Diann Wingert | The Real 50 over 50

About me

Diann Wingert became a business strategist, coach, and mentor after a 20-year career as a no-BS psychotherapist.

Her mission is to help women with big ideas and busy brains get focused, fired up, and flame retardant. Diann is an expert on women who are twice exceptional like herself (ADHD + gifted), encourages women to embrace standing out instead of fitting in, and embraces the opportunity in aging to grow bolder, not just older.

She is the creator of The Boss Up Breakthrough, host of The Driven Woman Entrepreneur Podcast, and is frequently referred to as “The Speaker of Uncomfortable Truths.”

What do you do and why do you do it?

I came to believe that what makes us different makes us special and that there are 3 reasons that half of all women at midlife are on medications for anxiety and/or depression:

  • the accumulated toll of 3 decades of feminine conditioning
  • once we are no longer under the influence of estrogen (the “tend & befriend” hormone) we realize that our life is half over and we never learned to think for ourselves or were given permission to do so or role models who are doing so, and
  • there aren’t enough older women who have the guts to tell the truth.

What changed for you after age 50?

Just about everything. After the estrogen evacuation (menopause), I realized that I was running out of time to make a real contribution and that conforming to the norm in order to fit in was just not working for me.

I changed careers, relocated, started a business, renegotiated my marriage, let go of friendships I had outgrown, got officially diagnosed with ADHD (after suspecting I had it for decades), started being unapologetically honest, and began practicing radical self-acceptance.

And I started a podcast during the pandemic to reconnect with my abandoned career goal of being in broadcasting (which I was talked out of at 20 by a male “guidance counselor” at UCLA, where I was earning a degree in communications.

What would you tell the 20 or 30-year-old YOU?

Guts don’t lie.

There is nothing wrong with you.

You are meant to stand out, not shrink to fit.

Most people follow the herd, “pick and stick” and live lives filled with unnecessary suffering because they don’t know who they are or what they want and lack to courage to find out.

You are an outlier. You are not a lone wolf. You need a wolf pack. You won’t find one that’s just right for you. Create your own.

What do you think you’ll tell yourself in retrospect at the end of your life?

Life is an orange. You squeezed the flesh, ate the rind, and then swallowed the seeds.

What impact do you think increased visibility can have on your business?

More of my people will find me.

Who or what inspires you and why?

Barbara Corcoran. She came from nothing, everyone underestimated her, she is a genuine self-made success. She’s also playful, funny, generous, and a great example of what is possible when you bet on yourself and ignore the doubters and the haters

Meet More of the Real 50 Over 50 Women

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