Reinventing Yourself Over 40 Isn’t Easy, But It Sure Is Worth It!

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Almost every woman I know is in the same situation: We had a career before we had kids, and now we want to (or have to) go back to work and don’t know what the heck we’re supposed to do! Women over 40 want flexibility and they want to feel good and be passionate about what they do professionally. So, that usually means reinventing yourself, and anyone who has ever experienced it will tell you that reinventing yourself over 40 isn’t easy.

This week’s Love Essentially is the story of New York real estate agent, Annette Akers, who reinvented herself and is as happy as can be. Here is the article, which includes tips on reinventing yourself over 40!

Do you love yourself enough to reinvent yourself?

by Jackie Pilossoph for Chicago Tribune Media Group

Eleven years ago, when Annette Akers up and moved to New York City after living her entire life in Illinois (19 years in Chicago), she was optimistic it was going to be great for her career.

“It was exciting, and I felt like moving to that market would help me grow with the company,” said Akers, who at the time was working in sales for a large medical device company.

But life took an unexpected turn. Claiming to this day that she was “bullied out of the company” by a male coworker who felt financially threatened by her success, Akers found herself out of a job two years later. A double whammy: It was during the 2007 recession.

“At first I wasn’t too worried about finding another job because it had always been easy for me in the past,” said Akers, who is now 50. “But when I started looking this time, I would always lose out to someone younger, and who was usually a male.”

During the years that followed, Akers tried starting her own company and performed contract work for medical companies. She ended up landing another medical sales job, but said it didn’t feel challenging or fulfilling. Akers said she felt frustrated and stuck. Then, one day, she had a realization. (click here to read the rest of the article, published in the Chicago Tribune and other major publications across the country.)

Like this article? Check out, “8 Job Searching Tips For Moms Going Back To Work After Divorce”

And, check out West Side Wednesdays, a creative marketing tool that Akers said has helped her business immensely!




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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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