The Cluttered Path
I planned my whole life out when I was 18 and NONE of it happened the way I drew it up. I'm 54 now: Former Marine Sergeant, engineer, tech sales guy, husband, dad, still in therapy, still working a corporate job, and still figuring this out. The Cluttered Path is the conversation I wish someone had with me at age 28. Career advice that isn't LinkedIn nonsense. Money talk without the crypto bros. Mental health without the eye-rolling. Faith without self-righteousness. Leadership lessons from a guy who's made ALL the mistakes so you don't have to. If your dad wasn't around, wasn't the talking type, or just couldn't relate to the world you live in, pull up a chair.
Episodes
Retirement isn’t the reward most men think it is. It’s an identity crisis waiting to happen.
In this episode, we sit down with Michael Kay, who has made it his mission to help men transition out of “work life” without losing themselves in the process.
Because here’s the uncomfortable truth: Most men don’t struggle with retirement because of money… They struggle because they don’t know who they are without being needed...
Smart, accomplished adults freeze when the rules of the game change. Dr. John Austin spent 20 years figuring out why, and he built a framework for navigating the unknown and conquering uncertainty.
In this episode we hear from Dr. Austin, Dean of the Honors College, PD Merrill Endowed Chair of Business at the University of New England, and author of the book "Certain About Uncertainty".
This is a conversat...
What if the "safe" path is actually the riskiest choice you'll ever make?
In this episode of The Cluttered Path, we sit down with Suzy May, a certified financial educator, Air Force veteran, mom of two, and full-time slow traveler who has visited over 55 countries. She didn't just dream about a different life, she built one intentionally, financially, and with her whole family in tow.
Suzy and her ...
Ever feel like your dream life is permanently “loading”? Bradley Charbonneau did, until one simple daily choice changed everything.
He was living a "successful life, but it felt empty. Bradley walked away from comfort to create a life that actually meant something. His experiment to write every day for 30 days evolved into a complete identity shift, and the birth of the “Every Single Day” and Repossible philosop...
What does it really take to build a fulfilling life after everything falls apart?
In this deeply personal episode, Todd Carswell sits with James to share his own story, from a fractured childhood and brutal military experiences to rediscovering faith, leadership, and purpose.
If you’ve ever felt powerless, stuck, or too far gone to start again, this conversation will remind you that your life can still be renewed...
Rand Timmerman survived harrowing combat as an infantry Marine in Vietnam. After the war, he found success as an attorney while battling PTSD, Alcoholism, and Shattered Faith. Later in life, he faced his demons, found grace, and teamed up with his brother to hike the Appalachian trail.
In this episode, Todd sits down with Rand to discuss his book A Spiritual Passage: The True Story of Two Brothers in Their...
Some stories punch through the noise because they’re honest, messy, and hopeful. Todd Cowles grew up with absentee parents, learned hustle the hard way, and nearly derailed himself with bad friends and worse choices. Then a rival reached out, a mentor stepped in, and a new path opened. Service, leadership, and the painstaking work of building his own self worth. A single pivot sent Todd to college, into the Air Forc...
In this episode, Todd talks with Cheryl Drury, host of Crack the Book Podcast, about how old words can sharpen modern minds. We dig into why reading classics isn’t simply nostalgia, it’s mental training!
Cheryl explains how reading Plato, Homer, and Shakespeare can push your limits, deepen focus, and crack open real mental growth in midlife. No fluff. Just ancient ideas proving their power in real life.
What if the problem isn’t that you need more… but that you’re carrying too much? In this episode of The Cluttered Path, Todd sits down with Paul Stryer, author of Living the Zero Life, to explore a radically different approach to minimalism, not about owning fewer things, but about releasing the emotional, financial, and psychological weight that quietly drains your life.
Paul shares his real journey through divorce...
Every New Year we aim for self improvement, but true personal growth comes from shifting your mindset, not from tapping into willpower. This video shares four of the best books I've read this year that truly changed my perspective on areas like money, relationships, and cultivating mindset.
I personally recommend these books for anyone looking to create lasting change heading into the New Year. I&apos...
What if your resume looks stellar, but your days feel hollow? We dive into the hidden costs of success (Anxiety, Insomnia, Quiet Dread) and show a measured way to pivot without blowing up your life. Our guest, career coach and therapist, Rachel Speckman, breaks down a practical framework for building a soul-aligned path where skills, values, and curiosity actually meet. You’ll hear how to translate vague dissatisfac...
Letting kids grow up isn’t easy. It’s beautiful, bittersweet, and takes a lot of courage. In this heartfelt episode, Dr. Jack Stoltzfus shares how parents can let go with love while staying deeply connected.
Parenting is full of moments that stretch the heart. None more so than watching your kids transition into adulthood. In this conversation with Dr. Jack Stoltzfus, we explore the common pitfalls and struggles tha...
From Victim to Victor: How Taking Accountability Transforms Your Life
Are you feeling stuck in your life despite trying hard to improve? Discover how shifting from a victim mentality to true accountability can change everything. In this episode, Todd interviews Robert J. Hunt, co-author of "Nobody Cares Until You Do," about the power of personal responsibility and overcoming blame and excuses.
Learn the st...
During WWII in war-torn Holland, a five-year-old watches Canadian soldiers hand out bread, butter, and cheese in a schoolyard. He decides that someday he will live in the land of his heroes. Decades later that child, John Brink, arrives in Canada with a suitcase, $25.47 in his pocket, and a desire to build his own company. What unfolds is a story of grit, passion, and the billion-dollar skill that changed everything...
What if confidence doesn’t come from hype, but from training yourself? We sit down with communication coach Jeff Callahan to carve out a practical path from social anxiety to authentic connection that's built on reps, helpful self-talk, and simple frameworks anyone can use. As a child, Jeff’s story began with a severe stuttering problem but today he has a thriving coaching practice featured by Inc., Time, and B...
What happens when you achieve everything society says will make you happy, only to discover it's left you feeling empty? Ray Martin, award-winning business leader turned nomadic explorer, discovered that his greatest achievement wasn't building a successful company — it was finding the courage to walk away from it all and build something better.
In this transformative conversation, Ray reveals how a planne...
In this episode, we delve into Andrew Profaci's incredible escape from the notorious Love Has Won cult, revealing the darkest corners of psychological manipulation and leading to the illuminating light of truth. As Amy Carlson's closest companion, Andrew witnessed firsthand how cult leaders exploit vulnerabilities through powerful psychological control, transforming ordinary individuals into devoted follow...
What happens when a former therapy skeptic sits down with a licensed psychotherapist? Prepare for an eye-opening conversation that challenges everything you thought you knew about mental health support.
Steve McCready, a licensed psychotherapist with a refreshingly practical approach, joins us to unpack why so many of us—particularly men—resist seeking help when we're struggling. From military boot camp experie...
Are your financial dreams feeling out of reach? What if I told you the secret isn't working harder or sacrificing more, but simply starting now and letting time do the heavy lifting?
In this eye-opening conversation with Chris Wilkens, Vice President and Financial Advisor at RBC Wealth Management, we uncover practical strategies that can transform your financial future regardless of when you’re starting. Chris ...
What happens when childhood trauma becomes your greatest teacher? Brandon Held's life story reads like a manual on resilience -- growing up in poverty, living with an abusive, alcoholic stepfather, losing his infant daughter, multiple failed marriages, surviving a suicide attempt, and emerging not just intact but mentally resilient and determined to help others.
Brandon's candid conversation reveals how he...
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