Billy Lahr returns to The Prestigious Initiative for a deeply honest conversation about living in the in-between. After 21 years as a teacher and dean, Billy stepped away from education—and four years later, he’s still experimenting, freelancing, promoting others, and wrestling with a question many high performers quietly carry: What if I don’t have a niche?
In this episode, Billy and Chris explore what it means to be a generalist in a specialist-driven world, the tension between quitting and gritting, and the emotional toll of constant experimentation and rejection. They talk about identity, generosity, self-promotion discomfort, and why wanting to see others win can be both a gift and a challenge. This is a real conversation about purpose, resilience, and staying in the arena when the path forward isn’t clear yet.
https://mindfulmidlifecrisis.systeme.io/jumpstartconvo
We love a good success story. The hero's journey. The triumphant arc where someone hits rock bottom, claws their way up, and emerges on the other side with a TED Talk and a book deal.
But what about the people who are still in the middle? The ones who took the leap, burned through their savings, tried things that didn't work, and are still standing there, hands dusty, asking "what's next?"
That's where my friend Billy Lahr is right now. And that's exactly why I wanted him back on the show.
Billy spent over two decades as an educator before stepping away to see what life looks like beyond a single identity. He's been traveling for four years, started and ended a podcast, moved to South Korea, taught business English, and is now building something new—slowly, carefully, without the pressure of a "launch."
When we first rescheduled this episode, Billy almost backed out. He told me, "I don't feel like I have much going for me right now."
And I said, "That sounds exactly like something my audience needs to hear."
Because the truth is, most of us are in the middle. Most of us are figuring it out. And pretending otherwise is exhausting.
So today, we're getting real about burnout, rejection, quitting, and why "follow your passion" might be the worst advice you ever got.
The Burnout That Broke the Camel's Back
Billy's story starts where a lot of teacher stories start: with a slow, grinding burnout that he didn't have the tools to handle.
"I really enjoy teaching where I got burnt out on teaching is when I started working in an alternative setting. I had students coming to me with socioeconomic, behavioral challenges, academic barriers, mental health barriers. Those challenges and the negativity—it was their experiences, not their fault—they were coming into my classroom and creating toxicity."
But here's the part that takes real honesty. Billy didn't blame the kids. He looked in the mirror.
"I myself was bringing in a lot of toxicity as well because I was not emotionally mature to handle groups of students like that. My mental health during that time was not great. So I couldn't be an emotional pillar of support for them."
This is the kind of self-awareness that most people never reach. He recognized that he wasn't just a victim of his environment—he was part of the problem.
After his dog passed away, Billy looked at his life and realized he had no wife, no kids, no mortgage. Nothing keeping him in place.
"I don't have any responsibilities. This is the time to do this."
So in September 2021, he took a leave. And he's never gone back.
The Failure That Cost Him Everything
Billy's first attempt at building something new was a podcast called The Mindful Midlife Crisis. Great title. Great concept. But when he tried to monetize it, everything fell apart.
"I listened to far too many podcast business coaches who tried to tell me, 'Hey, you got to sell, you got to sell, you got to sell.' And it ruined the podcast. I listened to those episodes during that season, and I'm like, these suck. I hate these episodes."
He was honest about the cost—not just emotional, but financial.
"It cost a lot of money to do all of that. That did not succeed. It did not make money."
So he walked away. But he didn't walk away blindly. He used a framework from Annie Duke's book Quit.
"What is the criteria that you need to meet in order for you to continue going with what it is that you are doing? And if you don't hit that criteria by this drop dead date, it's okay to walk away for good."
That's the difference between quitting and knowing when to pivot. Billy didn't give up on his dream. He just gave up on a version of it that wasn't working.
The Generalist's Dilemma
One of the richest threads in our conversation was the tension between being a specialist and a generalist. Billy embodies the struggle.
"The issue for me, the challenges that I face as a generalist, is just being stretched too thin. I want to do—there's a Nine Inch Nails song, he says, 'I want to be everywhere. I want to know everything. I want to do something that matters.'"
That line hit me. Because I feel it too. There are so many things I want to learn, so many paths I want to explore. But the world tells us to pick one. To niche down. To be the expert.
Billy's response? He changed his LinkedIn profile to reflect where he's going, not where he's been.
"I don't have a niche because, like Walt Whitman says, 'I am large, I contain multitudes.' So I am an educator, but in that role, there are many sub-roles. I can be your English teacher, but I'm also a certified mindfulness meditation teacher. I'm also a certified personal trainer. I've been traveling for the last four and a half years."
This is the manifesto of the generalist. Not knowing one thing deeply, but knowing enough about many things to connect with many people.
I shared my own experience with this.
"This is my third podcast. I had a podcast with my buddy about how to teach martial arts. And everybody in the podcast world says, 'You got to really nail down the niche.' I'm here to tell you, if you're too far down a niche, nobody listens to it because it's so far down that it doesn't connect with very many people."
The dinner party test: if you can only talk about one thing, you're not invited back.
Rethinking Passion, Hobbies, and Purpose
Billy pushed back hard on the "follow your passion" narrative.
"This whole idea that do something that you love and you'll never work a day in your life—that's complete and utter nonsense. If you do something that you love, you're probably going to spend more time doing it. You're going to put in 10, 12 hours because you enjoy doing it. And it's going to feel like a lot of work."
He offered a different equation. Passion isn't the starting point—it's the destination.
"Passions are a byproduct. First, understand your strengths, weaknesses, opportunities, and threats. Build awareness around what you are good at. Second, what you are curious about. And how you can connect those two things to a community of people who are curious about the same thing. Once you have those three things, then you know what your purpose is in that season of life."
And then he added the ingredients nobody talks about.
"If you want to turn it into a passion, you need consistency, you need discipline. But the two things that nobody ever mentions is you need patience and you need self-compassion."
This is where Billy has struggled most—and where most of us struggle too. We want results now. We want the audience now. We want the money now. But real passion takes time.
He also made a crucial distinction between passion and hobbies.
"What I see is people too often conflate hobbies with passion. Passion to me is that focus, that consistency, that discipline. But it's more important to dabble in hobbies and just enjoy them. Hobbies have that element of connection and community and play. And there's that saying: you don't stop playing because you grew old; you grew old because you stopped playing."
He shared something that broke my heart a little.
"When I ask my corporate clients what their hobbies are, if they're parents, a lot of them will say, 'I used to have hobbies, but now my hobbies are my children.' It makes me really sad to think that. If you ask an 8, 9, 10-year-old what their parents like to do for fun, they should be able to answer that question."
This hit home. Our kids need to see us as full people, not just parents. They need to see us playing, exploring, being curious. Because that's how they learn to do the same.
The Values Auction and Knowing What You Want
Billy's current project is something called the Jumpstart Conversation Series. One of the exercises he runs is a "values auction."
"Everybody gets 1,000 Billy bucks. And you get to bid on what values are most important to you, but you have to bid against other people who also value that same thing. So how much of your limited Billy bucks are you willing to spend on those values?"
He shared a fascinating insight from a recent session.
"Exciting life went for 100 Billy bucks because it was the first one and people were saving their money. But financial security went for 600 because there was a bidding war. Then you get to inner peace. Does financial security buy inner peace? Notorious B.I.G. says, 'Mo' money, mo' problems.'"
The auction forces you to confront what you actually value—not what you think you should value. And often, the results surprise you.
The Power of Connection and Self-Awareness
Near the end, Billy circled back to what matters most.
"The longest running study on happiness shows us that people who have good connections, strong connections, strong friendships, are the happiest people. Especially coming out of COVID, there's still this residual disconnect in this AI and digital day and age. We need this interaction."
His call to action was simple but profound.
"Get clear. Get aware of what your strengths and weaknesses are. Let those things guide your curiosity, and let that curiosity find your community. In doing so, you're going to be on a path toward a more fulfilling and enriching lived experience."
And he left us with a definition of mindfulness that cuts through the noise.
"Mindfulness is being in the present moment without judgment. When you're spiraling and you catch yourself, that's mindfulness. You're bringing awareness to the present moment and saying, 'Oh hey, I'm spiraling right now. Let me pause. Let me create space so that I can respond as opposed to react.'"
Permission to Be in the Middle
Billy Lahr doesn't have a tidy ending. He doesn't have a seven-figure business or a bestselling book. He's in the middle, building something slowly, with patience and self-compassion.
And that's exactly why this conversation matters.
Because most of us are in the middle. Most of us are figuring it out. And pretending otherwise is the fastest path to burnout.
If you're in that messy middle today, take Billy's words to heart. Get curious about yourself. Find your community. And give yourself permission to not have it all figured out yet.
You can find Billy on LinkedIn (Billy Lahr) or Instagram @mindful_midlife_crisis. And if you're interested in the Jumpstart Conversation Series, reach out. He'd love to connect.
Until next time, keep showing up—even when the path isn't clear.
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