Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black


ON ADVENTURE PODCAST | EPISODE 71

Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black

          

Episode Description

What does it actually take to step on a plane alone, head somewhere most people would call risky, and come home a different woman?

Amanda Black is the founder of the Solo Female Traveler Network, a community of more than half a million women that started as a small Facebook group during her expat years in Australia. Ten years and roughly thirty tours a year later, she leads women into places the average traveler tends to avoid: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan, and beyond. Bali was the first trip. Seventeen women signed up. Nine of them ended up with the company logo tattooed by the end of it.

We talk about why she leans into destinations perceived as less safe, what real risk actually looks like versus the version we imagine, and why she pushes back on the idea that travel is simply safe or unsafe. Risk, she argues, is a spectrum and a muscle, and most women have a lot more capacity to build it than they have been told.

We also get into the quieter side of all this. The cobblestone cafe in Sighișoara, Romania, where women who had known each other only a few days started telling the truth about how lonely life back home really feels. The Golden Eagle Festival in Mongolia, where she felt like she had walked into a movie set with no electricity. The unexpected pattern she keeps noticing across every trip, every country, every group: people are not really upset about the hotel room. They want to belong.

Amanda also shares why she launched Kindred Community, a smaller, slower offering built around connection retreats in Southern California, and what almost a decade of leading women into the wild has taught her about courage, capability, and the kind of friendships that get a logo tattooed on someone’s wrist.

Episode Highlights

00:00  Welcoming Amanda Black, founder of the Solo Female Traveler Network

01:00  Building a community of 500,000+ women and running tours in 25 countries

03:00  Why she leans into destinations perceived as less safe: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan

05:00  How strangers become a travel family inside the first 48 hours of a trip

08:00  From a Facebook group in Australia to a first Bali trip where 9 of 17 women got the company logo tattooed

12:00  Talking honestly with women about safety, fear, and the gray areas of real risk

15:00  Risk on a spectrum: why “safe or unsafe” is the wrong question, and how to build the muscle over time

17:00  Mongolia and the Golden Eagle Festival: stepping into a place that felt like going back in time

20:00  What solo travel reveals about how strong and capable women really are

22:00  The hidden business lesson behind a decade of tours: everybody just wants to belong

24:00  A cobblestone cafe in Sighișoara, Romania, and the loneliness that surfaces when women finally feel safe to share

27:00  Kindred Community and the next chapter: building belonging closer to home

Connect with Amanda Black

Bonus for Listeners (Free Travel Quiz):

https://thesolofemaletravelernetwork.com/where-should-i-travel-next-quiz/

The Solo Female Traveler Network

Website: thesolofemaletravelernetwork.com

Instagram: @solofemaletravel

TikTok: @sofetravel

YouTube: @sofetravel

Amanda’s TEDx Talk

Shared Firsts: Redesigning how we find belonging

youtube.com/watch?v=xSaVJH2b5H0

Amanda’s Website

meetamandablack.com

Kindred Community

Website: kindredcommunity.co

Instagram: @kindred.sd

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

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Episode 70: Saying Yes to the Right Invitations with Colin Stroud


ON ADVENTURE PODCAST  |  EPISODE 70

Episode 70: Saying Yes to the Right Invitations with Colin Stroud

                              

Episode Description

What if your next great adventure is not a destination at all, but a willingness to say yes to the breadcrumbs life keeps dropping in front of you?

Colin Stroud is a 26-year-old credit card rewards consultant, founder of Go Somewhere, and one of the fastest growing voices on LinkedIn in the points and miles space. He grew up in Fort Wayne, Indiana, the son of an OB/GYN and a nurse midwife who met delivering a baby together, and he was on track for a more traditional path until a six-week Spanish immersion trip to Oviedo at 16 cracked the world wide open. From there it was Italy on a $380 flight, a Catholic mission to Poland, an unlikely run at Ave Maria University in south Florida, an early marriage and a baby on the way before he had even graduated, and a first job in life insurance case design that he knew almost immediately was not it.

What followed is a story about paying attention. A coworker mentioned the Chase Trifecta. A LinkedIn post about points went viral and got picked up by The Washington Post. A side hustle turned into consulting calls, then into a community for business owners, then into a full-time business helping families and entrepreneurs unlock travel they thought they could not afford.

We talk about why early travel rewires you, what it actually takes to leave a steady paycheck, the difference between dopamine and meaning, why family life and entrepreneurship feel like the truest adventures of his life right now, and the surprising decision he and his wife made after almost moving to Hawaii. Colin makes a strong case that the go somewhere life is not always about getting on a plane, and that learning to be rooted where your feet are can be its own kind of expedition.

 

Episode Highlights

00:00  From cheap flights as a teenager to a full-time business helping people unlock travel

06:00  World Youth Day in Poland, six weeks of Spanish immersion in Oviedo, and catching the travel bug

14:00  Marriage, a baby on the way, and a first job in life insurance that did not fit

18:00  Discovering the Chase Trifecta and stepping into the points world

23:00  The first viral LinkedIn post and a Washington Post quote that changed everything

25:00  Quitting in November 2024 and going full-time on Go Somewhere

30:00  Almost moving to Hawaii, pumping the brakes, and rethinking what travel does for young kids

34:00  Why family life and entrepreneurship are the truest adventures of his life right now

39:00  Measuring yourself: finally finding feedback after years of feeling stuck

47:00  The two ingredients behind a viable internet business: clear writing and consistent humility

55:00 What adventure means now and where to find Colin online

 

Connect with Colin Stroud

LinkedIn: linkedin.com/in/colinstroud

Website: gosomewhere.world

Newsletter: The Go Somewhere Newsletter at gosomewhere.world

Email:

 

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

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Episode 69: No One Was Waiting at the Finish Line with Madison Blagden


ON ADVENTURE PODCAST  |  EPISODE 69

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden

 

   

   

Episode Description

What would it take to walk 10,000 miles in a single calendar year? Not across a lifetime. Not spread over a decade. One year.

Madison Blagden is a long-distance hiker and content creator from Massachusetts who went from a pre-med student with zero backpacking experience to one of the most prolific endurance hikers in the country. After completing the full PCT (2022), the Eastern Continental Trail from Key West to Newfoundland (2023), and the Continental Divide Trail (2024), she did all three Triple Crown trails back to back in 2025, border to border, logging over 10,000 miles in a single calendar year. She documented every step herself through daily YouTube videos, Instagram shorts, and blog posts, all edited on the road.

Starting in the Florida Keys in January, she pushed through Hurricane Helene damage on the AT, Sierra snowpack, desert heat, a debilitating hip injury in the White Mountains, and a flash flood that hit her tent in the middle of the night in the desert. The miles are extraordinary. But this conversation goes deeper than the miles.

We talk about what happens between the ears when the body wants to quit, the difference between healthy internal ambition and ego-driven achievement, how the most meaningful finish lines are the ones where nobody is waiting for you, what a flash flood teaches you about calm under pressure, the spiritual dimension of pushing past absolute exhaustion, and why you will never be 100 percent ready, and that is not a reason to wait.

 

Episode Highlights

       00:00  Introduction: Walking 10,000 miles in one calendar year

       02:00  Madison’s background: pre-med to PCT with no backpacking experience

       04:00  Van life, COVID, and two years of traveling in a 19-foot RV

       09:00  Comparing the AT, PCT, and CDT: terrain, culture, and difficulty

       14:00  Hurricane Helene’s impact on the Appalachian Trail and trail recovery

       19:00  Planning a 10,000-mile year: budget, timing, and keeping it flexible

       24:00  How a 5,600-mile year sparked the idea to go even further

       31:00  Funding the hike through daily content creation on the road

       34:00  Healthy ambition vs. ego-driven achievement

       39:00  Internal motivation: the David Goggins voice and the gentle encouragement

       42:00  37 miles a day for nine weeks: the math behind finishing the CDT before snow

       48:00  Hip injury in the White Mountains and the lesson in letting go

       51:00  Flash flood survival and what it reveals about fight-or-flight

       57:00  Nervous system training and calm under pressure

       01:02:00  Surrendering control: giving it up to the trail and the universe

       01:05:00  Spiritual experiences that emerge only at the edge of physical exhaustion

       01:10:00  Coming off trail softer: how big accomplishments quiet the ego

       01:15:00  Closing encouragement: you will never be 100 percent ready, so go

       01:20:00  The expanding ceiling of human limits and what comes next for Madison

 

Connect with Madison Blagden

Instagram & YouTube: @madisonblagden

Website: madisonblagden.com

Substack: substack.com/@madisonblagden

The Trek: thetrek.co/author/madison-blagden

 

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

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Episode 67: How to find God in Solitude, Silence and Wilderness with Bishop Mark Beckman


In this final installment of our series on spirituality and adventure, I sit down with Bishop Mark Beckman, the 4th Bishop of the Diocese of Knoxville, to explore what happens when faith is formed not just in quiet rooms, but in wild places. From hiking solo through old-growth forests to walking hundreds of miles on pilgrimage, Bishop Beckman shares how discomfort, silence, and physical effort can open us to something deeper than words.

We talk about the moments that push us to the edge of our capacity—storms in the backcountry, long days of walking, fear at high elevations—and how those experiences can shape trust, humility, and presence. This conversation is a reminder that adventure doesn’t only take us outward into the world, but inward toward meaning, mystery, and a deeper awareness of God.


Episode Timeline

  • [2:22] – Bishop Mark Beckman’s calling to ministry and how the outdoors shaped his faith from an early age

  • [6:45] – Discovering God’s presence through solitude, silence, and hiking alone in the woods

  • [10:48] – Forming a men’s backpacking group and finding unexpected community on the trail

  • [16:05] – Walking the Camino de Santiago and learning trust one step at a time

  • [22:40] – Pushing through fear and physical limits on a 14,000-foot peak in Colorado

  • [30:12] – Retreat, silence, and wilderness as pathways to deeper spiritual awareness

  • [38:05] – Suffering, endurance, and how hardship can deepen us instead of hardening us


Links & Resources


If you enjoyed this episode, I’d really appreciate it if you’d rate, review, follow, and share the podcast. And don’t forget to subscribe to our YouTube channel for full episodes and additional content — it’s one of the best ways to support the show and stay connected. Until next time, stay safe and stay on adventure.

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Episode 64: Adventure, Spirituality, and the Search for Something Bigger with Reed Dunn


In today’s episode—the first in a brand-new series exploring the deeper meaning behind our outdoor experiences—I sit down with my longtime friend, pastor, everyday explorer, and deep thinker, Reed Dunn, for one of the most meaningful conversations I’ve had on this podcast. This first installment leans less on adrenaline and more on the why—why we’re drawn to the outdoors, why hardship shapes us, and why so many of us pursue experiences that push us into awe, wonder, and transcendence.

Reed and I dig into the spiritual side of adventure—what it means to connect with something beyond ourselves, whether you call that God or a higher power. We unpack the way wilderness confronts our limits, how beauty can shake us awake, and why disciplines of “no” might be more important today than ever. And of course, we talk about Reed’s years of backpacking, his favorite place in the world, and the moments that have stayed with him long after the trip ended.


⏱️ Timeline Summary

Here are the top moments from the episode:

[00:16:00] – Kicking off the conversation: why I wanted Reed on the show and how his story fits into “the meaning side” of adventure.
[00:26:00] – Reed’s early backpacking years—Colorado, Arkansas, the Buffalo River Trail, and how those experiences shaped him.
[00:35:00] – The memory of his favorite place on earth: a glacial lake, seven waterfalls, and the power of remembering without a camera.
[00:36:00] – A deep dive into spirituality: what it means to connect with transcendence, how nature becomes a pathway, and why anyone—regardless of belief—can access it.
[00:46:00] – Religion vs. spirituality: Reed breaks down the difference between learning about God and meeting God—and why both matter.
[01:13:00] – Exploring hardship, asceticism, and the spiritual importance of limitation. Why “telling yourself no” opens doors to meaning.
[01:22:00] – The connection between ancient spiritual practices, desert monks, and modern adventurers who push themselves to the edge in search of something more.


🔗 Links & Resources


🙌 Closing Remark

If this conversation stirred something in you, inspired you, or made you think differently about why we chase adventure in the first place, I’d love for you to rate, follow, share, and review the podcast. It helps more everyday explorers find these stories—and it keeps great conversations like this one coming.

Thanks for listening, and keep living your adventure on purpose.

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Episode 63: Walking Into a New Life – How a 100+ Pound Transformation Led to Ultra Endurance Success with Lisa Decker

In this episode of the On Adventure Podcast, I sit down with ultra-endurance athlete Lisa Decker, whose story is a powerful blend of resilience, transformation, and the relentless pursuit of hard things. Lisa didn’t come from a traditional running background—yet she discovered the world of ultra running through community, curiosity, and a willingness to push herself beyond her comfort zone. What followed is a decade-long journey that includes a 120-pound weight-loss transformation, countless ultras, and the life-changing experience of completing the legendary Vol State 500K across Tennessee.

We dive deep into what motivates someone to walk 314 miles in the July heat, how finding the right community can unlock new levels of confidence, and why endurance challenges often lead to profound personal growth. This episode is packed with insight about mental toughness, identity shifts, overcoming self-doubt, and discovering what you’re really capable of when you take that first step—literally.

If you’re searching for inspiration, endurance storytelling, personal transformation, or insights about long-distance running and mindset, this episode delivers.


⏱️ Timeline Highlights

[2:15] – Lisa’s early life in California, her outdoors-focused upbringing, and how nature shaped her love of adventure.
[6:40] – Discovering the trail and ultra running community through Team RWB and why it instantly felt like “home.”
[14:30] – How she balances 10-hour pharmacy shifts with ultra training, and why walking ultras became her key to success.
[17:45] – The unexpected moment on the Vol State ferry that led to forming a five-person pack and transforming the entire race experience.
[23:10] – Kind strangers, roadside hospitality, skunk encounters, and what surprised her most during the 500K journey run.
[28:40] – Doing ultras while overweight, finishing last, and why showing up anyway built the foundation for her transformation.
[36:50] – The mental battle of “head trash,” the power of community support, and why being honest about struggles matters.
[49:00] – Future adventure goals, including walking the Caminos in Europe and exploring the world on foot.
[58:30] – How endurance sports shifted her personal identity, career goals, and even her vision for where she wants to live next.


🔗 Links & Resources

Featured Organizations & Topics


💬 Final Thoughts

If this conversation inspired you or helped you rethink what’s possible for your own life, please rate, follow, share, and review the podcast. Every bit of support helps new listeners discover these stories—and it keeps the adventure going.

And don’t forget:

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Episode 61: Why Adventurers Quit – 3 Mental Traps and How to Beat Them with Vol State 500K Finisher MAJ (Ret.) Vincent Antunez


Enduring the Impossible with Vincent Antunez

This episode is a deep dive into the mind and mission of Vincent Antunez, DSc, PA-C – a retired U.S. Army Major, ultra endurance athlete, and founder of Trail Toes. From grueling military deployments to multi-day ultramarathons across the globe, Vincent shares how pain, persistence, and preparation have shaped every step of his journey.

We talk about what it takes to push beyond the limits of your body – and more importantly, your mind. Vincent shares raw, powerful stories of suffering and success on the course, the lessons that endurance sports teach about humility and resilience, and the gear and mindset strategies that keep him (and his feet) moving forward. This one is packed with wisdom from the front lines – of both battlefields and ultramarathons.

🎧 Don’t forget – we’re now on YouTube! Be sure to subscribe to the channel and hit that bell so you never miss an episode. And of course, follow the show wherever you get your podcasts.


⏱️ Episode Timeline:

[1:12] – How Vincent met ultrarunning legend Lisa Smith-Batchen — and helped her complete her historic Badwater Quad
[3:44] – A military career across decades and continents
[6:57] – How a post-midnight beer run in Germany accidentally became his first marathon
[11:42] – Why he keeps showing up, even without formal training
[13:58] – The 3 reasons people drop out of ultras (and how to beat them)
[20:31] – Innovative tips for staying cool and blister-free on brutal courses
[24:49] – Trail Toes and how Vincent created it in Afghanistan
[38:11] – The psychology of endurance: crews, quitting, and the right kind of pressure
[52:05] – Why Vincent keeps coming back to these events — and what they continue to teach him


🔗 Links & Resources:


If you enjoyed this episode, please take a moment to rate, follow, and review the podcast — and share it with a friend who’s always pushing their limits. Every download helps more everyday explorers find their way forward.

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Episode 58: How to run through Death Valley in July at age 80 with Bob Becker


In this captivating episode of On Adventure, I sit down with the legendary Bob Becker ultramarathoner, race director, and age-defying adventurer – to unpack his incredible journey from late-blooming runner to becoming the oldest finisher of the Badwater 135, one of the world’s toughest ultramarathons.

At 80 years old, Bob proves that it’s never too late to rewrite your story, conquer deserts, and inspire generations. Whether you’re an aspiring endurance athlete, race organizer, or simply someone looking for motivation to stay active, this episode delivers.


🕓 Timestamps & Topics Covered

  • [00:04:00] Introduction – Welcoming Bob Becker and setting the stage.

  • [00:06:00] Late Bloomer in Running – Bob started serious running at 57!

  • [00:07:30] First Ultra: Marathon des Sables – 150-mile Sahara race to celebrate turning 60.

  • [00:09:00] Why Ultras? – The deep camaraderie and the life-changing community.

  • [00:13:00] Training Without Mountains – How Bob trains for elevation in flat Florida.

  • [00:18:30] From Running to Race Directing – Launching the iconic Keys 100 and Daytona 100 races.

  • [00:23:00] Life After Real Estate – How Bob turned adversity during the financial crisis into purpose.

  • [00:27:00] Jungle Racing in the Everglades – Creating and running a now-legendary trail race.

  • [00:34:00] Enduring Support – His wife’s unique but wholehearted support.

  • [00:38:00] Intergenerational Adventure – Racing with his granddaughter.

  • [00:39:30] Movement as Medicine – Encouraging older adults to “just start moving.”

  • [00:40:00] Nutrition & Heat Strategy – Vegan lifestyle and fueling for the long haul.

  • [00:47:00] Inside Badwater 135 – The heat, the altitude, the brutal beauty.

  • [00:54:00] History in the Making – Becoming the oldest finisher in Badwater history.

  • [01:00:00] Mental Grit – Mantras, bear crawls, and mindset hacks.

  • [01:05:00] Lessons from the Trail – What Bob’s learned from every finish line.


🏆 Key Takeaways

  • 🧠 Age is not a limitation – Bob didn’t start running seriously until his late 50s.

  • 🌱 Vegan athlete – Nutrition was key to training, racing, and recovery.

  • 🥵 Badwater veteran – 6x Badwater runner; oldest finisher at age 80.

  • 🛠️ Creative training methods – Pulling tires across bridges to simulate hills.

  • 💪 Mental strength over miles – Bear crawled the last mile of Badwater in 2022.

  • 🧡 Inspiring generations – Encourages others, especially seniors, to stay active.


✨ Notable Quotes

“If someone else can do it, why can’t I?” – Bob Becker

“The finish line is glorious. It’s a bragging right you carry forever.”

“You’re never too old to start moving. Start walking, gardening – just move.”


🔗 Connect with Bob Becker


🎧 Enjoyed this episode? Don’t miss out on more inspiring conversations with adventurers, endurance athletes, and game-changers just like Bob Becker.


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Episode 57: Barefoot Running, the Badwater Double FKT, and Chasing the Grid with Ken Posner


In this episode of the On Adventure Podcast, I sit down with Ken Posner—ultrarunner, author, former Army Ranger, and corporate financial analyst—to explore the transformative power of pushing physical and mental boundaries. Ken shares stories from his extraordinary journey completing the “grid”: summiting all 35 high peaks of New York’s Catskills in every month of the year. Along the way, he stripped away technology, embraced barefoot running, and found a deeper connection with nature and himself.

This episode isn’t just about extreme endurance. It’s about rediscovering who we are when the noise of the modern world fades away. We unpack how doing hard things in nature can bring clarity, strength, and a more balanced life. Whether you’re curious about barefoot hiking, intrigued by minimalist living, or seeking inspiration to shake up your own routine, Ken’s story will move you.

Timeline Summary:

[2:22] – Ken’s shift from corporate life to ultra endurance running in his late 30s
[4:00] – Why he started running barefoot and what kept him going
[7:45] – The joy, mindfulness, and sensation of barefoot movement
[10:10] – Balancing high-tech corporate work with minimalist, analog outdoor living
[19:00] – The metaphor of “signal vs. noise” and how nature helps us tune in
[28:30] – Pain vs. suffering: building resilience through chosen challenges
[35:00] – The Badwater Double: a 292-mile journey through Death Valley and back
[47:30] – How the mountains called him at age 50 and led to chasing the grid
[54:00] – The spiritual and transformative lessons learned through mountain pilgrimages

Links & Resources:

Closing Remark:

Please check out Ken’s website and support him by purchasing his new book! 

If this episode sparked something in you, share it with a friend who could use a little adventure in their life. Be sure to follow, rate, and leave a review of the podcast and well as our new YouTube channel—it helps us reach more everyday explorers just like you. Thanks for tuning in!

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Traveling on Purpose: Turning Luxury Vacations into Meaningful Milestones

For many families, vacations are about rest and recreation – time to unwind, see the world, and enjoy hard-earned success. But for those with significant resources, there’s an opportunity to take travel beyond luxury and create something far more lasting: purposeful travel.

Purposeful travel blends the comfort and adventure you expect with intentional goals – strengthening family bonds, serving communities in ways that leave a legacy, or cultivating personal growth through quiet reflection. These trips become milestones, remembered not just for where you went, but for how they shaped your family’s story.

Here are three purposeful approaches that resonate especially well for families who want their travel to matter as much as their investments:

  1. Multi-Generational Adventures that Forge Family Connection

When a family spans multiple generations, gathering everyone under one roof – or even in one country – can be rare. A purposeful family trip creates an intentional space to connect across ages, combining luxury comfort with shared challenges or experiences.

Think of chartering a private expedition yacht in Alaska where grandparents and grandchildren alike participate in guided wildlife research. Or a curated trek through Patagonia, complete with private guides and lodges, where each family member contributes – whether it’s navigating a trail or preparing a shared meal one evening.

The goal isn’t just to “go somewhere” but to actively create shared experiences that knit generations together and build the family narrative. These trips often spark traditions that become part of the family’s legacy.

How to get started:

• Engage a travel advisor who specializes in high-end, family-oriented experiences to ensure logistical ease and privacy.

• Choose a cause or skill that resonates with your family values – conservation, cultural preservation, or even an artistic pursuit.

• Plan structured reflection time, like nightly fireside conversations or a shared family journal to capture insights along the way.

  1. Personal Retreats for Renewed Perspective

Wealth often comes with significant complexity…it’s the often-overlooked paradox of ‘more.’ The pressures of leadership, decision-making, and public life can be relentless. Purpose-driven solo retreats – or even couples retreats – offer rare opportunities to disconnect from constant demands and recalibrate priorities.

Picture a guided silent retreat in the Swiss Alps with world-class amenities, or a secluded desert lodge designed for deep meditation and personal reset. These environments strip away distractions and offer clarity, allowing you to return not just refreshed, but re-centered on what matters most.

How to get started:

• Consider retreat centers that balance privacy with top-tier wellness programming – places that honor both comfort and introspection.

• Recommendations from friends that have gone before are helpful!

• Build a loose itinerary: include guided mindfulness sessions, private hikes, or curated reading lists to deepen the experience.

• Plan for post-retreat integration: a few days of quiet transition before re-engaging fully with work and family life. This is always important so we don’t blow right back into life as usual.

  1. Philanthropic Travel with Measurable Impact

For many affluent families, travel is also a chance to align lifestyle with legacy. Philanthropic adventures – sometimes called “impact travel” – allow you to explore remarkable destinations while supporting initiatives that matter to your family.

Imagine funding and participating in a reef restoration project in the Maldives, or helping construct sustainable water systems in a remote African village – while your family experiences the local culture and learns firsthand about the challenges and solutions. These trips can instill gratitude and broaden perspective for younger generations, while also tangibly advancing causes you care about.

How to get started:

• Partner with established philanthropic travel organizations to ensure projects are ethical, sustainable, and genuinely needed.

• Define your family’s core values (education, conservation, community) and seek projects that align with them.

• Combine service with adventure – balance meaningful work with opportunities to explore and celebrate the destination.

Why This Matters for Families of Means

There is no question that I am bent towards looking at vacation as an escape. I do not think that there is anything inherently wrong with viewing time away from daily life in this light. Sometimes, it is exactly what is needed for recharging.

However, the broader point here is that there is another angle that can be considered. Purposeful travel reframes vacations from “escape” to “investment” – not in dollars, but in relationships, perspective, and legacy. It creates shared experiences that deepen connection, foster gratitude, and remind everyone what your resources are really for: living a meaningful life, not just an affluent one.

These trips also help younger generations see wealth differently – not as entitlement, but as responsibility and opportunity. They become part of the family culture, shaping how future decisions about giving, living, and investing are made.

Next time you plan a trip, ask: What could this mean for our family beyond rest and luxury? The answer might turn your next vacation into one of the defining chapters of your family’s story.