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Work & Purpose

In Midlife, Take a Second Bite of the Cherry

Advice from the 'Generation Cherry' author on finding meaning in your life


There’s an expression in the United Kingdom that can be especially apt for Americans in their 50s and 60s: “Take a second bite of the cherry.” Basically, it means to take a second chance at something.

Tim Drake, a 74-year-old British motivational speaker and former advertising executive, has just written a book on how to do it. In Generation Cherry: Powerful Strategies to Give You a Second Bite of the Cherry, Drake lays out ways to adopt a “fresh mindset for a fresh opportunity.”

According to Drake, “The first bite of a cherry is nice. But the second is even better. Having a second bite of the cherry means once you have one bite, you’re not finished.”

Tim Drake
Tim Drake

Boomers and Generation Cherry

He uses the cherry metaphor in a second way, too. “The cherry is about the boomers hitting the jackpot,” said Drake, who has dubbed that cohort Generation Cherry. “In our youth, we were fully employed. We could get a job anywhere anytime. And many of us had pensions. It was a great time to be alive.”

Then things changed.

“Now the whole thinking is shrinking austerity, globalization and inequality of income, which is a terrible outcome of globalization,” said Drake.

But rather than moan about this state of affairs, boomers should instead exploit trends to keep working and lead fuller, more meaningful lives, advises Drake, who also co-wrote You Can Be As Young As You Think: Six Steps to Staying Younger and Feeling Sharper.

His Own Second Bite of the Cherry

Drake took a second bite of the cherry after the sports shoe shop he and a friend opened went bust.

As he describes it in Generation Cherry, shortly before his 50th birthday, “a gentle cruise towards a successful and comfortable retirement turned into a bit of a whitewater ride.” He had two young girls and no job.

“I had to take stock of what my life had been about,” said Drake. Since then, he has set up think tanks, written several books and become a self-employed consultant. Drake works four days a week.

There are two keys to getting a second bite of the cherry, according to Drake.

generation cherry2 Keys to a Second Bite

The first is what he calls “enlightened thrift,” which Drake refers to as “prosperity alongside frugality.” It’s about spending wisely.

“My feeling is that everything that’s important in life is free — things like walking and friendship and music. We need to get back to what is important and not worry about what the size of our car is,” said Drake.

The other key, Drake believes, is living the “four autonomies” — earning money (perhaps through gig economy jobs), continually learning, giving to others and recharging your batteries by staying in shape physically and mentally.

“Autonomy is about having control of your life,” said Drake. “With autonomy, you can control when you work and how you work. That could mean being your own boss or working from home.” Self-employment, Drake maintains, can also help your avoid age discrimination by employers.

Mastermind Groups and Body Age

Drake’s a big fan of forming a “Mastermind Group.” That’s a group of people you trust and respect — either in person or online — whose members generously help each other.  “It’s great if you’re going through a bad patch because it keeps your spirits up,” said Drake.

Finally, Drake suggests, pay less attention to your actual age and more attention to your “Body Age” (how fit you are) and your “Brain Age”  (how sharp you are). Several websites let you take an online quiz to estimate your Brain Age.

Drake — who runs, plays tennis, swims and goes to the gym regularly — estimates his Body Age is “late 50s or early 60s.” And his Brain Age? “I hope it’s about 26 or 27.”

Richard Eisenberg
By Richard Eisenberg
Richard Eisenberg is the Senior Web Editor of the Money & Security and Work & Purpose channels of Next Avenue and Managing Editor for the site. He is the author of How to Avoid a Mid-Life Financial Crisis and has been a personal finance editor at Money, Yahoo, Good Housekeeping, and CBS MoneyWatch.@richeis315

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