EPISODE · Feb 25, 2026 · 1H 11M
How to Nomad with a 9-5, First Time in Asia, and Betting on Myself | 11 - Dirt Path Wanderers
from The Dirt Path · host Grayson Harris
"Going into entrepreneurship feels like a trust fall with your future self." Today our host, Grayson Harris, starts his trust fall by launching his first business: Engineered Flexibility - helping engineers go nomad without sacrificing their careers. Ready to engineer your way onto the dirt path? You want to nomad but don't want to sacrifice your career?Apply for a free 9-5 Nomad Strategy Call here: https://docs.google.com/forms/d/e/1FAIpQLScm0rDg_qf24ss6OOpJQxNJcZCcLmLrIuiGPKHKEflanppDEw/viewformIn our first Dirt Path Wanderers update, Paige joins Grayson to pull back the curtain on the messy, beautiful reality of life on the dirt path. Different than our typical interview format, this episode is a back-and-forth conversation like we often have at the house. We reflect recent life updates like Paige's first time in Asia, Grayson's journey from leaving his dream job to launching his business (Today on pod release day!), and Grayson leaves us with his full playbook for how to nomad with a 9-5.Key TakeawaysThe Power of Subtraction: Why true clarity and health often come from chiseling away societal expectations rather than adding more to your plate.The 9-5 Nomad Playbook: Grayson’s tactical framework for negotiating being able to travel abroad while working remotely, including building "A-Player" leverage and preemptively solving tax and legal worries for your employer.Wherever You Go, There You Are: How travel acts as a mirror that "calls you out" on the habits and excuses you can no longer blame on your hometown.Timestamps(00:00) New Format Kickoff: Dirt Path Wanderers Updates (03:41) Paige's first time in Asia(07:20) Sensory Overload & Getting Used to the "New Normal" (09:04) Chiang Mai vs. Koh Phangan: Culture vs. Expat Bubbles (15:11) The Year of Disconnecting (19:20) Energy Management: Wiggle Room in a 9-5 vs. Entrepreneurship (21:37) Building the Ultimate Koh Phangan Routine (31:38) "Lost Soul" Energy: Transitioning with Clarity (34:57) Wherever You Go, There You Are (37:04) Elephants & Monks(42:47) Launch Day Fears: Tackling the Unknown (49:26) Engineered Flexibility: Helping Engineers Go Nomad (55:28) The 9-5 Nomad Playbook(01:09:11) Stop Ignoring the Voice Related Links:Paige's Interview Episode: 2 - The power of your personal brand on LinkedIn: Paige GoldsteinPaige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/Grayson's Story (From Engineer to Nomad): [4 - Digital nomad as an Engineer: Grayson Harris]Grayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/Support the podcast:Follow us on Instagram: @thedirtpathpodcastSubscribe on YouTube: The Dirt Path PodcastEmail your questions ([email protected])
What this episode covers
"Going into entrepreneurship feels like a trust fall with your future self." Today our host, Grayson Harris, starts his trust fall by launching his first business: Engineered Flexibility - helping engineers go nomad without sacrificing their careers. Ready to engineer your way onto the dirt path? You want to nomad but don't want to sacrifice your career?Apply for a free 9-5 Nomad Strategy Call here: https://docs.google.com/forms/d/e/1FAIpQLScm0rDg_qf24ss6OOpJQxNJcZCcLmLrIuiGPKHKEflanppDEw/viewformIn our first Dirt Path Wanderers update, Paige joins Grayson to pull back the curtain on the messy, beautiful reality of life on the dirt path. Different than our typical interview format, this episode is a back-and-forth conversation like we often have at the house. We reflect recent life updates like Paige's first time in Asia, Grayson's journey from leaving his dream job to launching his business (Today on pod release day!), and Grayson leaves us with his full playbook for how to nomad with a 9-5.Key TakeawaysThe Power of Subtraction: Why true clarity and health often come from chiseling away societal expectations rather than adding more to your plate.The 9-5 Nomad Playbook: Grayson’s tactical framework for negotiating being able to travel abroad while working remotely, including building "A-Player" leverage and preemptively solving tax and legal worries for your employer.Wherever You Go, There You Are: How travel acts as a mirror that "calls you out" on the habits and excuses you can no longer blame on your hometown.Timestamps(00:00) New Format Kickoff: Dirt Path Wanderers Updates (03:41) Paige's first time in Asia(07:20) Sensory Overload & Getting Used to the "New Normal" (09:04) Chiang Mai vs. Koh Phangan: Culture vs. Expat Bubbles (15:11) The Year of Disconnecting (19:20) Energy Management: Wiggle Room in a 9-5 vs. Entrepreneurship (21:37) Building the Ultimate Koh Phangan Routine (31:38) "Lost Soul" Energy: Transitioning with Clarity (34:57) Wherever You Go, There You Are (37:04) Elephants & Monks(42:47) Launch Day Fears: Tackling the Unknown (49:26) Engineered Flexibility: Helping Engineers Go Nomad (55:28) The 9-5 Nomad Playbook(01:09:11) Stop Ignoring the Voice Related Links:Paige's Interview Episode: 2 - The power of your personal brand on LinkedIn: Paige GoldsteinPaige's LinkedIn: https://www.linkedin.com/in/paigegoldstein/Grayson's Story (From Engineer to Nomad): [4 - Digital nomad as an Engineer: Grayson Harris]Grayson's LinkedIn: www.linkedin.com/in/grayson-harris-786087148/Support the podcast:Follow us on Instagram: @thedirtpathpodcastSubscribe on YouTube: The Dirt Path PodcastEmail your questions ([email protected])
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How to Nomad with a 9-5, First Time in Asia, and Betting on Myself | 11 - Dirt Path Wanderers
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