In this episode of The WHY Matters Podcast, we unpack the beautifully chaotic life of full-time travelers and what it really means to "sell it all and go." From ditching suburban routines to chasing connection across continents, WorldTowning founders Jessica and Will dive deep into the emotional, financial, and relational side of radically redefining home.
Through honest stories, hard-won lessons, and powerful reframes, we explore how choosing an unconventional life can lead to greater alignment, tighter family bonds, and a new definition of freedom. Whether you're a digital nomad, travel dreamer, or just rethinking what stability looks like, this episode invites you to challenge the script and make intentional choices — even when they’re scary.
@01:54 Leaving Suburbia – The “aha” moment that sparked their world travels
@06:27 Fitting Into Boxes – Why society’s version of success wasn’t cutting it
@10:16 Financial Reality – What selling everything really bought them
@16:43 Raising Kids on the Road – The ups, downs, and surprising benefits
@23:05 Conflict & Growth – What travel taught them about relationships
@29:48 Unexpected Anchors – When freedom needs a little structure
@36:21 Home Is a Feeling – Letting go of the white-picket-fence myth
@42:33 Advice for the Hesitant – What they wish they’d known before leaping
Ready to redefine what “normal” looks like? 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 info@thewhymatterspodcast.com or call 424-442-9295.
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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
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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
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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.
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