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Starting Over: 11 Lessons From Women Who've Switched Careers in Mid-Life

Laura Ingalls Wilder didn’t write her first Little House on the Prairie book until she was 65. Grandma Moses didn’t begin to paint until she was 76. When she first got up the nerve to do stand-up comedy, The View co-host Joy Behar was a newly divorced English teacher in her 40s with an 11-year-old daughter. You know Julia Child as the famous chef who brought French cuisine into the American home, but did you know that Child didn’t publish her first cookbook until she was nearly 50, and that before that, she was a copy editor — and a spy who worked for the CIA?

Many of us have fantasies about changing our lives, of doing something entirely different, but many of us worry that it’s too late. However, famous women — as well as women living right in our neighborhoods — have shown us by example that, as English writer George Eliot (who didn’t publish her first novel until she was 50) says, “It’s never too late to be what you might have been.”

Here are tips, strategies, advice, and words of inspiration from women who have successfully made the leap into their second acts. 

1. Tell yourself, “There’s always a way.”

Ann Anderson Evans, 76, of Hoboken, NJ had been a legal secretary for the previous 18 years when boredom, lack of fulfillment, and an acquaintanceship with a man in Zimbabwe led her to pursue her dream of writing. It was 2004, the African country was in turmoil, and Ann thought, “If he can be a successful businessman in Zimbabwe, then I can be a successful writer in New York.” She quit her lucrative secretarial job, used her M.A. in linguistics to teach composition, and in her spare time, wrote her first book, Daring to Date Again, which was published by SheWrites Press in 2014. It has since won three awards. Ann says, “Leaving my job as secretary was probably dumb, but sometimes you have to skate on very thin ice and just hope it doesn’t break, even when it begins to crack beneath your feet.” She keeps in her pocket an expression that a chess champion said: “There’s always a way.” 

2. Identify a career about which you can feel passionate — and that pays the bills. 

Trina Dye, 54, of Studio City, California, earned her BFA from CalArts in piano performance and had done most of her coursework for the MFA there, and then went on to tour with many musicians, including the Daniel Lentz group and Mel Powell, who worked with Benny Goodman in the ‘40s. But she gave up her dream of being a concert pianist when she had three children, as she has always gladly put her children first — and when she needed to support them as a single parent, jobs that merely paid the bills followed. As her children grew, she completed her MFA in music and began to publish an award-winning blog titled Middle Cinnamon Roll, about positive, punishment-free parenting. Now, at 54, her writing and research has led her to want to pursue her dream of becoming a clinical psychologist. “I am extremely excited at the prospect of a new career in something I am truly passionate about and in an area where I believe I can really help others.” Trina will begin her coursework this fall, after which she will work in a field that feeds her family — and feeds her soul as well. 

3. Ask yourself, “If not now, when?”

Marian Palaia, 62, of Missoula, Montana (and sometimes San Francisco) had worked as a Peace Corps volunteer in Nepal, a truck driver, an English teacher in Ho Chi Minh City, a bartender, a “chip girl” in a (poker) card room, a waitress, a gas station attendant, and most recently, as Program Director for the University of Montana at the Office for Civic Engagement — all before she became an acclaimed author. She attended the prestigious MFA program in Creative Writing at the University of Madison and received her MFA in Fiction there in 2012; her novel, The Given World, was sold at auction to Simon & Schuster and published in 2015. Marian had been writing for much of her life, but by the time she began applying to MFA programs when she was 54, she says she hadn’t written anything of substance in years. “It became a matter of, If not now, when?”

Everything about her “second act” has brought Marian satisfaction and joy — the writing, the great reviews (People magazine called The Given World “complex and haunting...vivid and unforgettable"), and being able to tell people she’s an author. When asked if it was worth all the challenges to get to this point, her answer is simple: “Can I say, Hell, yeah?”

4. Don’t focus on how long achieving your goals will take; the time will pass anyway. 

Kara Tsukerman, 35, of Atlanta, Georgia, had been working as a hair color specialist at Van Michael Salon for 10 years when she returned to college in 2014 after an 11-year break. When she arrived at her first class and took a seat, she was terrified, and when her professor said that the final exam would be a paper, she almost dropped the course. It was only three pages, and writing it was one of the hardest things Tsukerman has ever done. After completing her undergraduate degree, she immediately enrolled in a joint MA/PhD program in sociology, and the class she is in now requires 20-25-papers of publishable quality, and yet she “won’t even sweat it.” This shows how far she has come — and how anyone can accomplish their dreams with persistence and hard work

Tsukerman is studying the prevalence of sex/labor trafficking among homeless and runaway youth in metro Atlanta. Her goal is to finish her PhD and then find a job where her research can influence policy-makers. She says that while going back to college and discovering sociology has been the greatest thing she has ever done in her life, there have been challenges as well: Her husband is extremely supportive, but she still feels guilty about the time that school takes away from their relationship; leaving her lucrative full-time job in the salon has also been tough financially; and being in graduate school can be alienating. “It’s often easier to talk to my friends at school than explain what I’m doing to the other people in my life that I care about,” says Tsukerman. She has the following advice for other women whose “second act” involves going back to school: “Don’t worry about how long it will take. I will be close to 40 when I am fully in a new career. But one day I’ll be close to 40 anyway, so why not also be doing something I love?”

5. Turn challenges into opportunity.

Keri Olson, 60, of Baraboo, Wisconsin, has had successful careers in the fields of tourism, health care, and county government when she chose, two years ago, to take some time off to write a book, Find Your Heart, Follow Your Heart: Get to the Heart of What Matters and Create Your Abundant, Authentic, Joyful Life (Balboa Press, July 2017), and to become a public speaker. “My experiences with cancer and benign tumors in my brain and spine have given me moments to pause, reflect on what matters, and then view the good that I have in my life with gratitude and joy,” she says. “I wanted to share that message with others through a book, my blog, my social media presence and speaking engagements.”   

Mary Mceniry, 47, of Cedar Rapids, Iowa was a stay-at-home mom, consignment shop owner, and volunteer when she and her husband divorced and she immediately got cancer — and she was forced to find a job with insurance. She went into education because of the insurance, but found that she loved working with kids. She feels she’s a part of a real community with the school, and she likes that her own children are proud of her. With her newfound freedom as a single parent, she has also become involved in community theater, has taken a cabaret class and an improv class, adopted cats (which her ex hated), owns her own “kick-ass Prius named Angela Lansbury,” bought herself Birkenstocks (she says is never going back to regular shoes), and has changed her political affiliation. “For 20 years I did what I thought I should do,” Mary says. “What you should do can be so different than what you love.”

6. Identify a need, and then fill it.

Shavon Pierce, 54, of Huntington Beach, California, had been a stay-at-home mom and volunteer PTA president for many years when she found herself in a situation familiar to many women. Her children were grown and her parents needed in-home assistance. They were never satisfied with the care they were receiving, however, and went through eight companies in seven years. Shavon and her husband decided to fill a need they saw and open their own company, Home Instead Senior Franchise in Long Beach. While there are some challenges, Shavon loves owning her own business with her husband, creating a legacy for her children, helping other people, and doing work about which she’s truly passionate.

7. Turn a lifelong passion into a career.

Angela Washington, 50, of Houston, Texas, was 42 when her mother died, leaving her heartbroken and with a small inheritance. Angela was a single mom working as a restaurant manager at the time, a job that “paid the bills, but was killing me on the inside,” she says. When her mother died, she was overcome with happy memories of the two of them cooking and baking together, and she decided to do something with her mother’s money to honor those memories, and to build a better future for her six-year-old daughter. She quit her job and started her own catering company, specializing in making weekday suppers for working women too busy to cook. “I was petrified,” she says. “I knew a lot about cooking and food, but I didn’t know the first thing about opening up a business. But I did research and talked to other women who had done it. It’s been eight years now, and I can finally say the business is a success, and I’ve never been happier. I’ve made my mama proud, my daughter proud, and most important, I’ve made myself proud.”

8. Leave behind old notes of failure and success — and embrace new ones.

Marcia Brenner, 48, of Chicago, Illinois, is what most people would call a born teacher. What has changed, midlife, is her subject: Marcia was a college instructor when she took her first Pilates class, which blew her mind and “tapped into my teacher’s brain,” she says. She spent the next three years becoming a Pilates teacher, not considering it a career change at the time; she simply wanted to learn Pilates for her own education and benefit. Ten years later, it’s become her full-time career. “I think the hardest thing about a career shift is leaving behind the fantasy definition of ‘success’ you (or the world you work in) have been measuring yourself by, and to do the hard work of figuring out what you, and only you, feel is important,” Marcia says. “What I really needed was to stop worrying about other people’s measuring devices, and get to know what my own were.” 

If you’re dreaming of making the plunge into your second act, but aren’t sure how, Carol Fishman Cohen, co-founder of the career reentry firm iRelaunch, has the following tips and advice. 

9. Figure out what you want to do all over again and get clarity on your career or “second act” goals. 

Maybe you fell into your first career without a lot of thought, or you were fulfilling someone else's expectations. What are your interests and skills now, at this later point in your life? A career assessment and some coaching may be in order. Don't forget you may have resources at your alma mater in alumni career services that can be of help.

10. Go public with your job search or "second act" intention. 

Tell everyone you know what you are thinking about so you can get input (and sometimes opportunities!) from a wide network of contacts. Don’t conduct your job or “second act” search solely from behind your home computer.

Carol Fishman Cohen’s other tips include connecting with people from your past as well as from your present; joining Toastmasters; and attending university and college lecture series (often free and open to the public) relevant to your chosen field.

11. Take the leap.

Perhaps the last word of advice should best come from Dolly Parton, age 72, of Sevier County, Tennessee, one of the most successful and honored country performers of all time. Parton, who is not only a famous singer, songwriter, multi-instrumentalist, and actress, but a record producer, author, businesswoman, and philanthropist (and wife to her husband of 52 years), advises: “If you don’t like the road you’re walking, start paving another one.” 

This post was written by Kelly Dwyer, a published novelist and freelance writer.

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