The Ongoing History of Alan Cross

What to Make of a Life in the Corporate Reckoning

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 Website [https://bit.ly/3P7xDiJ] LinkedIn [https://www.linkedin.com/company/growth-mixtape] Instagram  [https://www.instagram.com/bob_mathers] The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/ [https://bobmathers.substack.com/] Links & Resources Jim Collins’ What to Make of a Life: https://www.jimcollins.com/books.html [https://www.jimcollins.com/books.html]

Find Yourself Right Where You Are with Bea Zanatelli

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. Connect with Bob Mathers Website [https://bit.ly/3P7xDiJ] LinkedIn [https://www.linkedin.com/company/growth-mixtape] Instagram  [https://www.instagram.com/bob_mathers] The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/ [https://bobmathers.substack.com/] Links & Resources Bea on LinkedIn: https://www.linkedin.com/in/beatrizzanatelli/ [https://www.linkedin.com/in/beatrizzanatelli/] Bea on Instagram: https://www.instagram.com/beatrizzanatelli/ [https://www.instagram.com/beatrizzanatelli/] Smart Goose Academy: https://smartgooseacademy.com/ [https://smartgooseacademy.com/]

The Life of a Digital Nomad at Sea with Linda Jackson

Today we talk to Linda Jackson, a self-described OG digital nomad who’s been living and working from a sailboat for over a decade… and not just weekend sailing either — we’re talking about crossing oceans, navigating cyclones, and building a life completely untethered from land. Linda is calling in from Fiji — yes, actually on an 80-foot sailing yacht — and what struck me right away is that this isn’t just a story about travel or adventure. It’s about designing a life on your own terms. Selling everything, letting go of the “stuff,” and figuring out how to blend work, curiosity, and freedom into something that actually feels like living. We get into what it really takes to live this way, the mindset required to handle uncertainty, and why most of us talk ourselves out of things long before we ever give them a shot. This conversation left me thinking a lot about the stories we tell ourselves… and what might be possible if we challenged a few of them. Please enjoy, Linda Jackson. Key Takeaways: * You don’t have to go “all in” to try something new — most big lifestyle changes can start as experiments rather than permanent decisions. * Letting go of physical “stuff” can feel surprisingly freeing — and often reveals how little of it actually matters. * The digital nomad lifestyle isn’t just about travel — it’s about designing work in a way that supports how you want to live. * Nature doesn’t care about your plans — Linda’s approach to sailing is a powerful reminder to respect reality, adapt quickly, and never get complacent. * “Head in boat” syndrome — being so focused on what’s right in front of you that you miss the bigger picture — applies just as much to life and business as it does to sailing. * Fear and perceived obstacles stop most people long before reality does — the barriers are often more mental than practical. * A shared vision matters — whether it’s a relationship or a business, alignment on the bigger goal is what makes long-term success sustainable. * You can blend work, adventure, and life together — it doesn’t have to be neatly separated into boxes like we’ve been taught. Connect with Bob Mathers Website [https://bit.ly/3P7xDiJ] LinkedIn [https://www.linkedin.com/company/growth-mixtape] Instagram  [https://www.instagram.com/bob_mathers] The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/ [https://bobmathers.substack.com/] Links & Resources Linda on LinkedIn: https://www.linkedin.com/in/eljay/ [https://www.linkedin.com/in/eljay/] Shellphone Chronicles on Substack: https://shellphonechronicles.substack.com/ [https://shellphonechronicles.substack.com/]

Do What You Want, Or Just Get Old with Whitney Boyd

Today I talk to Whitney Boyd as part of a special series where I talk to friends about things I’ve always been curious about.  And they get to do the same.  I bring two topics, they bring two topics and we surprise each other - no notice and no preparing answers in advance.  It takes courage and I give Whitney a lot of credit for going through with it. Truth be told, she wasn’t 100% sold on the whole idea.  But as you’ll hear, there is nothing Whitney can’t do.  She’s humble, thoughtful and hilarious.   I can’t explain why, but something magical happens when you put the right people in front of a microphone and press record.  Although we didn’t plan it, there was a theme that emerged.  It’s about getting older and watching your kids go through things that it feels like yesterday we just went through.  How hard it is to let them make mistakes.  And how much we can learn about ourselves after all these years, as we relive our childhoods vicariously through them. Please enjoy, Whitney Boyd. KEY TAKEAWAYS * Just because you’re good at something doesn’t mean you’re meant to do it — and knowing the difference matters more than we admit. * The idea that we should constantly push outside our comfort zone is worth questioning. Sometimes comfort isn’t the enemy. * Kids often tie their identity to the thing they do most — and when that’s taken away, it can leave a real gap. * Parenting is full of invisible emotional moments — like grieving the end of a chapter your kid might not even be thinking about. * The things that occupy our thoughts the most (work, appearance, logistics) aren’t always the things we wish did — and that gap is worth paying attention to. * Relationships evolve, but expressing things like “I love you” can feel strangely harder as we get older — even when it matters more. * Life stages sneak up on you — one minute you’re raising kids, the next you’re balancing that with caring for aging parents. * Big life decisions (like where to live) are often less about possibility and more about the stories we tell ourselves about what’s practical or allowed. Connect with Bob Mathers Website [https://bit.ly/3P7xDiJ] LinkedIn [https://www.linkedin.com/company/growth-mixtape] Instagram  [https://www.instagram.com/bob_mathers] The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/ [https://bobmathers.substack.com/] Links & Resources Vienna Waits - https://vienna-waits.com/ [https://vienna-waits.com/] Whitney on LinkedIn: https://www.linkedin.com/in/whitneyboyd/ [https://www.linkedin.com/in/whitneyboyd/] Whitney on Instagram:https://www.instagram.com/vienna_waits_studio/ [https://www.instagram.com/vienna_waits_studio/]

The Ongoing History of Alan Cross

Today we talk to Alan Cross, a legend in the music world and the voice behind The Ongoing History of New Music—a show that’s been shaping how we understand music for over 30 years. If you grew up loving music, there’s a good chance Alan helped you make sense of it—connecting the dots between artists, movements, and moments that changed everything. But this conversation isn’t just about looking back. It’s about how dramatically music has changed… and what that means for all of us. We get into everything—from the explosion of alternative rock in the early 90s, to the moment Napster flipped the entire industry upside down, to why music today feels so different than it did when we were growing up. Alan shares what we’ve gained, what we’ve lost, and why the future of music might be more fragmented—and more confusing—than ever. This felt like a masterclass in music, culture, and how technology quietly reshapes the things we love. Please enjoy, Alan Cross. Key Takeaways * The Power of Storytelling in Music: Alan’s success comes from making music feel human—turning songs into stories that pull you in, even if you didn’t think you cared about the artist. * Why the 90s Changed Everything: The rise of alternative rock wasn’t random—it was the result of cultural shifts, new data (SoundScan), and a wave of artists ready to redefine the industry. * Napster’s Ripple Effect: What seemed like a side experiment in file sharing ended up dismantling the traditional music business—and the industry never fully recovered. * Streaming Changed How We Value Music: With everything available instantly and cheaply, music lost its financial value—even though its emotional impact remains. * Algorithms Are Limiting Discovery: Instead of expanding our taste, streaming platforms often trap us in familiar sounds, making it harder to discover something truly new. * From Tribes to Playlists: Music used to define identity and community. Today, younger listeners mix genres freely, shifting music from a social signal to a personal experience. * The Death of Mystique: Social media has erased the distance between artists and fans, removing the mystery that once made rock stars feel larger than life. * The Future is Fragmented: With thousands of micro-genres and endless choice, music is becoming more personalized—but also harder to navigate and share collectively. Connect with Bob Mathers Website [https://bit.ly/3P7xDiJ] LinkedIn [https://www.linkedin.com/company/growth-mixtape] Instagram  [https://www.instagram.com/bob_mathers] The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/ [https://bobmathers.substack.com/] LINKS & RESOURCES Alan’s website: https://www.ajournalofmusicalthings.com/ [https://www.ajournalofmusicalthings.com/] Ongoing History of New Music Podcast: https://curiouscast.ca/podcast/126/ongoing-history-of-new-music/ [https://curiouscast.ca/podcast/126/ongoing-history-of-new-music/] Uncharted: Crime and Mayhem in the Music Industry: https://curiouscast.ca/podcast/1296/uncharted-crime-and-mayhem-in-the-music-industry/ [https://curiouscast.ca/podcast/1296/uncharted-crime-and-mayhem-in-the-music-industry/] CFNY: The Spirit of Radio documentary: https://www.ajournalofmusicalthings.com/the-cfny-the-spirit-of-radio-documentary-is-coming-to-theatres/ [https://www.ajournalofmusicalthings.com/the-cfny-the-spirit-of-radio-documentary-is-coming-to-theatres/]