Finance to the Final Frontier
The Trevor Sherman
By: Chase Muro
Trevor Sherman did not set out to become a hiking and rafting guide in Alaska.
A few years ago, he was studying finance at Midwestern State University in Wichita Falls, Texas, following a path that seemed far removed from leading visitors down trails and across rivers in Skagway. But after a couple of years in college, Sherman began questioning whether finance and the desk-bound career that could follow was really the life he wanted.
The answer eventually became clear.
“No, not at all,” Sherman recalled thinking when someone asked whether he wanted to become a financial advisor.
He left school and returned home, where he spent about eight months living with his two sisters.
Sherman saw the arrangement as one of their last opportunities to live together before they moved into the next stages of their lives. But during that period, he also began thinking about what his own next stage might look like.
He wanted something temporary. Something different.
Then he discovered seasonal work.
His first seasonal job took him far from Texas to Glacier National Park in Montana, where he worked at the front desk of a hotel. It was unlike anything he had experienced before. He spent his free time hiking among mountains, alpine lakes and blue water, quickly falling in love with Glacier.
He loved it enough to return for another season.
The second time around, Sherman worked as an employee experience coordinator. Part of the job involved leading hikes for other employees. Suddenly, something clicked: the activity he already loved could actually become his work.
“When I realized I can get paid to do some hikes,” he recalled, he knew guiding was something he wanted to pursue.
From there, Sherman began looking for guiding opportunities, particularly in a place he had long wanted to experience: Alaska.
A Long Way From Home
For Sherman, leaving Texas was about more than finding a job.
Before going to Glacier, the farthest he had lived from home was Wichita Falls, about two hours away. Montana represented a roughly 24-hour drive and an enormous leap into unfamiliar territory.
His mother initially had concerns, but Sherman remembers her crying because she was proud of him for taking such a big step away from home. Over time, she became one of his strongest supporters.
Sherman said his mother had not had many opportunities to travel herself, and he hopes that someday his own travels might help bring her to places such as Montana or Alaska.
“She’s been my biggest supporter,” he said, adding that much of his family has encouraged him to pursue the lifestyle while he is young.
That journey eventually brought Sherman to Skagway, where his days can begin as early as 6:30 in the morning.
Before a tour starts, there is paperwork to prepare and waivers to sign. Then comes meeting guests at the dock, driving them to the trail, hiking and eventually taking them on a scenic rafting trip before returning them from the tour.
At the busiest times, Sherman can lead two tours in a day, six days a week.
The schedule can be exhausting.
But the reason he keeps doing it can often be seen on the faces of the people he guides.
Seeing Alaska for the First Time—Again and Again
Sherman first discovered one of his favorite parts of guiding while leading employees on hikes during his second season in Glacier.
By then, he had already explored many of the places around him. He worried that returning for another summer might make the scenery feel ordinary.
Then he began showing it to other people.
Watching someone encounter a towering mountain or waterfall for the first time allowed Sherman to experience some of that wonder again himself. Now, in Alaska, the same thing happens with guests who may have traveled thousands of miles for what could be a once-in-a-lifetime trip.
Sometimes, the memory they take away is something grand. Other times, it is surprisingly small.
A guest might tell Sherman that they loved the rafting, the hiking, or even seeing a red squirrel along the way.
“And I’m like, you know what?” Sherman said. “You’re right. That was really awesome.”
Those moments help make the difficult parts of the job worthwhile.
Seasonal guiding can mean extremely long hours. Sherman described working about 120 hours during one pay period. Staffing shortages can make the workload even heavier, particularly toward the end of the season as employees leave or move on.
There is also the physical toll. After two tours, feet can ache. Rowing a heavily loaded raft can strain the back. Sherman said he has dealt with soreness from the repetitive physical demands of the work.
And sometimes the challenge is not the hours or physical strain.
Sometimes it is getting one person safely down a trail.
“I Enjoyed It, Trevor”
One group in particular has stayed with Sherman.
The tour included only three guests, one of whom was a man in his early 80s. From the moment Sherman met him at the dock, the man made it clear that the excursion was not his first choice. The tour he had wanted was unavailable, Sherman recalled, so he had ended up on the hiking and rafting trip instead.
He did not seem happy about it.
Then they reached the trail.
Within the first few steps, the man already needed help.
Sherman quickly realized the hike was going to require his full attention. He spent much of it holding and pulling the guest by the hand, worrying with nearly every step about whether the man would make it through safely.
It became one of the most stressful tours Sherman had led.
But something changed along the way.
By the end, the man who had begun the trip not wanting to be there had a simple message for his guide:
“I enjoyed it, Trevor. Thank you so much.”
For Sherman, that was enough.
The guest had enjoyed himself. He had completed the experience safely. A tour that began with reluctance ended as a success.
It is an example of what Sherman finds meaningful about the job: helping someone experience a place differently than they might have expected.
And Alaska offers plenty left to experience.
More Than Skagway
As impressive as Skagway can be to a first-time visitor, Sherman is quick to point out that it represents only a small part of Alaska.
“There’s more to Alaska than Skagway,” he said.
Looking at a map reminds him just how much remains beyond the place where he currently works. For visitors coming from heavily developed areas, Skagway might already feel like the edge of civilization—the “last frontier.”
To Sherman, it is only the beginning.
His time guiding has also changed the way he thinks about people and their relationship with the natural world.
Sherman grew up in South Dallas, Texas, where he remembers open space and a field behind his childhood home. Today, he said, that field has become a housing complex.
Watching development replace spaces he remembers has sometimes left him wondering whether people care enough about disappearing ecosystems and wildlife habitat.
Then he meets his guests.
People come from different places and backgrounds, but Sherman repeatedly watches them find beauty in nature.
Seeing that gives him hope.
“I think a lot of people find beauty in nature,” he said. “They want to find that beauty.”
Sherman hopes those experiences do not end when visitors leave Alaska. Maybe seeing an extraordinary landscape will encourage someone to care more about protecting the environment back home.
For him, that appreciation has become deeply personal as well.
A Second Therapy
Guiding means Sherman spends much of his life outside, and those hours have given him more than a paycheck or a career direction.
They have given him a place to think.
“Being outdoors is like a second therapy for me,” he said.
Even during a workday, Sherman can find brief moments when everything slows down. Sometimes it happens on the river: a slight breeze, low clouds, rain, and a stretch when he can stop rowing and simply drift.
In those moments, the noise in his head fades.
Job stress, conflicts with coworkers and worries about life back home can temporarily disappear. Whether he is on the raft or hiking alone, being outside gives Sherman a chance to process what is happening in his life and emerge feeling refreshed.
“I can walk away from it feeling refreshed, like I can keep going,” he said.
Perhaps that is fitting for someone whose life changed because he was willing to leave a familiar path and see where another one led.
Sherman does not know exactly where that path goes next. As his Alaska season winds down, he is considering winter work in the Pacific Northwest, Washington or Montana. Looking further ahead, he hopes to return to Alaska and guide rafting trips around Denali.
The uncertainty seems appropriate for a life built around seasonal work.
There is always another season. Another landscape. Another group of strangers arriving at the dock.
And another story waiting to be heard.
Everyone Has a Story
When asked what the phrase “Everyone Has a Story” means to him, Sherman returned to an idea at the heart of guiding: empathy.
Walk past a stranger in a city, and that person might simply be another face. Meet a coworker or a guest briefly, and it can be easy to see only the role they occupy.
But learning someone's story changes that.
“You start to see the human side of them,” Sherman said.
The person stepping off a cruise ship is not simply another tourist. The guide leading a tour is not simply a few hours of entertainment.
Each has family and friends. Each has aspirations. Each has struggles.
And once you understand that, Sherman believes, empathy grows.
“You are more,” he said, “because you have family, you have friends, aspirations, you have struggles.”
For Sherman, a career that began with leaving finance behind has become a life spent helping people experience wild places, and, in the process, continually rediscovering them himself.
Sometimes that happens beneath mountains.
Sometimes it happens floating quietly down a river.
And sometimes it happens simply by taking the time to learn the story of the person sitting beside you.
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Thanks, Trev, for taking me along, sharing your story, and reminding me that sometimes the best paths in life are the ones you never planned on taking.