itself is exhaling. It's the kind of scene that stops you, a moment that says, pay attention, because in between the storms and the sun there's beauty, there's clarity, and there's always something to be learned, if we're willing to look up. If you'd like to read the full Rivr Notes article, including all the amazing photographs, you can find it at OnRivr.com.
Andy:That's Rivr without an e. 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 viewpoints 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. Rivr Conversations is an OnRivr, LLC production.