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For Daniel Ryan, turning 40 and 50 came and went. But sometime around his 61st birthday last July, he said he had an “old man crisis.”

He did some simple math, and quickly concluded that living another 20 years would be considered a “full life.” Even if he remained healthy for another 15 years, he figured he might only be able to maintain his active lifestyle of skiing, hiking and mountain biking for another decade. “Looking at the rest of my life this way hit me like a ton of bricks,” Mr. Ryan said.

Five months later, he retired. After spending 36 years in sales and marketing at MillerCoors, the beer company, he was in the enviable position of having a pension and ample savings. The challenge, he said, is that his wife, Cheryl, 58, is still fully engaged in her interior design business, where she often logs 12-hour days. So he has to negotiate both his new play schedule and his wife’s work schedule.

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