Real estate agent Michael Pitcairn explains how he successfully transitioned from a six-year career in Charleston to Big Sky, Montana.

In 2017, Michael Pitcairn made a life and career-changing decision. He and his wife, Stephanie, would leave friends, family, and everything they knew in Charleston to embark on a new journey 2,304 miles away in Big Sky, Montana.

Pitcairn had established himself as a top broker at State Street Real Estate, garnering attention for his creativity, tenacity, and record-breaking year where he sold $5.4 million in real estate — more than any other agent in his office.

Despite his success in Charleston, Pitcairn was willing to leave it all behind for a chance to live and work in the mountains of Big Sky, an up-and-coming ski town he discovered after his wife’s parents bought a home there.

The Pitcairns and their son, Grayson. (Photo credit: Cynthia Kehoe Photography)

“I’ve always had a love for the mountains, and actually, my wife and I did a ski season in Lake Tahoe,” he told Inman. “I always wanted to get back to the mountains but didn’t have a family connection. We were thinking about raising a family, and Charleston just wasn’t the right fit for us.”

His in-laws’ purchase gave the young couple the push they needed to pursue their dreams on the frontier. Soon after moving to Big Sky, Pitcairn started working for L&K Real Estate, a seven-person indie brokerage that specialized in selling second homes and commercial properties, alongside development opportunities.

“In the last two or three years, Big Sky has begun to be put on the map,” he said. “Our downtown has had a lot of new, commercial buildings being constructed, and our resort, Big Sky Resort, has put in a lot of new lifts.”

“I’m glad we moved here and that we’ve hit this tipping point where Big Sky has been discovered,” he added. “It’s quite the time to be involved in real estate in Big Sky.”

Although the town was buzzing with interest from visitors, Pitcairn said it didn’t make it any easier for him to break into Big Sky’s highly seasonal real estate market, especially since there are only 2,176 permanent residents.

“It’s been a tough [transition], and it’s been a lot of hard work,” he said.

Pitcairn and two of his latest clients.

Pitcairn began his ascent by assisting his broker with transactions and open houses, something that reminded him of the years he spent helping his parents, who are investors, repair and maintain rentals.

“I started helping at the age of 10 or 12,” he said. “[My siblings and I] did everything from painting, and I think we actually replaced countertops in one of them. We had a bunch of yard work for one property, and it sparked my interest in and love of real estate.”

Pitcairn dug into the work ethic he learned as a child to survive his first year, which included sharpening his social media and email marketing skills, volunteering and participating in as many community events as possible, and learning how to leverage his client base in Charleston to kickstart his career in Big Sky.

Continuing to stay in touch with my database in Charleston has been important,” he explained. “Big Sky is a second-home market. Probably 70 to 80 percent of our market is second, third, fourth or fifth homes. People from Charleston have been buying ski homes out here in Big Sky.”

He also used his shifts at open houses to build name and face recognition, which yielded two sales worth $580,000 and $800,000, respectively.

“The big thing is trying to get walk-in buyers’ information without being too aggressive,” he said. “You want to make sure they don’t forget about you after they walk out that door.”

Although he’d already begun to get some traction, Pitcairn’s big break came in December 2019 when one of his marketing videos went viral.

The new father had received a Santa suit from his parents, their way of helping him continue a longstanding Christmas tradition of surprising children with a visit from St. Nick.

“I was thinking about buying [a suit] that morning, but the suit they sent me arrived that morning,” he said. “It was a crazy coincidence because I wanted to dress up and start that tradition for my child.”

“But I began thinking, ‘Wow, we can somehow use this to our marketing advantage and make something fun for the holidays.’ I thought seeing Santa doing a bunch of extreme sports would be entertaining and hilarious.”

So, Pitcairn called L&K Real Estate’s marketing partner, Outlaw Partners, to film him snowboarding, sledding, and riding a timbersled, a snowmobile dirt-bike hybrid.

“We sent it to our database and people really got a kick out of it,” he said. “It also went viral in our little community here, and I ended up getting on the front page of our local newspaper with my Santa suit and timbersled bike.”

Although the video certainly helped Pitcairn’s business, he said the video also serves as a reminder of something very important — making time to have fun.

“I don’t like to take things too seriously,” he said. “Life is about having fun and enjoying it while you’re here.”

We’re highlighting agents with extraordinary stories through a new series, Agent Plus. Do you know someone who should be highlighted for their work inside and outside of the office? Send your nominations to

Email Marian McPherson

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