Send us a text

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 [email protected] 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 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 [email protected] 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 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 [email protected] 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 [email protected] 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 [email protected] 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 [email protected] 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

Send us a text

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 [email protected] 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, we dive into Largo’s journey of questioning a childhood dream and discovering a new path forward. From his earliest memories, he wanted to be a pilot -  but when reality didn’t match the dream, he made the bold choice to step away and rethink everything. Through honest reflection, Largo shares how he moved from disappointment to curiosity, and how critical thinking became his compass for navigating big life decisions.

This is a story about more than walking away from flying planes -  it’s about growing up, challenging assumptions, and realizing that changing your mind can be the bravest thing you do.

@02:35 The Dream – Why Largo always wanted to be a pilot
 @07:48 Reality Check – The moment things shifted
 @13:12 Reframing – Letting go and looking deeper
 @19:45 Critical Thinking – A new way of approaching decisions
 @26:20 Support – Family, friends, and mentors
 @31:55 What’s Next – Exploring new passions and possibilities
 @38:40 Weekly Challenge – Question one belief you’ve always held

Leave us a voice message! Share your thoughts or questions at [email protected] 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, we share the story of how a dusty, empty building in rural Cambodia became a bright and welcoming library. Jessica, Largo and Will,  talk about the two-year journey - raising money, carrying six suitcases of books, painting in the heat, and working side by side with kids, volunteers, and the local community.

From replacing the roof to adding shelves, beanbags, and fairy lights, this project was about more than fixing up a space - it was about bringing joy, learning, and hope to hundreds of children. And it all started with one teenager’s vision.

@07:11 The Vision – Where it started
@13:02 Support – Donations and grants
@18:28 Fixing Up – Roof, paint, and shelves
@22:45 Community – Kids and helpers join in
@31:12 Challenges – Heat and deadlines
@37:16 Opening Day – Chalk and ribbon-cutting
@41:10 Next Steps – More books and teachers
@48:57 Weekly Challenge – Do one small thing

Before and After Pictures of the Library here.

To Donate books for the library:
Trask
P.O. box 242
Old Orchard Beach, Maine 04064

FREE College Application Session
This program will be offered FREE for families! When you register, a Zoom link will be emailed to you.
• Wednesday 8/20 at 1pm EST/5pm GMT
• Wednesday 8/20 at 6pm EST/10pm GMT
• Thursday 8/21 at 8am EST/12pm GMT

Fill out the Google Form to register for these free and helpful sessions!

Leave us a voice message! Share your thoughts or questions at [email protected] or call 424-442-9295.

The fabulous Luena Foundation who gave us guidance and recognized Largo with a Young Changemakers Grant.

https://luena.org/arts-education/education-arts-young-changemaker-largo-sueiro-cambodia-library

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

Support the show

Send us a text

In this episode of The WHY Matters Podcast, we lace up our boots for a deeply human look into long-distance hiking, family bonds, and personal transformation. Jessica and her son Largo, share our experience hiking over 2,000 miles of the Appalachian Trail, all while juggling remote schooling, teenage growth, and the realities of life after a decade abroad.

From trail names to trail magic, we dive into what it really means to strip away the noise of modern life and walk, literally, into a slower, more connected way of being. This is a story of resilience, reinvention, and what happens when you step outside your comfort zone with the people who know you best. Whether you're dreaming of the thru-hike life, craving a digital detox, or curious what it’s like to spend half a year in the woods with your teenage kid, this episode is packed with honesty, insight, and a few laughs.

@01:54 Life After 68 Countries – How nomadic travel shaped their worldview
@06:20 School on the Trail – Balancing AP exams and miles
@10:47 Trail Names & Meaning – Meet “Sunshine” and “Captain”
@14:30 The Mental Game – What really gets you through 2,000 miles
@18:01 Family Dynamics – Lessons from a mom-son thru-hike
@22:45 Hiking With WiFi – Making compromises to make it happen
@26:12 Breaking the Mold – Why adventure can’t wait for retirement
@30:00 Final Thoughts – Would they do it again?

Ready to rethink adventure, effort, and what it means to come home? Press play.

Want more stories like this? Check out Zero to Travel for deep dives into nomadic living and purposeful exploration.

Leave us a voice message! Share your thoughts or questions at [email protected] 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:

Support the show