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Before we begin, we want to share something important.

This episode originally aired when our close friend Doug was very much alive, sharing his perspective with the warmth and curiosity that defined him. At the time, none of us knew this conversation would become a memory we would one day hold so dearly.

Doug is no longer with us, and that still feels unreal. He had a rare way of making people feel seen, bringing lightness even to heavy conversations, and reminding us that life is not about perfection, but presence.

We are re-releasing this episode in honor of Doug. Not as a goodbye, but as a thank you.

In this conversation, we talk with Doug, an experienced meditation practitioner and teacher, about the impact meditation has had on his life. He shares his journey into meditation, lessons from silent retreats, and practical guidance for anyone curious about starting a practice.

If this is your first time hearing Doug, we hope you feel what we felt knowing him. If you have listened before, we hope you hear it differently this time.

This one is for you, Doug. We love you. Namaste.

Leave us a voice message and send it over to us at info@thewhymatterspodcast.com

You can call us and leave us a voicemail at 424 442 9295.

Doug’s Udemy Course: https://www.udemy.com/course/mantra-meditation/?referralCode=C292FCAF98C545866D17

01:15 Introducing Our Special Guest: Doug

08:14 Doug's Journey into Meditation

11:52 Understanding Meditation and Its Benefits

16:30 Doug's Meditation Training and Teaching

22:18 The Challenges and Realities of Meditation

26:38 The Power of Meditation During COVID

28:14 Experiencing a Silent Retreat

37:07 Daily Meditation Practices

41:48 Starting Your Meditation Journey

47:43 Final Thoughts and Reflections

PATREON

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If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

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10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

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In this episode of The WHY Matters Podcast, we unpack a lesson they learned the hard way - that sometimes, resilience isn’t about pushing harder, it’s about stopping.

From hemorrhoid surgery to burnout on the road, they get real about the hidden cost of “sucking it up” and why our culture glorifies being busy. Through stories from their sailing years, cross-country hikes, and even parenting two ambitious kids, they explore the fine line between perseverance and self-betrayal - and how true endurance requires recovery.

They also challenge the myth that rest is weakness, arguing instead that the power to rest is the power to endure.

@04:12 – When perseverance turns into burnout
@09:26 – The trail story that changed Jessica’s view of rest forever
@13:05 – Why they stepped off the boat (and what it cost them)
@16:05 – The guilt of slowing down and losing followers
@18:46 – Passion vs. punishment: knowing when to pause
@20:23 – The shame cycle of productivity
@22:26 – How our “suck it up” culture gets passed on to our kids
@27:25 – Redefining resilience: why recovery is strength
@29:16 – Missing deadlines, guilt, and the courage to rest anyway

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www.tiktok.com/@worldtowning

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In this episode of The WHY Matters Podcast, Will and I unpack one of the most asked questions we get as full-time traveling parents — how on earth did our kids become trilingual?

What started as a simple desire to expose our children to different cultures turned into a years-long journey through French immersion programs, homeschooling abroad, and more than a few unforgettable (and painful) teacher experiences. From Boston to Costa Rica to France, we share the real story behind raising multilingual kids — what worked, what didn’t, and what it really costs (financially and emotionally).

@04:18 – Why we believe language is the bridge between worlds

@08:14 – The surprising lifelong benefits of learning a second (or third) language

@18:24 – How we accidentally discovered France’s free immersion education system

@27:42 – What we paid at each stage — from $580/month preschool to free public school abroad

@43:11 – The honest truth about bad teachers, language tears, and firing tutors

@59:20 – Myth-busting: why kids don’t just “pick up” a language on the playground

@1:10:45 – Our biggest takeaways and why giving your child another language is the best gift you’ll ever give

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www.tiktok.com/@worldtowning

Support the show

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In this episode of The WHY Matters Podcast, Will and I dive into a topic close to our hearts - celebrating homeschooling milestones.

It all started with a post from a mom whose son’s homeschool graduation went unnoticed. That moment opened a deeper conversation about how nontraditional learners - homeschoolers, deserve to be recognized just as much as traditional students.

From Avalon’s graduation in the middle of the Caribbean to Largo’s upcoming celebration, we share how families can create meaningful, personal traditions that honor effort, growth, and adventure.

@04:28 – Why this topic hit home and what inspired the episode
@06:50 – Why families often overlook homeschool achievements
@09:59 – Surprising stats showing homeschoolers thrive academically and socially
@13:30 – How we celebrated Avalon’s graduation at sea
@20:08 – Finding meaning (and joy) even when others don’t show up

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www.tiktok.com/@worldtowning

Support the show

Send us a text

In this episode of The WHY Matters Podcast, Will and I open up about what aging has been teaching us - and why waiting for “someday” to chase big adventures is a mistake. A tough volcano trek in Guatemala showed us firsthand that our bodies don’t bounce back like they did in our 30s. That wake-up call, paired with the wisdom (and regrets) of older travelers we’ve met along the way, pushed us to make one of our biggest decisions yet - attempting a thru-hike of the Appalachian Trail.

@05:18 India Trip – Why it was our hardest journey yet
@11:30 The Wake-Up Call – Struggling on a volcano at 50+
@13:20 The Big Reveal – Committing to the Appalachian Trail
@17:22 Aging & Recovery – Injuries, slower healing, and reality checks
@21:14 Lessons from Retirees – Why waiting can mean missing your chance
@24:19 Do It Now – Stories of loss, legacy & seizing the moment

This isn’t just about adventure - it’s about aging with intention, choosing meaning over comfort, and creating memories while we still can.

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www.tiktok.com/@worldtowning

Support the show

Send us a text

In this episode of The WHY Matters Podcast, Will and I share what it was really like to spend five months living in one Holiday Inn room - not on vacation, but as a family navigating work, school, and life together in a tiny space. From cooking without a kitchen to dealing with noisy neighbors and even “Weed Alley,” we open up about the challenges, the laughs, and the lessons we’ll never forget.

We get real about:
@01:08 Why a Hotel – How we ended up in a Holiday Inn for months
@05:34 Small Space Living – RVs, boats & now a single room
@09:47 Culture Shock – Returning to the U.S. after a decade abroad
@13:06 Scary Moments – Confrontations, safety, and hotel drama
@15:37 Finding the Good – Pizza, bagels, gyms & small joys
@17:53 Raising a Teen – Sharing one room with a 17-year-old
@21:29 Staying Sane – Privacy hacks, Panera Bread, and date nights
@25:31 Minimalism – Learning to live with less (and love it)
@29:26 Making Memories – Why it was worth it for our son’s dream

For us, this isn’t just about surviving hotel life - it’s about choosing meaning over comfort, and creating family memories in the most unexpected places.

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www.tiktok.com/@worldtowning

Support the show

Send us a text

In this episode of The WHY Matters Podcast, Will and I get real about what it means to live like “working retirees” in our 40s and 50s while raising kids and traveling full time. Most people wait until their 60s to start chasing bucket-list adventures, but we’ve chosen to do it now — blending work, parenting, and travel into one messy, magical, and challenging lifestyle.

From crossing oceans on a sailboat to hiking the Andes and even through-hiking the Appalachian Trail, we’ve had incredible experiences with our kids — but it hasn’t been easy. We open up about the highs and lows of working seven days a week while on the move, why energy and health shape how we use our time, and the lessons we’ve learned about family, money, and what really matters.

For us, this isn’t about waiting for “someday.” It’s about creating a meaningful life while we still have the energy, curiosity, and kids at home to share it with.

@03:24 Why Now – Adventure in our 40s & 50s

@07:45 The Journey – Oceans, mountains & kids

@09:50 The Reality – Hard work behind the dream

@12:41 Die With Zero – Rethinking money & time

@21:35 Kids & Time – Making the most of these years

@24:27 Mental Sharpness – Staying curious & adaptable

@28:20 Who It’s Not For – The sacrifices required

@31:18 What You Can Do – Mini retirements & money shifts

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www

Support the show

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In this episode of The WHY Matters Podcast, Will and I open up about the stories behind our tattoos and the meaning they hold for us. What might look like simple body art is actually a reflection of family, love, travel, and identity. From my first strawberry tattoo at 17 to Will’s dolphins for our kids, and the travel-inspired sleeve I’ve been building along the way, each one carries a piece of our journey.

For us, tattoos aren’t just decoration, they’re a living journal of who we are, where we’ve been, and what matters most.

@04:32 The History – Where tattoos began and how views have changed

@06:40 First Impressions – Our early tattoos and what people thought

@17:10 Personal Stories – The strawberry, dolphins, and butterflies

@26:00 Travel Ink – Tattoos from Ecuador, Costa Rica, and India

@30:00 Anniversary Ink – Matching tattoos in Japan

@35:06 Love & Family – Vows, kids, and tattoos as journals

@42:02 Tattoo Tips – Safety, regrets, and what we’ve learned

Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.

PATREON

https://www.patreon.com/worldtowning

If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you!

GROUP TRIPS

https://worldtowningvoyages.com/

Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and minds alongside a community of like-hearted individuals.

COACHING

https://worldtowning.com/learn-2/

Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else.

NEWSLETTER

https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa

10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life.

MERCHANDISE

Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/

OUR SOCIALS

Instagram: https://www.instagram.com/worldtowning/

YouTube: https://www.youtube.com/worldtowning

Facebook: https://www.facebook.com/worldtowning
Tik-Tok: https://www.tiktok.com/@worldtowning

Support the show