The Steeper Path with Lenn Pryor

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/ [https://www.embracenow.co/] * LinkedIn: https://www.linkedin.com/in/janetjisunlee/ [https://www.linkedin.com/in/janetjisunlee/] Follow The Steeper Path: * LinkedIn: https://www.linkedin.com/in/lennpryor/ [https://www.linkedin.com/in/lennpryor/] * YouTube: https://www.youtube.com/@TheSteeperPath [https://www.youtube.com/@TheSteeperPath] * Website: https://www.lennpryor.com [https://www.lennpryor.com] Produced 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/@TheSteeperPath * Website: https://www.lennpryor.com Produced by Lagom LLC | Hosted by Lenn

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/ [https://thestreams.com/] * SoundCloud: https://soundcloud.com/streams-91848138 [https://soundcloud.com/streams-91848138] Follow The Steeper Path: * LinkedIn: https://www.linkedin.com/in/lennpryor/ [https://www.linkedin.com/in/lennpryor/] * YouTube: https://www.youtube.com/@TheSteeperPath [https://www.youtube.com/@TheSteeperPath] * Website: https://www.lennpryor.com [https://www.lennpryor.com] 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/@TheSteeperPath * Website: https://www.lennpryor.com Produced by Lagom LLC | Hosted by Lenn

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 [https://www.google.com/search?q=http://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 [https://www.google.com/search?q=http://www.LinkedIn.com/in/xiaolankruk]. * Emailing her directly: Xiaolan.kruk@natfin.net [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/@TheSteeperPath * Website: https://www.lennpryor.com Produced by Lagom LLC | Hosted by Lenn

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.burgess [https://www.instagram.com/coach.joel.burgess/] * Medium: joel-burgess-coach.medium.com [https://joel-burgess-coach.medium.com/] * Community: Elevated Coaching Collective [https://www.skool.com/@joel-burgess-7514] 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/@TheSteeperPath * Website: https://www.lennpryor.com Produced by Lagom LLC | Hosted by Lenn

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 burnout * Why you can't think your way into confidence—you have to feel it * The psychology of trust from her groundbreaking "Think Big" youth program * How Rio Carnival's matriarchal roots create cellular transformation * The incredible story of a man who overcame 60 years of body shame in front of 90,000 people If 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 [https://completeconfidence.co]  Experience Carnival: https://experiencecarnival.rio [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/@TheSteeperPath * Website: https://www.lennpryor.com Produced by Lagom LLC | Hosted by Lenn