Reading · Happy on Purpose

Welcome to Happy on Purpose, a bestselling newsletter about happiness, habits, and midlife. Tap the ❤️ button to spread the joy!

Taylor Swift got married last weekend, and there’s one thing I can’t stop wondering: does she ever imagine what her fifties will look like?

Probably not—why would she?!

She’s young, beautiful, and supremely accomplished, living a turbocharged version of the fairy tale we’re raised on: a thriving career, a romantic wedding, followed by smiling babies, and a comfortable, bustling family home.

Taylor’s life is too electric, too full of newness and possibility, to spend time picturing a decade that feels impossibly far away—and that isn’t exactly heralded as something to look forward to…

I grew up in the 80s and 90s, watching middle-aged women characters in movies and TV shows who were deeply unappealing: the ice-cold boss who made the young heroine’s life a misery, the nagging moms wearing unflattering jeans, or the divorced and widowed women who, ignored by men, moved in with their friends.

At Taylor’s age, I dreaded midlife: I imagined myself careworn, wrinkled, chewed up by life. Except for the sororal delights of a houseful of women, it seemed clear that a life worth living ended sometime around 40…

But life, as I keep learning, is full of surprises, and one of the best is how much I love being in my 50s. This period feels magical: we’ve accrued wisdom, are strong enough to remain physically active, and our children are becoming independent and self-sufficient.

Of course, no phase of life is perfect: midlife means facing the sobering realities of aging: declining parents, the end of certain dreams, and the limitations of our bodies, which, if viewed optimistically, are also timely reminders that life is precious and to be savored.

Here are the surprising things I love about being in my fifties, and fittingly, for a post that started with Taylor Swift, there are 13—because, as every Swiftie knows, that’s her lucky number!

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1. FOMO has lost its power. At 51, I’m not interested in counting the number of friends I have or invitations I receive. Hearing about a glamorous party I wasn’t invited to no longer fills me with jealous yearning — instead, I’m relieved I didn’t have to stay out late! I’m focused on nurturing relationships with the people I care about and who care about me: making time to be together without distractions, celebrating milestones, and taking trips we’ve fantasized about.

2. I’ve stopped trying to look like a twenty-something. It’s an enormous relief to know that wrinkles and cellulite are expected on a 50-something face and body, and to stop measuring how I look and feel by the yardstick of a beauty standard set by the young. I judge my appearance against the women I actually spend time with, not women I only know from a screen.

3. Reading glasses! While it was an adjustment to learn to buy them in multiples and stash them all over the house (and car, and purse!), I like the subtle sense of authority and intelligence that wearing reading glasses lends me. Plus, they frame my eyes in a way that my thinning eyebrows no longer can!

4. I’ve given myself permission to stop doing things I never actually liked. In my late thirties, I finally admitted that I disliked skiing and stopped trying to do it. Acknowledging that fact was surprisingly freeing—and opened the door to some more personal truths I was previously too embarrassed to acknowledge: I don’t like staying up late; I don’t value variety in my diet; any night can be for going out, and any night can be for staying home! It’s nice to accept that the time has come to firmly discontinue relationships, habits, and obligations that drain and depress me. Without apology.

5. There’s a compelling reason to do scary things. With age comes the acute awareness that “waiting for the right time” is no longer a valid excuse for not prioritizing our desires. The reminders are impossible to ignore: our parents aging, children leaving home, our bodies developing aches and pains. I like knowing that I don’t have forever to do things, and that if I want to achieve certain goals, there’s no longer a good reason to put them off. I secretly dreamed of being a writer my entire life but didn’t attempt it until I was 45. I started Happy on Purpose at 48 and Tennisette at 51!

6. Late-blooming is a genuine advantage. While our culture glorifies the precocious prodigy and the college dropout entrepreneur, research shows that older founders and creatives are equally—if not more—successful. A fascinating MIT study analyzed 2.7 million entrepreneurs and found that a 50-year-old is twice as likely to build a highly successful company as a 30-year-old.

7. Saying no is easier. It’s taken me half a century to learn that when I’m asked to do something, it’s perfectly acceptable to reply “I’m sorry, I can’t make it” without a long-winded explanation of why. Sometimes an explanation is warranted — when the invitation is from a close friend or family member. But most of the time, thanking someone and simply declining is sufficient.

8. My children are interesting people! While parenting teens is not for the faint of heart, getting to know your children as real people—with opinions, quirks, and genuine interests—is one of the great rewards. At this point, my kids know things I don’t, and it’s refreshing—and gratifying—to be able to ask their advice and benefit from their knowledge. It’s a delight to find myself beginning to see them as confidantes and friends vs. dependants.

9. Asking for help is not intimidating. For years, I felt it was a sign of weakness to need help, or to admit I didn’t know something. I’d spend large portions of meetings squirming when topics came up that I didn’t understand, wishing I were invisible rather than simply asking for an explanation. I now know that if I have a question, someone else probably does too—and that asking is almost always faster and less painful than pretending.

10. Being truly known by old friends. One of the deepest comforts of midlife is the sense of being truly known by friends who’ve been in my life for decades. It’s the payoff for all the years of ups and downs, as we navigated romantic relationships, careers, petty jealousies, insecurities, and instability, while building our lives. It is a rare privilege to have people in my life who’ve stuck around since childhood—by choice—through all the phases and changes of life.

11. There is still so much to learn. It is a joy to have arrived at an age where I know a few things yet am humbly aware of the vast expanse of knowledge beyond me — and am eager to continue learning and growing. I like that I no longer feel the need to pretend to know everything (except, occasionally, with my kids.)

12. Using the good stuff! In my fifties, there is simply no reason to “save up” anything for later: I’m using the expensive shampoo and fancy candles, and wearing my nicest clothes and jewelry, with enormous satisfaction!

13. I’m not afraid of what comes next. I know old age will bring wisdom and joy (and grandchildren if I’m lucky!), along with difficulties and heartbreak, and I aspire to do it with grace and intention. Aware I’m likely to experience some years of illness and cognitive decline, I want to be prepared—both for my own comfort, and to ease the emotional, logistical, and financial burden on my children. This means actively planning for my older years: I’m looking at it as yet another, fascinating adventure in life…

1. 📺WATCH. With the World Cup soccer and Wimbledon tennis in full swing, we’re mostly watching sports on TV right now! Also worth watching: The Agency, Season 2, starring Michael Fassbender, Richard Gere, and Jeffrey Wright, is a tense thriller set at the CIA’s headquarters in London. This show has hit its stride in season 2 with excellent performances by the entire casts, and several highly intriguing international plot lines. I’m making a date with my sofa to enjoy The Five Star Weekend, a limited series set in Nantucket and based on one of Elin Hilderbrand’s bestselling books. Jennifer Garner, D'Arcy Carden, Gemma Chan, Regina Hall, and Chloë Sevigny on a girls weekend in a very fancy house sounds delightful! I’m also hoping to see The Invite at the theater this weekend. Starring Olivia Wilde, Seth Rogen, Penélope Cruz, and Edward Norton, it’s about a dinner party for 2 couples and looks wild, funny, and unpredictable!

2. 📚READ. I’m thoroughly enjoying The Shampoo Effect, about a group of close-knit friends who grew up together on a New England beach. The insights into long friendships and the dynamics of marriage and parenting are spot-on, and hilarious. For more in the love and marriage category (and in honor of last weekend’s T&T wedding!), here are 12 novels set during weddings; and here are three summer vacation themed ideas!

3. 🎉Fashion for a classic Americana summer: 25 chic red, white, and blue options—with stars and stripes galore—for every occasion, from tennis court to cocktails!

4. Minimalist Packing Tips For Your Next Trip. I love Shira Gill’s sensible advice on how to simplify our lives.

5. 📚Life goals: a 30-year book club! Eight members, over 300 books read, twenty-one children, one grandchild, and zero divorces. “A couple of times over the years, Book Club has had to come together and reevaluate: Is this still working for everyone? Are we meeting one another’s needs?”