The Growth Mixtape: Chasing Curiosity and Sharing Boundless Insights from Ideas that Matter

Today I talk to Josh Woll, a documentary filmmaker with more than twenty years behind the camera who, six years into sobriety, built a second practice helping other people stop drinking and reconnect with their creativity.

What drew me to this conversation were two things that have consumed my life over the last couple of years that I had never heard anyone put together before.  Plenty of people write about sobriety. Plenty write about creativity. Josh is the first person I'd come across who treats them as the same conversation, and it felt like he was speaking to my soul. We get into his story, from a disastrous teenage DUI to the Orange Theory moment that first cracked things open.

You don’t have to be sober to need this conversation.  Because it’s really about rediscovering yourself, and clearing whatever fog is standing in your way.

Key Takeaways

• Sobriety and creativity are the same conversation. Most people silo them. Josh's whole premise is that putting the drink down doesn't just remove a problem — it clears space, sharpens presence, and reconnects you to the creative self that was there all along.
• Alcohol is a mirage. It feels like freedom, confidence, and relief from anxiety — and it quietly delivers the opposite. The things it seems to solve, it makes worse. It just takes a long time to see it.
• Everyone quits eventually — the only question is when. A reframe from the episode: nobody drinks forever. Seen that way, the decision isn't whether, it's how soon you want the life on the other side of it.
• Nobody can talk you into it — but the right moment and the right people help. Josh didn't do AA; a coach's offhand comment at the gym ("you won't progress if you keep doing that") was the first crack, and going public with a year off gave him accountability.
• "I'm not creative" is a story, not a fact. Josh's position, which echoes across these retreat-adjacent episodes: everyone is born creative; most people just haven't sat down and tapped back into it. Creativity is less a talent than a recovered childhood default.
• Two different creative journeys. The contrast between host and guest is the richest thread:
• We're afraid of our own power. One of Josh's essays-in-progress ("love doesn't need a drink") circles the idea that what really scares us isn't our weakness but our light — and that sobriety is one way of stepping into it.
• Do the hard things on purpose. From a five-day, 4,500-metre trek to Machu Picchu to a daily practice of meditation and sunrise walks, Josh's throughline is feeling the fear, letting it move through you, and taking the step anyway. The growth is on the other side of the discomfort.
• Trust the timing of your life. It's tempting to grieve the years you "wasted" before you made the change. More useful: you weren't ready sooner, and the path played out the way it needed to. Be grateful you made the call when you did.
• Awareness is the real practice. Josh's 30-day Reset isn't about white-knuckling four weekends — it's about getting curious about why you reach for the drink, peeling back the layers in a safe space, and building from there.

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• The Sober Creative on Substack: https://substack.com/@thesobercreative
• Josh’s website: https://www.joshwoll.com/
• Josh on Instagram: https://www.instagram.com/josh.woll/
• Josh on LinkedIn: https://www.linkedin.com/in/josh-woll
• This Naked Mind by Annie Grace — a major influence on Josh's decision to stop.
• One Year No Beer — the public-accountability approach that shaped his first year.
• Chef's Life (PBS, dir. Cynthia Hill) — the Emmy- and Peabody-winning series Josh worked on.
• The Kyle Larson "double" documentary (Amazon) — among Josh's recent film work.
• Julia Cameron's The Artist's Way — referenced as a dream guest/influence.

Today I talk to Rachel Druckenmiller, keynote speaker, songwriter and recording artist I met at a recent songwriting retreat.  You know those people you meet that seem kind and approachable, and then as you learn more you realize, oh I think she’s a really big deal.  Well, that’s Rachel.  In the 3 short months since we first met, she lived out a childhood dream of singing the national anthem for her hometown Baltimore Orioles.  We hear about all the seemingly small things she said yes to, things that didn’t seem to have any point to them, but together landed her on that field in front of 31 thousand people.  And when she got that opportunity, she didn’t waste it. She went all in.  

She also talks for the first time about the song she wrote at the retreat, something so deeply personal she had never said it out loud before.  But when she put her phone on airplane mode and reconnected with herself and nature, it just poured out of her.

This is a conversation about the power of saying your dreams out loud, borrowing other people's belief in you when your own runs short, and why, now more than ever, authenticity beats perfection every time.

Key Takeaways

• Say your dreams out loud — you never know who's listening. Rachel once told a stranger at a conference that her dream was to "speak and sing in stadiums." That offhand admission set off the chain of events that eventually put her on the field at Camden Yards. Kept-inside dreams can't be caught by the right person.
• Be strategic with your yeses — but don't let strategy veto what makes you feel alive. Her first anthem gig failed every strategic test. Rachel's gauge: if it's going to make you feel alive, do it.
• You already have the evidence — use it. Rachel had practised the anthem 200+ times and already sung it once in that exact stadium. Scale spooks us into forgetting we've done a version of the thing before.
• Borrow other people's belief in you. When her own confidence wavered, Rachel deliberately reached out to people who understood high-stakes performance.
• An anthem is a celebration, not a funeral march. Rachel's whole preparation was built on one intention — "renew joy" before every line — and on singing with her whole body, face, and hands.
• Alienating people is a sign of good art. (Peter Katz's line, which lands twice in this episode.) Rachel worried her retreat song was too specific to relate to. The specificity is exactly why it connects, with mothers and non-mothers alike.
• In the age of AI, imperfection is the signal. A little grit, a note caught slightly under — the human imperfections are what make people trust the art now.
• "Allow the unfolding." Rachel takes intentional action toward what she wants, then stays receptive to how it shows up rather than forcing it. Every action is a vote for the person you want to become (a nod to James Clear) — she spent years saying she wanted to be a singer while casting no votes; the last eighteen months have been nothing but votes.
• Get out of the audience of your own life. The through-line of Rachel's year: building a foundation strong enough to support a bigger life, and choosing to participate rather than observe. Legacy doesn't require the path everyone assumes — she points to the late Dolly Parton, who mothered millions without children of her own.

Resources & References

• Peter Katz's Heartstrings Songwriting Retreat — https://heartstringsretreats.com/
• Rachel's retreat song: "The Life I Didn't Choose" on Spotify: https://open.spotify.com/track/5JvSkBhrN7XxZORK8OYngF
• Rachel singing the national anthem at Camden Yards: https://www.youtube.com/watch?v=FTvSn44UR4s

Connect with Rachel Druckenmiller

• Website: racheldruckenmiller.com
• Instagram: https://www.instagram.com/rachel.druckenmiller/
• LinkedIn: https://www.linkedin.com/in/rachelbdruckenmiller

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Welcome to another solo episode, where I gather up conversations with friends, clients and guests that won’t go away and keep organizing themselves around specific themes.  This one is about something almost everyone I talk to is wrestling with: how to stand out and become memorable. Whether you're chasing a new job, a promotion, an investor, a creative breakthrough, or just trying to figure out what's next — at some point you're going to have to stand out among everyone else doing something similar to you. And in a world engineered for us all to blend into a thousand shades of grey, that's harder than it should be.

I walk through why we lose the ability to stand out, why your own life is the only thing nobody on Earth can copy, and the difference between telling your story and excavating it. Then I get practical: the exact three-step exercise I ran fifty people through at Cansbridge, the one you can do today with a pen, some paper, and — I'm not joking — a box of crayons.

Key Takeaways

• The game is rigged for sameness — so change the game. When everyone's playing the blend-in game, the only winning move is to stop playing it and make a bold choice that gives people something to react to.
• Give them something to react to. Olivia Wilde's casting-director story is the template: the actors who stopped trying to guess what the director wanted and instead showed what they could bring got remembered — and got the call a month later, even when they didn't land that part. Contrast is what gets remembered.
• A real client example. A customer success leader with a military background had always hidden that part of her story, afraid it read as rigid. In her final interview she led with it—the idea that the mission never changes even when the plan blows up.
• AI is a catalyst, not the cause. Everyone using the same three tools to sound unique is why we all sound identical — but this problem predates AI. Blending in was always the default.
• Your life is the only thing nobody can copy — but telling isn't enough. You have to excavate. Telling your story recounts what happened. Excavating it digs into what it reveals about how you're wired and what you can offer that no one else can.
• Two symptoms, one disease. Symptom one: we don't believe there's anything special about our story. Symptom two: most of us don't actually want to stand out — we live in quiet fear of it. The disease underneath both: we've lost the childlike curiosity we were born with. A five-year-old paints an orange sky and doesn't care what you think — until a thousand tiny corrections teach us there's a right answer and we'd better find it.
• Encodings and your constellation. We each carry a unique combination of the things that feel more natural to us than they do to other people — like stars forming a constellation only you have. The most fulfilling lives aren't built by grinding at something until you're good at it; they're built by aligning your work with what you were born to do.
• The three-step exercise (about 30 minutes, pen and paper — or crayons):

1. Clear the decks. Five minutes of stream-of-consciousness writing. No stopping, no editing. Get the noise out.
2. Build your storybank. Three moments that changed something in you — not accomplishments, not the highlight reel. (And don't make them all sad — joy excavates just as well as loss.)
3. Excavate. For each, ask what it reveals about you, not what happened. Look for the thread running underneath.
4. Uncover your Category of One. Draft one statement — "I believe…" is a useful scaffold, not a rule.

• Say it out loud within the hour. A statement you've never spoken is just journaling. Test it on a real human and watch their face.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Jim Collins’ What to Make of a Life: https://www.jimcollins.com/books.html

Cansbridge Fellowship Conference Workshop: https://cansbridgefellowshipconference.com/

Today I talk to Rob Szabo — a four-time Juno-nominated (and one-time Juno-winning) musician, producer, and composer who has spent over thirty years making a living doing the thing most of us are told to give up on. He's played in bands since before he was legally allowed to be there, sold thousands of tapes out of the back of a car in the '90s independent music boom, produced some fifty albums, and — in a plot twist nobody could have planned — writes music for the Paw Patrol movies, including a hair metal song he sings as the villain.

Rob and I grew up in the same town, a year apart, and somehow never crossed paths until a couple of months ago at Peter Katz's songwriting retreat. He was the first person I met when I walked in the door, and I've been wanting to have this conversation ever since.

I came into this thinking I'd ask Rob about the Junos and Paw Patrol and the fairy-tale career. Instead we went straight down the rabbit hole I've been obsessed with lately — creativity as a practice, not a talent you're either born with or not. We talked about the childlike well of creativity we all get told to bury, learning to be comfortable with waste, doing the work as an end in itself, and the constant negotiation of showing up to the practice even when you don't feel like it. If you've ever told yourself "I'm just not a creative person," this one's for you.

Please enjoy, Rob Zabo.

Key Takeaways

• Creativity is a practice, not a gift. We're all born with a deep well of it — it just gets dulled over the years as we're told to be serious and grow up. The good news: it's still there, and you can rebuild access to it like any other habit.
• The things worth doing are the ones you don't run a cost-benefit analysis on. Rob's most meaningful work came from committing to things as an end in themselves — not justifying the means to an end. If you're trying to justify it, it's probably not the thing.
• Beware getting really good at something you never wanted to do. Chasing security by doing "adjacent" work is how you wake up an expert at the wrong thing, with no time left for what you actually care about.
• Get comfortable with waste. Most creative work never gets seen — the sketches, the fifty songs recorded so twenty make the album, the dozens of revisions. In a productivity-obsessed culture that demands immediate results, learning to tolerate waste is one of the hardest and most essential shifts.
• Faith is part of the deal. Sitting down for two hours with no idea whether anything useful will come out — and doing it anyway — is an act of faith that the reps eventually produce fruit.
• Lower the stakes to beat resistance. "Let's write a shitty song today." Some of the best work comes when you're just fooling around and the pressure's off.
• Novel settings short-circuit the inner critic. Nature, water, a boat on a lake, a walk, a shower, driving — occupying your conscious brain just enough gets you out of your own way.
• Recognition matters less than you think — to everyone but you. The Junos, the followers, the accolades: nobody's paying as much attention as you are. Rob flags his Juno on LinkedIn knowing it eases a client's mind, while holding lightly to the fact that it doesn't mean what people think it means.
• Once you release something into the world, what happens next isn't about you (a Rick Rubin idea we both wrestle with). We're hardwired to crave the validation anyway — which is exactly what makes social media so insidious.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Rob Szabo’s website: https://www.robszabo.com/

The Creative Act: A Way of Being by Rick Rubin: https://sites.prh.com/thecreativeact

Bird by Bird by Anne Lamott: https://www.penguinrandomhouse.com/books/97395/bird-by-bird-by-anne-lamott/

Peter Katz's Heartstrings Songwriting Retreat: https://heartstringsretreats.com/

Michelle Grocholsky is back for her second time on the show, and this one's a different format than her first. Instead of a traditional interview, we each brought two topics we were excited to explore, didn't share them ahead of time, and just pressed record to see what happened.

Michelle works in equity, diversity, and inclusion, and she's someone I've had dozens of conversations with over the years — but there's something about doing it with a microphone on and other people listening that makes even close friends nervous. We both admitted to that jitteriness up front, and I think that's part of what made this land where it did.

We got into a belief I no longer hold (that I'm not a creative person), the whiskey-fuelled childhood moment that may have quietly turned my volume down, Aristotle's three kinds of friendship and how our circles change as we age, my nearly-five-years of sobriety and the conversations it forced with myself, and Michelle's decision to walk away from social media almost entirely — and what that clarified about who actually shows up for her.

Please enjoy, Michelle Grocholsky.



Key Takeaways

• The beliefs we hold most firmly about ourselves are often the ones we've never examined. Bob spent his life believing he wasn't creative and needed to borrow ideas from others — only to discover a deep well of untapped creativity once he got sober and had the space to look inward.
• Rick Rubin's reframe cuts through a lifetime of self-limiting stories: never say you're not good at something. All you actually know is whether you've tried it or not. Everything else is a fabrication we've accepted as fact.
• The gap between how the world sees us and the stories we carry about ourselves can be enormous. When Bob talked about "rediscovering" his creativity, friends who'd known him for years were baffled — to them it was never in question. The work isn't building the muscle; it's turning the volume back up on what was always there.
• Aristotle's three kinds of friendship — utility, pleasure, and virtue — are a useful lens for the friendships that shift as we age. We need all three, and the mix changes over time, but the enduring "friends of virtue" (where you can be fully yourself) are the ones worth deliberately cultivating.
• Deep, virtuous friendships often come from unexpected places — Michelle's most precious friend is a man in his seventies she met at a coffee shop, generations apart with little on paper in common. Sometimes you have to be "the weirdo at the coffee shop" and risk a few no's to find real connection.
• Existing pleasure friendships can deepen — but usually only at an inflection point (a diagnosis, a decision, becoming a parent, getting sober). And when you go vulnerable first, sometimes the door stays closed, and that's okay. No single person fulfils every need.
• On sobriety, the hardest conversations were with himself, not others.
• The unexpected gift of sobriety wasn't better sleep (still working on that) — it was comfort in his own skin.
• Michelle's case against social media: it enables "lazy friendships" (people who know your milestones without ever asking about your life), fuels comparison against curated fictions, and quietly steals the hours you'd need to exercise, read, or call your mom.
• The clarifying, uncomfortable truth: when Michelle left social media, most people forgot her birthday and few showed up for her biggest career milestones.
• You can't have it both ways with applause. If you let likes and recognition feed you, you'll be gutted when the applause stops.
• Real connection is a skill people are actively losing.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Michelle on LinkedIn https://www.linkedin.com/in/michelle-grocholsky/

Welcome to another a solo episode — where I pull together threads from conversations with guests, clients, and friends that keep organizing themselves around a theme, and try to make sense of them out loud so you have space to insert your own stories.

Today's thread is the rise of the retreats. They seem to have come out of nowhere — nobody talked about them before COVID, and now everyone I know is either going on one, saving up for one, or running their own. I've done two in the last ten months, and both were transformational. So I want to sit with a paradox: these retreats are helpful, they're necessary, and it's completely messed up that we need them at all. We've engineered our lives to be so full of distraction, comparison, and anxiety that we'll pay thousands of dollars to sit on a rock in the woods for three days and remember how we're actually meant to live.

I also share the story behind the song I wrote at Peter Katz's Heartstrings retreat — a song about my mom, dementia, and a playlist that brought her back to sixteen for a five-hour car ride — and then get practical about how to bring the best of these reset experiences home instead of leaving them in the woods.

If you stick around to the end, you get the world premiere of "Play Me Some Elvis." Mom, this one's for you.

Key Takeaways

• The retreat paradox: these experiences are genuinely necessary in the world we've built, and the fact that we need them at all is evidence of how badly we've engineered our lives. Both things are true — they help, and we should never have needed them.
• The magic isn't the programming — it's the white space. The best retreats resist the urge to pack every hour, striking a deliberate balance between a bit of group inspiration and long stretches of solitude to digest it. The content you could get anywhere (even from ChatGPT); the conversation plus the room to reflect is what you're actually paying for.
• Arthur Brooks' distinction between complicated and complex problems reframes all of it. Complicated problems (how does a jet engine work, how do I hit a million in revenue) have answers, and tech is great at them. Complex problems — love, happiness, meaning — have no answer; the point is to keep searching. We've overdeveloped the brain that solves the first kind and let the other atrophy.
• Being bored and quiet isn't wasting time — it's where the neglected side of your brain finally gets to work. We smother it in "digital slop," listening to podcasts while folding laundry, terrified of an unoccupied minute. That compulsion is exactly what blocks the answers we're looking for.
• It's not up to you what you create — your job is to be open and notice. Bob showed up with rock-and-roll song ideas he'd planned in advance; the actual song only arrived once he disconnected and gave his mind space. The best material was sitting just under the surface of a busy life, waiting for room to surface.
• Peter Katz's mic-drop line: "That's not the real world. This is the real world." We pay to live intentionally for 3 days out of 365 and call the other 362 normal. Maybe the version of us that shows up in the woods — honest, brave, unapologetic — is the real one, and the job is to smuggle as much of it back as we can.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Waypoint Retreat: https://vienna-waits.com/retreat

Heartstrings Retreat: https://heartstringsretreats.com/

The Meaning of Your Life, Arthur Brooks: https://www.arthurbrooks.com/the-meaning-of-your-life

Play Me Some Elvis on YouTube: https://youtu.be/aNwCbPw9df0?si=81Z4ZAtkOT-yXFDr

Today Greg Boyd is back on the show, and this time we tried something different.

Greg is a friend and cofounder of Vienna Waits with his wife Whitney, and if you've listened before you know our first conversation went to some deep, tearful places. This one uses a format I've been experimenting with: we each bring two topics, we don't share them ahead of time, we turn off the notifications, press record, and see what happens. It's vulnerable and a little terrifying, because I have no idea what someone's going to spring on me.

That's exactly why I love it.

We ended up covering songs that snap us back to another time and place, why men so often suck (and what we owe our kids as their fathers), the ugly, rarely-admitted feeling of not being happy when good things happen to people close to us, and Jim Collins' What to Make of a Life — the idea that you can only discover what you're built for through doing, never by being told.

What struck me most is how these unscripted conversations keep circling back to the same core themes without either of us planning it. 

Please enjoy, Greg Boyd.

Key Takeaways

• A song can be permanently rewired by a single powerful experience, not just repeated listening. Greg's decades-long association with the Tragically Hip's "Bobcaygeon" was rewritten in one night by a musical that reframed it as an immigrant falling in love with Canada.
• On why men suck: separate nature from nurture. The nature side you can't control, but the nurture side often comes down to a lack of role models — men modelling the less-shitty behaviours we actually want our sons to carry forward.
• The bar for being a "good dad" is embarrassingly low ("80% is just showing up"), while the bar for moms is far higher — the invisible load moms carry that dads simply aren't expected to. Worth naming, because pretending otherwise perpetuates it.
• Greg's sharpest theory: men are as insecure as everyone else, but grow up in an environment where insecurity isn't allowed. Masking that insecurity with achievement is what produces a lot of "successful" men who still aren't good ones.
• Own the good in your kids. When Bob credited his wife for his sons' kindness, Greg pushed back — deflecting all the credit to your partner perpetuates the exact "no good role models" problem. Claim that kindness came from you too.
• The hard, honest one: sometimes we can't be happy for the people closest to us, and quietly feel better when things don't go their way. It's more common than anyone admits — and it's a signal, not a character flaw.
• That jealousy fades when you're "in frame." Once you get clarity on what you're actually built for, other people's success stops threatening you, because you're finally in your own lane instead of eyeing theirs.
• You can't think or plan your way to knowing what you're good at — you discover it through action. Which means being 55 and "stuck" doesn't mean you're limited; it means there are countless things you're gifted at that life just hasn't asked you to do yet.
• An app that tells you what to do with your life misses the entire point. The messiness of the search is the value — being handed the answer at 20 would rob you of ever truly believing it.
• Bob's answer to "what do you wish people said about you behind your back": he helps me see things in myself I didn't know were there, and he's a good dad. Greg's: he's kind. Both trace back to the same root — being someone whose work leaves good people in the world.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Vienna Waits - https://vienna-waits.com/

Vienna Waits on Instagram:https://www.instagram.com/vienna_waits_studio/

Greg on LinkedIn: https://www.linkedin.com/in/gregboyd-vienna-waits/

Waypoint Retreat 2026: https://vienna-waits.com/retreat

Today we talk to Will Giangrande, founder of The NextGen Playbook and someone who has made it his mission to help bridge the gap between generations in the workplace.

I met Will a little over a year ago, and despite being nearly the youngest person in the room, he struck me as an old soul. He's spent the last few years helping leaders better understand Gen Z, but what I loved most about this conversation is that he flips the usual script. Instead of a fifty-year-old HR professional explaining how to relate to younger workers, here's someone from inside that generation translating both directions — and refusing to point fingers about which generation has it figured out.

We covered everything from dating apps and long-distance relationships to remote work, feedback, work-life boundaries, purpose, AI, and why a 25-year-old might already be wrestling with questions previous generations didn't start asking until midlife.

More than anything, this conversation reminded me that most of the friction between generations comes from misunderstanding. We're all just products of the world we grew up in — and if we can stay curious and ask one more question, we usually find we have more in common than we think.

Please enjoy, Will Giangrande.

Key Takeaways

• Every generation has accused the one behind it of being lazy, entitled, and bound to ruin everything. Will literally collects these quotes and has audiences guess which era they're from — the complaints are ancient.
• "Gen Z" isn't one group. Smartphones and COVID created sub-generations inside the label: someone who got a phone at 15 forms relationships differently than someone five years older, and where you were during the pandemic (17 or 22) changed everything.
• Most workplace tension is a projection problem. We assume the only upbringing we ever had — the way we learned to communicate and build relationships — is the "normal" way, and judge everyone else against it.
• Wanting feedback isn't neediness. In a remote setting, the hallway moments and quick door-knocks vanish, so mentorship has to be scheduled and asked for. That makes it look constant and formal when it's really just become visible.
• The work-life boundary fight isn't about laziness either — it's about control over time, not fewer hours. The 9-to-5 is an industrial-era leftover, and younger workers are the first to feel empowered to push back on it. Most of us never felt we could.
• Your first job becomes the baseline. Whatever you experience first — remote or in-person, one set of norms or another — quietly becomes the standard you judge every job after it against.
• Purpose is arriving early. The questions about meaning and balance that used to trigger a midlife crisis at 45 are now showing up in people's twenties — and with longer lives and AI reshaping work, careers are becoming less linear. Reinvention and curiosity may matter more than sticking to one path.
• We make sweeping claims about millions of people from a sample size of five. Social media magnifies the differences between us; honest conversation tends to shrink them.
• The simplest way to bridge the divide: stay curious and ask one more question. You never know where it leads.

Connect with Bob Mathers

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LinkedIn

Instagram 

The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

NextGen Playbook Website: https://thenextgenplaybook.com/

Will Giangrande on LinkedIn: https://www.linkedin.com/in/will-gian/

The Next Gen Playbook on Instagram: https://www.instagram.com/thenextgenplaybook/

Will Giangrande on YouTube: https://www.youtube.com/@WillNavigates20s

Welcome to another solo episode, this time on the collective midlife crisis we’re all going through and how to navigate it with the help of Jim Collins’ new book, What to Make of a Life.

Lately, I’ve been having the same conversation over and over again with leaders, founders, and people in every stage of their careers. They’re successful on paper, but something feels off. The things that used to work don’t seem to work anymore, and there’s this growing sense that there has to be something more.

In this episode, I share an idea I’ve been calling the “Corporate Reckoning” — the collision of COVID, AI, and economic uncertainty — and why so many of us feel like strangers in careers we’ve spent our lives building.

And I talk about Jim’s new book that arrived at exactly the right moment, one that gave me language, hope, and a completely different way of thinking about what our best work might still look like.

This one is deeply personal, a little messy, and very much a work in progress.

Please enjoy.

Key Takeaways:

• We’re living through a “Corporate Reckoning” — the combination of COVID, AI, and economic uncertainty has fundamentally changed how we work and what’s expected of us.
• Many people feel like strangers in careers they’ve spent decades building because the strengths that made them successful were designed for a world that no longer exists.
• The traditional career path our parents experienced is disappearing. Reinvention isn’t optional anymore — it’s becoming a normal part of modern life.
• Jim Collins’ concept of “encodings” suggests that each of us has unique, innate capabilities that are revealed through the experiences of life, and we have far more of them than we realize.
• Our best work may still lie ahead. Many of the people Collins studied discovered entirely new strengths and did their most meaningful work later in life.
• Being “in frame” means using the gifts that come most naturally to us. Being “out of frame” often creates the restlessness and dissatisfaction so many people are feeling today.
• Major events in our lives — what Collins calls “cliffs” — often force us to uncover strengths we never knew we had.
• Feeling lost, uncertain, or confused isn’t unusual. We all spend time in “the fog,” and recognizing that can make the experience feel a lot less lonely.
• Looking back at our stories can help us uncover patterns, strengths, and clues about what we’re uniquely meant to contribute.
• Curiosity may be one of the most important tools we have for building a bigger, more meaningful life.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Jim Collins’ What to Make of a Life: https://www.jimcollins.com/books.html

Today we talk to Beatriz Zanatelli — entrepreneur, founder, immigrant, and one of the most intentional people I know.

Bea and I have known each other for years, but this conversation felt different.  It’s a perfect example of what can happen when people show up with genuine curiosity and no expectations about where it might lead.

What came out of it was a conversation about identity, confidence, intuition, childhood insecurities, building a life in a new country, and the strange ways we slowly grow into ourselves over time.

Bea shares the story behind her obsession with the CN Tower — which turned out to be way more emotional and meaningful than I expected — and we talk about the difference between following data versus following your gut when making big life decisions.

This one felt deeply human. Vulnerable, funny, emotional at times… and honestly just a really beautiful conversation between two friends trying to figure life out in real time.

Please enjoy, Beatriz Zanatelli.

Key Takeaways:

• The things that make us feel different as kids often become the things we grow to love most about ourselves.
• Confidence isn’t having all the answers — true confidence is being comfortable saying “I don’t know.”
• Intuition can be just as powerful as data when making big life decisions. Sometimes your body knows before your brain catches up.
• The CN Tower became a symbol for Bea of possibility, belonging, and building the life she dreamed about for her family in Canada.
• Vulnerability and curiosity are the foundation of real trust and connection.
• Breaking generational patterns takes awareness, courage, and intentional choices over time.
• Purpose-driven work feels different — as Bea says, Smartgoos became “my soul in the shape of a business.”
• Most of us never fully “figure it out” — even later in life, there’s still uncertainty, insecurity, and constant growth.

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Bea on LinkedIn: https://www.linkedin.com/in/beatrizzanatelli/

Bea on Instagram: https://www.instagram.com/beatrizzanatelli/

Smart Goose Academy: https://smartgooseacademy.com/