Advice to Aging Millennials as They Reach 40

What generational war? No matter what generation a person is part of, eventually (if she’s lucky), she’ll reach 40. Here are some words of wisdom for those on the cusp of this milestone age.

By Katherine Lanpher
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Oh, it's happening

Ah, millennials. Has there ever been a generation so maligned? They’re blamed for “killing” everything from paper napkins to mayonnaise to golf. They ushered in the co-working space with kitchens stocked with LaCroix and cold brew on tap. They’ve shaped the way we talk, shop, eat, drink, and work. But there’s one reality that millennials can’t change: Aging.

That’s right, the first millennials start turning 40 next year. (Yes, yes, yes, the Pew Research Center technically starts the millennial generation in 1981, but we stand by our story. Ok, boomer?)

Take heart, aging millennials! We rounded up advice for you from a cohort of cool women who last saw 40 in the rear-view mirror as they sped toward their glorious present lives. 

“Make Mistakes,” says author Laura Lippman, 60

The New York Times bestselling author of more than 25 mysteries, novels and short story collections remembers exactly where she was in her life when she turned 40: “Trying to accept that I was in a marriage I needed to leave, not quite ready to accept that I was in a job I needed to leave.”

If that sounds like a lot of change for someone of any age to take on, take heart and listen to her life now: She’s in a successful second marriage, raising a nine-year-old daughter and just now finishing her first book of essays My Life as a Villainesswhich comes in May 2020.

Recently on Twitter, she comforted a writer sad about turning 30 with these wordsI didn't publish my first novel until I was 38, I didn't leave my day job until I was 42, I had the best career of my life — SO FAR — at age 60.

Oh, and she started tennis lessons last year. 

Her advice to those turning 40: “Make all the mistakes.”

Translation: “Embrace action over inaction. Don’t stay anywhere just because it’s safe and familiar unless you genuinely love it.”

“Stop Living for External Expectations,” says writer Shannon Huffman Polson, 47

By the time she was looking at 40, Polson had already lived several lives. After college, she joined the Army, becoming one of the first women to fly an Apache attack helicopter. She was assigned to Fort Bragg, in North Carolina, the only woman in a regiment of 120 pilots. She commanded two flight platoons. 

Then, it was off to Dartmouth to get an MBA. She dove into the corporate jungle and then tragedy struck: her father and stepmother were killed in a rare grizzly bear attack in the Alaskan Arctic. Her travels — both inward and outward — as she traversed her grief form the backbone of her first book, North of Hope: A Daughter’s Arctic Journey.

When she turned 40, she was editing that book, expecting her second child, and completing her MFA

And now? She, her husband, and their two sons live in the Methow Valley in eastern Washington, where they founded a lay-led Episcopal church and are raising funds to build a library. And she’s finishing a second book, this one based on her own experience and interviews with other women in the military. The Grit Factor: Courage, Resilience and Leadership in the Most Male Dominated Organization in the World will be published in 2020 by Harvard Business Review Press. 

Her advice on turning 40 applies to all of us: “When that whisper inside tells you that you are living for external expectations, or worried about other people’s expectations, then you smile, and turn toward your own true north.”

“Follow Your Instincts,” says novelist Jane Isay, 80

When Jane Isay turned 40, she barely had time to notice. She had entered her first excutive job in publishing and was commuting to Manhattan from New Haven, Conn., every day while raising two sons, then ages 9 and 13. 

You’ve probably read a book she helped bring to life. Friday Night Lights? She was the editor of the book that prompted the hit tv series. She gave us many great psychology books including Reviving Ophelia by Mary Pipher. 

But it was after she retired at 65 that she found her own voice as a writer with four books on families and relationships: Walking on Eggshellsabout adult children and their parents; Mom Still Likes You Best about adult sibling relationships; Secrets and Lies: Recovering from The Truths That Change Our Lives, on how to navigate family secrets; and her latest, which came out in paperback in 2019, Unconditional Love: A Guide to Navigating the Joys and Challenges of Being a Grandparent Today.

And now? She’s working on chapter books for girls in the 4th grade.

Her advice is succinct and to the point: “Find meaning. Follow your instincts and stick to your values.”

Use your voice. Whose permission do you need to speak your mind, other than your own?

Journalist Rachel Jones

“Stop Playing Small,” says journalist Rachel Jones, 59

The distance between Jones’ life at 40 and her life now can be measured several ways. For one, there was that 10-year stint in Africa, where she lived in Kenya and Uganda and trained health journalists there and in nine other countries. So she’s in D.C. now and she turned 40 in D.C. but in between? She traveled the world. 

She also turned 40 three weeks after 9/11. So, as she says, “the fact I COULD turn 40 seemed like an incredible privilege.”

All that travel and gratitude turned out to be great training for her current gig as Story Editor at Global Press Journal, a D.C.-based international news service that trains and mentors women in 20 countries so they can report the news they find important, not just what a Western journalist thinks is important.

In just one day, Jones can edit writers from Nepal, Uganda and the Democratic Republic of Congo. She looks back at her near 20 years of travel and work and realizes: “It's like the Universe was giving me a tryout phase to decide what my purpose was.”

Advice? She’s got plenty.

Speak up. Use your voice. Stop deferring. 

“Whose permission do you need to speak your mind, other than your own? I cannot tell you how many meetings I attend where grown-assed professional women whisper into the microphones, or refuse to stand up when making a comment, or are just visibly uncomfortable when the focus is on them.”

Don’t be like them, she says. “Stop playing small. You'll regret what you didn't say more than what you did, I promise you.”

“Recapture Your Confidence,” says humorist Julie Schumacher, 60

Schumacher’s first published short story was written for an undergrad writing assignment while in college and since then she has published novels for both adults and children. But she hit the national spotlight in 2015 with Dear Committee Members, a satiric look at academic life told throught a series of letters of recommendations. 

She must have hit a nerve: the book became a best-seller and garnered her The Thurber Prize for Amerian Humor. She was the first woman to win it. In the aftermath, she’s written a comic novel sequel called The Shakespeare Requirement and even a satirical coloring book Doodling for Academics

When she’s not making you smile, Schumacher is a faculty member in the Creative Writing Program and the department of English at the University of Minnesota.

It’s hard to recall what she was doing when she was 40, she says, in the middle of academic meetings and raising two daughters. 

“I was exhausted all the time,” she says. “It was a blur.”

Her advice? Don’t worry about getting older.

“It’s going to happen whether you worry about it or not,” she says. “Do you want to color your hair? Go ahead. Or don’t — it looks good either way. You want to wear those weirdly hideous pants to the coffee shop? Yes, do it!”

Most importantly, she says, “It’s time to recapture the confidence you had in your preteen years.”

“Forget the Nonsense Thrown At You,” says financial executive Anne Simpson, 61

Simpson is the director of global governance at CalPERS, California’s public pension fund and in September was named by TIME as one of 15 women leading the global fight against climate change. How’s that, you say? What does a public pension fund have to do with global warming?

“Money talks,” as Simpson told TIME. CalPERS has nearly $400 billion in investments, which means it can push for change. And with Simpson at the helm as the portfolio manager, it has. She also helps lead Climate Action 100+, an investor initiative that pushes the most harmful greenhouse gas emitters to change course.

You don’t really expect a woman with Oxford and The World Bank on her resume to be so down-to-earth, but Simpson calls herself a prune.

“It’s essentially a well-preserved plum,’’ she says. “And as a maker of jam, I am all about the sweetness and delight of preserves.”

She remembers turning 40 very well: she was in London, celebrating with her friends and children, when she was informed that her marriage was at an end. She moved her family to the United States and started over. 

“Being 40 and divorced with three kids is not any one’s idea of a picnic,” she says. 

But if you find yourself in a similar situation she wants you to know: Hang in there. You’ll be ok.

Her overall advice? Be kind. First, to yourself. 

“We live in a world where women are in a mess of advice,” she says. “Be pretty but not alluring. Be clever — but not too much. Be strong — but without upsetting anyone. Understanding what it means to work in this world, to reproduce the human race and navigate the danger, and manage still to be kind to others, which women generally are, is an extraordinary feat that each woman accomplishes,” she says.

So, in conclusion: “Forget the nonsense thrown at you.”

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