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The WHY Matters

The WHY Matters

Written by: WorldTowning
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About this listen

Hey friends, this is Jessica and Will from WorldTowning. You’re listening to the podcast that shares the highs, the lows, and the “what the heck just happened” of our decade-long full-time travel lifestyle and how it has changed us. On The WHY Matters, we dig deep into the WHY behind our choices and the positive results they leave. If you are ready to spread your wings, have a laugh, and take the insights of full-time travelers into your everyday life, then this podcast is for you.


© 2026 The WHY Matters
Self-Help Social Sciences Success Travel Writing & Commentary
Episodes
  • #45 – The Power of Meditation with Our Dear Friend Doug - A Tribute
    Jan 7 2026

    Send us a text

    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

    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/

    Support the show

    Show More Show Less
    54 mins
  • #44 - Taking a Rest - The WHY Matters Podcast
    Nov 12 2025

    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 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

    Show More Show Less
    40 mins
  • #44 - Raising Trilingual Kids: The Real Cost, Chaos, and Magic of Multilingual Living
    Oct 22 2025

    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 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

    Show More Show Less
    1 hr and 10 mins
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