In the summer of 1959, Richard “Richie” Olsen took a job at Goodale Construction, a summer gig that gave him his first chance to take the helm of a backhoe.

Sixty-four years later, Mr. Olsen has never strayed far from the role, still enjoying a career spent digging holes, driving excavators and paving roads, first with his late brother John and then his son Keith. Along the way, he founded a family excavation company and eventually stepped into the public side of things, serving as the West Tisbury highway supervisor for the last 25 years.

Now in his 80s and near retirement, Mr. Olsen reflected on his long career in a Gazette interview.

“I’ve always thought, stick with what you know,” he said. “This is all I’ve done all my life. It’s all I’ve ever known.”

West Tisbury highway department: Jesse Oliver IV, Richard Olsen, Kevin Hatt and Louis Slingerland IV.

Ray Ewing

West Tisbury highway department: Jesse Oliver IV, Richard Olsen, Kevin Hatt and Louis Slingerland IV.

Ray Ewing

Born in Tisbury, Mr. Olsen’s Island roots run deep. On the back wall of his highway department office hangs a poster advertising a movie about Zebulon Northrop Tilton, a famed schooner captain born in Chilmark in the 1860s.

“That’s my ancestor,” Mr. Olsen explained.

While his forefathers mastered the sea, Mr. Olsen’s command always remained tied to the land. It’s a charge undertaken with reverence, handling an excavator with the seriousness of any captain.

“An excavator is like the extension of your arm,” Mr. Olsen said. “You don’t think about what you’re doing, you see what you’re doing. You just work it like a hand, and you don’t even think when you’re picking something up with your hand.”

In his six-plus-decades of excavation work, Mr. Olsen claims he has never gotten a machine stuck in a position he couldn’t escape.

“I had backhoes in pretty scary situations, you know, mud all over the tires,” he said. “But if you keep your mindset, you can get them out.”

Recently, Mr. Olsen hung up his hard hat for good, trading the seat of an excavator for a seat at a desk, both in town and in his continued involvement in the family business.

“I’m too old, I just can’t do it anymore, he said. “That’s all I’ve ever known, so it’s hard to give that up.”

The highway supervisor has seen plenty of changes in the business over the years. There’s been a huge transition from cranes to hydraulic excavators. There’s also been an injection of comfort into the machinery when internal heating and radio were added.

Mr. Olsen got his first taste of municipal work behind the wheel of a snowplow. He had some experience already, previously clearing snowy roads for the state before leaving because of the slow pay schedule.

“I figured I’d rather be plowing for the town since they pay every two weeks,” he said.

Soon after, the previous town highway supervisor retired and Mr. Olsen stepped into the position.

A glance around Mr. Olson’s office behind the town fire station reveals his deep interest in the role. On his bookshelf, thick highway maintenance textbooks share space with decades of yellowed West Tisbury annual reports. On his desk sits a bright yellow excavator model.

It is largely an organizational position, Mr. Olsen said, coordinating contractors and knowing where roadside brush needs to be cut. The department has come a long way since he took the job, growing from one employee and one truck to three workers, a pickup, a bulldozer and a dump truck.

But the most important part of the job has stayed constant for the last quarter century: cruising around West Tisbury, keeping an eye on the roads.

It’s the part of the job Mr. Olsen has enjoyed the most.

“Just by driving around, you know what needs to be done,” he said. “I haven’t gotten tired of it.”

Mr. Olsen says he plans to stay in the position for about a year longer, though that’s a claim he has made before. Walking out of his office on a sunny morning, Mr. Olsen smiled.

“It’s always a nice day for a drive,” he said.