The Dirt Path

Grayson Harris
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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. 6일 전

    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

    36분

  2. 6월 24일

    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/

    1시간 16분

  3. 6월 16일

    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

    48분

  4. 6월 10일

    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

    47분

  5. 6월 3일

    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

    1시간 4분

  6. 5월 27일

    Traditional Hotel Executive to Empowered Female Solo Traveler | 24 Ann-Marie Plumb

    Ann-Marie Plumb is a digital nomad of nearly three years who started her life over in her mid 30s and launched a blog to inspire women to stop following the rules. After 18 years climbing the corporate hotel ladder in London, she walked away from her relationship and her career simultaneously to build a freelance copywriting business and travel the world on her own terms. Expect to hear: • How to successfully transition from a corporate career to freelance copywriting • The unique challenges of dating while constantly changing locations • Why hitting the reset button on your life in your 30s is incredibly empowering • How solo travel builds unshakeable confidence and independence for women • Why releasing the need to plan years in advance opens you up to better opportunities Timestamps: (00:00) The realization that sparked a complete life reset (02:00) Climbing the corporate ladder in London and feeling unfulfilled (06:17) Quitting a relationship and a career at the exact same time (10:38) Why breakups are a common catalyst for women to start traveling (15:01) Building confidence and self reliance through solo travel (18:18) The unfiltered truth about digital nomad dating (26:55) Should you date locals or stick to other digital nomads? (33:17) Why waiting for a partner to start traveling is a huge mistake (37:40) How to build a freelance copywriting business in three months (43:43) Freelancing freedom versus working a remote nine to five (48:16) Letting go of strict planning to embrace life's opportunities (53:15) Why choose the Dirt Path in life? 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 Ann-Marie: • Instagram: @areuokay_annie: https://www.instagram.com/areuokay_annie/ • Website and blog: www.areuokayannie.com http://www.areuokayannie.com/ Support the podcast: • Follow us on Instagram: @thedirtpathpodcast https://www.instagram.com/thedirtpathpodcast/ • Email your questions: thedirtpathpodcast@gmail.com

    55분

  7. 5월 20일

    Ranking Nomad Hubs in South East Asia | 23 - Wanderers

    In this episode of the Dirt Path podcast, Grayson and Paige analyze their recent five months living as digital nomads in Southeast Asia. We evaluate the day to day realities of working remotely from three major hubs: Chiang Mai, Koh Phangan, and Bali. We systematically break down the core variables of this lifestyle. This includes managing time zone overlaps with US based clients, tracking the real cost of living, assessing local transportation and walkability, and comparing the overall quality of life. We conclude by ranking these three destinations based on our operational needs and personal preferences as online entrepreneurs. Expect to hear: •Time Zone Management: Strategies for coordinating with US clients and optimizing productivity while based in Southeast Asia. •Cost Analysis: How to maximize the value of your budget for housing, food, and preventative wellness services. •Transportation Infrastructure: The reality of relying on scooters and ride apps versus the availability of walkable infrastructure. •Destination Profiles: A direct comparison of the culture, environment, and remote work viability of Chiang Mai, Koh Phangan, and Bali. 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 Reflections 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: https://www.instagram.com/thedirtpathpodcast/ Email your questions: thedirtpathpodcast@gmail.comm

    59분

  8. 5월 13일

    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 Connect with Ivan: Website: https://croanalyticslab.com/ LinkedIn: https://www.linkedin.com/in/ivan-pika-ba87535a/ Want to engineer your way onto the nomad dirt path without sacrificing your career? Book a free call: https://calendly.com/grayson-engineeredflexibility/30min Support the podcast: Follow us on Instagram: @thedirtpathpodcast Email your questions: thedirtpathpodcast@gmail.com

    1시간 6분
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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)

정보

  • 제작진
    Grayson Harris
  • 방송 연도
    2025년 - 2026년
  • 에피소드
    30
  • 등급
    무삭제판
  • 저작권
    © Grayson Harris
  • 웹사이트 보기
    The Dirt Path