What Churchill Knew About Getting Older

I confess right here that I’m a Winston Churchill fangirl. That might be the strangest sentence I’ve ever written but it’s true. For my 53rd birthday, my family ordered a custom ice cream cake that incorporated a Winston Churchill quote (my first obsession) and birdwatching (my second obsession). There’s probably no truer and weirder testament to their love for me, but that’s how we roll.

Cake with Happy Bird-Day Written on it
Proof of a Family’s Love (or Insanity) (Birds on Side of Cake), 2021

There’s so much to love about Winston Churchill: complexity, paradox, eccentricity, brilliance, courage, and more than a few fatal flaws. And I’ve just scratched the surface.

Although he was born into the British aristocracy at Blenheim Palace, Churchill wasn’t born with a silver spoon in his mouth. His parents could be neglectful and cruel, even for that period in history. They were spendthrifts, leaving him with virtually no inheritance. He had to earn a living from his writing, and managed his money poorly.

In fact, Churchill’s adult life was pockmarked with failure and struggle from beginning to end. It was especially challenging from ages 40 to 90. And yet, he kept going. And as I look at it from the vantage point of midlife, I’ve wondered, how?

When he was 40, Churchill’s enthusiastic support of the Dardanelles campaign in WWI resulted in hundreds of thousands of casualties and his removal as First Lord of the Admiralty. His wife Clementine said of that time, “I thought he would never get over the Dardanelles. I thought he would die of grief.” He was effectively cast out of productive public life for many years, grief-stricken, humiliated, and with his career in tatters.

To keep going — to climb out of the abyss — he threw himself into two oddly paired projects:

He wrote The World Crisis, a six-volume comprehensive account of the First World War, including his role in it and the lessons he learned.

And he started painting.

Casting about for a new purpose, he trained a critical eye on both the dark and the light. On the ugliest and the most beautiful. On the gritty and the glorious. He set out to dissect both sides, unsparingly.

Winston Churchill learned that in getting older, we can finally hold a view of the world where shadow and sunshine coexist. We finally realize that both sides are capable of teaching us and of healing us. We’re finally able to see — and embrace — the world as it is, and find solace in all of it.

In April, I realized a lifelong dream to visit Winston Churchill’s country house, Chartwell, in Kent, England. I saw where it all happened, where the books were written, where the paintings were painted. I saw the great sweep of Churchill’s life, the bitter and the sweet. And I understood, for the first time, how he kept going.

“When I get to heaven I mean to spend a considerable portion of my first million years in painting, and so get to the bottom of the subject.”
Sir Winston Churchill

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Helping you thrive in your 50s and beyond. Advice, tools, and inspiration for navigating midlife and post-work life (with just a tiny bit of travel thrown in).