SECOND CAREERS

Can You Have A Second Career As You Enter Your Late Sixties?

I am about to find out.

Jill Ebstein
Crow’s Feet: Life As We Age
4 min readAug 14, 2024

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Blue sky with some white billowy clouds
Photo by Kumiko SHIMIZU on Unsplash

I turn 67 this fall, which I consider the beginning of my late sixties. It is also when I ask myself whether I can embark on a second career.

The second career, were I to have one, would be nothing like my first.

My first career relied on my MBA, analytical skills, salesmanship to find and retain clients, diplomacy on multiple fronts, and paranoia that I might have just serviced my last client.

Paranoia is what makes you reach out, again, to the one who said, “Maybe in six months…” You never forget the remotest of possibilities.

One of my favorite business reads was Andy Grove’s Only the Paranoid Survive. I could relate. When my phone wouldn’t ring, and the emails wouldn’t come, I’d call my husband at work and sing,

“Nobody likes me. Everybody hates me. I’m gonna go eat worms.”

He would tell me to knock it off and do something fun. “Isn’t this what they call ‘beach time?’ It won’t last, so enjoy it.”

He was right, and I tried hard to enjoy the symbolic beach. Sometimes, I succeeded.

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Crow’s Feet: Life As We Age
Crow’s Feet: Life As We Age

Published in Crow’s Feet: Life As We Age

“The longer I live, the more beautiful life becomes.” (Frank Lloyd Wright) Non-fiction pieces, personal essays and occasional poems that explore how we feel about how we age and offer tips for getting the most out of life.

Jill Ebstein
Jill Ebstein

Written by Jill Ebstein

I’m about dogs, our lovable and peculiar families, business, and writing in a wide lane, including fiction. I’m a positivity washer too. www.jillebstein.com