After I Was Dropped on a Mountain in Alaska, I Realized What's Missing From My Retirement Plan
A birthday skiing trip revealed a scary truth about planning for retirement — we're so focused on making sure we don't run out of money, we don't think about running out of friends, even though the data says it matters just as much.
The helicopter approached low and loud, rotor wash blasting snow in every direction. The pilot set us down on a spine of untouched powder at 7,129 feet atop the Chugach Range, Alaska.
The door slid open. Cold air hit our faces. The guide unloaded our skis, the helicopter retreated, and the silence that replaced it was the kind you find only in places that humans rarely touch.
Above us, the sky was bright and blue. The temperature crisp. The winds calm. Snow conditions "dialed." Fresh powder in every direction. And around me, grown men were grinning like little kids, because they were about to drop into some of the best skiing on the planet.
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I'll say this plainly. For those who ski, this is as good as it gets. A bluebird day, a competent pilot, a knowledgeable guide, a group of friends you trust, all in an Alaskan mountain range.
There isn't much in life that tops it. It's pure joy, pure presence, pure shared experience. The kind of spectacular day you remember for the rest of your life.
That's what my friend had built for us: He was turning 60, and he'd invited the people he shares meaningful relationships with to celebrate. Not a dinner. Not a golf outing. The whole thing: Mountains, helicopters and powder, in Alaska, with people he cares about.
There were 24 of us. Not all of us knew one another. Some were old friends. Some were meeting for the first time. But there was a core group from Aspen who had known one another for decades. Most of them had moved there as young adults and, over time, built their lives together in the same place.
What I saw over the next few days tipped the scales on my views of aging.
What I saw
After each full day of epic heli-skiing, we gathered in the lodge. Everyone was tired in the best possible way. Legs burning. Faces wind-burned. All glowing with the particular kind of glow you get after doing something hard together and coming out successfully on the other side.
At dinner, stories celebrating the birthday man would start the way they always do. One friend stood up, drink in hand, and told a story from years ago. Then another. And another.
The stories were funny. Outrageous. Sometimes unbelievable. But the content wasn't what made them remarkable. It was the way they landed.
There was a continuity I don't often see. Nobody was performing. Nobody was trying to impress. Nobody was competing for the room. They listened to one another. They built on one another's stories. They laughed fully.
And underneath it all was something you rarely see among men: Real emotion. Not forced. Not performative. Just honest. Based on shared experience.
Part of that was the day we'd just had together. Men who have just shared a peak experience are different men. They're open. They're grateful. They're fully present. The walls come down on their own.
But the deeper current running through the room had nothing to do with a single day. These were men talking about their lives. Coming of age together, building careers, raising families and experiencing life together. And still showing up for one another decades later.
That's rare. And the questions I couldn't stop asking myself were: Why here? Why them?
The friendship problem hiding in plain sight
American men have a friendship problem, and it gets worse with age. And the ability for men to maintain connections as they age is a larger problem than most recognize.
In 1990, 55% of American men reported having six or more close friends. Today that number is 27%. The percentage of men with zero close friends has jumped fivefold, from 3% to 15%.
The decline cuts across all age groups, but it hits hardest in the years leading up to and after retirement.
AARP's 2025 study found that 40% of Americans age 45 and older are lonely, up from 35% in 2018. And here's the data point most retirement planners aren't tracking: men report higher loneliness than women, 42% versus 37%. After 60, isolation deepens fast.
A Pew analysis found that Americans 60 and older spend roughly seven hours a day alone, or more than half their waking hours. For those living on their own, alone time climbs to 10 hours a day.
Researchers call it a "friendship recession." I'd call it something more direct: A "friendship depression," because the health consequences of isolation are staggering.
In 2023, the U.S. Surgeon General declared loneliness a public health epidemic, warning that social disconnection carries mortality risk comparable to smoking 15 cigarettes a day.
Harvard's 85-year Study of Adult Development reached one conclusion: relationships are the strongest predictor of health and longevity. Not wealth. Not genetics. Not IQ. Relationships.
And here's where it becomes a financial conversation. AARP found that social isolation among older adults costs Medicare an estimated $6.7 billion in additional spending every year. Isolated older people face 31% higher mortality risk. And a quarter of Americans over 65 are considered socially isolated right now.
We plan obsessively for our financial retirement with concerns about market risk, sequence-of-return risk, inflation risk and healthcare risk. Social connection does not appear in any of these models. And yet its failure can quietly undermine everything these models are designed to protect.
I thought it was intentional — I was wrong
So, "Why here? Why them?" My first instinct was to credit the birthday man. He'd built these relationships. He'd kept them alive across decades. He'd organized the trip. Surely this was a story about intention and discipline.
But the more I thought about it, the less that held up.
Intention matters. But intention alone is almost never enough. If it were, most people would be thin, rich and well rested. They're not. And it wasn't discipline either.
It was something stronger, and it was obvious: their environment. Eighteen of these men bonded through Aspen, Colorado. This is a place that makes the healthy choice the easy choice.
They'd built their lives in a place where running into your friends was the default, not an event. Where shared experiences stack without anyone having to schedule them. Where decades of connection occurred simply because of where they lived.
Aspen did the heavy lifting. The birthday man just didn't leave.
And when it came time to celebrate a milestone, he did something most men never think to do: He designed the environment. He picked the trip that would unlock the most joy in the people he loved.
He knew exactly what a week of heli-skiing in Alaska with old friends would do to a group of men in their 50s and 60s. He built the conditions, and let the rest happen by itself.
The lodge scene wasn't an accident. It was the predictable output of a well-designed environment, just on a compressed timeline.
The Blue Zones were telling us this all along
In places called Blue Zones, Dan Buettner has spent 20 years studying how the environment is such a strong driver of healthy aging.
Blue Zones are communities where people routinely live longer and are happier than the rest of us. They are located in Sardinia, Italy; Okinawa, Japan; Nicoya, Costa Rica; Ikaria, Greece; and Loma Linda, California.
The line from his research I can't get out of my head is this: "Blue Zone health and longevity aren't pursued. They ensue from the right environment."
Read that again. The people who live longest and are the happiest in the world aren't trying. They're not cold plunging, taking supplements, tracking their glucose or reading self-help books on happiness.
They simply live in places where the healthy choices for movement, food, engagement and purpose are the default. Longevity and happiness are side effects.
Buettner goes further. He points to the Danish Twin Study, which found that only about 20% of how long you live is genetic. The other 80% is lifestyle and environment.
Of all the environmental factors his team has studied across five continents, social engagement is the one that matters most. Buettner's view is that longevity and happiness ultimately come down to the quality of your social network.
The clearest example is Okinawa, home to some of the longest-lived women on the planet. Okinawans form lifelong social groups called moai. Children are assigned to a moai of about five friends around age five, and that group stays together for the rest of their lives.
- They meet regularly
- They pool money
- They show up when somebody's spouse dies or somebody runs out of cash
Buettner documented one moai that had been together for 97 years, with an average age of 102.
When one member misses a gathering, the others walk across the village to check on them. That's what a lifelong friendship infrastructure looks like when it's baked into the environment. Nobody has to remember to do it. It just happens.
This is what I saw in that Alaska lodge. It was the product of an environment where engagement is baked into the environment. Not codified, not ancient, not ritualized. Simply a group of men living in a place that made deep friendship by default, and who had the good sense not to walk away from it.
My problem wasn't intention — it was ZIP code
Sitting there, I had to admit something I didn't love admitting.
I don't have that exact experience. And it's not because I didn't want it.
I grew up in Minneapolis. Great city. Walkable. Green. Safe. Buettner, who is from Minnesota himself, calls it a "light blue zone" for its parks and its bike infrastructure. By most measures, it's one of the healthiest places you can live in America.
But it's not Aspen.
My life in Minneapolis was open, distributed and mobile. My friends came from different phases and different places. Careers scattered us. Families absorbed our time.
- We had intention
- We had affection
- We had history
What we didn't have was an environment that kept throwing us into the same room, ski lift, bike trail, bar or restaurant.
I used to think that was my failure. Watching those men in Alaska, I realized it wasn't. It was physics. The environment I built my life in wasn't designed to sustain the kind of friendships I was trying to maintain. I was paddling upstream. They were floating down.
That's the part Buettner is right about, and it's the part most of us miss. Willpower is a terrible long-term strategy. The environment wins. Every time.
A broader view of retirement
We constantly think about retirement, physically and financially. But we don't think enough about the environments that quietly determine both.
Retirement isn't just a financial transition. It's a restructuring of time and environment. The workplace disappears. The routines dissolve.
If you haven't built something underneath, you're staring down a 25- or 30-year stretch with a shrinking circle and expanding hours. That's the setup for everything retirement is supposed to prevent.
The question isn't just whether you can afford retirement. It's whether you've built the environment you want to live in once you get there.
Design the environment — the rest follows
I'm not going to give you a list of tips. This isn't a self-help column.
What I will say is this: Blue Zone research and 85 years of Harvard data point at the same conclusion, and it's the one most retirement plans ignore. Willpower is a lousy long-term strategy. Environment is the real one.
If you want to arrive at 70, 80, 90 with the kind of life worth funding, stop trying to force it through discipline. Design the conditions instead.
- Where you live
- Who you live near
- What routines you build into your week
- What communities you actually show up to, not once, but every week, for decades
And once in a while, plan a week of peak experience with the people who matter. A trip. A mountain. A helicopter. Something worth telling stories about 20 years later.
What does the right environment actually look like? Look at the structures that have always done this work.
- Walkable neighborhoods where you cross paths with the same faces every week
- Faith communities, where Buettner's research shows attendees live four to 14 years longer than non-attendees
- Club sports like golf, tennis, cycling, masters swimming and pickleball that put the same people in the same room on a recurring schedule for years
- Second-home communities where the same families return season after season
The pattern is always the same: Proximity, repetition and shared experience over time.
Which means geography itself deserves a place in the retirement planning conversation. Most financial plans treat "where do you want to live" as a lifestyle question. Beach vs mountains. Taxes vs weather.
The research suggests it's actually a structural input to your friendships, your health and ultimately your medical costs. The town you choose may matter as much as the portfolio you build.
The birthday man in Alaska didn't have extraordinary willpower. He had an ordinary willingness to stay in the place that made the rest of it possible and an instinct for building the kind of environments where his friendships could do their best work. That turned out to be enough.
Longevity is not the enemy. Unprepared longevity is. And "unprepared" doesn't just mean broke.
It means showing up at 70 with a full brokerage account and an empty room, wondering where everybody went.
Related Content
- Blue Zones: A Blueprint for Adapting Health and Financial Security into Longevity
- Want to Live Longer? Here's What Works
- Healthy to 100: Secrets from Countries Where Retirees Age Best
- The Surprising Truth About Loneliness and Longevity
- The Retirement Risk No One Likes to Talk About: You, Still Here
