in: Family, Featured, People

• Last updated: September 26, 2021

The Churchill School of Adulthood – Lesson #6: Don’t Be Afraid to Start a Family

The Winston Churchill Header.

Of the many “contradictions” of Churchill’s life, one of the most interesting is that while he loved high-flying adventure, and relished danger, risk, and excitement, he was also, as a friend put it, “tremendously domestic.” Nothing gave him more happiness and satisfaction than his family, and while he loved traveling the world, he could sincerely say that “A day away from Chartwell is a day wasted.”

Yet the more one looks at his life, the less contradictory these two impulses seem. Not only was Churchill’s family life an adventure in and of itself, but it in fact made possible his other escapades and accomplishments.

A Lionhearted Couple Unites Their Lives

Young Winston and clementine Churchill.

“[My marriage] was much the most fortunate and joyous event which happened to me in the whole of my life.” -WC

Churchill was 34 years old when he got hitched. Making it with the ladies hadn’t been high on his list of priorities as a youth; he had far too many other interests, ambitions, and adventures to which to attend. He had sought marriage and courted a few women to be sure, but they had not returned his advances, until at last he found himself talking to one Clementine Hozier at a dinner party in March 1908. They had met briefly four years earlier; this time they fell for each other.

Clementine left shortly after the party for a trip abroad, and a smitten Churchill wrote to tell her “how much I liked our long talk on Sunday and what a comfort and pleasure it was to me to meet a girl with so much intellectual quality and strong reserves of noble sentiment.” This letter was followed by many other affectionate missives, to which Clementine responded in kind.

They were engaged by August. Churchill sent a letter to his future mother-in-law (Clementine’s parents were separated, and her father not in the picture) to ask for her consent and blessing in the marriage. “I am not rich nor powerfully established,” Churchill wrote her, “but your daughter loves me and with that love I feel strong enough to assume this great and sacred responsibility.” Winston and Clementine tied the knot the following month, and their wedding marked the beginning of a lifelong love affair. “In September 1908,” Churchill later recalled, “I married and lived happily ever afterwards.”

Winston and clementine Churchill walking together.

Lovers, companions, and friends, the Churchills’ marriage was a mix of healthy codependence and striking independence. They adored each other and professed their utter reliance on one another, but also happily partook in divergent pursuits. They slept in separate bedrooms – though that was normal for the time (and interestingly, is becoming more common today; a quarter of new homes are being built with separate his and hers bedrooms). As Churchill was a night owl and Clementine an early riser, their individual bedrooms allowed the couple to create and carry out their own morning routines. Each had their own preferred hobbies as well; Churchill enjoyed reading, painting, and gardening, while Clementine enjoyed more active pursuits and was fond of tennis, skiing, swimming, and even hunting boar. More unconventionally, they also vacationed separately – each taking their own desired trips.

Yet if their independence was unique, so was the depth of their devotion. They each put their spouse first. Beginning with Winston’s marriage, Manchester writes, “the overarching figure in his life had been his wife, and none of his other relationships, not even his love for his children, held him as closely as the matrimonial bond.” Unique for the women of her time, who typically offered the lion’s share of their affection and attention to their children rather than their husbands, Clementine too prioritized her relationship with Winston above all else; her daughter Mary recalled that he and his career “consumed the cream of her thought and energy.”

Winston and Clementine Churchill sitting on couch.

Together they could boast of a wonderful compatibility. Churchill rejoiced in the fact that “the sun has never yet gone down on our wrath. Never once have we closed our eyes in slumber with an unappeased difference.” They could talk about current events, and also be quite playful. Each had a pet name for the other – she was Cat or Kitten, he Pug or Pig – and the Churchills would often adorn letters to each other with drawings of their namesake animals.

It was in fact their great love for each other that motivated their mutual support of their respective pursuits. Clementine did all she could to aid Winston in his goal of becoming prime minister. But Winston didn’t wish his wife to lose herself altogether in furthering his aims, but to find her own fulfillment as well. In their tenth year of marriage, he wrote to her:

“My dearest sweet I hope and pray that future years may bring you serene and smiling days, and full and fruitful occupation. I think that you will find real scope in the new world opening out to women, and find interests which will enrich your life. And always at your side in true and tender friendship as long as he breathes will be your ever devoted, if only partially satisfactory, W.”

When she was in her 40s, Churchill encouraged Clementine to go alone on an exotic voyage that sailed to Komodo, stopping at many other sparsely developed islands along the way. While she was gone, Churchill wrote his wife:

“I think a lot about you my darling … and rejoice that we have lived our lives together; and have still some years of expectation in this pleasant vale…. I feel this has been a great experience and adventure to you and that it has introduced a new background to your life, and a larger proportion; and so I have not grudged you your long excursion.”

Then he added:

“But now I do want you back.”

When the Churchills returned from their respective adventures, the party crossing the threshold to Chartwell would cry out their affectionate mating call — “Wot!” — and the spouse in residence would echo a warm “Wot!” in return.

An Enduring Love

Winston and clementine Churchill outside smiling.

The Churchills’ romance lasted a lifetime, and is perhaps best displayed in the mountain of notes they wrote to each other, both when apart and together. As Manchester observes, even after many decades of marriage, Clementine’s “intimate letters to Churchill, and his replies, were as charming as an exchange between honeymooners.” Here are a few examples that demonstrate the depth of their love and affection, and the fact that they never sunk into complacency in their relationship; both Winston and Clementine ever wished to make each other happy and to overcome their human failings to be even more to each other than they were:

1909, after one year of marriage

Winston to Clementine:

“My darling I so want your life to be a full and sweet one, I want it to be worthy of all the beauties of your nature. I am so much centered in my politics, that I often feel I must be a dull companion to anyone who is not in the trade too. It gives me so much joy to make you happy—and often wish I were more various in my topics.”

1913, after five years of marriage

Clementine to Winston:

“My sweet and Dear Pig, when I am a withered old woman how miserable I shall be if I have disturbed your life and troubled your spirit by my temper. Do not cease to love me. I could not do without it. If no one loves me, instead of being a Cat with teeth and claws, but you will admit soft fur, I shall become like a prickly porcupine outside and inside so raw and unhappy.”

Winston’s reply:

“I loved much to read the words of your dear letter. You know so much about me and with your intuition have measured the good and bad in my nature. Alas, I have no good opinion of myself. At times, I think I could conquer everything—and then again I know I am only a weak vain fool. But your love for me is the greatest glory and recognition that has or will ever befall me: and the attachment which I feel towards you is not capable of being altered by the sort of things that happen in this world. I only wish I were more worthy of you, and more able to meet the inner needs of your soul.”

1918, after ten years of marriage

Winston to Clementine:

“Ten years ago my beautiful white pussy cat you came to me. They have certainly been the happiest years of my life, and never at any moment did I feel more profoundly and eternally attached to you. I do hope and pray that looking back you will not feel regrets. If you do it [is] my fault and the fault of those that made me. I am grateful beyond words to you for all you have given me. My sweet darling I love you very dearly.”

1935, after 27 years of marriage

Clementine to Winston:

“Oh my Darling, I’m thinking so much of you and how you have enriched my life. I have loved you very much but I wish I had been a more amusing wife to you. How nice it would be if we were young again.”

Winston’s reply:

“In your letter from Madras you wrote some words very dear to me about my having enriched your life. I cannot tell you what pleasure this gave me, because I always feel so overwhelmingly in your debt, if there can be accounts in love. It was sweet of you to write this to me, and I hope and pray I shall be able to make you happy and secure during my remaining years, and cherish you my darling one as you deserve, and leave you in comfort when my race is run.”

Given the Churchills’ commitment to never rest on their relationship laurels and to ever work on being better partners, it is not surprising that they managed to remain faithful to each other for almost six decades, until Winston’s death at age 90. One can practically count on two hands the number of famous men who stayed true to their wives, and there were naturally women who tried to woo Winston as well, but he was fairly oblivious to such overtures. Clementine was enough for him; “I feel there is no room for anyone but you in my heart–you fill every corner,” he told her.

Churchill ultimately had so many other passions in his life – in his career, philosophy, and marriage alike — to be interested in petty flings, a fact he made clear in a response to a letter from Clementine in which she worried he would stray during his many travels:

“We do not live in the world of small intrigues but of serious and important affairs. I could not conceive myself forming any other attachment than that to which I have fastened the happiness of my life here below … You ought to trust me for I do not love and will never love any woman in the world but you and my chief desire is to link myself to you week by week by bonds which shall ever become more intimate and profound.

Beloved I kiss your memory—your sweetness and beauty have cast a glory upon my life.

You will find me always
your loving and devoted husband,

Young Again: Winston’s Playful and Affectionate Parenting

Winston Churchill with Wif and daughter on patio.

The Churchill’s first child, Diana, was born nine months after their honeymoon. Diana was followed by Randolph, Sarah, and Marigold. Marigold tragically took ill and passed away when she was 3. Clementine gave birth to her last daughter, Mary, in 1922.

Churchill found true joy in being a father and absolutely adored his children. “Of all his roles,” Manchester writes, “the warmest, and most endearing, was that of paterfamilias.” Winston’s own parents had been cold, remote, and sometimes cruel, and he determined that his children would have a much different upbringing.

Accordingly, family life at Chartwell was full of fun and affection. Winston bestowed endearing nicknames on each of his children: Diana was “Puppy Kitten,” Randolph “the Chumbolly,” Sarah “Mule,” and Mary “Mouse.” The Churchill family had their own way of greeting each other as well; in place of hello, they’d call out “Wow-wow!” or “Miaow!”

Despite his appreciation for decorum and the weight of his responsibilities, Churchill never hesitated to get down on his children’s level to play with them. He’d read to them at night and tell them stories by the fire. Together they’d make snowmen, construct model bridges, and build hideouts in the woods. And Winston was always up for joining in their games. One of his favorites was “gorilla”: Churchill would hide behind a bush or up in a tree and leap out as the children approached. Growling and swinging his arms like a primate, the future prime minister pursued the children, and whoever he caught lost the game. As his nephew recalled, “The realism was alarming but we squealed with delight and enjoyed this exclusive performance hugely. Few people can say that they have seen an ex–First Lord of the Admiralty crouching in the branches of an oak, baring his teeth and pounding his chest with his fists.”

During the war, and with his children grown, Churchill did not have many opportunities for fun and games, but he still made time to see his family, and often went home to have dinner with them. Spending time with his children was a true balm during the stress of the crisis, and he found their presence immensely comforting and strengthening. No matter what else was going on in the world, Manchester writes, “His awareness of them was constant.”

Takeaways from Lessons #6

Winston and clementine Churchill standing outside posing.

Presenting marriage and family as an imperative tends to be a sensitive, and often unpopular, subject these days. So let’s get something clear right at the outset: while I personally feel that getting married and having children constitutes one of the best, if not the best way to cultivate the kind of generative selflessness that constitutes a fundamental marker of adulthood, these commitments are not at all necessary to becoming a grownup. The capacity to bring people and projects to life can be developed in other ways, and mature traits like personal responsibility, reliability, autonomy, and self-control are hardly exclusive to the domestic set.

The title of this lesson was thus chosen intentionally, as the takeaway is this: if the opportunity for marriage and children is a possibility for you, rather than being wary of it, embrace it if you can. For family life can truly offer some of the greatest satisfactions of adulthood:

Family life centers you. Ideally, your home becomes a refuge and sanctuary from the stresses and pressures of the world outside it. You can leave the day’s setbacks and annoyances at the doorstep, and be reminded of what really matters. Here are the people who know and love you best. Here you can be utterly yourself. Here you can create your own schedule, your own atmosphere, and your own traditions. “Here firm,” as Churchill put it, “though all be drifting.”

Winston Churchill with wife and grandchildren on outdoor swing.

Family life offers meaning and motivation. As we talked about in our series on the 3 P’s of Manhood, for thousands of years, men found their identity as members of a tribe, and were motivated to protect, procreate, and provide for the good of their people. These days, we’re more likely to find ourselves as fragmented parts of a network, rather than whole members of a community, but the family continues to offer a tiny tribe to which to belong and make one’s way through the world. Few things feel as real and satisfying to me as knowing “We are the McKays,” a merry band with its own mission and purpose. And nothing motivates me more to be a better man than wanting to do right by my wife and kids – to provide for them both material comforts and an example of character and strength.

It’s no coincidence that when the lives of 268 men were studied over a 75-year span, it was found that those who achieved the most professional and personal success, and led the happiest and most fulfilling lives, were those with the greatest capacity to foster loving relationships, especially within their families.

Family life renews your youthful energy. The effect of having children on your life constitutes a real paradox: on the one hand, they’re a huge responsibility and can really tire you out, but on the other hand, they also reacquaint you with some of the long-forgotten pleasures and energies of your youth. For the first time in a couple decades, you find yourself building with blocks, going down playground slides, and coloring with crayons. Holidays, which can become rather stale as you grow up, become re-imbued with fun. And kids become the best instructors in how to live more romantically; you get to re-experience the world through their fresh eyes, and partake of their excitement in learning and seeing things for the very first time.

Winston and clementine Churchill on deck of Boat.

Family life feels transcendent. Both getting married and having children opens up dimensions of the human experience that would otherwise be inaccessible. Your heart almost physically seems to expand in size, and it feels as though chambers of your love that you were hitherto unaware of are unlocked. As Manchester writes of Churchill, only Clementine and his children could tap into these hidden places of his soul:

“The only people who saw the intimate Churchill—who knew the power and depth of his love, which lay within him like a vast reservoir eternally replenishing itself, available to them in boundless measure when they were parched or careworn—those few whom he cherished, were his family.”

As one’s 20s and 30s wear on, and the once-fresh routine of work/travel/friends gets repeated in an endless loop, a feeling of having reached a plateau often sets in, along with the question: “Is this all there is?” The answer to this searching feeling is no, for a new world can be discovered and explored within the bonds of family.

It’s a world that can sometimes feel transcendent, that can lift you out of an existence that so often feels crowded with tiresome superficialities. Love is the one thing that unfailingly feels of a nature not of this world. Even someone like Churchill, who doubted the existence of a spiritual realm, experienced his love for his wife as “profound” and “eternal” and hoped for an afterlife so that their relationship could continue. “If there is anywhere else,” he told Clementine, “I shall be on the look out for you.”

For me, my family doesn’t just spark my spirituality, but in many ways is my spirituality. In a world that can often seem flat and meaningless, it is the one thing that perennially replenishes the freshness of my life, and seems the most mystically “meant to be.”

Embrace the Adventure of Marriage

Winston and clementine Churchill standing next to Airplane.

Family life ideally begins with marriage, but many young adults are increasingly reluctant to take this step. Fewer Millennials are married now than previous generations were at the same age: 26% compared to 36% of Generation X, 48% of Baby Boomers, and 65% of the members of the Silent Generation. Pew researchers project that if trends continue, the Millennial generation will include a record number of folks who never get married at all.

This modern wariness about getting hitched is often rooted in a fear that one’s relationship will end in divorce. Yet the ironic thing about marriage, is that while it may very well constitute, as Joseph Barth puts it, “Our last, best chance to grow up,” the modern perspective on it is thoroughly adolescent.

Folks today often see getting married as a kind of Russian roulette – an endeavor based purely on chance in which one has no idea as to whether it will work out or not.

A better, and surely more inviting way to see marriage is as an adventure. If, as we discussed in our last lesson, the elements of an adventure are 1) a chance for failure/harm, 2) the inability to completely plan out what will happen and how things will go, and 3) challenge and the calling forth of your deeper abilities, then marriage certainly fits the criteria to a T:

Risk. Might your marriage fail? It might. And yet the dangers of matrimony are regularly over-exaggerated.

Contrary to popular belief, divorce rates are not going up, but have actually been declining for three decades. And the well-known “fact” that 50% of marriages end in divorce is a myth as well. According to a report by The New York Times, “About 70 percent of marriages that began in the 1990s reached their 15th anniversary” and “If current trends continue, nearly two-thirds of marriages will never involve a divorce.” For the college-educated, the numbers are even more optimistic: among those who married in the early 2000s, so far only 11% have parted ways.

Even these much less dire numbers can be reduced down further. As with any adventure, potential risks can be mitigated through thorough planning and staying vigilant on the journey. Couples that make thoughtful, intentional decisions about their relationship while dating end up with higher-quality marriages. And of course marrying the right person is huge in reducing your chances of divorce. Rather than being akin to a game of Russian roulette, the dangers of a potential partner are almost always evident while you’re dating…if you’re willing to acknowledge such red flags with open eyes.

While it is indeed possible for a woman to do a complete 180 after you’re hitched, the chances of marrying a bad apple with no previous warning signs at all is probably about that of dying in a car accident. And nobody goes around saying, “Dude, you should give up driving altogether – too dangerous.” The relatively small risk is worth how far a vehicle can take you.

As with all adventures, some risk is inherent in marriage. But it wouldn’t be such a compelling adventure without it!

Winston and clementine Churchill riding Horses Horseback.

The Unknown. Part of what makes marriage an exciting adventure is that you don’t know where the journey is going to take the two of you. Life is thoroughly unpredictable. When Kate and I got married, we had no idea where we’d end up living, what our kids would be like, or that we’d be running a website about manliness together!

Venturing into the unknown can be a little scary, but it’s much less so when you have a constant companion by your side. Friends come and go, but your spouse will always be there. It’s terrifically fun to dream about future goals and make big, life-changing decisions together. And when the hard stuff comes, you’ve got someone with which to share the burden. Being a grownup can sometimes feel like pulling a mighty heavy plow, and there’s no greater asset in the task than being yoked next to someone who’s just as dedicated to planting and growing a beautiful life as you are.

Winston and clementine Churchill touring war ruin with group of Men.

“Thus the world wages–good, bad and indifferent…and only my sweet Pussy cat remains a constant darling.” –From a letter from Winston to Clementine

You don’t have to take my word for it either; a recent study found that getting married makes people happier and more satisfied with their lives, and that this buoying effect is particularly pronounced when the couple goes through periods of stress and hardship. So too, the study found that those who feel they are married to their best friend, get twice as much life satisfaction from their marriage.

Churchill knew this comforting, centering effect of marriage well, and felt he could not have achieved his many adventures or accomplishments without Clementine’s companionship:

“My ability to persuade my wife to marry me was quite my most brilliant achievement…Of course, it would have been impossible for any ordinary man to have got through what I had to go through in peace and war without the devoted aid of what we call, in England, one’s better half.”

As the old proverb goes, “Shared joy is double joy; shared sorrow is half sorrow.”

Challenge and the calling forth of your deeper abilities. Marriage is really a classroom of personal development. If you’re dedicated to becoming an ever better spouse, slowly your rougher edges get rounded off, your more selfish impulses get refined. You learn to compromise, to forgive, and to have more empathy. You learn to create a relationship that’s entirely yours, and to not care if it doesn’t match up with what others are doing. Maybe your marriage will look like the Churchills, where you retain a lot of your independence; maybe you’ll discover happiness in spending 24/7 together, as we have. Crafting the unique nature of your relationship will be part of the journey. The important thing is to accept the challenge to never get complacent about becoming a better lover and friend. As with any great adventure, if you get your attitude right, you’ll come out the other side a different person than you were at the start.

Winston and clementine Churchill sitting on small couch.

The Churchills on Winston’s 80th birthday.

Ultimately, life is an adventure, and any adventure is more enjoyable when shared. When your story unites with another’s, the narrative becomes all the richer. Your memories become wonderfully intertwined, and this shared past becomes one of the most valuable things you accrue along your journey. As Churchill wrote to his beloved wife:

“What it has been to me to live all these years in your heart and companionship no phrases can convey. Time passes swiftly, but is it not joyous to see how great and growing is the treasure we have gathered together, amid the storms and stresses of so many eventful years?”

Read the Entire Series

The Winston Churchill School of Adulthood Is Now in Session
A Prerequisite Class on Becoming the Author of Your Own Life
Lesson #1: Develop a Mighty Moral Code
Lesson #2: Establish a Daily Routine
Lesson #3: Live Romantically
Lesson #4: Cultivate a Nostalgic Love for History
Lesson #5: Don’t Give Up Your Sense of Adventure
Lesson #7: Work Like a Slave; Command Like a King; Create Like a God
Tips on Hustling, Leadership, and Hobbies from Winston Churchill
Conclusion: Thought + Action = An Awesome Adulthood



The Last Lion Trilogy by William Manchester

Clementine Churchill: A Biography of a Marriage by Mary Soames

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