The Third Chapter
What Retirement Actually Looks Like in the Lakes Region
There is a patio not far from my house where, most days between June and September, at four o’clock exactly, my lovely clients and friends are pouring a gin and tonic or a pomegranate martini. I know this because I have driven past it enough times to set a watch by it. I join when I’m able, and I give a little honk when I drive by but can’t stop. The couple who owns the patio are semi-retired and my morning commute often sees them updating the landscaping or supervising a contractor as they renovate the small house near my favorite swimming hole. They’ll head back to a warmer Southern state in the late fall…maybe. For now their calendar has exactly one fixed appointment a day, and it is cocktails at 4 pm.
I used to think that was what retirement looks like, wherever you are, but certainly up here. The reward lap. Projects you do for love not for money. Water, a cocktail shaker, maybe a boat that costs more than many people’s first house. A return to the way some classes lived in bygone times, resting and pursuing genteel habits like embroidery and golf. And, sure, there might also be some passion projects or a consulting gig here and there, but mostly, your time is your own.
What I’ve learned from living here for several years now is that this is a story. It is not the story. The stories that comprise even my small circle of friends and acquaintance are much more varied.
Last fall at a dinner party, I met a woman who hasn’t pulled a paycheck in a decade. But she spends three afternoons a week in a courtroom with attorneys and judges and social workers, advocating for a kid who isn’t hers, because she is a CASA volunteer and she decided, somewhere around seventy-two, that she had spent enough of her working life being useful to a company and wanted the next bit to be useful to a small person that might not have anyone else in their corner. Nobody pours her a drink at four. She is usually still in her car or gathering information from pediatricians and teachers or hanging out with a child at a park or getting ice cream just because they can.
Then there is my neighbor, who in his 90s has seen changes to this region I can only guess at. We eat a meal together about once every six weeks or so and in the spring, I was allowed to join his gentleman’s breakfast club at Linos as a one-time special guest. Around the table was an amateur historian and local geneologist, a volunteer docent at Wolfeboro’s WWII museum, a gentelman who hand built the “cabin” on Lovell that his great grandkids now enjoy during the summer months, and the organizer of the annual Chooch festival which brings model train enthusiasts to nearby Union, NH from as far as Pennsylvania and New York.
There is a newcomers club, and there is a writers center that one friend is building out of a a website, meeting rooms at the library and sheer dedication. Both exist because someone decided, well into their retirement, that not knowing anyone yet wasn’t a permanent condition. I could write a whole piece about either one. I probably will.
Some of my friends are only half here. They keep the house through the summer and close it up in October, and by November they are in South Carolina, or Florida, or somewhere in Texas near a grandchild, and by May or June they are back, and the lake tells them when its time to open up each year. This isn’t retreat. It’s a second geography, built on purpose, and most of them will tell you the Lakes Region summer is the whole reason the other five months are bearable.
Other friends stayed for the grandkids and built their whole third chapter around a school pickup schedule. Their calendars are fuller now than when they worked. They are there for every dance recital or travel soccer game. They sew gymnastics leotards and bandage ice hockey injuries. They give the kids ice cream for dinner every so often and remind their parents that this too shall pass, whatever the crisis of the moment is. There is a particular kind of tired that comes from being genuinely needed by an eight-year-old, and most of them would not trade it for cocktails every day at 4…at least most of the time.
And then there are the friends for whom none of this is a choice in the way it sounds like a choice. They are on a fixed income in a place where the taxes went up again this year. They know the veterans’ tax credit paperwork by heart because they’ve filed it every year since they qualified. They know which town employee processes fuel assistance fastest and which one takes until December. Meals on Wheels comes on Tuesdays. They are not the sad ending to somebody else’s story about boats and cocktail hour. They are the same people, the same generation, sometimes the same street, navigating a version of this place that asks something different of them.
That is the part I want to be honest about, because it would be easier to just tell the story about boats and cocktails and faces stretched to the sun. Retirement here is not one thing dressed up in six different outfits. It is genuinely different lives, running in parallel, sometimes overlapping at the transfer station or the church supper or the museum gift shop, where the man who runs the tours might ring up the sale for the woman waiting on her fuel assistance approval, and neither of them thinks anything of it, because that is just how life is in a community that means many different things to many different people.
I don’t think the Lakes Region hands anyone a third chapter. I think it gives you the raw materials, a lake, a season, a small enough population that showing up matters, and then it is entirely up to you, or your circumstances, what you build with them. Some people build a boat life. Some people build a courtroom advocacy practice out of thin air at sixty-five. Some people build a way to get through February on eleven hundred dollars a month with their dignity intact, which might be the hardest retirement project of all.
If you’re thinking through what your own next chapter might look like here, whichever direction that’s leaning, I’m always happy to talk. Even if you’re just thinking out loud.
🧭 Jenn
Keys to the Lakes
This is part of an ongoing series about what the third chapter of life actually looks like in the Lakes Region, for the people who chose it.



