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.
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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.

“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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Hosted by Josh Self, financial advisor and everyday explorer.

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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.

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


ON ADVENTURE PODCAST  |  EPISODE 69

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

 

   

   

Episode Description

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

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

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

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

 

Episode Highlights

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

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

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

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

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

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

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

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

•       34:00  Healthy ambition vs. ego-driven achievement

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

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

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

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

•       57:00  Nervous system training and calm under pressure

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

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

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

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

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

 

Connect with Madison Blagden

Instagram & YouTube: @madisonblagden

Website: madisonblagden.com

Substack: substack.com/@madisonblagden

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

 

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Hosted by Josh Self, financial advisor and everyday explorer.

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