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

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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?

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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: [email protected]

- Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

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

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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

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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: [email protected]

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.

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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

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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: [email protected]

- Follow Grayson on LinkedIn: www.linkedin.com/in/grayson-harris-786087148/

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.

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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

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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: [email protected]

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

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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

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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: [email protected]

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

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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

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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: [email protected]

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: [email protected]

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: [email protected]

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: [email protected]

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 travel

• The reality of managing a North American team while living in Asia and working from 10 PM to 3 AM

• How the digital nomad experience changes when you transition from solo travel to traveling with a partner

• Why moving to a new city every week is a trap and why slowing down is essential for remote workers

• Practical advice for taking the leap into remote work if you are stuck in a cold winter climate

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

Connect with Stephanie:

Instagram: @steph.zum

https://www.instagram.com/steph.zum/

Support the podcast:

• Follow us on Instagram: @thedirtpathpodcast

• Email your questions: [email protected]