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.

“Will We Be Okay?” The Question Beneath the Question

Of all the questions we’ve heard in this work over the years, the one that’s been coming up most often lately isn’t really a question – it’s a feeling. The words around it shift depending on who’s asking and what kind of week they’ve had.

“Will we be okay?”

Sometimes it sounds like a market question. Is the portfolio set up for this? Sometimes it sounds like a household question. If we have to absorb a few more shocks, how do we look? Most of the time, when we listen carefully, it’s neither. It’s a question about whether the plan can hold.

We want to talk about that question – because it deserves a real answer, not a market forecast.

What clients are really asking

When we sit with someone who’s worried, the surface question is almost never the deepest one. The surface might be should we cut back on travel this summer? The deeper question is does our life still have room in it for the things that matter to us, if conditions keep getting harder?

That’s not a market question. That’s a planning question. And it has a real answer.

Resilience isn’t a guess

A financial plan, built well, doesn’t depend on the next twelve months going a particular way. It’s designed to absorb the months we can’t predict. That’s the whole point.

The pieces that actually answer the “will we be okay” question aren’t headlines – they’re structural. A cash reserve sized to your real fixed expenses, not the version of your budget on a calm day. A clear picture of which expenses are truly fixed and which feel fixed because they’re habits. An understanding of which goals are non-negotiable and which are timing-flexible. A goal that can wait six or twelve months without doing damage is fundamentally different from one that can’t. And a relationship between your portfolio and your actual time horizons – money you need soon shouldn’t be at the mercy of money you don’t need for fifteen years.

When those pieces are in place, the answer to “will we be okay” is mostly already written. It’s not a prediction. It’s a structure.

What we’d say if you asked us today

We’d say what we always say – it depends on the plan you’ve already built, and we can walk through it together. We’d look at your fixed-expense floor. We’d look at where your goals have room to flex. We’d look at the cash reserve relative to today’s prices, not last year’s. And we’d revisit time horizons.

That conversation is rarely as scary as the one in your head.

A small word on the headlines

Consumer sentiment hit an all-time low in May – lower than during the 1970s oil crisis, lower than 2008, lower than the early days of the pandemic. That’s a fact worth knowing, mostly because it means two things at once. If you’re feeling unsettled, you’re not imagining things, and you’re not alone. And feelings are not forecasts. The economy will do what it does. Your plan can be ready for a wider range of outcomes than you might think.

If “will we be okay” has been a question on your mind, we’d love to sit with it. That’s what we’re here for.

Your Photos Are Part of Your Legacy – But Is Your Family Prepared?

Guest post by Teresa Cox: Simple ways to organize, preserve, and share your family’s memories – now and for the next generation

When most people think about leaving a legacy, they focus on financial assets – investments, property, estate plans.
But in my experience, families often aren’t prepared to pass on the most meaningful
assets: the photos, the stories, the family traditions, and the moments that capture a life
over time.
Today, photos are everywhere – on phones, computers, external drives, and across
multiple websites or cloud services. At the same time, many families have decades of older
memories – photo albums, printed photos, slides, and home videos – tucked away in closets
or attics, slowly deteriorating or becoming harder to access.
There’s rarely a single place where everything lives. And often, no one else knows how to
access it – or has a clear plan for how those memories will be organized, preserved, and
shared.

Most of the families I work with aren’t in crisis.

They’re simply at a stage of life where they’re starting to think more intentionally about the future – especially parents who have spent years documenting their children’s lives and want to make sure those memories are organized, protected, and easily shareable with the next generation.

3 Simple Ways to Begin Preserving Your Family’s Memories

1. Bring Your Photos Together

Over time, photos tend to get scattered across devices, platforms, and accounts.

It’s very common to have photos on your phone, older computers or hard drives, in cloud services like iCloud or Google Photos, and in printed albums or storage boxes.

Rather than leaving everything spread out, begin thinking about how to gradually bring your photos together into fewer, more centralized locations.

If your printed photos and older media are stored in multiple places around your home, consider consolidating them into one general area.

Labeling boxes can also be incredibly helpful – especially with timeframes like years or decades, if known. Even simple labels make it much easier to navigate your collection.

If you happen to know family connections for older or heritage photos – like which side of the family they came from or who is pictured – that information can be incredibly meaningful to future generations. It doesn’t have to be perfect – just capturing what you know is often more than enough.

2. Make Your Photos Accessible

Once your photos are more centralized, the next step is making sure they can be accessed when needed.

For digital photos, this may involve sharing passwords or using built-in legacy settings for your online accounts.

If you use an iPhone, Apple offers a Legacy Contact feature.
If you use Google services (Android), there’s a similar tool called Inactive Account Manager.

Accessibility also means that someone else could step in and understand what you have. Even simple organization and clear labeling can make a big difference.

Most people don’t realize how difficult it can be for someone else to piece all of this together without guidance – but a little bit of planning now can make things much easier later.

3. Share and Preserve What Matters Most

Once your photos are more organized and accessible, the next step is to begin sharing them intentionally.

This doesn’t have to be complicated or time-consuming. In fact, some of the most meaningful moments come from simply pulling out old photos or home videos and enjoying them with your children or grandchildren.

Many families have older memories – slides, printed photos, and home movies – that haven’t been viewed in years. Digitizing these items not only preserves them, but makes it possible to easily watch, share, and enjoy them again.

There’s something incredibly special about seeing old family videos come to life – hearing voices, watching personalities, and experiencing moments that might otherwise be forgotten.

You might also consider creating something simple but meaningful, like a small photo book that tells the story of your life or your family. It doesn’t require hundreds of photos – just a thoughtful collection that captures the moments and people who matter most.

The goal isn’t perfection. It’s making sure your memories can be experienced, shared, and enjoyed – both now and for years to come.

If this is something you’ve been meaning to get to “someday,” consider this your gentle nudge to take a small first step – whether that’s gathering your photos into one place, labeling a few boxes, or sharing a favorite memory with your family.

Many people don’t realize there are professionals who specialize in organizing and preserving photo collections – this is the kind of work I help families with every day. 

If you’d like guidance or support along the way – even just a starting point – I’m always happy to help.

Teresa Cox
Photo Concierge Services

photoconciergeservices.com

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:

 

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AI Will Not Replace a Great Advisor. It Will Almost Certainly Replace a Good One

And why some clients will need a human in the room more than ever. 

I want to say something that I think a lot of people in my industry are afraid to say out loud.

Artificial intelligence is going to replace a great many financial advisors over the next decade. Probably most of them. The advisors who run a tidy practice doing solid, competent work – gathering documents, building plans in commercial software, rebalancing portfolios on a quarterly schedule, screening for tax-loss harvesting opportunities, drafting client letters that sound like every other client letter – those advisors are in real trouble. Not because they are bad at their jobs. Most of them are quite good. They are in trouble because the things that make them good are the things AI can now do faster, cheaper, and at three in the morning.

I am not predicting this from a distance. I use AI every day in my own practice. Anyone in my industry who tells you the technology is overrated has not actually used it. It is not overrated. It is one of the most consequential tools to come into financial services in my career, and it is improving on a timescale that should make every advisor pay close attention.

So let me be clear about what I am claiming and what I am not. I am not claiming that the human advisor disappears. I am claiming that the bar for being worth what you cost is rising quickly and that the people who used to settle for a good advisor will, before long, get a better version of that good advisor for free, or close to it, from a chatbot. The gap that survives is between the great advisor and the AI. And great is harder to define than most of my colleagues like to admit.

What AI is genuinely good at – and what “good” advisors mostly do

If you sit down and list the actual tasks a competent advisor performs in a typical week, a sobering thing happens. Most of them are tasks AI either already does well or is about to. Pulling in a client’s documents and summarizing what is in them. Comparing two retirement scenarios. Calculating a Roth conversion. Drafting a quarterly letter. Researching a tax law change. Evaluating an annuity contract. Building a cash flow projection. Spotting a missed beneficiary designation.

None of this is glamorous work, but it is most of the work. And it is the work that, until very recently, justified a full time person doing it. That justification is eroding. Software that costs a client $30 a month can now do a credible first pass on most of these tasks, and within a few years it will do a near-final pass. The advisor who built a career on being the diligent middle layer between the client and the financial machinery is being replaced from underneath by a tool that does the diligent middle layer for free.

That is the bad news. Now the good news, which is also the more interesting news.

The clients AI cannot serve well

There is a category of client for whom AI will never fully be enough, and the reason has nothing to do with technology. It has to do with the structure of the problems they are trying to solve. In my experience, three characteristics tend to define this group. Many of the people I work with fit these characteristics. The clients who need a great advisor likely have all three.

First, complicated financial situations. I am not talking about a household with a 401(k), a Roth IRA, and a mortgage. AI handles that beautifully. I am talking about the business owner whose personal balance sheet is wound around an operating company, a holding LLC, a real estate entity, and a buy-sell agreement that has not been updated since the partner left. I am talking about the family that has wealth flowing across two generations, with trusts that were drafted in different decades by different attorneys with different assumptions. I am talking about the executive whose compensation includes restricted stock, performance shares, deferred comp, and a non-qualified plan that interacts with their cash flow in ways that change every year. AI can produce a remarkably good overview of any one of these pieces. Where it struggles is in the connective tissue, the place where the entity structure, the estate plan, the tax exposure, the family dynamics (always the gasoline on the fire!), and the operating reality of a closely held business all touch each other. That is where decisions actually live, and that is where the analysis is messy enough, and the data is incomplete enough, that you need a human who has seen this kind of mess before.

Second, a high regularity of consequential decisions. Some clients live a financial life with very few decision points. They save into their plan, they hold a diversified portfolio, they rebalance on a schedule, they retire on a date, and most of the work is just steady execution. They benefit enormously from a sound plan and a low-cost portfolio, and frankly, AI can carry a lot of that load. But other clients face a steady drumbeat of real decisions. Should I take the buyout offer or hold out for a better one? Do I exercise the options now or wait? Should we sell the second home or keep it? Do we lend to our son’s startup or write a check we cannot ask back for? Do I move the trust to a different state? Do I take the partnership stake? Do I retire in eighteen months or push it three more years? When decisions of this kind arrive every few weeks rather than every few years, you do not need a tool. You need a thinking partner, someone who knows your situation cold, who you trust, who you can call on a Tuesday afternoon and say, here is what I am turning over in my head, what am I missing? That kind of relationship is not something a chat window provides, no matter how clever the chat window gets.

Third, high consequences and costs attached to those decisions. A wrong move on a $40,000 401(k) contribution is forgivable. A wrong move on a $40 million liquidity event is not. A misread on the timing of a Roth conversion can cost a few thousand dollars; a misread on the structure of a business sale can cost seven figures and a strained relationship with a sibling. When the dollar amounts get large enough, or when the decisions become irreversible enough, the value of being right goes up, and the value of being wrong goes up faster. Clients in this position are not paying for information. They are paying for judgment under pressure, and they are paying for someone to share the weight of the decision with them. That is fundamentally a human service. It always has been. AI does not change it. If anything, AI raises the stakes, because the people on the other side of these transactions…the buyer, the IRS, the opposing trustee, the estate attorney…are using AI too, and the playing field at the high end is getting more sophisticated, not less.

What “great” actually means now

I have been thinking a lot about what separates the advisors who will thrive in the next ten years from the ones who will not, and a lot about the clients who will need them. It is not credentials. It is not technical knowledge.  AI is a great equalizer on technical knowledge, and the playing field there is collapsing fast. There is no longer a scarcity premium added to knowledge.  The advisors who will thrive are the ones who do the work AI cannot do, and that work has a specific shape.

It is the work of being a thinking partner before a decision, not just a report generator after one. It is the work of pushing back when a client wants to do something you believe will hurt them, and doing it in a way they can hear. It is the work of holding a conversation across years, remembering what the client said three Christmases ago about their daughter, and connecting it to what is being decided this Tuesday. It is the work of judgment in places where the data is incomplete, the stakes are real, and the answer is not in any model. It is, in a word, presence.  The kind of presence that does not scale, cannot be automated, and is exactly the thing that the right kind of client will pay for as long as I am alive to provide it.

If you are a client of mine reading this, I want you to know I take this seriously. I am using every AI tool I can get my hands on, not to replace what I do for you, but to free up more of my time and attention for the part of the job that actually matters when your number is called. The diligent middle work…the research, the modeling, the document review, the first drafts…should be done faster and cheaper every year. That is good for you. The real work, the conversation that happens when something hard is on the table and you need someone in the room with you, is exactly where I want to be spending more of my time, not less.

And if you are reading this and wondering whether you have the kind of financial life that justifies a great advisor – whether the complexity, the decision velocity, and the stakes really warrant the relationship – that is a fair question to ask. For some people, the honest answer is no. A good chatbot, a target-date fund, and a disciplined savings habit will get them where they are going. For others, the answer is firmly yes, and the cost of being wrong about it is too high to leave to a tool that, however brilliant, has no skin in your game.

Knowing the difference is itself a financial decision. And it might be the most important one you make this year.

 

On Adventure: Lessons from the Edge

Two Walks Off the Well-Marked Path

What a 10,000-mile hiker and a credit card points cosultant have in common – and what it means for the rest of us.

If you had told me, when I started the On Adventure podcast, that two of my favorite recent conversations would be with a long-distance hiker who walked the equivalent of more than four cross-country trips in a single calendar year and a Midwestern dad who built a thriving business around airline points, I would have raised an eyebrow. On paper, they have almost nothing in common. But spend an hour with each of them and you start to hear the same note ringing underneath the very different music.

Madison Blagden and Colin Stroud both did something that scared them. They both stepped off a well-marked path. And they both came back changed – not because of the mileage or the revenue, but because of what those experiences taught them about who they actually are when the safety rails come off. I think there is a lot in their stories that the everyday explorer – and frankly, the everyday investor – can put to work this week.

Madison: Walking 10,000 Miles, Planning Almost None of It

Madison Blagden spent last year on her feet. Through-hiking the Appalachian Trail, the Pacific Crest Trail, and the Continental Divide Trail in a single calendar year is itself an audacious goal – only a handful of people have ever done it. Madison didn’t stop there. She set her bar at over 10,000 miles, walking from Florida to Newfoundland and weaving the three big trails together into a feat that no woman had previously completed. She finished. She also raised the women’s record by a couple thousand miles in the process.

What surprised me most, though, was not the scale of the accomplishment. It was her relationship to planning. Here is someone who built her year around weather windows, snowpack, and resupply logistics – and her advice to anyone considering something hard was, in her words, plan as little as you have to. Whatever you think it will cost, double it and save that much. Then go.

Her reasoning is worth sitting with. So many things will happen that you cannot predict, she said, that the energy you spend trying to control them is energy you will need later for the things you actually have to face. The hikers who do best on a long trail are the ones who can pivot – who do not get emotionally locked into a schedule or a route. The ones who white-knuckle a plan tend to suffer more, finish ragged, or quit. Madison described last year’s mid-season injury as the moment she finally let go of the last bits of control she was still holding. From that point forward, every setback, every weather change, every wrench in the gears became something she just folded into the trip.

If you have ever opened a financial plan and felt the urge to nail every variable to the wall – the exact return, the exact retirement date, the exact tax outcome – Madison’s advice translates directly. A good plan is a flexible one. Whatever you think things will cost, plan for more. Then walk.

Colin: The Quiet Quit That Wasn’t Quiet at All

Colin Stroud’s adventure looks nothing like Madison’s, and that is the point. A few years ago, Colin was sitting in an insurance brokerage in Indiana, watching his wife and two of his brothers-in-law build real audiences on the internet. He was good at his job, but it bored him, and he had been passed over for a promotion he wanted. Around the same time, he had stumbled into the world of credit card points and travel rewards as a way to take his young family on a vacation they otherwise could not afford. He started writing about it on LinkedIn, mostly to see if anyone would care.

They cared. The Washington Post quoted him after one of his earliest posts. People started asking if he would get on the phone for an hour to walk through their points strategy. He charged forty-five dollars. Then a little more. Then more. About fifteen months later, he resigned from his W-2 job and went all in on a one-person consulting practice he calls Go Somewhere. Today he is running consulting calls, building a private community for business owners, and partnering with another points expert to scale a white-glove travel-research service. He does not yet know how big it gets. He does know that nothing in his prior career – the standardized tests, the promotions he did not get, the jobs he was not great at – comes close to what he is feeling right now.

What hooked me in our conversation was Colin’s description of why entrepreneurship lit him up the way it did. It was not the income, though the income matters. It was the daily measurement. Every day he gets feedback on whether he is where he thought he was. Every post, every sales call, every new client tells him something true about his actual capability. He used the word ikigai – that overlap of what you love, what you are good at, and what people will pay you for – and said for the first time in his life, every part of him feels activated at once.

Colin also said something I want every entrepreneur and every parent listening to this to take seriously. He has experienced more dopamine, more excitement, more flow from building this business than from any travel destination he has ever been to. And his family life, while quieter, is the most meaningful thing he does. Travel, in other words, is not the adventure. The adventure is the life he is building around the people he loves. The travel is just a way to bring them with him.

What the Everyday Explorer Can Take Home

Different as they are, Madison and Colin pointed me toward the same three lessons, and I think they apply just as much to the way we manage money and build a life as they do to long trails and online businesses.

The first is that uncertainty is not the enemy. It is the proof that you are doing something real. Madison built her year around variables she could not control. Colin walked away from a paycheck without knowing what would replace it. In both cases, the willingness to live with not-knowing was what unlocked the experience. We tend to treat uncertainty in our financial lives as a thing to be eliminated. It cannot be. The better question is whether your plan can absorb a surprise without breaking – and whether you have left yourself enough margin, financially and emotionally, to keep walking when the weather turns.

The second is that the people who do the most talk about it the least. Madison observed that on trail, the loudest people in the room have usually done the least. The ones with the real accolades sit quietly in the corner. I have seen the same dynamic in money. The truly wealthy people I have worked with rarely tell you anything about it. The ones loudly counting their wins are usually the ones with the most to prove. If you are doing the work, the work will speak. You do not have to.

The third – and this is the one that has stuck with me longest – is that the cliff edge is the whole point. When I asked Madison what she would say to someone standing on the edge of a decision that scared them, her answer was just, do it. Not because every adventure works out. Some do not. But because nobody she has met in the trail community regrets going and finding out it was not for them. The ones with regret are the ones who stayed home. Colin’s version of the same line was that everyone has a hundred-thousand-dollar idea sitting in their Google Drive, and most people will never act on it.

You probably have a version of this too. A trip you have been talking about for five years. A career move you keep telling yourself you will make next year. A conversation you have been avoiding. A plan you have been afraid to commit to on paper. The everyday explorer is the person who, knowing they cannot control the outcome, takes the next step anyway – and trusts that whatever shows up next, they will figure out how to keep walking.

That, more than anything else, is what I keep hearing from the guests on this podcast. And it is the kind of mindset I want for the people I am lucky enough to work with at Ridgeline. A flexible plan. A long view. The honesty to admit you cannot know everything in advance. And the willingness to walk into the unknown anyway, because the alternative – staying parked at the trailhead, indefinitely – is not actually safer. It is just stiller.

On Adventure: Lessons from the Edge

What Hurricane Helene Taught a Free Solo Climber About the Life You’re Already Living

Most of us will never free solo a 3,000-foot cliff on the Napali Coast or spend a night alone in the Appalachian wilderness with nothing but a pair of shorts. But Robbie Lenfestey — wilderness survival instructor, ecologist, and founder of Mandala Springs retreat center — would argue that every one of us is already standing on a ledge of our own. The question is whether we’ve trained our nervous system to meet the moment.

In his return to the On Adventure podcast, Robbie shared what happened when Hurricane Helene tore through his corner of the North Carolina mountains in the fall of 2024 — and how a lifetime of deliberately pushing his edges prepared him for the worst night of his life. Alone on his tractor in the pelting darkness, digging channels to divert floodwater from his structures, he felt massive boulders rolling in the creek bed and heard entire mountainsides give way in explosive cracks above him. Landslides were happening on every side. There was nowhere to go. And yet something inside him remained still.

That stillness, Robbie explains, is flow state — the same theta brainwave pattern found in master meditators and elite athletes. He first discovered it as a young man doing things most people would call reckless: free soloing without ropes, walking into the forest at night to navigate by sound and feel alone. What he learned is that when the stakes are absolute, the mind quiets itself. Thought drops away, and all that remains is the next move. Over decades, he turned what was once a byproduct of extreme risk into a skill he can access at will.

What the Everyday Explorer Can Learn

So what can the Everyday Explorer take from someone who has mastered the extreme?

Start with the Breath

Robbie points to one of the simplest and most underused tools available to any human being: conscious breathing with an emphasis on the exhale. Inhaling activates the sympathetic nervous system — the fight-or-flight accelerator. Exhaling engages the parasympathetic system, the body’s built-in brake. Simply slowing down and lengthening your exhale in a tense moment can shift your entire physiology. It’s kindergarten-level entry into something profound, and it works whether you’re standing on a cliff or sitting in a difficult conversation.

Build Emotional Intelligence Like a Muscle

Drawing on Internal Family Systems therapy, Robbie described the practice of stepping back from a triggered emotion rather than being consumed by it — creating enough separation to ask the feeling where it started. That flash of anger when your partner says something pointed? It probably has nothing to do with what was said and everything to do with a protective pattern wired in childhood. Working through those patterns doesn’t bury the emotion. It dissolves the hook so the emotion no longer hijacks the moment.

Protect Your Attention

In a world engineered to capture and commoditize human attention, Robbie sees reclaiming it as a quiet act of rebellion. Walking in the woods without a phone, practicing peripheral vision, engaging the senses in unfamiliar ways — these aren’t esoteric exercises. They expand the attentional capacity that makes flow state, presence, and deeper experience possible in ordinary life.

The Grief That Waited

Perhaps the most striking insight from the conversation is what happened six months after Helene, when a neighbor led a bonfire gathering and asked everyone to name what they had lost. Robbie — the man who had held everyone together through weeks of crisis — sat down on the ground and wept. The grief had been there all along, waiting for a safe moment to surface. Mastering the extreme doesn’t mean bypassing the human experience. It means developing the tools to move through it fully, on your own terms, when the time is right.

The real frontier, Robbie suggests, isn’t a cliff face or a hurricane. It’s the edge of what we’ve habitually come to believe is possible — and the willingness to step beyond it.

Four Common Money Questions, Answered in Plain English

At Ridgeline Wealth Advisors, we believe financial literacy should feel practical, not intimidating. Here are four common questions we hear, with straightforward answers to help you think clearly about cash, investing, and market headlines.

Is investing in gold or other metals worth it?

Maybe for some people as a small, specialized part of a broader plan—but not as a guaranteed shield against inflation or market stress.  Gold has had significant price swings and has not reliably tracked inflation over long periods. If someone is focused specifically on inflation protection, Treasury Inflation-Protected Securities, or TIPS, have historically been a more direct inflation-linked tool, though no approach is perfect.

Possible benefits of precious metals can include:

  • Diversification in some environments
  • A tangible asset some people find psychologically reassuring
  • Potential value during certain inflationary or crisis periods

But there are also tradeoffs:

  • Prices can be volatile
  • Gold is not an investment…there are no future expected cash flows so no way to discount cash flow to determine a fair present value share price.  It is pure speculation.
  • Metals generally do not pay interest or dividends
  • Physical ownership can involve storage, insurance, and transaction costs
  • Tax treatment can differ from stocks and mutual funds

At a high level, physical gold and many precious metals are generally taxed when sold. Some structures may be treated as collectibles, which can mean different tax treatment than stocks. Some gold ETFs may also be taxed differently depending on how they hold the metal. In some states, sales tax may apply when buying physical metals.

In short, precious metals may have a role for some investors, but they are not a one-size-fits-all solution.

What does it really mean when the stock market drops, and when should we worry?

A market drop usually means investors are willing to pay less for many publicly traded companies than they were willing to pay before. That can feel unsettling, but downturns are a normal part of investing and the ‘price of admission’ to get higher expected returns in the long-term. Short-term volatility by itself is usually not a reason to abandon a long-term plan. The better question is often not, “What is the headline today?” but, “Have my own needs changed?”

The S&P 500 is a widely followed index of 500 large U.S. companies, so it is often used as a quick snapshot of how large U.S. stocks are doing. But indexes are not available for direct investment and do not reflect actual portfolio expenses.

Market declines can be uncomfortable, but they are also part of how long-term investing works. For many people, the more important issue is whether their own liquidity needs, time horizon, or risk tolerance have changed—not whether markets are simply having a difficult week.

Is it ever okay to keep cash in a shoebox or under your mattress?

A small amount of physical cash for convenience is a personal choice. But for reserve cash, source materials support prioritizing liquid, interest-earning, FDIC-eligible options over storing large amounts at home.  An emergency fund, or protective reserve, exists to help cover unexpected expenses and near-term spending needs without forcing you to sell long-term investments at the wrong time. The exact amount depends on your situation, but the core idea is simple: keep enough cash accessible for real-life surprises.

There is also a tax angle. Money in a savings account may earn taxable interest. Cash at home does not generate taxable interest because it earns nothing. But that comes with tradeoffs: cash at home is easier to lose, steal, or destroy, and it can be harder to document.

How does a CD work?

A certificate of deposit, or CD, is a bank savings product. You agree to leave money at the bank for a set term—such as 3 months, 1 year, or 5 years—and in exchange the bank pays a fixed interest rate. If you take the money out early, the bank will usually charge an early withdrawal penalty. When the CD reaches maturity, you can typically:

  • Withdraw the money
  • Move it into a new CD
  • Let it renew automatically, depending on the bank’s terms

At a high level, CD interest is generally taxable as ordinary income in the year it is credited or made available, even if you do not withdraw it. Banks typically report that interest on Form 1099-INT. Early withdrawal penalties may be deductible on a federal return, and state tax treatment can vary.

Closing Thought

Good financial decisions often start with matching the tool to the goal: cash for short-term needs, savings vehicles for reserves, and long-term investments for long-term objectives.  Most financial options are not bad tools to have in the toolbox as long as you know when it’s appropriate to use which tool.  Don’t let me find you trying to fix your mirror with a hammer…it won’t go well.  Neither will using the incorrect financial tool.

Q2 Letter to Clients

Where Things Stand

The first quarter of 2026 tested the patience of even the most disciplined investors. A combination of rising energy prices, geopolitical uncertainty, and a pullback in the large technology companies that led markets higher in recent years produced the worst quarterly performance for U.S. stocks since 2022. The S&P 500 declined approximately 4.6% for the quarter, the Nasdaq Composite fell roughly 7.1%, and the Dow Jones Industrial Average dropped in similar fashion. Meanwhile, the Russell 2000 index of smaller domestic companies held up notably better, finishing the quarter roughly flat. At the sector level, energy was the clear standout, posting its best quarterly gain on record as oil prices surged. These numbers are a useful reminder that diversification across asset classes, market capitalizations, and sectors continues to serve long-term investors well, even when individual parts of the market come under pressure.  It is very difficult to capture the value in diversification if you are holding individual stocks.

Much of this quarter’s volatility was driven by the conflict in the Middle East. The war in Iran and disruption around the Strait of Hormuz sent oil prices sharply higher, contributing to renewed inflation concerns and creating uncertainty across global markets. Brent crude posted its largest monthly percentage increase on record during March, and the ripple effects were felt well beyond the energy sector. As the quarter drew to a close, reports emerged suggesting that both U.S. and Iranian leadership may be open to ending hostilities, and markets rallied meaningfully on the final trading day of March. Whether that optimism translates into a lasting resolution remains to be seen. No one knows with confidence how current geopolitical conflicts or trade disruptions will ultimately play out, and reacting emotionally to that uncertainty is rarely helpful for long-term investors. For a useful overview of how Q1 unfolded across the major indexes, Reuters published a helpful summary via U.S. News & World Report.

Why Staying the Course Matters

Markets are forward-looking. By the time a recession, policy shift, or geopolitical event becomes front-page news, much of that information is often already reflected in prices. This is one reason why making portfolio changes in response to headlines can be counterproductive. A diversified portfolio is designed with uncertainty in mind. Consider that the S&P 500 has now posted a negative first quarter in back-to-back years, yet history shows that a down first quarter has been followed by a positive full year far more often than not. Markets have historically moved through wars, recessions, political change, and crises while continuing to reward disciplined long-term investors over time. There is no proven way to consistently time the market, and missing even brief periods of strong performance can meaningfully affect long-term outcomes. For investors interested in the historical context around negative first quarters and what tends to follow, Motley Fool published a thoughtful analysis at fool.com.

For that reason, we will not adjust portfolios in response to market whims or short-term movements. Short-term declines do not necessarily lead to down years, and many years with significant intrayear drops have still finished with positive calendar-year returns. In fact, one of the most notable themes of Q1 was the divergence in performance across different parts of the market. While large-cap technology names bore the brunt of the selling, small-cap domestic companies in the Russell 2000 were largely insulated from the geopolitical disruption, and the energy sector delivered exceptional returns. This kind of rotation is exactly what a well-diversified portfolio is built to capture. Staying invested and focused on the long term helps ensure you are in position to benefit when markets recover and leadership shifts.

Planning Opportunities

Market turmoil can still serve a useful purpose if it prompts a review of the things that actually matter. Short-term market moves are not, by themselves, a reason to change a well-constructed long-term allocation. But when your life changes, it may be appropriate to revisit your financial plan. Retirement timing, spending needs, charitable goals, liquidity needs, estate intentions, and tolerance for risk can all justify thoughtful updates. If your plan still aligns with your values, goals, and time horizon, staying the course is often the most appropriate response.

Periods like this can also create planning opportunities worth evaluating in the context of your broader strategy. Depending on your circumstances, volatility may create room for disciplined rebalancing, tax-loss harvesting, cash-flow review, or future Roth conversion planning.

What Your Plan Is Really For

Most importantly, we would encourage you to focus on living your great life right now. Your financial plan is not meant to compete with your life; it is meant to support it. Even in periods of turmoil, your plan should prepare for important transitions, care for the people you love, and continue making progress toward the life you want to live. That may mean spending meaningful time with family, protecting time for travel or rest, supporting a cause that matters to you, or simply being more present in your day-to-day life. The headlines matter, but they are not the whole story. A well-built plan allows you to keep perspective and remember what your money is for in the first place.

As always, we are here to help you think through decisions in the context of your long-term plan rather than the emotion of the moment. If anything in your life has changed, or if you would like to revisit your plan together, please reach out.