Stewarding Significant Wealth: Navigating Complex Financial Decisions

At a certain point, the financial conversation shifts.

For most people, the early stages of building wealth are focused on accumulation. Growing a business, investing consistently, and creating a sense of security. But when wealth reaches a level of real significance, the questions change. It becomes less about whether you have enough and more about what you do with it, how you protect it, and whether it continues to reflect what actually matters to you.

That is the work of stewardship. And it looks very different from standard financial planning.

The complexity is real

Ultra-high-net-worth families face a different set of decisions than most financial plans are built to address. A portfolio may span public investments, real estate, private companies, philanthropic structures, and multigenerational planning. Each layer adds another decision point. Taxes matter more. The structure of asset holdings matters more. Family dynamics matter more.

And here is something that surprises many people: the margin for costly mistakes does not shrink just because there is more money on paper. In some ways, it grows. Complex wealth requires more coordination, more intentionality, and a plan that is built around your specific situation, not a template.

Tax planning is not an afterthought

For families managing significant wealth, tax planning is often where the most valuable work happens. Not because every decision should be made to save taxes, but because the tax consequences of major decisions deserve to be considered before they are made, not after.

The most effective planning weaves together investment strategy, estate considerations, charitable giving, and liquidity needs. When those pieces are coordinated, families can be much more deliberate about timing, ownership structures, and how different assets fit into the larger picture.

Beyond a traditional portfolio

Many families at this level begin exploring opportunities outside of a standard investment portfolio. Real estate, private companies, alternative investments, and family-office-style structures can all offer meaningful diversification and long-term potential. But they also entail greater complexity, more due diligence, and a need for clarity about how each piece fits the overall plan.

The question worth asking is not just “What is the return on this?” It’s “How does this serve the life and legacy we are building?”

Using wealth well, right now

One of the most common patterns we see is this: families who have worked hard to build significant wealth end up waiting too long to use that wealth intentionally. There is always a reason to hold off. Another milestone to hit. Another uncertainty to resolve first.

But wealth is most powerful when it is engaged with intention now. That might mean funding the experiences that matter most to your family. Supporting causes that align with your values. Helping the next generation understand both the opportunity and the responsibility that comes with what they will inherit. Sometimes it simply means giving yourself permission to live fully into the life your planning has made possible.

Good stewardship is not about being cautious to the point of paralysis. It is about making decisions that are values-aligned, tax-aware, and built to last, while also actually living.

The real work

At the highest levels of wealth, financial planning is not primarily about performance. It is about making sure the decisions you make today reflect who you are and what you want your wealth to do.

That requires a plan that accounts for complexity, a team that understands the landscape, and the clarity to know what you are building toward. Not just financially, but in life.

Wealth creates opportunity, but it also creates responsibility. If your financial picture has grown more complex and your planning has not kept pace, it may be time to revisit whether your strategy truly reflects the life you’re building. Reach out to our team to start the conversation.

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 66: The Adventure Within – Finding Strength, Meaning, and Hope through Adversity with Hilal Kanaan


In today’s episode, I sit down with Dr. Hilal Kanaan – neurosurgeon, son of Palestinian immigrants, and someone whose daily work places him in the quiet but profound landscapes of human suffering, endurance, and compassion. While he isn’t chasing adventure in the traditional sense, Hilal spends his days navigating a different kind of wilderness: the emotional and spiritual terrain of walking with people through their hardest moments.

We explore the kind of toughness that’s forged not on trails or mountaintops, but in operating rooms, hospital corridors, and the inner worlds shaped by personal history, faith, and humility. Hilal shares what it was like growing up between cultures, how his parents’ story of resilience shaped him, and what strength has come to mean inside a profession where asking for help can be the bravest move of all. This conversation broadened my understanding of what “adventure” can truly mean – and I think it’ll do the same for you.

⏱️ Episode Timeline Highlights

[00:00] Opening the conversation with Dr. Kanaan and framing a different kind of adventure.
[02:00] Growing up in Kalamazoo as the son of Palestinian immigrants.
[04:00] The mix of chaos, tragedy, resilience, and optimism woven into Palestinian identity.
[07:00] Balancing two cultures and the intentional ways his parents raised their family in America.
[11:00] The parental tension between comfort and necessary challenge.
[15:00] Identifying “the ghosts in the nursery” – what we inherit, keep, and let go of.
[17:00] The book Hilal created for his kids to help them understand God, compassion, and curiosity.
[24:00] Faith as a language for gratitude rather than certainty.
[29:00] What it feels like to accompany patients through their darkest moments – and how their faith shapes him.
[35:00] The humbling lesson of asking for help when a case goes sideways.
[44:00] Hilal’s message to anyone facing hardship: your feelings are valid…and this is not the rest of your life.

🔗 Links & Resources

🙏 Closing Thoughts

If this episode resonated with you, it would mean so much if you’d rate, follow, and review the podcast — it truly helps others discover these conversations.

And don’t forget: we’re building more content on YouTube, including full episodes, clips, and behind-the-scenes insights.
👉 Find and subscribe to our YouTube channel to stay connected.

Until next time — stay safe, and stay On Adventure.

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Planning 2026 with intention: 10 financial and life considerations for the year ahead

The start of a new year naturally invites planning. But for most people, planning quickly turns into optimization – more efficiency, better returns, tighter projections.

The more meaningful work often starts earlier than that.

Before adjusting numbers, it’s worth stepping back to ask whether your financial life is aligned with the life you want to live. As we look ahead to 2026, with several new planning rules and legislative changes becoming active under the OBBBA framework, this is an ideal moment to reset both direction and strategy.

As a kid of the ‘90’s and a David Letterman fan, I always waited for the part of the show when he revealed his (sometimes crazy, but almost always funny) Top 10 List.  Here is my attempt and a nod to Mr. Letterman with 10 financial and life planning considerations worth reviewing as you prepare for the year ahead, with a particular emphasis on building margin, clarity, and adventure into 2026.

1. Define What You Want 2026 to Feel Like

Before reviewing accounts or projections, clarify the experience you want the year to deliver.

Do you want 2026 to feel spacious or packed? Grounded or mobile? Predictable or exploratory?

Financial plans are most effective when they support a clearly defined life vision. Without that anchor, even strong financial results can feel disconnected.

2. Plan Adventure First, Not Last

Adventure is often treated as optional – something to squeeze in if time and money allow.

In practice, that usually means it doesn’t happen.

Whether adventure for you means extended travel, meaningful family trips, endurance events, or simply more time outdoors, plan it intentionally. Block the time on the calendar. Estimate the cost. Create a dedicated savings bucket.

When adventure is designed into the plan, money becomes an enabler rather than a gatekeeper.

3. Understand What’s Changing Under the OBBBA

Several provisions tied to recent federal budget and benefits legislation are now becoming relevant for 2026 planning. While the specifics vary by household, common planning areas affected include retirement contribution limits, including updated catch-up provisions for certain age ranges; required minimum distribution rules and beneficiary timelines impacting inherited retirement accounts; income thresholds for tax credits and deductions, with tighter phase-outs at higher income levels; and sunsetting provisions from earlier tax law, increasing the importance of proactive, multi-year tax planning.

The key takeaway is that understanding these changes early creates flexibility. Waiting until year-end often removes good options.

4. Revisit Your “Enough” Number

As income and assets grow, old targets often linger long after they stop serving your life.

Revisit what level of income actually supports your desired lifestyle, how much work is enough, and which trade-offs are no longer worth it.

Clarifying “enough” is often the most powerful financial decision you can make.

5. Align Cash Flow With Experience, Not Habit

Instead of asking where to cut spending, ask where your money is working well for you.

Which expenses consistently add meaning or enjoyment? Which ones feel automatic or outdated?

Redirecting cash flow toward experiences, travel, and flexibility often improves quality of life without increasing overall spending.

6. Strengthen the Safety Net

Adventure is easier to pursue when the foundation is solid.

The new year is a good time to review emergency reserves, insurance coverage, estate documents, and beneficiary designations.

These items rarely feel urgent – until suddenly they are. Proactive review reduces stress and creates confidence.

7. Simplify Where Complexity Has Crept In

Over time, financial lives naturally become more complex.

Multiple accounts serving similar purposes, legacy strategies that no longer apply, and complexity that adds confusion without value can quietly accumulate.

Simplification improves clarity, reduces friction, and makes decision-making easier when life changes quickly.

8. Use Tax Planning to Support Lifestyle Decisions

With updated thresholds and evolving rules, tax planning for 2026 should align with life choices.

This may include timing income around travel or sabbaticals, evaluating Roth strategies during lower-income years, or coordinating charitable giving with tax efficiency.

The goal is not minimizing tax in isolation, but ensuring tax decisions support the life you want to live.

9. Decide What to Stop Doing

Borrowing from the annual review approach popularized by Tim Ferriss, one of the most powerful planning exercises is deciding what to stop.

What commitments, habits, or financial behaviors create stress without meaning, consume time without return, or reflect an outdated version of you?

Stopping often creates more freedom than starting something new.

10. Build Margin Into the Plan

Finally, leave room.

Margin in your calendar allows spontaneity. Margin in your cash flow absorbs surprises. Margin in expectations builds resilience.

A plan with no margin may look efficient, but it is fragile. A plan with margin can flex and support opportunity when it appears.

Final Thought

Planning for 2026 isn’t about predicting every outcome. It’s about creating a framework strong enough to support responsibility and exploration.

When financial planning is aligned with experience, when adventure is treated as essential rather than optional, and when decisions are made intentionally rather than reactively, money becomes what it was always meant to be – a tool in service of a well-lived life.

The top 8 financial items to review before the end of the year

As the year draws to a close, many people feel an instinct to wrap things up. It’s a natural moment to pause, take inventory, and make sure nothing important is left undone.

In financial planning, year-end reviews aren’t about scrambling or chasing last-minute tactics. Done well, they’re about clarity – confirming that your financial decisions still align with the life you’re building.

Here are the most important areas worth revisiting before the calendar turns.

  1. Taxes: Reducing Regret, Not Just the Bill

    Year-end tax planning isn’t about perfection – it’s about intention. This is the time to review realized gains and losses, assess whether tax-loss harvesting makes sense, and confirm that income timing aligns with your broader strategy. For many families, charitable giving also plays a role here – not as a tax trick, but as a thoughtful extension of their values.

  2. Required Minimum Distributions (RMDs)

    For retirees and those nearing retirement, RMDs deserve careful attention. Confirming distributions are made on time, in the correct amount, and from the appropriate accounts is critical. It’s also worth reviewing how RMDs integrate with your overall cash-flow plan. This is ideally done in the first half of the year, but if you haven’t gotten to it yet, do not delay. The penalty for missing your RMD is significant!

  3. Charitable Giving with Purpose

    Year-end giving often happens quickly. A pause can make it more meaningful. Review how and where you give, and whether you’re giving still reflects what matters most to you. Going back to your RMD’s, if you are over 70.5, you can consider using a Qualified Charitable Distribution (QCD) from your IRA to fund those giving goals!

  4. Portfolio Alignment and Risk Exposure

    Markets have a way of feeling louder in December. Year-end is a natural time to rebalance, reassess concentration, and confirm that your portfolio still supports your long-term plan. Have you set aside enough funds in safe cash and short-term bonds to match several years’ worth of coming expenses? If you’re not sure, we should talk.

  5. Estate Planning and Beneficiary Reviews

    Time with family has a way of surfacing important questions. Review beneficiary designations, trustee and executor choices, and guardianship decisions if applicable. Your beneficiary designations on retirement accounts, insurance policies, etc. are legal agreements between you and the financial institution. This means that what ever is on file will trump what is stated in your will, so make sure they line up!

  6. Retirement Readiness Beyond the Numbers

    For those approaching retirement, year-end reflection often brings deeper questions. Financial readiness and emotional readiness don’t always arrive at the same time. Both deserve attention. I’ve seen the emotional transition into retirement impact clients much more significantly than the financial transition. Make sure you have spent time preparing yourself for both.  If you are only focused on what you are retiring away from and haven’t spent any time thinking about what you want to retire towards, then you’re not ready.

  7. Simplification and Organization

    Many people enter a new year craving less complexity. Consolidating accounts and reducing unnecessary financial clutter can create a surprising sense of relief. Everyone has a financial ‘junk drawer’, where things accumulate over the years, but have no rhyme or reason or coordination. Spend time emptying out the junk drawer to assess what you have and then be intentional about what you keep and what you get rid of.  Does it serve you anymore? 

  8. Family Support and Legacy Planning

    Supporting adult children or aging parents requires balance. These decisions are rarely about math alone – they’re about boundaries and stewardship. I have noticed that there is no magic formula or one-size-fits-all approach. Every family dynamic is different and requires a thoughtful, intentional approach to what is best for everyone.

Closing the Year Well

A thoughtful year-end review isn’t about checking boxes. It’s about asking:
Does our financial plan still serve the life we want to live?  If it doesn’t or you’re not sure, give us a call….we’re here to help.

Changes to charitable giving from OBBBA

Obviously, there were many changes to the tax code with the implementation of the One Big Beautiful Bill Act (OBBBA) earlier this summer.  No matter what your level of wealth, but especially for the ultra-high-net-worth, if you are charitably minded, you should pay attention to these changes to take full advantage of the tax code under the new bill.  Here’s what’s about to shift in charitable giving when OBBBA kicks in for the 2026 tax year, and how thoughtful donors can adapt to keep generosity impactful and tax-smart.

OBBBA was signed into law in July 2025 and includes several provisions that directly touch charitable deductions starting January 1, 2026. In short, the law changes who benefits, how much is deductible, and when timing really matters.1

What’s changing in 2026
  1. A new universal charitable deduction for non-itemizers:
    For the first time since the temporary CARES-era rules, non-itemizers will get a modest above-the-line deduction: up to $1,000 for single filers and $2,000 for married filing jointly for cash gifts to qualified charities. This creates a floor of benefit even if you don’t itemize.2
  2. A 35% cap on the tax benefit for top-bracket donors:
    This one gets wonky really quick…If you’re in the 37% marginal bracket, the value of your itemized charitable deduction will be capped at 35% beginning in 2026. Practically, a $100,000 gift produces a $35,000 income reduction instead of $37,000 under current rules. High earners should revisit multi-year giving plans with this cap in mind.3
  3. A new charitable deduction floor for individuals:
    Beginning in 2026, itemizing individuals can only deduct charitable gifts to the extent total annual giving exceeds 0.5% of their contribution base (generally AGI). Amounts below that floor aren’t deductible. The first 0.5% is basically throw-away contributions…no tax savings.  There are carryforward interactions and some relief for pre-2026 carryovers.4
  4. SALT cap dynamics can change the math of itemizing:
    OBBBA raises the state and local tax (SALT) deduction cap to $40,000 for 2025 and then increases it slightly each year through 2029 before snapping back to $10,000 in 2030. That higher cap in 2025 can push more households into itemizing for that year, which affects whether you should bunch charitable gifts into 2025 or stage them differently across 2026 and beyond.5
Strategy moves to consider now
  1. Bunch 2025 giving, then smooth 2026+:
    If you planned significant gifts in the next 12-24 months and you’re a high earner, consider accelerating into 2025 to avoid the 35% cap and the 0.5% floor that begin in 2026. Using a donor-advised fund lets you make the large, potentially pre-2026 contribution for tax purposes while pacing grants to charities over several years. This can also pair well with 2025’s higher SALT cap to maximize itemizing in one year.6
  2. For non-itemizers, plan to use the new universal deduction annually:
    Households that typically take the standard deduction should plan to give at least $1,000 ($2,000 MFJ) in cash each year to capture the new above-the-line benefit starting in 2026. Keep good receipts and ensure gifts go to qualified organizations. If your giving is sporadic, consider consolidating into a single calendar year to clear any administrative thresholds and simplify tracking.7
  3. Re-optimize appreciated asset gifting:
    Gifting highly appreciated securities still avoids capital gains tax and can be combined with a DAF to streamline execution. But because 2026 introduces a 0.5% floor for itemizers, coordinate the size and timing of appreciated stock gifts so that your total giving clears the floor and captures the full intended deduction. Large, fewer-and-farther-between gifts may be more efficient than many small ones post-2026.8
  4. Lean on QCDs for IRA owners age 70½+:
    QCDs remain a standout tool because they reduce taxable income directly rather than relying on itemized deductions, which helps regardless of floors or caps. If you’re charitably inclined and subject to RMDs, map out a multi-year QCD plan to satisfy some or all of your RMD while supporting charities.9
  5. Mind carryforwards and pre-2026 gifts:
    If you already have charitable deduction carryforwards, note that amounts carried into post-2025 years from gifts made before January 1, 2026 are not subject to the new 0.5% floor when used. Work with your advisor to prioritize using those carryforwards efficiently alongside any new giving.10
Bottom line

Generosity still works. What’s changing under OBBBA is the path to getting full tax value from your gifts. For 2025, ultra-high-net-worth families may benefit from front-loading into a DAF and harvesting appreciated positions before the new cap and floor arrive. For 2026 and beyond, standard-deduction households can finally claim a modest benefit each year, and retirees can keep leaning on QCDs to simplify taxes and amplify impact. The best plan is coordinated: tax bracket, SALT position, portfolio gains, and charitable goals aligned on a multi-year calendar.

Episode 55: From Conservation to Kilimanjaro – A Life of Meaningful Struggle with Tom Hicks


What does it really mean to suffer with purpose? In this episode of On Adventure, I sit down with conservationist and ultra-endurance athlete Tom Hicks – a man whose journey is as layered as the landscapes he climbs. From leading anti-poaching efforts across Africa and Asia with the David Shepherd Wildlife Foundation to tackling brutal challenges like Ironman races and high-altitude expeditions, Tom’s life is defined by intentional hardship, deep introspection, and relentless forward motion.

We dive into the heart of resilience, why discomfort can be transformative, and how a former rugby coach found meaning in the mountains. Tom also shares his connection with previous On Adventure guest Holly Budge and his plans to lead a new team to the summit of Kilimanjaro. Whether you’re an aspiring adventurer, a mindset junkie, or someone wrestling with self-doubt, this episode delivers a powerful reminder: growth is never linear, and purpose is often found in the pain.

Episode Highlights:

[3:00] – Fighting global wildlife crime: Tom’s work with the David Shepherd Wildlife Foundation
[8:00] – The brutal truth about poaching, organized crime, and the risks of field conservation
[12:00] – From being told he’d never succeed to becoming a conservation leader
[18:00] – Mentoring the next generation: the importance of presence and vulnerability
[24:00] – The “circuit breaker” mindset tool to quiet negative inner voices
[29:00] – What drives us to endure suffering in pursuit of meaning
[38:00] – A life-or-death lesson on Lenin Peak – and why good decision-making matters
[45:00] – Remembering Dixie Dansercoer and how it reshaped Tom’s risk tolerance
[54:00] – Emotional regulation in chaos: the power of calm leadership
[59:00] – Balancing ambition, burnout, and building a team for Kilimanjaro

Links & Resources:

Connect with Tom:
Have questions about conservation, endurance training, or joining the upcoming Kilimanjaro team? Reach out to Tom directly on LinkedIn or Instagram – he’s always happy to connect with fellow adventurers and curious minds.

Enjoyed this episode?
If Tom’s story sparked something in you, take a second to rate, follow, and review On Adventure. And be sure to follow us on Instagram, Facebook, and LinkedIn for behind-the-scenes content, updates, and inspiration from the trail. Plus – don’t miss new episode drops and bonus video content on our brand-new YouTube channel. Hit subscribe and join us for the next great adventure.

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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.

Episode 50: What My Son Taught Me About True Strength and Courage with Hudson Self


In this heartfelt episode of the On Adventure Podcast, I sit down with a younger Everyday Explorer, my son Hudson, for a conversation that redefines what adventure truly means. While we often explore tales of physical challenge and bold travel, this episode takes us on an inward journey—a story of persistence, identity, and the courage to live fully despite daily challenges. Hudson lives with Prader-Willi Syndrome (PWS), a rare genetic condition, and he brings us into his world with sincerity, wisdom, and humor.

We talk about what it’s like to grow up with PWS, the unique joys and struggles that come with it, and how it’s shaped Hudson’s perspective on life. He shares how adventure isn’t just found on mountaintops or across oceans—it’s in the relationships we build, the obstacles we face, and the love we share. From exploring WWII history in Europe to dreaming about the Great Wall of China, Hudson reminds us that the truest adventures are often the ones that take place in our own hearts and homes. This episode is not just a story of difference—it’s a story of belonging, resilience, and the extraordinary power of being seen and included.

⏱️ Timeline Summary

  • [0:00] – Meet Hudson Self and an introduction to Prader-Willi Syndrome Awareness Month

  • [1:00] – Hudson’s heartfelt presentation on living with PWS

  • [3:00] – Sharing his passions and personal joys beyond the diagnosis

  • [5:00] – The importance of inclusion and being treated like everyone else

  • [7:00] – Discussing the constant challenge of hunger with PWS

  • [9:00] – How PWS brought meaningful relationships and mentors into Hudson’s life

  • [10:00] – Visiting historical sites in Europe and the emotional impact of Normandy

  • [12:00] – Dreaming of a future adventure to the Great Wall of China

  • [13:00] – Favorite memories from a Jurassic-themed trip to Hawaii

🔗 Links & Resources

🎧 Closing Thoughts

This episode is a powerful reminder that adventure comes in many forms. If Hudson’s story moved you, inspired you, or made you think a little differently, please consider rating, following, and sharing the podcast from our YouTube (this is brand new!), Instagram and Facebook pages (this is new too!). And don’t forget to leave a review—we’d love to hear from you.

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Episode 48: Beautiful rebellion and choosing creativity over conformity with Thad Cockrell


In this episode of the On Adventure Podcast, I sit down with singer-songwriter and creative visionary Thad Cockrell for a conversation that took an unexpected but deeply inspiring turn. Thad opens up about his journey from wrestling mats and seminary halls to Nashville stages and international acclaim—all while forging a career based on creativity, authenticity, and saying a bold “yes” to uncertainty. We explore what it means to create from love rather than fear, and how rebellion, doubt, and wonder can be sacred tools on the creative path.

From Thad’s bold decision to sell his album for $100 directly to fans, to the moment Jimmy Fallon discovered his song in a hardware store, this conversation will challenge the way you think about success, security, and what it means to truly create without an agenda. Whether you’re an artist, entrepreneur, or just someone seeking a more intentional life, this episode is packed with insight and soul.

⏱️ Timeline Summary:

[1:45] – Thad on how creativity is a daily act of defeating doubt
[4:00] – Why you can’t conform and create at the same time
[9:55] – The childhood moment that sparked Thad’s unexpected path toward music
[14:20] – Discovering Neil Young and realizing, “This is what I’m supposed to do”
[24:30] – Moving to Nashville and the wild story of unexpected community support
[33:50] – Thad’s transformative shift from insecurity to creating from security
[44:00] – How he released his latest album for $100 and made more than 13 years on Spotify
[49:50] – What it means to create from the present moment with no need for external validation
[56:00] – Thad’s big dream: building a new music economy and going platinum without streaming

🔗 Links & Resources:

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