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/

Today I talk to Whitney Boyd as part of a special series where I talk to friends about things I’ve always been curious about. And they get to do the same. I bring two topics, they bring two topics and we surprise each other - no notice and no preparing answers in advance. It takes courage and I give Whitney a lot of credit for going through with it. Truth be told, she wasn’t 100% sold on the whole idea. But as you’ll hear, there is nothing Whitney can’t do. She’s humble, thoughtful and hilarious.

I can’t explain why, but something magical happens when you put the right people in front of a microphone and press record. Although we didn’t plan it, there was a theme that emerged. It’s about getting older and watching your kids go through things that it feels like yesterday we just went through. How hard it is to let them make mistakes. And how much we can learn about ourselves after all these years, as we relive our childhoods vicariously through them.

Please enjoy, Whitney Boyd.

• Just because you’re good at something doesn’t mean you’re meant to do it — and knowing the difference matters more than we admit.
• The idea that we should constantly push outside our comfort zone is worth questioning. Sometimes comfort isn’t the enemy.
• Kids often tie their identity to the thing they do most — and when that’s taken away, it can leave a real gap.
• Parenting is full of invisible emotional moments — like grieving the end of a chapter your kid might not even be thinking about.
• The things that occupy our thoughts the most (work, appearance, logistics) aren’t always the things we wish did — and that gap is worth paying attention to.
• Relationships evolve, but expressing things like “I love you” can feel strangely harder as we get older — even when it matters more.
• Life stages sneak up on you — one minute you’re raising kids, the next you’re balancing that with caring for aging parents.
• Big life decisions (like where to live) are often less about possibility and more about the stories we tell ourselves about what’s practical or allowed.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

Links & Resources

Vienna Waits - https://vienna-waits.com/

Whitney on LinkedIn: https://www.linkedin.com/in/whitneyboyd/

Whitney on Instagram:https://www.instagram.com/vienna_waits_studio/

Today we talk to Alan Cross, a legend in the music world and the voice behind The Ongoing History of New Music—a show that’s been shaping how we understand music for over 30 years.

If you grew up loving music, there’s a good chance Alan helped you make sense of it—connecting the dots between artists, movements, and moments that changed everything. But this conversation isn’t just about looking back. It’s about how dramatically music has changed… and what that means for all of us.

We get into everything—from the explosion of alternative rock in the early 90s, to the moment Napster flipped the entire industry upside down, to why music today feels so different than it did when we were growing up. Alan shares what we’ve gained, what we’ve lost, and why the future of music might be more fragmented—and more confusing—than ever.

This felt like a masterclass in music, culture, and how technology quietly reshapes the things we love.

Please enjoy, Alan Cross.

Key Takeaways

• The Power of Storytelling in Music: Alan’s success comes from making music feel human—turning songs into stories that pull you in, even if you didn’t think you cared about the artist.
• Why the 90s Changed Everything: The rise of alternative rock wasn’t random—it was the result of cultural shifts, new data (SoundScan), and a wave of artists ready to redefine the industry.
• Napster’s Ripple Effect: What seemed like a side experiment in file sharing ended up dismantling the traditional music business—and the industry never fully recovered.
• Streaming Changed How We Value Music: With everything available instantly and cheaply, music lost its financial value—even though its emotional impact remains.
• Algorithms Are Limiting Discovery: Instead of expanding our taste, streaming platforms often trap us in familiar sounds, making it harder to discover something truly new.
• From Tribes to Playlists: Music used to define identity and community. Today, younger listeners mix genres freely, shifting music from a social signal to a personal experience.
• The Death of Mystique: Social media has erased the distance between artists and fans, removing the mystery that once made rock stars feel larger than life.
• The Future is Fragmented: With thousands of micro-genres and endless choice, music is becoming more personalized—but also harder to navigate and share collectively.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

Alan’s website: https://www.ajournalofmusicalthings.com/

Ongoing History of New Music Podcast: https://curiouscast.ca/podcast/126/ongoing-history-of-new-music/

Uncharted: Crime and Mayhem in the Music Industry: https://curiouscast.ca/podcast/1296/uncharted-crime-and-mayhem-in-the-music-industry/

CFNY: The Spirit of Radio documentary: https://www.ajournalofmusicalthings.com/the-cfny-the-spirit-of-radio-documentary-is-coming-to-theatres/