The Sub-Gen Problem: Why 2 People Born 5 Years Apart Aren't the Same GenZ with Will Giangrande

The Sub-Gen Problem: Why 2 People Born 5 Years Apart Aren't the Same GenZ with Will Giangrande

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 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 NextGen Playbook Website: https://thenextgenplaybook.com/ [https://thenextgenplaybook.com/] Will Giangrande on LinkedIn: https://www.linkedin.com/in/will-gian/ [https://www.linkedin.com/in/will-gian/] The Next Gen Playbook on Instagram: https://www.instagram.com/thenextgenplaybook/ [https://www.instagram.com/thenextgenplaybook/] Will Giangrande on YouTube: https://www.youtube.com/@WillNavigates20s [https://www.youtube.com/@WillNavigates20s]

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/]