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The Pacific Crest Trail is worth every step. Just ask Tampa Bay’s Bob Doyle

What would happen if you left work for six months to take on the challenge of a lifetime? A St. Petersburg business owner found out.
Bob Doyle on the Pacific Crest Trail in Northern California in May. [Courtesy of Bob Doyle]
Bob Doyle on the Pacific Crest Trail in Northern California in May. [Courtesy of Bob Doyle]
Published Nov. 27
Updated Nov. 27

Bob Doyle sits behind a tidy desk at his financial planning firm in St. Petersburg, wearing a crisp shirt and slacks with nary a wrinkle. Lean, with trimmed white hair, he could play the role of a veteran drill sergeant.

In real life, he’s a certified public accountant in the serious business of looking after other people’s money. One client described him as staid and steady.

That all changes as he recounts his time on the 2,650-mile Pacific Crest Trail. His voice rises. His cadence quickens. He can’t reveal the details fast enough — readying the firm for his six-month absence, reconciling his commitment to clients with a desire for adventure, training for long days on the trail and tackling the daunting logistics, including mailing 28 boxes of supplies to post offices along the route.

Twice he tears up. Once when he explains how he nearly quit. The second as he describes his final moments on the trail.

He’s been home for only five weeks. The transition to regular life is taking some time, he says. His mind is still half in the mountains out west. One clue: He’s wearing sneakers instead of dress shoes, the same brand he used for the hike.

• • •

Bob Doyle on the Pacific Crest Trail. [Bob Doyle]

The Pacific Crest Trail snakes from Mexico to Canada, passing through six national parks, 25 national forests and 19 major canyons. Adventurers like Doyle who plan to walk the entire length — known as thru-hikers — battle 110-degree heat in the southern California desert and snowstorms in the Sierra Nevada mountains. They must be strong enough to survive at least 420,000 feet of elevation gain, the equivalent of walking up Mount Everest from sea level 14 times.

More than half of thru-hikers don’t finish. They get injured, mentally fatigued, or they run out of time or money. Doyle, 56, hired a trainer who put him through thrice-weekly circuit workouts. He also walked a lot, spending days putting in 18 miles at Fort De Soto Park.

“You can get in shape on the trail, but your feet have to be ready to do 20 miles on Day 1,” he said.

In 2014, he hiked the 211-mile John Muir Trail in California. He fell in love with the west — the mountains, the huge skies. And his knees held up. The trip made him think he could take on a bigger challenge.

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Before leaving for the Pacific Crest Trail, Doyle had to get his work life in order. In 2005, he and his wife, Jill, founded Doyle Wealth Management, which now has 23 employees who manage more than $1 billion in assets. Many of the 750 clients entrust the firm with their money because they like Doyle. They respect and rely on him. The trip, though, would mean taking six months off to hike a far-away-trail with little internet or phone access.

Financial advising is an analytical field, full of certified public accountants and other professionals with initials after their names poring over elaborate spreadsheets. But Doyle knows that the business is not all about numbers or beating the stock market. Good advisers relate to their clients. They understand their needs and hopes. A year before he left, he started making sure clients who dealt directly with him got to know other senior advisers at the firm. He also knew that his wife, the firm’s chief financial officer, could handle any emergencies.

“She's the smarter of the two of us anyway,” he said.

• • •

Most thru-hikers have a trail name. Doyle’s was Daddy Llama, given to him years earlier by one of his two adult daughters as they walked a section of the Appalachian Trail. Some hikers like to go solo. Others create a trail family, strangers they hike with or camp with at the end of each day.

Doyle met his first “family member” at the airport in San Diego, as the two men walked out with backpacks. He and Two Times — from Lancaster, Penn. — started at the U.S.-Mexico border on March 23. They soon added Sunshine, a tall, red-headed man and recent graduate of Oregon State University, and Oreo, a German woman traveling the world.

Bob Doyle (left), whose trail name was Daddy Llama, with his "trail family", Two Times, Oreo and Sunshine. [Bob Doyle]

Like many thru-hikers, Doyle took an ultra-light approach. His gear weighed 15 pounds, minus food and water. He wore lightweight running shoes. He refused to carry extra batteries for his headlamp. He eschewed gloves and instead covered his hands with extra socks when the temperatures plunged. His one luxury item: an inflatable pillow that weighed 1.6 ounces.

Doyle quickly fell into a routine. Rise before the sun, break down the tent, drink some iced coffee, and start walking. He loved watching the sun come up, but he also needed a head start on his three 20-something companions. He’d meet them along the trail or at the nightly campsite. He didn’t wear a watch, nor did he care much about time. He couldn’t easily communicate with the outside world, nor it with him.

After a week, the trail had vanquished the little stresses of regular life — tomorrow’s appointments, the next red light. He’s smiling in nearly every photo. He’s dancing in several videos. He played Twister in the southern California desert.

Bob Doyle's trail family plays a game of Twister at their campsite on the Pacific Crest Trail. [Bob Doyle]

“Your brain is scrubbed,” he said. “It’s joyous.”

Except for the snow, which came late in the season and covered long stretches of the trail in central and northern California. The Florida native never got used to the uneasy footing.

In early June, near the town of Mount Shasta, two southbound hikers painted a grim picture ahead — steep and slippery slopes with rocks at the bottom. You’ll need an ice ax to arrest a fall, they warned.

Doyle called his wife.

I’m done, he told her. The snow is too much.

How do you feel? Jill asked.

I’m in good shape physically.

You know you don’t have a deadline?

So what? he felt like saying.

The snow will melt, she said. Take some time off.

Bob Doyle's tent in Lassen Volcano National Park along the Pacific Crest Trail. Parts of the trail received a lot more snow than usual. [Bob Doyle]

Jill flew out and they spent several days touring Oregon. Two weeks after the phone call, he returned to where he left the trail.

He never again thought about quitting.

“So simple — the snow will melt,” he said with watery eyes. “But it saved me. It really did.”

• • •

Doyle called the office every 10 days from the small towns along the way. He had left word with the other advisers that he would talk with anxious clients during those call-ins. No one took him up on it. The advanced planning and a reliable team took care of everything. Six months, Doyle discovered, isn’t that long in the big picture. The business didn’t suffer at all.

“We teach our clients to think long term,” he said smiling. “I guess they’re listening.”

Many clients followed the adventure on Facebook, including Maureen Kolar. She described Doyle as serious and committed “but not the most humorous man on the planet.”

“To see him dancing with young people on the trek just proves that we should all seek new challenges,” said Kolar, who lives in St. Petersburg with her husband. “It makes us better people.”

The snow in the Sierra Nevada mountains was so deep that many thru-hikers this year including Doyle jumped ahead to northern California and continued walking to Canada. They then returned and completed the section they skipped, the snow having receded.

On their last night, Doyle and Two Times camped 4 miles from the road in Kennedy Meadows, near the Sequoia National Forest, that marked their finish line. Doyle woke early on Sept. 24, six months after taking his first steps on the trail. He sauntered down the path, singing Great is Thy Faithfulness over and over, blaring out the line Morning by morning new mercies I see.

Two Times caught up and the men walked the last couple of miles together. When they saw the road, they danced the last few hundred yards to I Just Want to Celebrate by Rare Earth and Elton John’s I’m Still Standing.

Doyle wept and then couldn’t stop smiling.

• • •

Doyle gets asked a lot why he wanted to walk 2,650 miles. He prefers to turn the question around. Why wouldn’t he do it, given that he has the means and the health?

Bob Doyle on the Pacific Crest Trail in spring 2019. (Courtesy of Bob Doyle) [Courtesy of Bob Doyle]

His older clients often regret the things they didn’t get around to doing. They tell Doyle some version of, “When I was your age, I wish I had …”. Their investment accounts include a couple of commas, but they cannot go back to their younger days.

Doyle heard the lament so many times that he took it to heart. He now fights against the flood of reasons not to plan the next adventure, whatever it might be.

The hard part is giving yourself permission, he said. That’s when the fun starts.

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