Today we talk to Linda Jackson, a self-described OG digital nomad who’s been living and working from a sailboat for over a decade… and not just weekend sailing either — we’re talking about crossing oceans, navigating cyclones, and building a life completely untethered from land.

Linda is calling in from Fiji — yes, actually on an 80-foot sailing yacht — and what struck me right away is that this isn’t just a story about travel or adventure. It’s about designing a life on your own terms. Selling everything, letting go of the “stuff,” and figuring out how to blend work, curiosity, and freedom into something that actually feels like living.

We get into what it really takes to live this way, the mindset required to handle uncertainty, and why most of us talk ourselves out of things long before we ever give them a shot.

This conversation left me thinking a lot about the stories we tell ourselves… and what might be possible if we challenged a few of them.

Please enjoy, Linda Jackson.

Key Takeaways:

• You don’t have to go “all in” to try something new — most big lifestyle changes can start as experiments rather than permanent decisions.
• Letting go of physical “stuff” can feel surprisingly freeing — and often reveals how little of it actually matters.
• The digital nomad lifestyle isn’t just about travel — it’s about designing work in a way that supports how you want to live.
• Nature doesn’t care about your plans — Linda’s approach to sailing is a powerful reminder to respect reality, adapt quickly, and never get complacent.
• “Head in boat” syndrome — being so focused on what’s right in front of you that you miss the bigger picture — applies just as much to life and business as it does to sailing.
• Fear and perceived obstacles stop most people long before reality does — the barriers are often more mental than practical.
• A shared vision matters — whether it’s a relationship or a business, alignment on the bigger goal is what makes long-term success sustainable.
• You can blend work, adventure, and life together — it doesn’t have to be neatly separated into boxes like we’ve been taught.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Linda on LinkedIn: https://www.linkedin.com/in/eljay/

Shellphone Chronicles on Substack: https://shellphonechronicles.substack.com/