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 edge
What being truly "unemployable" actually looks like in practice — and what it costs you
The loneliness and isolation nobody talks about when they romanticize life off the grid
Why flexibility isn't just a nice-to-have — it's the only way this life works
How she found creativity through art and writing, and why it changed everything
How she almost turned her Substack into a job she didn't want
What 150 rejection letters taught her about doing creative work on your own terms
The drowning iguana in Mexico that changed her outlook and became a book
Why "nothing's forever" is the most liberating business strategy she knows
Chapters
00:00 Introducing Linda Jackson
00:37 How the OG digital nomad earned her title
05:30 The journey to becoming unemployable
10:29 Subconsciously designing a life you love
11:17 Embracing flexibility and imperfection
14:29 The downsides to being a digital nomad
17:15 Navigating financial trade-offs
19:59 You don't need to monetize everything
22:54 Rediscovering joy in writing
28:28 Small acts of kindness, big impact
31:22 Being willing to course correct
32:13 Navigating life as a crew of 2
35:29 Trusting your captain (or boss)
37:06 Advice to start working for yourself
Where to find Linda
Substack
LinkedIn
Website
Verde’s Very Lucky Day
For more from The Unemployment Diaries