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

Website

LinkedIn

Instagram

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/

Welcome to another solo episode, and I’m really proud of this one. It’s quite personal. If you’ve ever struggled to get something off the ground, or have started something you loved only to have it turn into a chore, this is for you.

The truth is I’ve been wrestling with what this podcast is actually about - what it’s supposed to be. Somewhere along the way, this thing I loved most in the world slowly turned into something that felt like work. In trying to make it valuable for everyone else, I lost what drew me to it in the first place.

So in this episode, I take you through that journey—from chasing my curiosity, to getting pulled into the self-help world, to a moment of clarity that finally revealed the answers I was looking for.

Listening to me fumble my way through this just might give you the inspiration you need to rediscover the passion you’ve lost.

Please enjoy.

Key Takeaways

• Following your curiosity is often where the most energy and joy come from—when you lose that, the work starts to feel heavy.
• Trying to make everything “useful” or “valuable” can strip the life out of creative work.
• Not everything needs to be actionable—sometimes stories and perspectives are more powerful than step-by-step advice.
• People take away different things from the same story, which is why leaving space for interpretation can be more impactful.
• The self-help cycle can keep us stuck—consuming ideas instead of actually applying them.
• You don’t need more answers—you likely already have them. What you need is space to think differently.
• Leading with curiosity might feel selfish, but it often creates the most genuine and engaging work.
• Sometimes the best thing you can offer is a break—a shift in perspective that helps people see their own lives more clearly.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

Links & Resources

https://growth-mixtape-podcast-with-bob.cohostpodcasting.com/episodes/the-untold-story-of-the-edmund-fitzgerald-with-john-u-bacon-chasing-curiosity-and-sharing-boundless-insights-from-ideas-that-matter

Alan Cross - https://www.ajournalofmusicalthings.com/

Today we talk to Anne Bonney, speaker, author and self-described discomfort zone guide.

I loved this conversation because it pushed on something I’ve been thinking about a lot lately. We hear all the time that growth happens outside our comfort zone, but Anne gives that idea a fresh twist. Instead of just leaving comfort, she talks about learning how to dance with discomfort — and more importantly, how to know when discomfort is helping us grow and when we’re just exhausting ourselves.

We talk about why hard things build self-trust, how the challenges we choose can prepare us for the ones life throws at us, and why confidence is really just evidence that we’ve survived difficult things before. We also get into silent retreats, relationships, leadership, and the stories we tell ourselves when change shows up uninvited.

This one was thoughtful, practical, and really fun.

Please enjoy, Anne Bonney.

Key Takeaways:

• Anne reframes the whole idea of a “comfort zone” by focusing instead on the discomfort zone — something we can move toward with curiosity instead of fear.
• Doing hard things builds self-trust. The more often we survive discomfort, the more evidence we have that we can handle what comes next.
• Not all discomfort is created equal. Sometimes growth means taking on a marathon or a big keynote, and sometimes it means having an honest conversation or asking for what you need.
• Comfort isn’t the enemy. It’s the place we rest so we can step back into challenge when we’re ready.
• Self-efficacy matters. Resilience grows when we believe there’s something we can do to improve our situation instead of waiting for life to magically get easier.
• Anne’s line, “thoughts are random, thinking is not,” is a powerful reminder that we don’t have to believe every story our brain tells us in moments of fear or uncertainty.
• The discomfort we choose can help prepare us for the discomfort we don’t choose — illness, grief, aging parents, relationship struggles, and all the other hard parts of life.
• Nobody else has it figured out, and you don’t have to do it alone. That might be the most comforting truth of all.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

Links & Resources

Anne Bonney website: https://yourchangespeaker.com/

Anne on Linkedin: https://www.linkedin.com/in/annebonney/

Anne’s TEDx talk: https://youtu.be/wSL6tVD__po?si=3xSBLDfCwTYUaTB7

Michael Easter, The Comfort Crisis

https://www.michaeleaster.com/the-comfort-crisis

https://www.amazon.com/dp/0593138767

Vipassana meditation retreats

https://www.dhamma.org/

David Goggins

https://davidgoggins.com/

Tim Ferriss

https://tim.blog/

Today we talk to three incredible women on a mission to completely reimagine healthcare, with community and the whole person at the centre.

This was our first recording in front of a live studio audience, and the energy in the room was incredible. Maddi Kohlberg, Dr. Tina Sestin, and Carmen Sutherland share how a chance meeting in a sauna, years of clinical burnout, and a deep belief in community all collided to create something new: the Generations Collective.

We talk about what’s broken in our current system, why so many of us feel isolated as patients and caregivers, and what it could look like to build healthcare around humans instead of appointments. This conversation is about perimenopause and pelvic health, yes — but it’s also about grief, belonging, accessibility, and the power of stories to build something better.

This one left me hopeful.

Please enjoy, Maddi Kohlberg, Dr. Tina Sestin, and Carmen Sutherland.

Key Takeaways

• A Chance Encounter Sparked a Movement: A conversation in a sauna led to the creation of Generations Collective — proof that when you follow curiosity and authenticity, powerful collaborations can form.

• Burnout Isn’t Failure — It’s Information: Tina shares how 15 years in practice left her exhausted and questioning a system where only those with money or benefits could access care. That discomfort became fuel for change.

• Healthcare Should See the Whole Human: Mind, body, spirit, family, finances, and community all impact health. Treating symptoms in isolation misses the bigger picture.

• Community Is Medicine: Maddie’s experience navigating her daughter’s medical journey — and the overwhelming support from her neighborhood — reinforced that healing doesn’t happen alone.

• Integration Changes Everything: Instead of siloed practitioners working back-to-back, Generations Collective envisions collaborative care — clinicians literally sitting at the same table to support each patient together.

• Belonging Is Foundational to Health: Carmen reminds us that beyond treatment plans and protocols, people need to feel seen, valued, and like they truly belong.

• Accessibility Matters: Quality care shouldn’t depend on income level. Reimagining healthcare means building models that make support available to more people.

• Regenerative Leadership Over Burnout Culture: If we want a better system, we can’t build it by sacrificing the people inside it. Taking care of each other is part of the mission.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

Links & Resources

https://www.generationscollective.ca/

https://www.instagram.com/generationscollective.ca/

https://www.linkedin.com/in/maddi-kolberg/

https://www.linkedin.com/in/tina-sestan-557b112a/

https://www.linkedin.com/in/carmen-sutherland-34604829/

Today we invite back Alyx Parks, a great friend, conviction coach, writer, fly fishing guide, and one of my favourite people to have unhinged conversations with.

This episode is a bit of an experiment. We both brought 2 topics to discuss, but didn’t tell each other ahead of time. No research, no prepared answers, no performance.

What came out was a wide-ranging, honest, funny, and surprisingly deep discussion about making friends after 30, tattoos and identity, fear of judgment, and why we’re all so afraid to just pick up the phone and call someone we miss.

Please enjoy, Alyx Parks - unhinged.

Key Takeaways

• Birthdays can bring a quiet kind of grief—not just about age, but about who we were, who we thought we’d be, and who we’re becoming.
• We’ve been conditioned to fear phone calls and doorbells, but random, agenda-free connection can be one of the greatest gifts we give and receive.
• Tattoos aren’t really about ink—they’re about identity, intention, permanence, and who we’re doing things for.
• Making friends after 30 is hard, vulnerable, and necessary—and sometimes it starts with simply saying hello or asking someone for coffee.
• Fear of failure is often really fear of judgment, and most of that judgment lives only in our own heads.
• Letting “future you” handle the hard moments can be a powerful way to move through fear and self-doubt.
• Growth often looks messy in real time—and cringing at your past self might actually be proof that you’re evolving.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

Links & Resources

https://www.wilderpath.co

https://www.linkedin.com/in/alyxparks

https://www.instagram.com/ontarioflygirl

https://www.ontarioflygirl.com/

Today, we talk to Sensi Graves and Brandon Scheid - extreme athletes, parents, partners, and now the subjects of a powerful new documentary - Windfall.

Two years ago, Brandon was in a speed flying accident that nearly took his life. In the days immediately following, Sensi learned she was pregnant with their first child. Together, they share their incredible journey of recovery, and how learning to live with Brandon’s traumatic brain injury has re-shaped their view of life and parenting.

This conversation is about more than the accident. It’s about identity, love, and how we move forward when life doesn’t go as planned. It’s about the quiet strength of caregivers, the stubborn resilience of the human spirit, and the role that community plays in helping us heal.

Please enjoy, Sensi Graves and Brandon Scheid.

Key Takeaways

Turning trauma into purpose: Brandon and Sensi share how they’ve made meaning from a life-altering accident—and why they wouldn’t take it back.

Two perspectives, one story: Sensi speaks as the partner and caregiver; Brandon shares what it's like to survive a crash you don’t remember, and come back a different person.

Brain injury recovery isn’t linear: From post-coma mania to long-term depression, Brandon opens up about the invisible impacts of TBI and how he’s still navigating the mental health journey.

Presence over purpose: In the middle of crisis, Sensi redefined success as simply taking care of herself, her baby, and her husband—nothing more.

Letting go of the “old you”: After his accident, Brandon couldn’t return to his old sports or identity, so he explored everything from drones to piano to punching balls while walking down the street.

What we focus on expands: Sensi talks about practicing radical gratitude—not to sugarcoat hardship, but to make space for joy amidst the mess.

We all molt: Brandon offers a surprisingly perfect metaphor about crustaceans—sometimes growth requires outgrowing your old shell, even when it hurts.

Vulnerability creates connection: Their willingness to be open, even in the messiest moments, is a powerful reminder that healing isn’t something we do alone.

Connect with Bob Mathers

Website

LinkedIn

Instagram

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

https://www.instagram.com/windfall_movie/

https://www.instagram.com/sensigraves/

https://www.instagram.com/brandonscheid/

https://www.sensigraves.com/

https://www.linkedin.com/in/sensi-graves/

The Body Keeps the Score by Bessel van der Kolk

Big Magic by Elizabeth Gilbert

The Rise of Superman by Steven Kotler