EPISODE · Apr 8, 2026 · 38 MIN
OG digital nomad who quit being employable | Linda Jackson
from The Unemployment Diaries · host Aisha Ommaya
What if the life you always wanted had no map, no guarantee, and no way back?Linda Jackson spent decades in tech sales and marketing, working for startups and surviving volatile bosses. Then she sailed out under the Golden Gate Bridge (just two weeks after 9/11) on a 34-foot sailboat with her husband and a one-year plan that turned into a lifetime.Today they live full-time aboard their sailboat in Fiji where she runs a consulting business from the middle of the Pacific Ocean (for now). No house. No car. No safety net. She's been doing this since before Starlink, before Zoom, before anyone called it remote work.And somewhere along the way, she discovered that the most important parts of her life had nothing to do with work at all.In this episode, Linda shares her story and:Why she walked away from employee life and what finally pushed her over the edgeWhat being truly "unemployable" actually looks like in practice — and what it costs youThe loneliness and isolation nobody talks about when they romanticize life off the gridWhy flexibility isn't just a nice-to-have — it's the only way this life worksHow she found creativity through art and writing, and why it changed everythingHow she almost turned her Substack into a job she didn't wantWhat 150 rejection letters taught her about doing creative work on your own termsThe drowning iguana in Mexico that changed her outlook and became a bookWhy "nothing's forever" is the most liberating business strategy she knowsChapters00:00 Introducing Linda Jackson00:37 How the OG digital nomad earned her title05:30 The journey to becoming unemployable10:29 Subconsciously designing a life you love11:17 Embracing flexibility and imperfection14:29 The downsides to being a digital nomad17:15 Navigating financial trade-offs19:59 You don't need to monetize everything22:54 Rediscovering joy in writing28:28 Small acts of kindness, big impact31:22 Being willing to course correct32:13 Navigating life as a crew of 235:29 Trusting your captain (or boss)37:06 Advice to start working for yourselfWhere to find LindaSubstackLinkedInWebsiteVerde’s Very Lucky DayFor more from The Unemployment DiariesStay up to date on InstagramGo behind the scenes on SubstackWatch on YouTube
What this episode covers
What if the life you always wanted had no map, no guarantee, and no way back?Linda Jackson spent decades in tech sales and marketing, working for startups and surviving volatile bosses. Then she sailed out under the Golden Gate Bridge (just two weeks after 9/11) on a 34-foot sailboat with her husband and a one-year plan that turned into a lifetime.Today they live full-time aboard their sailboat in Fiji where she runs a consulting business from the middle of the Pacific Ocean (for now). No house. No car. No safety net. She's been doing this since before Starlink, before Zoom, before anyone called it remote work.And somewhere along the way, she discovered that the most important parts of her life had nothing to do with work at all.In this episode, Linda shares her story and:Why she walked away from employee life and what finally pushed her over the edgeWhat being truly "unemployable" actually looks like in practice — and what it costs youThe loneliness and isolation nobody talks about when they romanticize life off the gridWhy flexibility isn't just a nice-to-have — it's the only way this life worksHow she found creativity through art and writing, and why it changed everythingHow she almost turned her Substack into a job she didn't wantWhat 150 rejection letters taught her about doing creative work on your own termsThe drowning iguana in Mexico that changed her outlook and became a bookWhy "nothing's forever" is the most liberating business strategy she knowsChapters00:00 Introducing Linda Jackson00:37 How the OG digital nomad earned her title05:30 The journey to becoming unemployable10:29 Subconsciously designing a life you love11:17 Embracing flexibility and imperfection14:29 The downsides to being a digital nomad17:15 Navigating financial trade-offs19:59 You don't need to monetize everything22:54 Rediscovering joy in writing28:28 Small acts of kindness, big impact31:22 Being willing to course correct32:13 Navigating life as a crew of 235:29 Trusting your captain (or boss)37:06 Advice to start working for yourselfWhere to find LindaSubstackLinkedInWebsiteVerde’s Very Lucky DayFor more from The Unemployment DiariesStay up to date on InstagramGo behind the scenes on SubstackWatch on YouTube
NOW PLAYING
OG digital nomad who quit being employable | Linda Jackson
No transcript for this episode yet
Similar Episodes
No similar episodes found.
Similar Podcasts
No similar podcasts found.