Lee McColgan’s career in finance was probably doomed as soon as he started visiting historic house museums. The first one he toured was the Fairbanks House, in Dedham, Mass., the oldest surviving timber-frame home in America, built in 1637.

It was 2014, and Mr. McColgan was living in Omaha, where he worked as a sales representative for a large investment company. Despite a rural childhood in Vermont and an interest in visual arts and building, he had spent much of his adulthood working in a cubicle: five years of “jacking in” at a call center outside Boston, followed by several more as a Midwestern “external wholesaler” pitching mutual funds to financial advisers.

In quiet desperation, Mr. McColgan took up woodworking as a creative outlet, building an oak chest in his garage. That experience, and the visits he made to historic houses whenever he was back in New England, inspired him to reassess his life and envision a different future, working with his hands.

He especially appreciated the solidity of early Colonial-era building: the big, hefty beams that can last hundreds of years, so long as bugs and moisture don’t get them; the dry-stone foundations that won’t weaken as long as the roof is kept in good repair. He was obsessed with quality and hated “cheap stuff.”