As Peter and Pam Esselstyn began to imagine the specifics of retirement from successful careers in Boston, they came to a consensus almost immediately. “Within about five minutes,” Peter recalls, “we decided to retire out West in a ski community.” More specifically, somewhere they could ski in and ski out. For the Esselstyns, the small hamlet of Crested Butte, Colorado, with only about 1,600 permanent residents and iconic ski slopes, was perfect.
After purchasing a lot in a ski community there in 2016, their original plan was to wait until 2024 or 2025 to retire. “But we just couldn’t talk about anything else except building a house,” Peter says. So, when they realized finances would allow them to retire earlier, the real planning began.
“One of the first questions you…