The Steeper Path with Lenn Pryor

Lenn Pryor
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Join me on The Steeper Path as we explore stories of individuals who defied conventional success to find a different kind of fulfillment. This podcast is a guide for anyone ready to choose a life of flow and meaning over a life of simply chasing rewards.

Episodes

  1. 4d ago

    Lizzie Parker and Rich Maddux: The Messy Middle

    Lizzie Parker has walked onto a live QVC set and was beamed into a hundred million households. She built a clothing line, landed on a reality TV show, sold into Nordstrom. She's also been on stage with Bill Gates in front of thousands of people.  Lizzie held senior product roles at Microsoft, Amazon, Google, and Cisco. Rich Maddux spent more than twenty years serving his country in the US Army, moved into logistics, then went back and earned an MBA he never believed, as a kid, he'd live to finish. By every visible measure, they had made it. This episode is about why they walked away from all of it in their fifties, and what nobody warns you about the part that comes after. Lizzie and Rich left their careers in San Francisco, traveled for three months, landed in Denver, and are now six months into something most people never get to attempt. Not retirement. Realignment. They have their basic needs met, no boss, no roadmap, and a wide open calendar, and they're discovering that all of that freedom comes with its own kind of weight. In this episode we get into the paradox of choice, and how having every option can leave you sitting at home doing none of them. The strange grief of an unproductive day, and why your body gets sick when the cortisol finally drops. The slow work of self-knowledge, of figuring out who you actually are after thirty years of being who the job needed you to be. We also tackle the financial reality underneath the dream, the planning, the downsizing, the honest conversations a couple has to be able to have before any of this is possible. There's a question in here that started Lizzie's whole pivot. What's a year of your life worth? She'll tell you the moment that question stopped being abstract. This is the work I write about in Breaking Asphalt. Alignment over achievement. The fit between who you are and what you actually do with your time. Lizzie and Rich are living that question out loud, in real time, in the messy middle, and they were generous enough to let us listen in. We'll check back with them in another six months to see what the laboratory has taught them. In this episode we explore: Why leaving a great career in your fifties is realignment, not retirementThe paradox of choice and the discomfort of unstructured timeRedefining success when no one is handing you the metrics anymoreThe perfect day exercise, and Lizzie's reframe into the perfect monthThe financial planning and partnership conversations that make any of this possible"What's a year of your life worth?" and the moment it gets realConnect with Lizzie Parker: https://www.linkedin.com/in/parkerlizzie/ Connect with Rich Maddox: https://www.linkedin.com/in/rich-maddux-5a28b1a1/ Follow The Steeper Path for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 42m

  2. May 14

    Janet Lee: When the Path Finds You First

    Janet Lee opened the conference room door, showed the founder to his seat, got him water, and watched him set up his laptop. When he looked up, he expected her to leave, assuming she was an admin. Instead, she sat down across the table from him and asked "What would you like to talk about today?" The shock on his face told her everything about the room she was in, and the room she was still building toward. This episode traces Janet's path from Garden Grove, California (the other Orange County, the one inland, the one with underfunded schools) to a violin audition that changed her trajectory, to Apple, to venture capital, to nine years in AR/VR, to the executive coaching practice she spent years circling before she finally committed. The shift that drives the whole story: from "let me prove you wrong" to "let me show you who I am." That's a short sentence. It took her two decades to get there. We talk about what her mom understood about discipline that had nothing to do with becoming a musician, why she left Apple at 24 without another job lined up, what the first time she put on a VR headset showed her about human connection, the Snap team council that cracked open coaching for her, the "could versus should" distinction and what it costs to ignore it, and what she changed her mind about when it comes to success. Connect with Janet: Website: https://www.embracenow.co/LinkedIn: https://www.linkedin.com/in/janetjisunlee/Follow The Steeper Path: LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 24m

  3. Apr 29

    Dave Streams: Running Toward the Life You Keep Postponing

    Dave Streams spent 12 years at Microsoft, then Yahoo, then Disney, then Amazon. He was good at the job. He made money. He moved his family across the country seven times. Then he watched his sister finish an Ironman in Oceanside, California. It was pitch black. Marines were setting up the course. U2 was on the PA. Athletes in wetsuits were walking into the water. He was done before the gun went off. This episode is about what happens when you finally stop accepting the narrative you've been handed about who you are and what you're capable of. Dave went from sedentary tech executive to Ironman finisher to 100-mile ultra marathoner, not because he was born athletic, but because he decided to stop believing he wasn't. He battled a rare eye melanoma, left Amazon, launched two companies, and now he's building Audira, a music tech startup that wants to do for the studio what GitHub did for code. We talk about what it costs to leave the cage, what it looks like to suck at something new, how endurance sports rewired the way he moves through everything else, the ADHD epidemic hiding in plain sight across the tech industry, and whether the only real test of alignment is a simple question: does work feel like work? It does not, for Dave Streams. Not anymore. Connect with Dave: Website: https://thestreams.com/SoundCloud: https://soundcloud.com/streams-91848138Follow The Steeper Path: LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comFollow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    2h 12m

  4. Feb 11

    Xiaolan Kruk: Money, Mapping, and the Courage to Move

    After a bit of an unplanned hiatus, The Steeper Path is back in your ears. This episode features a guest who embodies the "steeper path" in more ways than one: Xiaolan (Charlene) Kruk. Charlene and I met nearly a decade ago when she was working for Samsung and I was working for Facebook (Meta).  She has navigated a journey that would intimidate the most seasoned travelers, moving from Shanghai to Korea (mastering the language and the corporate culture at LG and Samsung), and finally to the United States. Her most recent breakthrough wasn't across a border; it was a career pivot into financial planning. In this episode, we dive into: The Courage of the Pivot: How Charlene navigated radical changes in culture, language, and career.The "A" in SEPARATE: Why Action Planning and a "responsible and sustainable financial plan" are the non-negotiables for any career transition.Facing the Money Monster: Why financial pressure is a primary blocker that can "stall creativity and progress" if left unmanaged.As I wrote in my book Breaking Asphalt, "Alignment without mastery is inspiration without impact". Charlene’s story shows you how to master the practical side of your dreams so you can finally stop driving on someone else’s track. Connect with Xiaolan (Charlene) Kruk:  Charlene is offering a free PDF guide on financial considerations before quitting your job. You can get yours by: Visiting her website: www.xiaolankruk.com (Write “steeper path” in the “what are your biggest goals” question box).Direct Messaging her on LinkedIn: www.LinkedIn.com/in/xiaolankruk.Emailing her directly: Xiaolan.kruk@natfin.net.Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 30m

  5. 12/04/2025

    Joel Burgess: Dancing Through Annihilation

    What happens when the thing that defined you is taken away? When the path you were on disappears, and you're forced to discover who you are without it? Joel Burgess was known to everyone around him as a force of nature. A semi-pro rugby player who powered through life with sheer brute force and will. A big man with a big presence.  The last one to leave the pitch or the pub after the match.  Then a devastating injury at the peak of his career didn't just end his rugby dreams—it shattered the entire identity he'd built around being unstoppable. What followed was a winding path through corporate life in Dubai to founding his own company in London which was wiped out during the COVID-19 pandemic, where he kept trying to apply that same force-of-will approach to success. But his body kept breaking down. His spirit kept suffocating. And eventually, he had to face a profound question: What if the way forward wasn't about pushing harder, but about surrendering to something deeper? In this raw, vulnerable and insightful conversation, Joel shares his transformation from someone who muscled through everything to someone who learned to lean into sensitivity, wisdom, and courage. From athlete to entrepreneur to leadership and business coach, his journey isn't a straight line to success. It's a steeper path of discovering alignment through annihilation. Now living in Portugal, he built the Elevated Coaching Collective, a community of heart-led coaches who he helps to master both the inner and outer game of building a business helping others. More than that, he's living proof that our greatest breakdowns can become our breakthrough, if we're willing to step forward with an open heart and learn to laugh at the annihilation. This isn't a story about hustle or willpower. It's about learning that resistance is the path. That anxiety and laughter are two sides of the same coin. That sometimes the way forward requires us to completely let go of who we thought we had to be and just dance. If you're in the middle of your own transformation, or questioning whether to keep forcing your way through or to finally surrender to who you really are, this conversation is for you. Connect with Joel: Instagram: @coach.joel.burgessMedium: joel-burgess-coach.medium.comCommunity: Elevated Coaching CollectiveFollow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 19m

  6. 10/31/2025

    Helen Parker: When Crisis Opens The Portal To A New Path

    What happens when a life-threatening health crisis becomes the greatest gift you've ever received? Helen Parker spent 14 years climbing the corporate ladder at O2 in the UK, building award-winning social impact programs while burning out repeatedly. Then emergency brain surgery in 2014 forced a complete stop—and became her portal to transformation. Today, Helen is a clinical hypnotherapist and co-founder of Experience Carnival, taking women on journeys of radical self-discovery through Brazil's Rio Carnival. Her Complete Confidence Method helps high-achieving women move from exhausting performance to embodied self-leadership. In this conversation, we explore: The "doer trap" and why over-performing leads to burnoutWhy you can't think your way into confidence—you have to feel itThe psychology of trust from her groundbreaking "Think Big" youth programHow Rio Carnival's matriarchal roots create cellular transformationThe incredible story of a man who overcame 60 years of body shame in front of 90,000 peopleIf you're tired of performing success and ready to feel it instead, this episode is for you. Connect with Helen:  Complete Confidence: https://completeconfidence.co  Experience Carnival: https://experiencecarnival.rio Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 27m

  7. 10/20/2025

    Leonardo Benitez: From Dig Sites to Digital Worlds

    From Ancient Temples to Digital Worlds: Leonardo Benitez's Journey from Archaeologist to Game Engineering Leader What happens when a childhood obsession with Indiana Jones transforms into a career unearthing ancient mysteries and then pivots completely into building some of the world's most successful mobile games? In this episode, I sit down with Leonardo Benitez, Head of Game Engineering at Scopely, the studio behind the phenomenon that is Monopoly Go! But before Leo was helping build games played by millions, he was decoding the astronomical secrets of ancient civilizations across the Americas. Leo's path has been anything but conventional. His passion for archaeology led him deep into the world of astroarchaeology, studying how ancient peoples built elaborate structures to track celestial patterns and organize their societies. To bring these ancient mysteries to life, he taught himself software development, creating specialized models and visualizations that could reveal patterns invisible to the naked eye. That technical curiosity opened an unexpected door. One interest fed another, pulling Leo from dig sites in South America into the creative world of animation and game development, starting with building Macromedia Flash games at Disney. Nearly 15 years later, he's leading engineering teams at one of mobile gaming's most successful studios. This conversation explores the connective tissue between seemingly disparate passions, the courage it takes to follow your curiosity into entirely new fields, and how the skills we develop in one chapter of life can become unexpected superpowers in the next. Whether you're contemplating a career pivot or simply curious about how great journeys unfold, Leo's story offers a masterclass in following the steeper path. Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 9m

  8. 10/09/2025

    John Bartleson: From Hip-Hop History to Market Rhythms

    What happens when you build your career at the intersection of culture and technology — then walk away to start over? John Bartleson’s journey from MTV and Roc-A-Fella Records to Wall Street and New York’s DJ scene is a story of reinvention, risk, and staying true to yourself. John Bartleson stumbled into an internship at MTV during its cultural peak, bringing early knowledge of the internet to an industry that barely knew it existed. That insight launched him into a career at the crossroads of music, pop culture, and digital innovation—from Paper Magazine to Island Def Jam and Roc-A-Fella Records, where he worked alongside Jay-Z and Kanye West as hip-hop reshaped the world. As music and media evolved, John helped Nokia and Telefónica bridge culture and technology on a global scale. Eventually, he made a radical pivot—leaving corporate life to trade the markets by day and spin tracks by night at some of New York City’s most vibrant clubs. In this episode, we explore: • The courage to reinvent yourself when the world (and your identity) are shifting • The tension between traditional success and creative fulfillment • How humility, agility, and curiosity can sustain a career across decades and disciplines John’s story is a masterclass in following the beat of your own life—proof that the steeper path often leads to the most meaningful destinations. Listen now and subscribe to The Steeper Path Podcast for more stories of people who’ve chosen the steeper path to greater goals. Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 32m

  9. 09/11/2025

    James Lucas: Building Businesses That Don't Trap You

    Most founders don’t fail because they lack talent or ideas. They fail because they build on someone else’s playbook. They are chasing speed, scale, and status instead of alignment. James Lucas has lived that reality. A repeat founder with a career spanning companies big and small, he’s helped scale startups, worked hands-on with early-stage teams, and learned the hard way what happens when you build on assumptions. That experience shaped his vision for Lunos: a founder-first partner that supports startups from idea to scale, helping entrepreneurs create businesses that actually work for them. Not ones that trap them in broken startup narratives. In this episode of The Steeper Path Podcast, James and I explore: How personal loss and career transitions shaped his definition of success.Why “alignment > achievement” is the real competitive advantage in entrepreneurship.What it takes to design a company that serves your life instead of consuming it.The founder-first philosophy behind Lunos and why it challenges conventional startup thinking.This isn’t just a conversation about startups. It is about choosing the steeper path, rejecting the easier, clearer path to lesser goals and building something that is aligned with who you are. 🎧 Listen in if you’ve ever asked yourself: Am I building the business I actually want or the one I think I’m supposed to? Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 14m

  10. 09/04/2025

    Andrew Molina: Four Strings, No Limits

    Ukulele virtuoso Andrew Molina joins host Lenn Pryor on the debut of The Steeper Path Podcast. We talk about passion, mastery, and choosing the harder road to create a life of meaning. The Steeper Path Podcast | EP 1 – Andrew Molina Welcome to the very first episode of The Steeper Path Podcast, where we explore what it means to choose the harder road to greater goals in life and how alignment, not just achievement, leads to a more meaningful life. Host, Lenn Pryor, is an executive coach and author of the upcoming book Breaking Asphalt: Choosing the Steeper Path to Greater Goals. After two decades leading teams in the tech world, Lenn now helps people break through barriers and find deeper success by aligning with who they truly are. This episode's guest is Andrew Molina, a Hawaii-based ukulele virtuoso who proves that the ukulele has no limits. His electrifying performances have taken him performing and teaching around the world. His four albums have all been nominated for Ukulele Album of the Year at Hawaii’s prestigious Na Hoku Hanohano Awards (The Hawaiian equivalent of the Grammys).  Andrew’s music blends genres effortlessly, from Hawaiian originals to Aerosmith’s Dream On, Led Zeppelin’s Stairway to Heaven, and even the Game of Thrones theme. He has been featured on the cover of Ukulele Magazine, in campaigns for Hawaiian Airlines, and continues to inspire the next generation through the Andrew Molina Ukulele Academy. In this episode, Andrew and I dive into his journey as a professional musician, what it takes to master a craft, and how to keep pushing creative boundaries. Andrew embodies someone who has walked the steeper path to greater goals in his life and continues to evolve, challenge, and grow himself in new ways.  You will learn much from the conversation.   “Andrew Molina is one of my favorite musicians. He works incredibly hard on his craft and approaches the ukulele in such a unique way.” – Jake Shimabukuro Learn more about Andrew:  https://andrewmolinaukulele.com/ Listen to Andrew's Music: https://open.spotify.com/artist/0RbvtOScVE4XNgbjVyHL1m? si=WKp7qWCpQpqATL13CmJG4Q Learn more about Breaking Asphalt: https://www.lennpryor.com/coming-soon-02 Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1h 20m

  11. Trailer

    The Steeper Path Podcast: Coming September 2025

    Join me on The Steeper Path as we explore stories of individuals who defied conventional success to find a different kind of fulfillment. This podcast is a guide for anyone ready to choose a life of flow and meaning over a life of simply chasing the clearer path to lesser goals. Follow The Steeper Path on social media for updates and behind-the-scenes content. LinkedIn: https://www.linkedin.com/in/lennpryor/YouTube: https://www.youtube.com/@TheSteeperPathWebsite: https://www.lennpryor.comProduced by Lagom LLC | Hosted by Lenn

    1 min

Trailer

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Join me on The Steeper Path as we explore stories of individuals who defied conventional success to find a different kind of fulfillment. This podcast is a guide for anyone ready to choose a life of flow and meaning over a life of simply chasing rewards.

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