The WHY Matters
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.
The WHY Matters
#40 - Living Our Retirement Dreams in Our 40s - The WHY Matters Podcast
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.
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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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