150 Miles At a Time

After a decade at Apple, Kevin Martin walked away to live on his own terms.

Author Note: When I first came up with the idea for naming this publication “Pressure Point”, I wanted to write about moments, stories, and the people behind them. I have always loved reading profiles, articles or pieces of writing telling another person’s story or providing a snapshot of a moment in time. I could write about well-known people, including athletes and coaches, or maybe even performers or executives. However, the idea of writing about someone who isn’t widely known, but still has a great story, appealed to me. I connected with Kevin, and once I learned about his journey, it resonated with me and felt like the perfect first profile to feature here. Kevin writes his own Substack Unmapped , which you should check out for much detail on his journey and his current adventure.

The sunlight reflecting off the snow-covered hills, the sharp cuts audible across the Telluride mountains from skiers and snowboarders making the most of the beautiful landscape. Many come here looking for fun and enjoyment with family and friends, a bright winter oasis centered on the outdoors and connection. As far as places to spend a weekend with your girlfriend’s family --- this was a great one. Kevin Martin, now over a decade into his career at Apple in their supply chain logistics department, was working remotely for the week. It would be the perfect break to recharge, get outdoors, and spend some quality time with loved ones.

At least that’s how it was supposed to go. The notifications started to build up slowly, and by Friday they were an avalanche rumbling down the mountains. Apple was scrambling from the impact of tariffs enacted by the Trump administration. While the family and friends were enjoying the holiday weekend, Kevin toiled away on his laptop. He hopped on call after call, trying to put out one fire after another. Things grew worse as the week went on; he fell back into the familiar cycle: available, on-call, wherever, whenever. In the worst moments Kevin saw another few years, more life moments missed, more difficult conversations with loved ones about why he was never really “present”.

The first holiday Kevin spent with his girlfriend’s family, the questions flooded in --- ‘Don’t they know it’s a holiday?’ ‘Can’t it wait until after dinner?’” Now, thirteen years later, there were no questions. This was how it was. The rest of the family connecting and enjoying the holiday, Kevin working.

My days at Apple are numbered, he thought, I just have to get through this, I am almost there.

The plan had been set in motion years earlier, but he still had to wait until he was 40. That was almost three years away. Another thirty-six months of constant stress and anxiety, of nonstop notifications pinging his iPhone. More internal meetings.

As he poured himself a cup of coffee, trying to rouse himself for another day, he watched the others head out to enjoy the mountain. The joy on their faces, their breath visible in the air from the laughter. Kevin had come to Telluride to connect with his partner, her family, and ultimately himself. Instead of being out there, in the place where he felt the most clear and at ease, with people he loved, he once again was stressed, angry, anxious. As someone so intently focused on planning and systems, Kevin knew his own system needed improvement.

The Telluride weekend wasn’t an unfortunate inconvenience; seemingly every day over the following weeks panic ensued, a new catastrophic problem identified. The COVID work craziness had been one thing, everyone was struggling to navigate the uncertainty of a new global pandemic, and honestly Kevin had just been happy to have a job. Now though, almost five years later, the rollercoaster ride was exhausting.

The decision that set Kevin Martin down his path toward the biggest moment of his life started nearly ten years before the Telluride weekend. It took place on a different mountain weekend, in the hills of Blue Ridge, Georgia.

In his words: “I was living for the weekends, and the weekends were mostly just recovery from how much I hated the week. Counting down to five o’clock, drinking until Sunday, repeat. A pretty hollow cycle.”

Like all great plans, it came together in the best or worst way imaginable depending on who you ask. A few too many beers deep, with some friends, in front of a burning fire pit. Maybe it was the alcohol talking (it most definitely was), but Kevin felt instantly compelled to answer the call to action his fellow inebriated compatriot was proposing to him.

You want to climb this?

The friend threw his iPhone in Kevin’s face, a picture of a massive mountain on the screen.

“Hell yeah, let’s do it”, Kevin responded.

The “this” in question was a mountain peak reaching fourteen thousand feet in elevation, one of the most challenging climbs in the United States. Sitting about sixty miles southeast of Seattle, Mt. Rainier represents a challenge for even the most experienced climbers. The decision to take this journey is not made under the most steadfast of mindsets, let alone mid drunken weekend. Kevin ignored all sense of logic and practicality and followed his intuition.

First though, he had to figure out how to not embarrass himself, and also not die.

We’ll probably forget about this tomorrow anyway.

Fighting the urge to back away from his drunken commitment, Kevin remained all-in, his heart racing as he submitted the $1,500 non-refundable deposit to the guide group who would lead his group up the mountain.

“My buddy had attempted something similar the year before with the same guiding company, hadn’t trained, and his whole group had to turn back because of him. I knew I didn’t want to be that guy. So I trained seriously for the first time --- bought the training bible for high-altitude mountaineering, built a plan, scared myself into shape.”

His passion reignited, the frustration and aimlessness gone. It was hard to dwell on his career path or frustrations with work when he was spending weekends building his physical and mental capacity. Those weekends filled with Bud Lights and hangovers? A distant memory.

“All of a sudden I had a reason to be awake that had nothing to do with Apple.”

Eight months after committing, Kevin traveled to Washington, proud of his consistency but apprehensive about the journey in front of him. Thirty pounds lighter, the by-product of thirty-two weeks of training, and clear-eyed about his purpose. None of which would help him much on a fourteen-thousand-foot climb in sub-zero temperatures and skin-tearing winds.

Why couldn’t I have taken up golf instead?

Steam coming off the coffee of his fellow climbers, getting ready to ascend to the summit --- Kevin found himself wishing he had been attracted to more easy-going hobbies. “Remember why you are doing this. Every part of you is going to want to quit, my job is to make sure you don’t,” the mountain guide reminded him. The climb to the top was excruciatingly difficult, his legs and back screaming out in pain. Kevin found himself constantly waiting for the guide to check in so he could ask to stop, but they soldiered on.

He thought about the months of training and reflected on how far he’d come to power him through the trip to the peak. His legs ached from the climb. One step at a time, the fear of falling or making a misstep kept him focused. “Here we are,” the guide finally said. Reaching the summit, exhausted and altitude-drunk, was euphoric. Looking out with mountains appearing above the clouds the realization hit Kevin:

I can’t believe I’ve worried about so many things that don’t matter. No one is going to care if their iPhone is a day late.

The years after Rainier were the best of Kevin’s life. He found meaning outside of work --- embracing yearly challenges that pushed and developed him mentally and physically. With the pressure of finding meaning eased, he actually excelled at work, steadily rising in stature and earning more responsibility. He became infatuated with the idea of financial independence, and the ability to live life on his own terms. The plan worked, almost too well. Money, as Kevin describes it, became a mental cage. Dramatic personal cost cutting, constant checking of Apple stock price and brokerage accounts, living and dying by the day’s market moves. The number Kevin started with that he would need to retire, replaced with constantly changing targets. He wondered about the people around him, and why everyone else wasn’t doing the same:

Kevin watched his colleagues and wondered why no one else was getting out. The answer, he says, surprised him: “slowly you find out --- no one had millions. They’d spent it all“. For Kevin, the rapidly appreciating stock price was his exit lever, but for others it was justification to themselves. “You walk through the Apple parking garage and it’s Porsches, Rivians, BMWs. The lifestyle creep is total and invisible from the inside. I don’t judge it --- there are real reasons people spend that way. But I just kept my life simple.”

Almost five years after looking out from the summit of Rainier, Kevin was back in a dark bar.

PING

The notifications kept hitting his phone, but Kevin left it in his pocket. His eyes glazed over, the neon haze of dive bars in Central Pennsylvania. Few more years, Kevin thought. Almost there. He checked his phone, ignoring the notifications, but scrolling to his financial accounts. The numbers stopped really having much meaning to him. The goalposts always felt like they were moving anyway.

Pennsylvania was supposed to be a promotion. The elevation in responsibility, the sheer amount of attention, the massive number of moving parts in the warehouse created pressure that was agonizing.

In 2018, with life trending in his direction, he agreed to an opportunity to lead a warehouse build-out in Pennsylvania. Leading the operations, being the self-described ‘boots on the ground’, he was ready to bring everything he’d learned on the mountains and the trails to the job.

Two years of missed deadlines, finger-pointing, and budget overruns followed. The project failed. Kevin’s professional identity had been built around solving and optimizing systems. Being flown up to Pennsylvania to lead a major effort, and then have it fail, was shattering to his self-image. The culture in the group became extremely negative, with stress and resentment surging. Burnout ran rampant; most people were either fired or quit. Kevin shouldered a lot of it internally, struggling to bear the responsibility of such a high-profile internal mess. Far from his home in Nashville, Kevin fell back into old habits.

After the trip with his girlfriend’s family to Telluride, Kevin drowned in work from January to April as Apple figured out how to navigate the impact of the Trump tariffs. Kevin, his girlfriend, and their dog loaded the car in Nashville and drove to Utah. Three weeks in a Park City Airbnb. No phone, no constant pings, just the three of them. Testing out what life post-Apple could actually feel like. Kevin’s head was clearer than it had been in years. On April 19th, 2025, he wrote himself a note he can still pull up: I AM LEAVING APPLE.

He told his plans to his parents, and expected at least one of them --- probably his dad --- to tell him he was crazy. Everyone agreed: he needed to leave. His dad told him to wait for the the last stock grant in a few months, then go.

October 15th - the day Kevin received his final Apple stock grant and the day he turned in his resignation to Apple. That afternoon, he finally communicated his decision in a one-on-one with his boss. When Kevin had quit previous jobs, superiors had been confrontational. This time was different. His boss was blindsided --- Kevin was ‘the one guy always kind of positive’ on a team where everyone hated their lives --- but supportive. In the weeks that followed, leaders Kevin barely knew opened up to him. Senior people making millions confided they were jealous, that they wished they could do the same. They just needed three more years.

Three more years. The same number Kevin had been telling himself before Telluride.

Kevin gave Apple a few more months, wanting to help his team manage the holiday rush before departing. His last official day was December 23rd, the Christmas holiday providing the first few days to enjoy his life without Apple for the first time in thirteen years. No more 4:30 AM wake ups, rushing from the gym to the office; getting pinged for calls after work.

A few weeks later, Kevin was sitting at home on a Sunday night. He didn’t know what day it was at first. Then he realized --- it was Sunday. For thirteen years, Sunday nights had meant dread, the countdown to Monday morning already ticking. This time, nothing. Just a quiet evening. If anything, he was excited about the week ahead.

Kevin woke up without an alarm for the first time in years. He and his girlfriend developed a morning routine, walking trails together without their phones. Never thinking of himself as a creative type, suddenly with time and space to think, Kevin realized he had a lot of things he wanted to write about. Days now starting with creative thinking, writing, and leaving his phone at home.

“When I left, I was swarmed with people asking how and why, some told me I needed to document my travels on YouTube etc., but I hate social media. It’s really bad for me. Writing on Substack seemed like a better way, and it’s grown rapidly and has been a way for me to connect with new and interesting people.”

Kevin says he doesn’t know what comes next professionally. Every time the question comes up, he circles back to the same frame: one chunk at a time. He named his publication ‘Unmapped’, because it’s how the rest of his life feels.

“I’m hoping the trails surface what’s next”.

After Colorado, he realized that “I don’t have the time to do that” was an excuse. The dream, the one he’d shared with friends and family for years, didn’t have to die just because he was older.

It’s the same approach he’s taking to the Appalachian Trail. He started 2026 aiming to hike a thousand miles --- a dream he’d buried, thinking he’d missed his window. Now he’s doing it 150 miles at a time.

Last month he met a seventy-five-year-old man, BT, who hands out snacks to hikers on the trail, “the least I can do is make sure they get a cold drink and treat along the way”. Then there was James, a twenty-year-old junior at Kevin’s alma mater who was considering opting out of the entry level business career path for working in a national park. The people he’s met are just as important as the miles he’s traveling.

A forty-seven-mile stretch of solitude forces him to step back, take a breath, and work through everything in his head.

He’s prepping for the next stretch --- 300 miles, three weeks, the longest consecutive section he’s done. Kevin is heading into the first stretch, a twelve day trail of solitude, carrying everything on him that survival will require. It’s hard to reconcile the man he describes himself as before Rainier with the one speaking now.

A few weeks into his new life, Kevin and his girlfriend went back to Telluride. One morning, Kevin awoke and looked at the clock: just before 7:00 AM. He got up and made coffee, the aroma filling the room of their small Airbnb. There weren’t any skiers out and about this time, but Kevin took in the scenery, thinking about how different his life was now from four months ago. When asked, the contrast is stark:

“The previous year was like being waterboarded in front of family members. This year felt like unlimited creative abundance.”

His girlfriend woke up, they shared coffee, and headed out for a hike with the dog. Kevin didn’t even check his phone before leaving the house. It was still plugged into the wall charging beside his bed.

When asked what comes after this 300 mile section he’s about to hike, Kevin answers:

“I’m not sure, I guess I’ll take it 150 miles at a time and figure it out”