The Dirt Path

Grayson Harris
  • 5.0 (2)
  • Self-Improvement
  • Updated Weekly

The Dirt Path Podcast celebrates those who choose to live and work differently. The world pushes us toward the "highway" of conventional jobs and lifestyles. But some brave people choose the "dirt path," with no signs or lights guiding the way. We interview these "dirt path trailblazers" to uncover: What led them to the path? Their biggest challenges and actionable tips for the "dirt path curious." This show is for anyone unaligned with their current job or lifestyle, seeking motivation to make a change. New episodes: Wednesday 6am EST (Video available on Spotify and YouTube)

  1. 2d ago

    Small Town Maine to Broadway via Relentless Adaptability | 32 Dennis St Pierre

    Dennis St Pierre is an actor, singer, dancer, and founder who spent over 20 years performing around the world including multiple appearances on TV and Broadway. Expect to hear: - Humble Beginnings and Recovery: Dennis' story of coming from a small town in Maine in a big family below the poverty line and how he overcame an early traumatic experience - Wild NYC Tales: Bartending at Studio 54, sleeping in his car for two years to attend dance classes, and getting career advice from Prince - The 4 Week Collapse: How Dennis went from finally achieving his ultimate career peaks on Broadway and TV to the lowest point of his life in less than a month - Break a Leg: The wild emergency call-up story that gave Dennis his second chance on the big stage as Jean Valjean in Les Misérables - Redefining Success: How Dennis's definition of success transformed over decades of pivots, why true talent is adaptability, and what lights his soul on fire today ------------------------------ Timestamps: (00:00) Relentless Adaptability (00:58) Returning to Maine (Interview Start) (05:18) Redefining Success Beyond the Stage (09:42) Small-Town Maine Roots & Hockey Concussions (14:19) The Burn Accident & Ballet Recovery (16:46) New York Hustle & Sleeping in a Car (22:51) The 4-Week Collapse: Ed & Les Mis Close (27:57) The Radio Theater Pivot & Losing Savings (36:22) "Break a Leg": Stepping In as Jean Valjean (41:30) Professional vs. Amateur Acting (48:59) Why the Ultimate Talent Is Adaptability (53:25) What Real Fulfillment Looks Like Today (57:09) Theater Beyond Entertainment: Emotional Catharsis (01:04:09) New Projects in Denmark & Actor Studio Helsingør (01:06:16) Why "The Dirt Path?" ------------------------------ Connect with Dennis: Dennis' website is coming soon! Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Email your questions: thedirtpathpodcast@gmail.com - Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

  2. Jul 15

    The Importance of Taking Your Destined Path | 31 Wanderers

    If you are dirt path curious, but not yet taken the leap, you are missing out on much more than you think. In this month's Wanderers episode, we talk about the importance of taking your destined path, past the obvious. We dive into how choosing location independence and career alignment naturally attracts the community, relationships, and opportunities meant for your true self. Expect to hear: - How we met: how taking the dirt path lead us to meeting each other - Showing up authentically online: why being your full self online will lead to aligned opportunities - LinkedIn authentic branding: Paige gives us her top 3 tips for building an authentic personal brand on LinkedIn ------------------------------ Timestamps: (00:00) Importance of taking your destined path (02:02) Grayson before meeting Paige (07:54) Paige before meeting Grayson (10:08) How we met on LinkedIn (18:55) What attracted one another (27:35) Change Environment Meet People (29:19) Authenticity Online Wins (32:24) Why LinkedIn Needs Realness (38:42) Authentic LinkedIn Tip 1: Profile Photo Refresh (42:14) Authentic LinkedIn Tip 2: Show Who You Are (45:18) Authentic LinkedIn Tip 3: Post for Future You (51:50) Monday Club In Person Events ------------------------------ Related Links: - Paige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/ - Grayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/ Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Email your questions: thedirtpathpodcast@gmail.com

  3. Jul 8

    Grieving an Unlived Life: How to Build Grit from Deep Loss | 30 Eric Hodgdon

    Eric Hodgdon is a 2x TEDx speaker, Amazon bestselling author, coach, and the founder of "The Grit Guy" who spent 25 years climbing the corporate ladder in IT before completely restructuring his life. CONTENT WARNING & DISCLAIMER: This episode contains deep discussions surrounding suicide and severe trauma. We believe these raw conversations are vital to share, but please listen with care. (If you or someone you know ever needs support, free confidential help is always available 24/7 by calling or texting 988, or visiting findahelpline.com). Expect to hear: • The Transition Curve Framework: The cyclical trap of building a business, moving from uninformed optimism to informed pessimism, and why 80% to 90% of people quit on their goals • The Catalyst of Shocking Loss: The heartbreaking retelling of losing his 15-year-old daughter Zoi to suicide in 2014, and how it became the catalyst for his own long-term healing framework • Micro vs. Macro Recoveries: Eric’s operational toolkit for down-regulating your nervous system out of chronic fight-or-flight • Grieving an Unlived Life: The moment Eric realized the true origin of his grief, and signs to lookout for on your journey towards greater purpose • Side-Hustle Method: The highway exit for calculated risk-takers looking to enter the dirt path of entrepreneurship ------------------------------ Timestamps: (00:00) Job Offer Reality Check (01:08) First P90X Success Story (Interview Start) (02:35) Grit Built in Repetition: Embracing the Boring Operational Tasks (06:45) From IT to First Break: The Newspaper Ultimatum (12:14) Corporate Costs and Lifestyle: Realizing You Are a Cog in the Wheel (14:50) Entrepreneur Leap and Optimism: The Illusion of the Corporate Exit (17:01) The Transition Curve Explained: Uninformed Optimism to Informed Pessimism (22:36) Finding Alignment in Funnels: Using Technical Skills for Market Demand (24:46) Loss That Changed Everything: The PIP, The Layoff, and January 2014 (29:39) Helping Others While Grieving: Forging Resilience Through Narrative Storytelling (34:00) Grayson's Ongoing Struggles: Nerve Damage, Layoffs, and Live On-Air Coaching (42:07) Nature as Nervous System Reset: Walking the Harraseeket Trail (44:42) Micro vs. Macro Recovery: Lower-Body Breathwork and 90-Day Sacred Boundaries (49:04) Zoi’s Lesson: Just Be & Breaking the Cycle of Commuter Rail Self-Blame (53:09) From Grief to Grit Guy: Building a Chapter on Your Own Terms (58:36) Highway vs. Dirt Path Signs: Listening to Physical Ailments and Gut Bio-Signals (01:06:40) Lessons from Near Failure: The $7,000 Boston Mastermind Workshop Disaster (01:12:11) Side Hustle vs. Leap: Utilizing Fragmented Time to Validate Market Demand (01:19:56) Why Choose the Dirt Path? ------------------------------ Connect with Eric: - Eric's Website: https://www.thegritguy.com/ - Eric's Instagram: https://www.instagram.com/thegritguy - Watch Eric's Tedx Talk: https://www.youtube.com/watch?v=ihp1_szQlM8 Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Email your questions: thedirtpathpodcast@gmail.com - Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

  4. Jul 1

    How to Become a Digital Nomad and Keep Your 9 to 5 | 29

    After living the digital nomad life for 5 years, and helping people live the life without leaving their careers, these are the 5 most common mistakes most people make when trying to achieve their ideal lifestyle and keep their job. In this episode, we do a deep dive and how-to on a specific dirt path: becoming a digital nomad as a corporate employee. Expect to hear: • Ditching the Binary Mindset: Why most corporate employees trap themselves in black-and-white thinking, and how "embracing the gray" allows you to build a custom lifestyle that supports both your career and your freedom • The Undercover Nomad Risk: Why keeping it a secret and going nomad undercover isn't a good idea • Proposing a Partnership vs. Asking Permission: How to talk with your boss and company in a way that will get a 'yes' • The 4 Corporate Roadblocks: The most common 4 things each company will bring up when you propose the idea of working remotely while traveling abroad ------------------------------ Timestamps: (00:00) New Episode Format - Dirt Path Deep Dive (01:32) Nomad with a Nine to Five (02:40) Five Mistakes and Playbook (04:39) Mistake One: Black and White Thinking (09:22) Mistake Two: Undercover Nomad (12:54) Mistake Three: Underestimating the Energy (17:23) Lifestyle Logistics and Commitment (22:12) Mistake Four: Asking for Permission (28:52) Mistake Five: After Yes Execution ------------------------------ Checkout my free playbook on how to become a digital nomad with a 9-5: https://www.engineeredflexibility.com/products/the-engineer-to-nomad-playbook Watch my full story on how I used this playbook to fully shift my life: https://youtu.be/dKHHTVmWFG4?si=sLmP9P3fyZYbSzOf Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/ - Email your questions: thedirtpathpodcast@gmail.com

  5. Jun 24

    Doubling Down Amidst Uncertainty & Building Community | 28 Mandy Reynolds

    Mandy Reynolds is a commercial real estate agent, developer, and the co-founder of Union + Co. coworking space in Bath, Maine. She shared her dirt path journey rescuing a historic, 24,000-square-foot "white elephant" building, creating a community cornerstone in a small town, and the mental stamina it takes to continue amidst massive uncertainty. Expect to hear: - Unconventional Path: How Mandy started her career doing ESG research, transitioned into real estate, and eventually co-founded a coworking space - Doubling Down Amidst Uncertainty: Why Mandy chose to invest more into Union & Co after a rocky start, and how they mentally persevered throughout. - Third Space Emergence: The rise of third spaces after covid and the unexpected impact a coworking space provides - Bigger than a Coworking Space: Mandy's vision of creating a community center point in a small town in Maine, and how they differentiate themselves from other coworking spaces. ------------------------------ Timestamps: (00:00) Bath Coworking Dream (01:05) Closing Deals Variety (02:13) Commercial vs Residential Real Estate (06:05) Maine Roots & The Border Town Reality (08:13) New Zealand Study Abroad & The Liberating Side of Travel (12:19) ESG Research Career & The SINS Blueprint (18:28) Remote Work Coworking & The Isolation Trap (21:21) Real Estate Turning Point & Build Maine (27:04) Broker Investing Dilemma & "Rich Dad Poor Dad" Influence (32:13) Union & Co Origins: A Historic Fairytale Downtown (37:04) Opening Day And First Members (40:58) Sticking With It: From 5 Founders to 2 (47:22) Why Coworking Matters: Getting Out of Your Bubble (55:12) New Building Redevelopment: Tackling a 24,000 Sq Ft Monster (59:25) Community Programs And Art (01:04:17) Advice For New Operators: You Must Own the Bricks (01:07:53) Frankisms And Farewell: Knowing How to Get Out ------------------------------ Connect with Mandy: - Union + Co Website: https://www.unionandco.me/the-team - Union + Co Instagram: https://www.instagram.com/unionandcomaine/ - Mandy's LinkedIn: https://www.linkedin.com/in/mandy-reynolds-aa779155/ Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Email your questions: thedirtpathpodcast@gmail.com - Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

  6. Jun 16

    Why We Stopped the Digital Nomad Life for a Small Town in Maine | 27 Wanderers

    After 5 years living the digital nomad life around the world, we decided to make a major life change: we are settling down in a small town in Maine. In this month's dirt path wanderer's episode, we are sharing why we are stopping full-time travel, why we chose Bath, Maine, and reflections from our recent trip to South Korea. Expect to hear: • The South Korea Safe Flex: why Koreans leave their most expensive possessions to save seats. • The 2-Year Prank: For 2 years Paige has been working towards this moment. It finally manifested in a big way. • No More Nomadding: why we are stopping full-time travel and how it will look for us going forward. • Why Bath, Maine: Out of everywhere in the world, why did we choose a small town in Maine for our new homebase. ------------------------------ Timestamps: (00:00) We Stopped the Digital Nomad Life (01:19) Reflections from our South Korea Vacation (04:06) Red Clay Barefoot Parks (10:21) Paige's 2 years prank on Grayson Comes to Fruition (13:53) Grayson’s South Korea Roses: walking and tranquility (19:23) Food highlights: Gochujang Octopus and Kimchi Burnout (24:35) Why We Paused Full-Time Travel (27:00) Searching for our New England Homebase (28:36) Returning to a Repeat Apartment for the First Time Ever (32:24) Needs vs. Wants: How Constant Moves Reveals Your True Home Base Non-Negotiables (35:41) Why Bath, Maine Checked Every Single Box (44:59) The Future of The Dirt Path: Local Artists, Craftsmen, and In-Person Interviews ------------------------------ Related Links: - Paige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/ - Grayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/ Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Email your questions: thedirtpathpodcast@gmail.com

  7. Jun 10

    8 Life Lessons From 5 Years as a Digital Nomad | 26

    I just celebrated my 5-year digital nomad anniversary (nomadiversary). Here are my 8 life lessons after living in 5 continents, 24 countries, and making 57 unique moves. For most of my time traveling the world, I was an electrical engineer working remotely in a traditional industry. I later transitioned to HR and recently stepped onto the dirt path as an online entrepreneur. Expect to hear: • The 5-Year Nomad Statistics: A breakdown of my last 5 years living around the world • Deconstructing the Fear Algorithm: How traditional media distortion and viral social media loops completely twist our perception of international travel safety • The Trap of Lifestyle Labels: Why obsessing over industry titles like "remote worker," "slow-mad," or "expat" can quietly sabotage your autonomy • Human Relationships vs. Remote Destinations: Why learning to love a new country is a lot like loving a partner • Conditioning the Mindset Muscle: The unexpected psychological benefits of facing constant micro-challenges and small discomforts while living abroad • The Ultimate Medium for Personal Growth: Why intentional, curious travel completely outperforms standard personal development books and podcasts for long-term self-improvement ------------------------------ Timestamps: (00:00) Celebrating a 5-Year Nomadiversary (01:13) My Nomad Stats: 5 Continents & 57 Moves (05:44) Lesson 1: Deconstructing the Media's Fear Algorithm (10:11) Lesson 2: The Illusion of Lifestyle Labels (12:51) Lesson 3: Designing Environments Around Specific Hobbies & Goals (17:53) Lesson 4: Trusting Your Lived Experiences Over Thoughts (22:21) Lesson 5: No Place Is Perfect (27:52) Lesson 6: Why Small Discomforts Generate Ultimate Empowerment (31:57) Lesson 7: "I’m the Problem" — The Confronting Mirror (36:05) Lesson 8: Curious Travel and the Art of Popping Cultural Bubbles (44:57) Celebrating 6 Months of the Podcast ------------------------------ Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/ - Connect with Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/ - Email your questions: thedirtpathpodcast@gmail.com

  8. Jun 3

    Moving Abroad With $0 and Building an Agency | 25 Den Kravchu

    Den Kravchu is a digital nomad from Belarus, a 3X founder, and a software developer who has generated $1M+ for his clients. We sat down in our shared villa in Bali to break down the reality of moving abroad with zero dollars, escaping enlistment, and the behind the scenes of building a tech business in today's fast-changing landscape. Expect to hear: - The High-Stakes Exit: Why Den decided to pack his life up and leave Belarus at 19 with zero dollars to avoid military conscription - The Culture Shock: What it actually feels like arriving in Asia for the first time and navigating a new reality - The Pull of Home: How he travels sustainably as a digital nomad and why he ultimately plans to return to his hometown - Building the Business: How he transitioned from freelance to agency scaling and learned the hard lessons of delegation - AI & Vibe Coding: His future vision for software engineering with advanced artificial intelligence right around the corner - The Platform Trap: How he successfully monetized 6 YouTube channels only to have them banned overnight ------------------------------ Timestamps: (00:00) Leaving With Nothing (01:10) Pancake Ritual (02:39) Kuala Lumpur Visa Run (04:31) Bali Visa Logistics (06:42) Bali Villa Life And Community (10:15) Belarus Roots And The Pull Home (13:05) Escaping Conscription (18:32) Freelance Leap To Poland (21:36) First Asia Trip Thailand (23:29) Culture Shock And Success (27:29) Travel For Productivity (31:20) Freelance To Agency (32:38) Winning Upwork Systems (34:29) Agency Scaling Leadership (40:27) Vibe Coding and the Risk of Blindly Relying on AI (46:23) Side Hustle Experiments (50:57) Travel Routine Today and Ready for Normalcy (59:16) Why the dirt path ------------------------------ Connect with Den: - Company Website: https://textura.agency/ - Den's LinkedIn: https://www.linkedin.com/in/den-kravchu-30ba86230 - Den's Instagram: https://www.instagram.com/thedzianis/ Support the podcast: - Follow us on Instagram: @thedirtpathpodcast - Email your questions: thedirtpathpodcast@gmail.com

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out of 5
2 Ratings

About

The Dirt Path Podcast celebrates those who choose to live and work differently. The world pushes us toward the "highway" of conventional jobs and lifestyles. But some brave people choose the "dirt path," with no signs or lights guiding the way. We interview these "dirt path trailblazers" to uncover: What led them to the path? Their biggest challenges and actionable tips for the "dirt path curious." This show is for anyone unaligned with their current job or lifestyle, seeking motivation to make a change. New episodes: Wednesday 6am EST (Video available on Spotify and YouTube)

Information

  • Creator
    Grayson Harris
  • Years Active
    2025 - 2026
  • Episodes
    33
  • Rating
    Explicit
  • Copyright
    © Grayson Harris
  • Show Website
    The Dirt Path