The Turnaround Decision

Summit fever has a financial cousin – and the cure is the same in both places. Decide what would make you turn around before you’re standing there.

There’s a phrase climbers use for the thing that gets people killed, and it isn’t weather or altitude or bad rope work. It’s summit fever – the pull that takes hold when the top is close and every reason to keep going suddenly sounds more convincing than it did at breakfast.

Stefan Gruber described it well in a recent On Adventure conversation. He’s turned back from the Grand Teton twice. What stayed with us wasn’t the turning around; it was how he thought about the times things worked out anyway. There’s a certain store of luck, he said, and it runs out eventually. Surviving a bad decision doesn’t make it a good one.

We’ve thought about that line a lot, because we watch a version of it play out at desks and kitchen tables all the time.

The Financial Version

Summit fever in a financial life doesn’t look dramatic. It looks like reasonableness, which is exactly what makes it hard to catch.

It’s the concentrated stock position that has done so well that selling any of it now feels like quitting early. It’s the business someone meant to step back from three years ago, still going, because this year is finally the year it all pays off. It’s the rental property that stopped making sense a while ago but has become part of how a person describes themselves. It’s the goal set at forty-five that nobody has re-examined at sixty, still quietly driving decisions.

In every case the pattern is identical. The commitment was sound when it was made. Conditions changed. And the reasons to keep going are being generated by the part of us that has already decided.

That’s the tell. When we notice ourselves reaching past the original reasons for new ones, something has usually shifted.

Why It’s Hard in the Moment

Standing a few hundred feet below a summit is the single worst place to evaluate whether you should be there.

You’re tired. You’ve spent real money and real time. Everyone around you has too. The thing you came for is right there, and the effort already sunk feels like an argument for continuing rather than what it actually is – gone either way, and irrelevant to the decision in front of you.

Financial decisions inherit all of it. Add in the fact that turning around usually means admitting the plan changed, which people hear as admitting the plan was wrong. It wasn’t. Conditions changed. Those aren’t the same thing, and conflating them is what keeps people on routes they’d never choose fresh.

Then there’s the quiet distortion Stefan named: if the last three times you pushed through it worked out, the lesson you absorb is pushing through works. The sample is too small and the stakes are too asymmetric for that to be a lesson at all.

Set the Criteria Before You’re Tired

Here’s the part climbers actually do, and the part most of us skip.

Serious parties set a turnaround time before they leave camp. Not a feeling – a time. If you aren’t at the summit by then, you go down, whatever the weather is doing and however good your legs feel. The whole point is that the decision gets made by the version of you that’s rested, unhurried, and not staring at the top.

The financial equivalent is the same move. Decide in advance what would change your mind, write it down, and let the calm version of yourself bind the tired one.

That might sound like:

  • “If this position passes a set share of our investable assets, we trim on a schedule – regardless of how it’s performing or what we think happens next.”
  • The business. “If I’m still working past a certain date, or if these specific conditions are met, we run a real conversation about transition – not a mental note, a meeting on the calendar.”
  • A property or venture. “If it hasn’t cleared this bar by this date, we sell. Not because it failed, but because that’s what we said.”
  • The plan itself. “We revisit the assumptions every year on a set date, including the ones we’re most attached to.”

The specifics belong to the family. The structure is what matters: a condition, a date, and an action, decided while nothing is on the line.

Turning Around Isn’t Failure

This is the piece worth saying plainly, because a lot of capable people carry the opposite belief.

Changing course is not the same as being wrong. Stefan will go back to the Grand Teton. The two attempts he walked away from didn’t cost him the mountain – they’re the reason he’s still available to climb it. Alex Potts, in another recent conversation, made the related point from the other direction: being fit enough to push harder isn’t the same as knowing whether you should. Experience is largely the accumulated ability to tell those apart.

The families we see handle change well aren’t the ones who never adjust. They’re the ones who built permission to adjust into the plan from the beginning, so that when the moment comes, it reads as judgment rather than defeat.

The summit will still be there. The point was never to reach it on this particular day. The point was to keep being someone who gets to go back.

If you’re carrying a decision like this right now – a position, a business, a goal you’ve outgrown but haven’t said so out loud – we’d be glad to sit down and think it through with you.

Ridgeline Wealth Advisors

This material is for general educational purposes and does not constitute investment, tax, or legal advice. It is not a recommendation of any particular strategy or security and does not account for any individual’s circumstances.

On Adventure: Lessons from the Edge

Two recent conversations from the On Adventure Podcast – and what they have to say about the lives the rest of us are building.

Every so often we like to step back from the individual episodes and notice the thread running between them. The two most recent conversations on the On Adventure Podcast came from very different places – a bike-shop classroom on the California coast and a rotating string of mountain towns out West – and yet they landed in almost exactly the same spot. Both are about choosing the harder, fuller life on purpose, rather than drifting toward comfort or putting it off for some vague day down the road.

That turns out to be a financial question as much as an adventuring one. So here are the two, and a bit of what stayed with us.

Episode 75: Hard Things Are Worth Doing with Justin Smith

Justin Smith teaches high school in Santa Cruz, where his classroom is a working bike shop – teenagers learning to fix bikes, build résumés, and solve real problems with their own hands. On his own time, he’s an ultra-endurance athlete who has ridden the 2,700-mile Tour Divide from Banff to the Mexican border in sixteen straight days, raced the Fiji Eco-Challenge, and lined up at the Ironman World Championships in Kona.

What we appreciated most was how ordinary he made all of it sound. Justin talks about the “pain cave” – the dark hours before sunrise on day two of a race, when the body starts asking what exactly you’re doing out here – not as something to conquer but as a room you learn to redecorate and settle into. Comfort, he says, is what gets sold to us. Hard things are what actually move the needle. The line he repeats to his students and his daughter has stuck with us: a ship is safe in its harbor, but that is not what ships were built for.

Listen to Episode 75 →

Episode 76: Do It While You Can with Stefan Gruber

Stefan Gruber grew up in Raleigh, studied engineering at Western Carolina, and today works a remote job for a technology company he’s been with for about six years. But the more interesting thing about Stefan is what the remote job makes possible. Where a lot of us build our lives around our work, Stefan has quietly done the reverse – he’s built his work around the life he actually wants to live.

For the last couple of years, that life has been a moving target, in the best sense. When his wife Sarah began travel nursing, the two of them packed a car and a trailer and started following her contracts – Bozeman, where they later got married in Glacier; Idaho; and now Colorado Springs, in the shadow of the Garden of the Gods. Almost everywhere they land, there’s climbing within twenty minutes of the front door. Stefan describes climbing the way Josh describes the trail: one of the rare activities where you’re so locked into the next move that everything else – work, stress, the noise – simply melts away. He’s an unusually good photographer, too, a habit that started when he found an old camera lens in his parents’ attic and went looking for the camera to match it.

He was refreshingly honest about the cost. Living on the move means no steady circle of friends – the hardest part, he admitted, of the whole adventure. But when Josh asked him to boil it all down to one lesson, Stefan didn’t hesitate: get out and do these things while you can. We only live once, we’re a little older every day, and the experiences, he said, end up meaning more than any car or house ever could.

That’s a sentence we think about a lot on the financial side of the desk. The only real value of money is in its use – spending it on what’s genuinely of value to you, whatever your version of that is. It’s easy to spend a whole career building bigger buckets for a someday that keeps receding, only to arrive less healthy, less able, or not at all. Stefan’s life is a working argument for the alternative: decide what matters, and go live some of it now.

Listen to Episode 76 →

What We Took From Both

Put the two side by side and the lesson from the edge is really one lesson. The worthwhile life rarely happens by default. It gets chosen – on purpose, against the pull of comfort, and without waiting for permission or for the perfect moment that never quite arrives.

That’s the heart of how we think about planning, too. A good plan isn’t about the number for its own sake. It’s about being able to do the hard, meaningful things on purpose, to stay present through the long stretches, and to spend a life – not just save for one. We’re grateful to guides like Justin and Stefan for the reminder.

If either of these resonate, they’re worth a full listen. And if you’d like to talk through what you want your own version of “do it while you can” to look like, we’re here and happy to help.

Ridgeline Wealth Advisors

Legacy Is Caught, Not Taught: Raising Kids Who Can Carry What You Build

There’s a line from a recent On Adventure conversation that we haven’t been able to shake. Talking about his own children, ultrarunner Aaron Saft said that legacy is something children catch rather than something we teach. He wasn’t talking about money – he was talking about the way his kids absorbed a love of the outdoors by watching, not by being lectured. But the more we sat with it, the more it felt like the truest thing anyone has said about passing on wealth.

Most families we work with have thought carefully about the mechanics of transferring assets – the wills, the trusts, the beneficiary designations. Far fewer have thought about the harder question underneath it: will the people who inherit this be ready to carry it? And that readiness, it turns out, is caught long before it’s ever formally taught.

The Quiet Curriculum

Children learn how money works in a household the same way they learn a first language – by immersion, years before anyone sits them down to explain it. They watch whether money is a source of tension or calm. They notice whether generosity is a habit or an afterthought. They pick up on whether work is something you resent or something you take pride in. By the time a family is ready to talk openly about the estate, the deeper lessons have usually already been absorbed, for better or worse.

This is good news and hard news at once. The good news is that you have far more influence than a single conversation could ever carry. The hard news is that you can’t outsource it to a document. A beautifully drafted trust can protect assets, but it cannot manufacture judgment, gratitude, or a sense of purpose in the person who receives them.

What Actually Gets Passed Down

When we ask families what they most hope to leave behind, almost no one leads with a dollar figure. They talk about work ethic. About generosity. About the sense that the family stands for something. The money is real and it matters – but it tends to be the vehicle, not the destination.

That reframing changes how a plan gets built. If the goal is simply to transfer the largest possible sum, the plan is an exercise in tax efficiency. If the goal is to transfer capacity – the values and the competence to steward what’s been built – then the plan has to include the people, not just the assets. That might mean bringing adult children into age-appropriate conversations earlier. It might mean letting them practice with real decisions while the stakes are still small. It might mean being honest about how the wealth was built, including the setbacks, so the next generation inherits the full story and not just the balance sheet.

Small, Repeated Signals

Because legacy is caught, the signals that matter most are usually small and repeated rather than grand and occasional. A family that gives together, even modestly, teaches generosity more effectively than a one-time gift ever could. A parent who talks openly about a financial mistake teaches resilience and honesty. A household where money is discussed calmly, without shame or secrecy, raises children who can do the same as adults.

None of this requires a fortune, and none of it happens on a deadline. It’s the accumulation of ordinary moments – the same way a hundred-mile race is really just one mile run a hundred times.

Where a Plan Fits

This is where the financial and the personal meet. The structures still matter enormously – thoughtful estate planning, clear documents, and a shared understanding of who does what and when can spare a family real pain down the road. But the structures work best when they sit on top of a family that has been quietly prepared to receive them. One without the other tends to disappoint.

If you’ve been thinking about what you want to pass on – and, just as importantly, to whom, and how ready they are – that’s a conversation worth having out loud. We’re here and happy to help you think it through.

This article is for general educational purposes and is not intended as legal, tax, or investment advice. Please consult your own advisors regarding your specific situation.

Ridgeline Wealth Advisors

The Owner’s Long Trail: Planning the Years Before You Sell

Ask a seasoned hiker about a big route and they’ll tell you the summit gets all the attention, but the descent is where people get into trouble. Ed Viesturs, the mountaineer, put it plainly: getting to the top is optional; getting down is mandatory. We think about that a lot when we sit with business owners, because selling or handing off a company is a lot like the descent. The years of climbing – building the thing, making payroll, growing it – get all the glory. The way down gets far less planning than it deserves, and it’s where the real risk lives.

For many owners, the business is the single largest asset they’ll ever hold, and often the least liquid. The transition from owning it to having sold it is one of the biggest financial and personal shifts a person can go through. It rewards the people who start early, and it tends to punish the ones who wait until a buyer is already at the table.

The Trail Starts Years Before the Sale

The most common regret we hear isn’t about price. It’s about timing – specifically, about how little runway an owner left themselves. The moves that most improve an eventual outcome tend to take years, not months: cleaning up the financials so the numbers tell a clear story, reducing the degree to which the business depends on the owner personally, building a management team that can run things without you in the room, and documenting the systems that live only in your head. A buyer pays more for a business that can thrive without its founder – and, not coincidentally, that same work makes the business easier and more enjoyable to run in the meantime.

Starting early also creates options. An owner with a five-year horizon can be patient, wait for the right buyer or structure, and walk away from a bad deal. An owner with a five-month horizon is at the mercy of whatever offer appears. Time, on this trail, is leverage.

Liquidity Is a Different Animal

There’s a particular disorientation that comes with turning an illiquid asset into a liquid one. For years, wealth has been tied up in something you could see, touch, and influence. After a sale, it becomes a number in an account – and suddenly the questions change entirely. How much is enough to support the life you want? How should proceeds be positioned when they arrive all at once, rather than earned gradually over time? What are the tax implications of the deal structure, and how do they ripple across the years that follow?

These aren’t questions to answer in the closing week. They’re far better handled in advance, when there’s still time to shape the structure of the sale itself rather than simply react to it. The decisions made before the transaction often matter more than the decisions made after.

The Question Nobody Puts on the Term Sheet

Then there’s the part that no valuation captures: who are you when the business is no longer yours? For many owners, the company isn’t just what they do – it’s a large part of who they are, the thing that organizes their days and their sense of contribution. We’ve watched financially successful sales leave people unexpectedly adrift, simply because no one planned for the identity transition alongside the financial one.

The owners who navigate this well tend to have thought ahead of time about what the next season is for. More time with family. A cause they want to pour into. A different kind of work, or the freedom to explore. The money is what makes those things possible, but it isn’t the thing itself – and knowing the difference ahead of time makes the descent far steadier.

Where We Come In

A good transition plan pulls all of these threads together: the operational work that makes a business more valuable and more sellable, the financial planning that turns a lump sum into lasting security, the tax and structural thinking that’s most powerful when it’s early, and the personal question of what comes next. None of it has to happen at once. But the sooner the trail is mapped, the more control you keep over how it ends.

If a transition is somewhere on your horizon – even a distant one – it’s worth starting the conversation now, while time is still on your side. We’re here and happy to help you think it through.

This article is for general educational purposes and is not intended as legal, tax, or investment advice. Please consult your own advisors regarding your specific situation.

Ridgeline Wealth Advisors

Episode 76: Summit Fever and Close Calls – Knowing When to Turn Back in the Mountains with Stefan Gruber


 

What happens when you build your work around the life you want to live?

In this episode of On Adventure, Josh talks with Stefan Gruber, a climber, photographer, traveler, and customer success professional at Levitate. Stefan shares how remote work and his wife Sarah’s career as a travel nurse have helped them create a life centered on movement, creativity, and outdoor adventure.

They discuss climbing, film photography, international travel, dangerous moments in the mountains, and the judgment required to turn around when conditions are not right. At the heart of the conversation is a simple message: meaningful experiences should not always be postponed.

In This Episode

  • Building a mobile life around remote work and travel nursing

  • Why climbing creates focus, presence, and flow

  • Traveling through the American West, Poland, and Nepal

  • The appeal of film photography and printed images

  • Balancing documentation with being present

  • Avalanche terrain, exposed climbing, and failed summit attempts

  • Summit fever, risk assessment, and the limits of luck

  • Future goals, including the Grand Teton and Colorado fourteeners

  • Why Stefan believes in doing things while you still can

Episode Chapters

00:00 – Colorado Springs and life on the move
Josh and Stefan discuss Colorado Springs, choosing temporary homes, and the possibility of eventually buying land in Colorado or Montana.

11:00 – Stefan’s career and lifestyle
Stefan explains how he moved from a long corporate commute into remote work and began traveling with Sarah during her nursing assignments.

17:30 – Climbing, travel, and flow
Stefan reflects on his Polish heritage, his early interest in travel, and the sense of complete focus he finds while climbing.

20:00 – Designing work around life
The conversation explores the freedom and tradeoffs of building a career that supports travel, adventure, and flexibility.

24:00 – Poland and international travel
Stefan describes Poland’s cities, mountains, coastline, affordability, and cultural growth, along with other memorable travel experiences.

36:30 – Photography and creative ambitions
Stefan explains how photography connects his travels and outdoor life. He also shares ideas for creating a travel channel with Sarah.

41:00 – Film, digital photography, and presence
They discuss the visual character of film, the value of printed photographs, and the tension between capturing an experience and fully living it.

51:00 – Risk, fear, and turning around
Stefan recounts dangerous moments involving avalanche terrain, exposed climbing, wildfire smoke, and two unsuccessful attempts on the Grand Teton.

57:00 – Summit fever and the limits of luck
The conversation turns to humility, decision-making, and why surviving a poor choice does not make it a good one.

1:04:00 – Survival psychology and photography advice
Stefan recommends Deep Survival by Laurence Gonzales and encourages new photographers to begin with whatever camera they can access.

1:11:00 – Favorite mountains and future goals
Stefan talks about the Tetons, Annapurna Base Camp, Denali, Everest, and his goals for the rest of 2026.

1:18:00 – Do it while you can
Stefan closes with his belief that health, time, and opportunity are uncertain, so meaningful goals should not always be saved for later.

Memorable Quotes

“Sometimes those limits find you.”

“There’s a certain store of luck, and it will run out eventually.”

“If it doesn’t happen today, it can happen another day.”

“Do it while you can.”

Key Takeaways

Build work around what matters.
Flexible work can create more room for travel, relationships, creativity, and meaningful experiences.

Turning around is not failure.
Good judgment sometimes means abandoning a climb or summit and returning under better conditions.

Luck is not a strategy.
A successful outcome does not automatically mean the decision behind it was wise.

Give photographs a life beyond the screen.
Printing images or shooting film can make photography feel more intentional and lasting.

Do not save everything for someday.
Adventure can be a major expedition or a small personal goal. The important step is beginning while the opportunity still exists.

Resources Mentioned

  • Deep Survival: Who Lives, Who Dies, and Why by Laurence Gonzales

  • Stefan’s Instagram page

About Stefan Gruber

Stefan Gruber is a climber, traveler, and photographer who works remotely for Levitate. He and his wife Sarah travel throughout the United States for her nursing assignments while pursuing hiking, climbing, skiing, photography, and international travel.

Keep Exploring

Subscribe to On Adventure in your podcast app and on YouTube for more conversations with people building meaningful lives through exploration, challenge, and curiosity.

Share this episode with someone who has been saving an important goal for “someday.”

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Episode 75: Hard Things Are Worth Doing with Justin Smith


Episode Description
What happens in the dark hours before sunrise on day two, when your body starts asking
what exactly you are doing out here?
 
Justin Smith teaches high school in Santa Cruz, California, where his classroom is a working 
bike shop. By day he runs a Career Tech Ed program through Project Bike Tech, teaching
teenagers to fix bikes, build resumes, and solve real problems with their own hands. On his own
time, he is an ultra-endurance athlete who has finished the 2,700-mile Tour Divide from Banff,
Canada to the Mexico border in 16 days straight, raced the Fiji Eco-Challenge with Team Curl,
competed at the Ironman World Championships in Kona, and returned three times to a 60-hour
swimrun across the Swedish archipelago.
 
In this conversation, Justin takes Josh inside the pain cave and the mental game of multi-day 
racing: the dark hours before sunrise on day two, the difference between the front country and
the back country, and why the body only truly comes alive on the second night. He explains how
a psychology degree and Outward Bound canoe trips led to a life built around adventure, why he
and his wife once lived in a tiny house they built on television, and how putting himself in hard
situations makes him a better dad, husband, and teacher.
 
They also talk about the people. From trail angels on the Pacific Crest Trail to a septic-truck 
driver in Southern California, Justin keeps returning to the connections that outlast the miles.
Most of all, this is a story about a simple idea he repeats to his students and his daughter: a ship
is safe in its harbor, but that is not what ships were built for, and the more you do hard things,
the more you realize hard things are worth doing.
 
Episode Highlights
• 00:00 Meet Justin Smith: high school teacher by day, ultra-endurance adventurer on
his own time
• 02:00 The bike shop classroom and the Project Bike Tech program in Santa Cruz
• 08:00 Building a tiny house on the TV show Tiny House Nation
• 14:00 The permission slip to not conform, and choosing the hard path on purpose
• 16:00 Comfort is what gets sold to us, but hard things are what move the needle
• 19:00 Meeting Roy Malone at the 2019 Fiji Eco-Challenge with Team Curl
• 20:00 The One Water swimrun across the Swedish archipelago, attempted three times
• 26:00 The Stagecoach 400 and sleeping on McDonald’s cardboard with no sleeping bag
• 31:00 Courtney Dauwalter’s pain cave, and learning to redecorate it instead of fighting it
• 38:00 Finishing the 2,700-mile Tour Divide in 16 days, from Banff to the Mexico border
• 43:00 The Pacific Crest Trail, meeting his wife, and hiking through grief in 2009
• 55:00 Orienteering, gut instinct, and trusting intuition when the map runs out
• 01:04:00 A ship is safe in its harbor, but that is not what ships are built for
• 01:12:00 The mantra: if you can’t get out of it, get into it, and find a way

About Justin Smith

Justin Smith is a high school Career Tech Ed teacher in Santa Cruz, California, where he leads a
bike shop program through Project Bike Tech, and a lifelong endurance athlete and adventurer.
A former NCAA swimmer, he has finished the Tour Divide, raced the Fiji Eco-Challenge and
multiple expedition-style adventure races, competed at the Ironman World Championships in
Kona, and thru-hiked the Pacific Crest Trail. He lives in Santa Cruz with his wife and daughter,
with whom he shares most of his adventures.

Connect with Justin Smith
• Facebook: www.facebook.com/smilingjustin
• Inspire Out: www.instagram.com/inspireout/

Connect with the On Adventure Podcast
Hosted by Josh Self, financial advisor and everyday explorer.
• Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms
• Follow on Instagram for short-form clips and behind-the-scenes content
• Connect on Facebook: On Adventure Podcast with Josh Self
• Connect on LinkedIn: Josh Self
• If this episode resonated with you, leave a review and share it with someone who needs
to hear it.

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On Adventure: What We Carry

Lessons from Gil Jackson and Aaron Saft

Every long walk is an exercise in deciding what matters enough to carry. Ounces add up over thousands of miles, and eventually you strip down to what is essential. In our two most recent On Adventure episodes, I sat down with a Cherokee language educator and an ultrarunning coach whose lives revolve around a version of that same question: out of everything you could hold onto, what is worth the weight?

Gil: Walking Home

Gil Jackson grew up in the Snowbird community of western North Carolina in the 1950s – no television, no car, one light bulb per room, and a tight-knit Cherokee community where everyone showed up when a neighbor needed help. When he left for college in Georgia, his mother laughed and said, “You’ll be back.” He was gone almost 40 years, then built a house 200 yards upstream from where he was born and poured himself into the work that now defines his days: keeping the Cherokee language alive.

Only about 130 fluent speakers remain, and they are losing roughly two and a half a month. Gil calls it the eleventh hour. He thru-hiked the Appalachian Trail in 2014 to experience some portion of what his ancestors endured on the Trail of Tears, and conceded the biggest difference: he got to come home. But what moved me most is what Gil does off the trail. He spends his days locating sacred Cherokee sites in the mountains and taking younger people to them, so the stories and routes are not lost. The elders who know where these places are can no longer reach them. The young people who can make the climb do not know they exist. Gil is the bridge.

Aaron: What Do You Need?

Aaron Saft has finished Hardrock, UTMB, Leadville, Western States, and the Bigfoot 200. But the moment from our conversation that will stay with me had nothing to do with a finish line. It was his description of what happens when you come across another runner sitting on a rock in the middle of a 100-miler. You do not ask, “How are you?” You can see how they are. You ask, “What do you need?” And then you give whatever you have. Aaron said it is not a decision people make in the moment. It is who the sport turns you into.

He pins an upside-down photo of his family to his quad so that when he looks down at mile 80, he sees his wife and kids looking back at him. His son now runs for the University of Portland. His daughter, a high school freshman, just competed at the state championships. When other parents ask how he got his kids into running, his answer is simple: he did not. He just showed them what was possible. He even rebranded his coaching business – from “MR Running Pains” to “Running is Life” – because the words we wrap around our work shape the experience. Training is 99 percent process and 1 percent celebration. If you cannot find joy in the process, you are missing the whole thing.

The Same Trail

Gil is preserving a language and the sacred geography of his people. Aaron is building runners who understand not just what to do but why. Both told me the point was never the miles. The miles were just the means of discovering what mattered enough to hold onto. Not every adventure happens on a trail. Some happen when you ask someone what they need and mean it, or when you pass along something that would disappear if you kept it to yourself.

Stay safe and stay on adventure.

— Josh

You can listen to the full conversations with Gil Jackson and Aaron Saft on the On Adventure podcast, available wherever you get your podcasts.

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.

Base Camp Thinking: What Mountaineers Know About Volatile Conditions

There’s a sentence Ed Viesturs likes to repeat, and we’ve been thinking about it a lot lately.

“Getting to the top is optional. Getting down is mandatory.”

Viesturs is one of the most accomplished high-altitude mountaineers in history – one of a handful of climbers to summit all fourteen of the world’s 8,000-meter peaks without supplemental oxygen. He’s said he didn’t make it home that many times by being brave at the wrong moments. He made it home by being disciplined at the right ones.

Markets aren’t mountains. But the principles people use to come home alive from volatile conditions translate surprisingly well to financial life planning. And in a stretch like this one – energy shocks, persistent inflation, consumer confidence at all-time lows – we keep returning to a few of those principles.

Base camp

No one summits straight from the road. The first thing you do is build a base camp – a stable, well-supplied position you can return to when conditions deteriorate. You sleep there. You eat there. You wait out storms there.

In a financial life, base camp is the cash reserve. It isn’t where you live – it’s what you fall back on when the weather turns. And the function it serves isn’t really about the dollar amount. It’s about giving you the freedom not to make decisions out of panic.

Households with an honest base camp don’t necessarily make different long-term decisions than households without one. But the experience of difficult conditions is fundamentally different. One is decision-making from a position of strength. The other is decision-making from a position of fear.

Acclimatize before you climb

Altitude doesn’t care how strong you are at sea level. The body has to be allowed to adapt to thinner air, in stages.

Building a financial life has a similar rhythm. Big decisions – a new house, a business move, an early retirement, a significant inheritance – work best when there’s time to acclimatize. To live with the implications. To stress-test how they feel. To see what assumptions hold and which don’t.

Most of the financial regrets we hear about aren’t bad ideas. They’re good ideas executed too quickly.

Pre-set turnaround thresholds

Climbers set turnaround times before they start the summit push. If you haven’t reached the summit by, say, 2 p.m., you turn around. Period. The decision is made in advance – in calm conditions, with clear thinking – precisely because at altitude, in bad weather, under pressure, the mind isn’t reliable.

A financial plan with pre-set thresholds works the same way. Rebalancing triggers. Cash buffer minimums. Withdrawal rate guardrails. Spending floors during retirement transitions. These aren’t constraints – they’re decisions made when your head was clear, so you don’t have to make them when your head isn’t.

The team you bring

No one solos K2 by accident. Every expedition has a team – sherpas, climbers with complementary skills, an extended network at lower altitudes. The team is part of the equipment.

In a financial life, the team is the people you’ve intentionally chosen to walk alongside you – the spouse you talk through decisions with, the CPA, the estate attorney, the advisor, the family members you trust. The point isn’t to outsource judgment. It’s to have other clear minds in the room when yours is tired.

One more thing

The mountains have a way of revealing what was already true. Volatile financial conditions do the same.

If your plan is built well, hard stretches are uncomfortable but not catastrophic. If it isn’t, hard stretches reveal what was missing – and they tend to do it at the worst possible moment.

We’d rather have those conversations now, in calm air, than at the top of the ridge.

When the Tank Costs More: Energy, Inflation and the Family Budget

Walk into almost any conversation with friends right now and the cost of things is bound to come up. The grocery bill. The fuel cost. The summer travel that suddenly feels more expensive than it did last year.

We want to make sense of what’s actually happening – without spin and without panic – and offer a calm way to think about the household budget through this stretch.

Where the pressure is coming from

A few things are converging.

Gas prices are up sharply. The U.S. national average for a gallon of regular sits around $4.48 in late May, an increase of nearly 50% since February. The driver is largely geopolitical – disruption to oil supply routes through the Strait of Hormuz, which historically handles roughly a fifth of the world’s seaborne oil.

Headline inflation is moderate but persistent. The Consumer Price Index for April came in at 3.8% year-over-year, up from 3.3% the month before. That doesn’t feel huge until you remember it’s stacked on top of several years of similar increases.

The cumulative effect is real. A common framing – a basket of goods that cost $100 before the pandemic now runs about $126. That’s where the “everything is more expensive” feeling comes from. It’s not your imagination.

Why oil ripples beyond the pump

Higher oil prices don’t only show up when you fill the tank – they show up indirectly in almost everything you buy. Nearly every product spends time on a truck. Shipping costs feed into grocery prices, into building materials, into the cost of a hotel room two states over. The pump price is the most visible piece of a broader effect.

That’s why the budget pressure right now isn’t only about gas. It’s about gas plus the things that gas touches.

The line we’d encourage you to draw

There’s a simple distinction worth making, and we find that families do better when they make it explicitly.

Essential – the things that have to be paid no matter what. Housing, utilities, basic food, insurance, transportation to work, medical.

Discretionary – everything else. Some of it is meaningful to you. Some of it has crept in through habit.

Both categories deserve respect. We’re not in the camp that says cut every latte. Discretionary spending is often where life happens. But knowing which line items are which gives you choices, and choices are what reduce anxiety in a stretch like this one.

Sticky vs. temporary

A second cut worth making – which price increases are temporary, and which are likely to stay with us for a while?

Gasoline is sticky in the sense that it stays elevated until the underlying supply story changes. We don’t know how long that takes.

Some household items are temporary – they spike for a season and ease back.

Some are structural. Housing, healthcare, insurance – these tend to grind higher over time regardless of headlines. They’re the line items that quietly do the most damage to a long-term budget, because they don’t make the news.

For most families, the leverage is in the structural line items. A modest, deliberate review of housing-related expenses, insurance, and recurring services often produces more breathing room than cutting variable costs.

A few starting places

Not advice for your specific situation – just a frame.

Re-price what you can. Insurance, internet, streaming, subscriptions – these are line items most households don’t revisit annually, and there’s often room.

Refresh the emergency cash number. The familiar “three to six months of essential expenses” rule still holds, but the dollar figure has moved. Your reserve from 2022 may now cover less ground than you think.

Be honest about discretionary creep – not to shame it, to see it. Choices are easier when you know what you’re choosing.

If you’d like to walk through any of this in the context of your own situation, that’s what we do. The numbers feel less heavy when there’s a structure around them.