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. 15H AGO

    Ranking Nomad Hubs in South East Asia | 23 - Wanderers

    Trading a traditional routine for the digital nomad lifestyle comes with a serious learning curve. Grayson and Paige just spent the last five months testing out three massive remote work hubs in Southeast Asia and they are ready to share exactly what they learned. In this episode, they broadcast from their villa in Uluwatu to reveal the unglamorous side of managing US client calls at midnight and the hidden reality of scooter heavy infrastructure. They also break down how affordable preventative wellness completely alters your daily routine and give their final verdict on whether Chiang Mai, Koh Phangan, or Bali claims the ultimate top spot for digital nomads.Expect to hear:• The Time Zone Trap: How to manage your energy and client calls when you are 12 hours ahead of the US.• The $35 Perfect Day: Breaking down the exact cost of living in Thailand and how affordable wellness completely changes your lifestyle.• Walkability vs. Scooters: The hidden daily routine shift that happens when you move to a scooter dominant island.• Destination Deep Dives: The raw truth about Chiang Mai, Koh Phangan, and Bali.• The Performative Trap of Bali: Why Uluwatu feels a little bit like LA and how the hyper wellness culture can sometimes lack soul.• Returning Home: What happens to your nervous system when you prepare to trade slow island life back for the US hustle.Timestamps: (00:00) Introduction to the Digital Nomad Lifestyle in Asia (02:27) Navigating Time Zones as Digital Nomads (09:11) Cost of Living and Affordability in Southeast Asia (12:56) Quality of Life Enhancements in Asia (19:20) Challenges of Walkability and Transportation (25:53) Experiencing Chiang Mai: First Impressions and Highlights (30:19) City Life vs. Nature Retreats (32:10) Koh Phangan: A Slice of Paradise (38:35) Bali: The Beauty and the Facade (44:08) Lifestyle and the American Dream (49:33) Ranking the Destinations: Personal ReflectionsRelated Links:Paige's Interview Episode: https://youtu.be/zJ3HnRGtcuc?si=lDBsOKnrlbgJ_GgbPaige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/Grayson's Story (From Engineer to Nomad): https://youtu.be/dKHHTVmWFG4?si=3Anp8u2_DojSO-bFGrayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/Ready to Engineer your way to the Digital Nomad Life, but without having to quit your job? Apply for a free 9-5 Nomad Strategy Call here: https://docs.google.com/forms/d/e/1FAIpQLScm0rDg_qf24ss6OOpJQxNJcZCcLmLrIuiGPKHKEflanppDEw/viewformSupport the podcast:Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast/Email your questions: thedirtpathpodcast@gmail.com

    59 min

  2. MAY 13

    The "Siberian Teddy Bear": Breaking Stereotypes and Escaping the Money Game 22 Ivan Pika

    Ivan is a conversion rate optimization and data analytics expert, currently ranking as the #1 freelancer in the analytics section on Upwork, and an avid world traveler who has explored 80+ countries. After scaling and selling a massive 60-person agency, Ivan has spent the last several years living as a digital nomad, intentionally downscaling his business to find true freedom. In this episode, we dive into Ivan’s dirt path transformation from navigating the mosquito-filled wilderness of Siberia to a stressful agency owner to working 5-hour days from Bali. We unpack his bold decision to walk away from endless hustle culture, the fascinating truth behind Russian traveler stereotypes, and why he chooses to spend his free time mentoring global startups for zero cost. Key Takeaways: • What’s the deal with Siberia? What it's actually like growing up in the remote wilderness and hunting for diamonds.• Anti-Hustle: Why Ivan intentionally limits his company's growth to work only 5 hours a day, trading money for time wealth.• Unlearning Stereotypes: The fascinating cultural reasons why Russians don't do "small talk" and why relying on stereotypes is just "brain laziness."• Power of Slow Travel: How staying in a country for 3 to 6 months completely changes your nomadic experience.• Community Hacks: How Russian expats use Telegram to build instant, tight-knit communities anywhere in the world.• Choosing the Dirt Path: Why doing things the hard and unconventional way is the ultimate secret to finding contentment. Timestamps: 00:00 - Intro & reality of growing up in Siberia 08:24 - Diamond hunting and surviving Siberian summer mosquitoes 14:26 - Leaving Russia and transitioning to long-term slow travel 20:07 - Visa struggles and the reality of a Russian passport 25:52 - Why Russians form tight-knit communities abroad 28:00 - The cultural truth behind the Russian "cold front" and small talk 35:28 - Dispelling traveler stereotypes 43:40 - The shared gear community in Georgia 47:20 - Leaving a 60-person agency to escape hustle culture 54:55 - Why Ivan mentors global startups for free 01:01:40 - Why the dirt path is just plain fun

    1h 6m

  3. MAY 6

    Digital Snowbird Lifestyle: Work 9 to 5 While Traveling the World | 21 Stephanie Zummo

    Stephanie is a COO who has mastered the art of balancing a demanding remote career with traveling the globe. For the past few years, she has been perfecting what we call the digital snowbird lifestyle by spending half the year in Montreal and the other half escaping the winter to explore the world as a digital nomad. In this episode, we talk about how Stephanie transitioned from a traditional office setup to working from beach towns and jungles across Mexico, South Africa, and Bali. We get into the actual logistics of managing a remote team across massive time zone differences and how her travel style has evolved over the years. Key Takeaways How the digital snowbird method gives you the best of both worlds between routine and travelThe reality of managing a North American team while living in Asia and working from 10 PM to 3 AMHow the digital nomad experience changes when you transition from solo travel to traveling with a partnerWhy moving to a new city every week is a trap and why slowing down is essential for remote workersPractical advice for taking the leap into remote work if you are stuck in a cold winter climateTags: #DigitalNomad #RemoteWork #DigitalSnowbird #TravelAndWork Timestamps 00:00 Getting off the news and protecting your mindset 05:15 The nomad community and crossing paths globally 09:45 Stephanie's origin story of working from anywhere 13:30 Testing the remote work waters in Mexico 15:50 Managing a Canadian team as a COO from abroad 18:15 Working the graveyard shift in Bali 24:45 Breaking down the digital snowbird lifestyle 32:15 Managing a split life and keeping up with friends back home 36:20 The pros and cons of solo travel versus traveling with a partner 41:50 The biggest mistake new digital nomads make 47:20 Highlights and challenges of working remotely from Asia 53:20 Advice for starting your own remote work journey 58:45 Why the dirt path is worth the trade offs Want to engineer your way onto the nomad dirt path without sacrificing your career? Book a free call with Grayson: https://calendly.com/grayson-engineeredflexibility/30min Follow Stephanie: https://www.instagram.com/steph.zum/

    57 min

  4. APR 29

    Lost in Life to Web3 Clarity Coach | 20 Remington Langston Rodney

    Meet Remi, a former Web3 tech recruiter and luxury car salesman who packed up his life to become a digital nomad and high performance coach in Bali. He is on the podcast today to talk about stepping away from the corporate grind and building a successful business from halfway across the world.We dive into Remi's wild journey from experiencing intense burnout as a competitive athlete and dropping out of college to finding his footing in sales and ultimately launching his own coaching company, The Reset Protocol. He shares the raw truth about what it really takes to reinvent yourself and why slowing down is the ultimate secret weapon for high performers.Key Takeaways:• How a harsh reality check in college sparked a seven year journey into personal development and entrepreneurship.• The hidden traps of the digital nomad lifestyle and why moving to a cheaper country requires strict discipline.• Why taking a step back to reset your nervous system actually helps you achieve your business goals faster.• A practical three step framework to audit your life, find alignment, and build sustainable daily habits.• How to stop tying your self worth to your daily productivity and output.Timestamps:00:00 Remi opening up about his childhood04:30 Chasing greatness in sports and the reality of early burnout12:00 College struggles and the wake up call16:00 Grinding through early jobs to fund a streetwear brand24:30 Pivoting to web3 recruitment and the power of networking29:00 The decision to move to Bali and nomad life41:30 Building The Reset Protocol and why founders need to slow down53:30 How to detach your self worth from your daily productivity01:03:00 Choosing the dirt path and creating a life you loveWant to engineer your way onto the nomad dirt path without sacrificing your career? Book a free call with Grayson: https://calendly.com/grayson-engineeredflexibility/30minSupport the podcastFollow us on Instagram: @thedirtpathpodcastEmail your questions: thedirtpathpodcast@gmail.comConnect with Remi:https://www.linkedin.com/in/remingtonrodney/ Coaching with Remi: https://www.theresetprotocol.xyz/

    1h 7m

  5. APR 22

    Navigating Impermanence and Fleeting Moments as a Digital Nomad Couple | 19 Wanderers

    Most travel vlogs show the laptop on a beach dream but skip the actual realities of the digital nomad life. Recording while living in Bali, Grayson and Paige get real about digital nomad loneliness at year 5, and the shedding phase that follows starting the dirt path. Expect to hear: - The Shedding Phase: Why entering the dirt path often feels really freaking lonely and how to navigate the in-between - Real-Time Nostalgia: The bittersweet feeling of knowing a moment is becoming a memory while you’re still in it - The American Hello: Why we need to find our identity beyond what we do and where we are from - Solo Travel for Couples: How short solo trips can balance the intensity of digital nomad relationships - Impermanence as a Practice: Using travel as a microcosm to learn the art of letting go - The High-Achiever Hamster Wheel: Grounding takeaways from going to Chris Williamson (Modern Wisdom) Live in Bali ------------------------------ Timestamps: (00:00) Digital Nomad Realities (00:59) Welcome Back Wanderers & Fleeting Moments (08:52) Identity Beyond Your Job (15:16) The Shedding after Starting the Dirt Path (20:49) Is it Worth Investing in Fleeting Connections? (27:29) Travel as the Ultimate Test of Impermanence (33:05) Redefining Relationship Norms: The Ubud Solo Trip (42:10) Independence vs. Comfort Zones as a Couple (48:13) Grounding Lessons from the Chris Williamson Live Show (54:46) Balinese Healers and the Water Purification Ritual ------------------------------ Related Links: - Paige's Interview Episode: https://youtu.be/zJ3HnRGtcuc?si=lDBsOKnrlbgJ_Ggb - Paige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/ - Grayson's Story (From Engineer to Nomad): https://youtu.be/dKHHTVmWFG4?si=3Anp8u2_DojSO-bF - Grayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/ Ready to Engineer your way to the Digital Nomad Life, but without having to quit your job? Apply for a free 9-5 Nomad Strategy Call here: https://docs.google.com/forms/d/e/1FAIpQLScm0rDg_qf24ss6OOpJQxNJcZCcLmLrIuiGPKHKEflanppDEw/viewform Support the podcast: - Follow us on Instagram: @thedirtpathpodcast - Email your questions: thedirtpathpodcast@gmail.com

    1 hr

  6. APR 15

    7 Figure Founder's Vipassana Breakthrough | 18 Alex Thomas

    Alex Thomas is a 7-figure founder and digital nomad of 6 years who sold his business for freedom. After his million-dollar exit, he turned to Vipassana and the spiritual path to find fulfillment and deeper meaning. Expect to hear: • Alex's journey to realizing a million-dollar Shopify store exit • How Alex overcame social anxiety by building his courage muscle • How being a digital nomad for 6 years has affected his spiritual path • How Vipassana retreats are a step function for spiritual growth Timestamps: (00:00) 7-Figure Exit: Why I sold my business for freedom (00:47) Connection Lab Card Game Question (06:17) Healing the Pain Body: Releasing emotions without the story (12:06) The Surrender Experiment: Trusting the flow of life (17:18) Digital Nomad Life: Leaving the New York 9-5 grind (21:39) Lessons from building a 7-figure Shopify store (24:15) Connection Lab: The mission to end loneliness (30:53) Social Experiments: Overcoming social anxiety with free hugs (34:51) The Courage Muscle vs. Core Confidence (39:13) Does nomadic travel help or hurt your spiritual path? (46:20) Meditation for Beginners: Watching the ego (51:54) What is Vipassana? Alex's various Vipassana experiences (53:05) Awareness of Awareness: The direct path to truth (01:01:26) Why choose the Dirt Path in life? Connect with Alex: • Instagram: @thisisalext • Connection Lab: @ConnectionLabTeam Support the podcast: • Follow us on Instagram: @thedirtpathpodcast • Email your questions: thedirtpathpodcast@gmail.com

    1h 5m

  7. APR 8

    From Luxury Fashion Buyer to Building a Freedom First Business | 17 Sophie Biggerstaff

    Sophie Biggerstaff is a business coach and the host of "The Freedom Method Podcast" (Previously known as “The Remote CEO Life”) who helps entrepreneurs build Freedom-First Businesses. She’s also been a digital nomad for five years and was voted 2025 Mental Health CEO of the Year. Sophie was a high-level Buyer for iconic luxury fashion brands like Burberry, Kate Spade, and Ralph Lauren, navigating global product strategies and massive budgets. However, after escaping a toxic corporate role in 2020 and battling severe burnout and illness while freelancing in Bali, she realized something had to change. Through pausing her mental health startup, TINAH (“Time Is Not a Healer”), and completely "burning down" her original consultancy, she learned the power of simplifying her life and is now on a mission to help others achieve true remote freedom. Key Takeaways The "Freedom First" Approach: Why you must design your life, boundaries, and desired income before building your business. Avoiding the Money Trap: How building a business purely for financial gain can easily turn entrepreneurship into just another stressful job. Navigating Burnout and Boundaries: How struggling with illness and time-zone demands in Bali taught her the crucial importance of simplifying and setting strict limits. Knowing When to Pivot: The lessons learned from pausing her mental health marketplace (TINAH) and completely restructuring her consultancy to prioritize alignment and well-being. Timestamps (00:00) Money Built Job Trap (00:47) What's a Fashion Buyer? (03:21) Regional Buying Strategy (04:30) Leaving School for Fashion (09:32) Corporate Exit in Lockdown (13:21) Freelance Leap and First Clients (14:38) Doubt, Savings, and Confidence (18:19) Why Corporate Wasn't It (21:12) Building a Remote Nomad Plan (24:56) Bali to Full Nomad Life (28:51) Burnout and Boundaries Reset (30:24) Burnout Hits in Bali (31:28) Redesigning Work for Sustainability (32:58) Mental Health History and Healing Tools (35:47) Founding TINAH (“Time Is Not a Healer”) (37:46) Pausing the Mission Project (39:43) Simplify Everything Lesson (42:31) Burning Down the Old Business (48:28) Pivoting Toward Freedom First (53:42) How to Choose Your Business Path (57:06) Podcast Moments That Expand Possibility (01:02:47) Why Choose the Dirt Path Want to engineer your way onto the nomad dirt path without sacrificing your career? Book a free call: https://calendly.com/grayson-engineeredflexibility/30min Guest Links: Website: https://www.itssophiebiggerstaff.com LinkedIn: https://www.linkedin.com/in/sophie-biggerstaff-business-coach Instagram: https://www.instagram.com/itssophiebiggerstaff Recommended Episode: Build a Six-Figure Business | The Freedom Method Podcast Support the podcast: - Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast - Email your questions: thedirtpathpodcast@gmail.com

    1h 6m

  8. APR 1

    From Google Ads Success to Depersonalization & Subconscious Healing | 16 Thibault Walter

    Thibault Walter is a French Google Ads expert who has spent 6 years in entrepreneurship, managing over €4 million in ad spend for more than 50 clients. He also recently embarked on his first stint abroad as a digital nomad. Thibault shares his dirt path journey from working in an ad agency to scaling e-commerce brands to millions in revenue as a freelancer. He later goes into his battle with depersonalization, derealization, and deep depression amidst his success and the natural healing he used to reclaim his life. Key Takeaways • The Prison of Success: Discover why hitting your best financial months can sometimes trigger a severe mental health crisis. • Depersonalization/Derealization (DPDR): Learn what it actually feels like to lose touch with reality and the steps to anchor back into your body. • The Nomad Trade-off: Understand the realities of maintaining deep relationships while traveling and the isolation of the entrepreneurial monk phase. • Subconscious Healing: Explore how moving beyond traditional talk therapy and utilizing heart-brain coherence and meditation can facilitate profound healing. • Choosing Yourself: Break the cycle of codependency and learn to prioritize your own needs and boundaries in relationships. Timestamps (00:00) Intro: Success vs. Emptiness (01:30) Growing up near Paris & the "Paris Syndrome" (07:00) The Obsessive Entrepreneur: From Pro Scootering to Google Ads (14:30) Making €400k in 3 weeks (and the pressure that follows) (21:00) The 1-Year Sacrifice: Building the foundation for freedom (31:00) Entering Monk Mode: High output vs. social isolation (41:45) The Onset of Depersonalization & Derealization (45:00) 10 Days of Silence: The Vipassana experience (51:30) Dr. Joe Dispenza & The Turning Point (57:00) Relationship Red Flags & Learning to Say No (01:02:00) Grayson’s own Empty moment in Cape Town (01:10:00) Starting the Nomad Life: Bali & Thailand (01:16:30) Why The Dirt Path is the only path worth taking Work With Me Want to engineer your way onto the nomad dirt path without sacrificing your career? Book a free call: https://calendly.com/grayson-engineeredflexibility/30min🔗 Connect with Thibault Walter • LinkedIn: https://www.linkedin.com/in/thibault-walter • Instagram: https://www.instagram.com/thibault_wltr⛺ Support the Podcast • Follow us on Instagram: https://www.instagram.com/thedirtpathpodcast • Email your questions: thedirtpathpodcast@gmail.com

    1h 20m
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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
    24
  • Rating
    Explicit
  • Copyright
    © Grayson Harris
  • Show Website
    The Dirt Path