Be happier, healthier, wealthier.

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Making a successful career pivot after age 50 can make you happier, healthier and wealthier than ever before. Photo by Jonas Kakaroto on Unsplash

After earning two academic degrees in journalism and bleeding newspaper ink from my veins for 25 years, I made a career pivot to digital communications.

It didn’t work out as planned. I was fired (for the first time in my life) at age 50.

It could have been the beginning of the end of a once-promising career. Instead, it was the beginning of a series of new beginnings, all requiring increasingly successful career pivots, thanks in part to the books I read.

What follows is my curated list of 10 books to help men over age 50 pivot to a place where they are happier, healthier and wealthier than ever before. It happened to me. It can happen to you!

Note: I include links for convenience, not for affiliate marketing. I don’t earn a single penny.

10 Books for Manly Career Pivots After 50

Reliable study paints alarming picture

An analysis of the federal Health and Retirement Study (done before a global pandemic dropped a bomb on the job market) showed 56% of Americans were pushed out of a job, one way or another, after age 50.

Include me in that statistic.

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Chart by the author using Canva. Sources: Data analyzed by ProPublica and Urban Institute.

Wait, there’s more!

Among workers over 50 who have lost one job, a third go on to lose two or more jobs.

Question: What are you doing to mitigate your risks and maximize your career opportunities after age 50?

See. Acknowledge. Ask.

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Life is about managing pain. What will you do if someone risks revealing their pain to you? Stock photo: Canva.

Do you know someone who is hurting, someone trying to get through their day, week and life managing their pain?

You probably do. It might be a family member, friend, neighbor, co-worker or the anxious person looking at you in the mirror. It might be someone grieving the passing of a loved one, the breaking of a relationship, the death of a vision, the shattering of hope, the relentlessness of racial discrimination.

Pain can feel like getting kicked in the stomach, leaving you breathless for a moment or several years. …

Can the 1973 hit inspire us still today?

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A 1973 song somehow made a yellow ribbon around a tree symbolize love, forgiveness, community, loyalty and hope. Photo: Canva.

In 1973, a nation divided over the Vietnam War, a growing Watergate scandal and racial issues took a step toward unity thanks to a song with a story everyone could relate to. We need a song like that now.

Perhaps the story of “Tie a Yellow Ribbon Round the Ole Oak Tree” can inspire someone to make a tune like that today. Or, to paraphrase Humphrey Bogart, maybe we need to “play it again, Uncle Sam.”

Sung by a Puerto Rican singer named Tony Orlando and two Black women from Motown collectively called Dawn, “Tie a Yellow Ribbon Round the…

“Happy hour” is now nap time

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Age is a state of mind, and your mind is, unfortunately, aging. Photo from Canva.

Are you a man turning 50 this year? Congratulations! Take it from me. It’s not that bad.

This could be the best decade of the rest of your life.

Like most things, it all depends on how you look at it.

I could say, “You’re not getting older; you’re getting wiser!”

But you have to be a Baby Boomer to understand that my clever play on words is a ripoff of the famous Clairol hair coloring slogan of the 1960s and early 1970s: “You’re not getting older, you’re getting better.”

Men turning 50 this year were born in 1971, meaning…

God’s plan to lift you up

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This often-overlooked verse promises a big payoff. Illustration by M.M. O’Keefe.

I call 1 Peter 5:6 my “lifetime verse” because the message of humble waiting for God’s perfect timing keeps coming back like a boomerang in my life.

In this reflection, I focus on what I’ve learned about 1 Peter 5:6 from my personal study of the Bible and life experience. Why? This often-overlooked verse promises a big payoff.

If you can grasp and embrace the recipe of 1 Peter 5:6, you are promised elevation, even exaltation, not by straining to pull yourself up some slippery career ladder, but by the power of a God who cares personally for you.


100+ digitally stitched-together YouTube renditions

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Montage made by M.M. O’Keefe on Canva, combining images of “The Blessing” on YouTube. Images from DJ Chuang’s YouTube playlist.

A hymn with more than 100 digitally stitched-together YouTube renditions called The Blessing has spread like a global fire, jumping cities, countries, continents and oceans.

Sometimes called “the Amen song,” The Blessing has empowered people with spiritual hope and unity in the midst of the COVID-19 pandemic.

According to author and podcaster DJ Chuang’s YouTube playlist, at least 145 digitally choirs from Australia to Zimbabwe have now recorded and released their own geographically focused versions of the song, some in languages other than English.

I’m a former journalist who was once the editor-in-chief of a news service that covers religion…

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My father, Maurice “Morey” O’Keefe on a cruise with me. Not shown: Dad’s best friend, “Percy Verance,” who never quit on him.

You’re smarter than you look!

Over the years, my father built up a collection of memorable idioms, jokes, maxims, proverbs, dates, and one-liners that he drew from for practically every occasion, delivered with a glimmer of amusement in his Irish eyes.

For example, when I came home as a kid with a sterling report card, I heard the quip, “Son, you’re smarter than you look.”

I never figured out if that was a compliment or an insult. I’m still not sure.

A life in search of meaning and humor

Maurice “Morey” O’Keefe built up this library of pithy quotes from a Siddhartha-like life looking for ultimate meaning in his journeys.

His life began…

His ‘velvet weapon’

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Author montage of photos assembled from the online exhibit, The “President and Humor,” at the Ronald Reagan Presidential Library.

Humor flowed from Ronald Reagan.

The 40th U.S. president charmed the public, disarmed political foes and alarmed the Soviet Union with a seemingly endless supply of funny jokes and sight gags.

The humor and wit of Ronald Reagan are on display and recorded for history in a refreshingly funny exhibit of 31 photos in the otherwise serious Ronald Reagan Presidential Library. The collection is titled “The President and Humor.”

The photos show Reagan’s humor at its best.

Ronald Reagan’s jokes sometimes jabbed, but they didn’t go for the jugular, in stark contrast to the mean-spirited digs and biting sarcasm that…

Ask for 20/20 hindsight

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Do you have 20–20 hindsight? Photo illustration by the author using an image from Canva.

One of my father’s memorable and quirky maxims was this: “Hindsight is 20/20.” It took me years to get what Morey O’Keefe, a Fulbright scholar turned semi-truck driver meant:

Life looks clearer in your rear-view mirror.

With time, you can sometimes see the domino effect of how one thing led to another to get you to where you are today. Not just the good stuff but the bad stuff and the in-between stuff.

What if you are a person of faith? Is there a way to look back on your life with eyes of faith to see not only what…

M.M. O'Keefe

I’m a communications VP, journalist & after-50 career and life coach who writes about faith, history and finding your purpose.

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