in: Character, Featured, Manly Lessons

• Last updated: September 26, 2021

The Churchill School of Adulthood — Lesson #5: Don’t Give Up Your Sense of Adventure

The Winston Churchill Header.

All his life, William Manchester writes, Churchill loved to look at maps, “as much for their utility as for their ability to stoke his imagination. Maps and naval charts lifted him away to far-off places and conjured images of heroic adventures long past.” Many have felt a similar affinity for the possibilities symbolized in maps; but unlike most men, Churchill did more than contemplate exploring distant lands — he got up and went.

Churchill saw his entire life as a romantic adventure – a hero’s journey. And, he felt, there was no greater, more romantic adventure than war — for war was the arena in which heroes were most readily forged.

Winston Churchill Quote Men who derive exaltation from danger.

His was not the fantasy of an armchair general; he intentionally sought out the battlefront his whole life through, saw action in several conflicts around the world, and came under fire over 50 times. Indeed, rather than extinguishing Churchill’s ardor for war, his firsthand experience only heightened it. By way of explanation he famously offered that “Nothing in life is so exhilarating as to be shot at without result.”

Churchill’s appetite for the excitement of combat was first whetted when he traveled to Cuba as a 20-something war correspondent. Writing in 1930, with the horrors of the Great War still fresh in his audience’s mind, he tried to explain how the prospect of witnessing a firefight might still emit an aura of romantic adventure:

“The minds of this generation, exhausted, brutalized, mutilated and bored by War, may not understand the delicious yet tremulous sensations with which a young British Officer bred in the long peace approached for the first time an actual theatre of operations. When first in the dim light of early morning I saw the shores of Cuba rise and define themselves from dark-blue horizons, I felt as if I sailed with Captain Silver and first gazed on Treasure Island. Here was a place where real things were going on. Here was a scene of vital action. Here was a place where anything might happen. Here was a place where something would certainly happen. Here I might leave my bones.”

Churchill goes on to describe what it was like to wake up on his first morning after being embedded with Spanish troops, who are preparing to march into the jungle in search of the enemy:

“Behold next morning a distinct sensation in the life of a young officer! It is still dark, but the sky is paling. We are in what a brilliant though little-known writer has called ‘The dim mysterious temple of the Dawn.’ We are on our horses, in uniform; our revolvers are loaded. In the dusk and half-light, long files of armed and laden men are shuffling off towards the enemy. He may be very near; perhaps he is waiting for us a mile away. We cannot tell; we know nothing of the qualities either of our friends or foes. We have nothing to do with their quarrels. Except in personal self-defence we can take no part in their combats. But we feel it is a great moment in our lives—in fact, one of the best we have ever experienced. We think that something is going to happen; we hope devoutly that something will happen; yet at the same time we do not want to be hurt or killed. What is it then that we do want? It is that lure of youth—adventure, and adventure for adventure’s sake. You might call it tomfoolery. To travel thousands of miles with money one could ill afford, and get up at four o’clock in the morning in the hope of getting into a scrape in the company of perfect strangers, is certainly hardly a rational proceeding. Yet we knew there were very few subalterns in the British Army who would not have given a month’s pay to sit in our saddles.”

After covering war as a journalist and experiencing the excitement of battle second-hand, Churchill sought out opportunities to involve himself as a combatant himself. He persistently petitioned his superior officers and anyone else who would listen for a position on the frontlines and eventually saw action in India, Egypt, and South Africa. One of the satisfactions of such adventures, Churchill found, was the way in which their inherent danger and action compelled a man to live simply and narrow his focus. Of his time during the Boer War, he wrote:

“We lived in great comfort in the open air, with cool nights and bright sunshine, with plenty of meat, chickens and beer. The excellent Natal newspapers often got into the firing line about noon and always awaited us on our return in the evening. One lived entirely in the present with something happening all the time. Care-free, no regrets for the past, no fears for the future; no expense, no duns [financial demands], no complications.”

Though Churchill left the military when he was 26 to make a career as a politician and writer, he missed combat and felt drawn back to the frontlines. Thus in 1915 when he found himself out of favor in Parliament, he rejoined the British Army and journeyed to the Western Front to command the 6th Battalion, Royal Scots Fusiliers. During this tour of duty, he intentionally subjected himself to danger by making 36 forays into “No Man’s Land,” the treacherous territory between the British and German trenches where nary another soul dared to step for fear of being picked off by the enemy.

While Churchill lived like a pampered pasha at home, he thoroughly enjoyed his time in the muddy, rat-filled trenches where the “cannonade and fusillade were unceasing.” “I do not know,” he wrote at the time, “when I have passed a more joyous three weeks… I share the fortunes of a company of Grenadiers. It is a jolly life with nice people; and one does not mind the cold and wet and general discomfort.”

Churchill, Manchester writes, simply had “a remarkable gift for romanticizing squalor.” For Winston, the danger and hardships were all part of the adventure.

A Note on Churchill’s Affinity for War (And Our Repulsion to It)

As we shall see, agreeing with Churchill’s equation of adventure with war is inconsequential to the takeaways of this piece. But as Churchill’s ardor for war is perhaps the hardest part of his personality for us to understand, it’s worth offering a little context for it.

To better understand Churchill’s perspective, a few things should be noted. The first is that that he grew up in a time without mechanized warfare, where combat was more gentlemanly, and as he puts it, “Nobody expected to be killed.” When war did become mechanized and mercilessly deadly, he fully acknowledged that its nature had fundamentally changed and that combat had “now become cruel and squalid.”

Secondly, he personally had no fear of death, calling it “only an incident, and not the most important that happens to us.” He (unfairly) projected such an attitude to others, and believed that all men would rather die doing something truly exciting than live out lives of “quiet desperation.”

Most importantly, while critics paint him as a warmonger, and assume that his penchant for glorifying war led him to try to instigate one, Manchester counters that “He was in fact the country’s number one peacemonger” and that “no man ever fought harder for peace.” Churchill championed the League of Nations in the belief that it would foster the collective security necessary to avoid another global crisis. And his untiring, lonely efforts in the 1930s to get Europe to wake up to the dangers of Hitler was nothing less than an attempt to foster actions that might prevent the same. Someone who hoped for war would have stayed quiet and gleefully relished the prospect of a coming armageddon; Churchill did the very opposite.

He was in fact dead set against men losing their lives in unnecessary wars. But, if war was inevitable, he saw no reason why such a fight should not be imbued with glory and honor and that men should approach battle as their ancestors had in ancient times.

That Churchill was able to view the unvarnished carnage of battle with clear eyes, and yet still see war as a romantic endeavor, is a concept many moderns will find nearly impossible to understand. Our inability to access such a viewpoint likely has much to do with the fact that only a tiny, tiny percentage of the present population has ever seen combat. Men who have, report that war is cruel and terrible…but also the most exciting, meaningful, and ultimately compelling thing they ever experience in their lives, and that they are often drawn back to it again and again. (To understand this paradox, I cannot recommend highly enough Sebastian Junger’s War).

The Maturation of Adventure

As Churchill grew older, got married, and had children, his life settled down a little more. His longing for adventure remained acute, but he found different, more generative ways to sate it.

One arena that offered him a new form of excitement and challenge was his writing; giving birth to the ideas in one’s head can truly feel like a heroic labor:

“Writing a book is an adventure. To begin with it is a toy, then an amusement. Then it becomes a mistress, and then it becomes a master, and then it becomes a tyrant and, in the last stage, just as you are about to be reconciled to your servitude, you kill the monster and fling him to the public.”

Winston Churchill standing speaking at meeting.

Churchill also found adventure in his political career. He got quite a rise out of running for election, trying to get legislation passed, and trading barbs with his fellow MPs. Giving speeches and debating under the pressure-cooker stresses found on the floor of Parliament was a form of verbal combat in which Winston had to always be on his toes. As he told a reporter, politics proved to be “almost as exciting as war and quite as dangerous.” When the newsman asked “Even with the new rifle?” Churchill replied, “Well, in war you can only be killed once, but in politics many times!”

While Churchill’s role as statesman required much memo-writing and report-reading, he also found opportunities to be more effective in his work, while adding greater adventure to his job. During WWII, he was always looking for ways to step away from his desk, and thus made numerous diplomatic trips abroad. He was, Manchester notes, “the first leader of any nation to undertake a transoceanic flight” and he logged far more air miles than the heads of the other Big 3 powers. These dangerous trips found him sprawled out on a tick mattress situated in the back of an unheated, seatless B-24, as the plane flew over enemy territory.

Winston Churchill in field watching Military drills.

Though Churchill’s penchant for adventure matured with his years, his enthusiasm for danger and risk could not be completely curtailed. While he couldn’t be out on the battlefield, he never stopped trying to immerse himself in the action. During the air raids of WWII, he eagerly – recklessly – would climb to the rooftop of his headquarters in London to watch the bombs fall from the sky. “There,” Manchester writes, with “gas mask at his side, armed with a glowing cigar and binoculars, he watched for bomb flashes. He counted the seconds until the crunch of the bomb reached him. Five seconds, one mile. Persuading him to leave the roof proved difficult at best.” The next day, he would venture out into the wreckage and rubble of the city, assessing the damage, and buoying the spirits of his besieged, beloved Englishmen.

Churchill would later call 1940 – a year in which ceaseless German bombings wreaked death and destruction on England – the time in his life he would most certainly repeat if he could. For it was a year, he said, when “it was equally good to live or die.”

While Churchill remained nostalgic for the exciting, meaning-laden years of WWII, he didn’t spend his later years sitting around longing for days gone by. Even into the last decade of his life, he continued to feed his wanderlust, making numerous trips to Sicily, Morocco, the French Riviera, Rome, Paris, New York, and Washington in the name of both pleasure and diplomacy.

Takeaways from Lesson #5

Winston Churchill quote curse ruthless time.

Keeping a sense of adventure as an adult is a necessary component of growing up well. Adventures, whether big or small, lend our lives a sense of interest, challenge, and excitement, and ensure our personal growth doesn’t grind to a halt.

They also help us to retain our youthful ability to live in the present. Last week we talked about how important it is to learn from the past and foresee the future, but the ultimate goal is to have that wide perspective, while still being able to concentrate on the here and now. Adventures often strip our lives down to the essentials (think of packing for a camping trip), and their inherent excitement and risk reminds us that we’re alive and of the fragile state of mortality. As Manchester shares, that was certainly adventure’s effect on Winston:

“Churchill squeezed the present for all it was worth. He believed meaning is found only in the present, for the past is gone and the future looms indeterminate if it arrives at all. Churchill was an old trooper who, whether at his easel, speaking in the Commons, or dining with his cronies, manifested the soldier’s creed: savor the moment, for it may be the last.”

For Churchill, the greatest form of adventure was war. But one need not share his romantic conception of combat to understand the need for more adventure in your own life. Adventure can indeed take many forms – it even did for Churchill himself.

But what is adventure, anyway? And how do you have more of it even as you embrace the responsibilities of adulthood?

What Is Adventure?

We plan on doing a whole post on the nature of adventure down the road, but for now, let’s just outline a few of its essential elements:

  • A chance for failure/harm. An adventure must have an element of risk – a chance that you may fail in the endeavor and/or become injured in some way. The most potent adventures carry the risk of physical harm or death, but financial, social, and emotional challenges can feel like adventures as well.
  • The inability to completely plan out what will happen and how things will go. If you know exactly how an endeavor will start, proceed, and end, it isn’t an adventure. An adventure must have an element of the unpredictable and unexpected.
  • Challenge and the calling forth of one’s abilities. An adventure can’t be completely easy, and must at times call upon your ability to dig into your deeper qualities and skills. Two of the most fundamental traits activated by a true adventure are resolution and courage, which are necessary to propel you on when the endeavor becomes scary and/or difficult.

How Do You Maintain a Sense of Adventure as an Adult?

Most children are naturally adventurous. In their imagination they’re a great explorer or archaeologist, even when they’re confined to scouting around the backyard. As adults, we finally have the freedom and resources to take the kinds of adventures we dreamt about in our youth. Yet the weight of our responsibilities can make us feel even more hemmed in than when we were kids, and we lose our drive to take action and our comfort with risk. Such challenges need not be fatal to our sense of adventure, however; every adult, in every situation, can have more of it, if they intentionally seek it out.

Evaluate how much adventure you personally need. These days we’re kind of taken with the notion that everyone should be a grand adventurer, and that if you’re not living like Indiana Jones, you’re going to suffocate under the weight of your boredom. But the truth is that everybody needs a different level of adventure in their lives to be satisfied. This isn’t just speculation, but a biological fact; people with a certain gene are more willing to take risks, and get more pleasure out of doing so. Churchill very likely had this gene. Another eminent man from history, Henry David Thoreau, likely did not; Thoreau hated being away from his hometown and rarely traveled outside it. He found his satisfaction in taking nearby hikes and staring at the water of a pond for hours on end, discovering new things.

So one of the keys of a happy adulthood is being honest with yourself as to whether you’re more of a Churchill or more of a Thoreau (or more likely, somewhere in-between). It can be just as damaging to write off adventure altogether, as it is to feel that you absolutely should have the desire to sail around the world and climb Everest. Putting such “shoulds” on yourself will only result in acute restlessness and FOMO.

If you’re someone who craves a great deal of adventure, then make seeking it a top priority.

If you’re someone who feels satisfied with a lower level of adventure, you should accept that, but also be vigilant about letting adventure drop out of your life altogether. Folks who have a less intense itch for adventure will often neglect to scratch it at all — especially as the responsibilities of adulthood crowd their lives.

Decide how you like to take your adventure. Adventure can take many forms, and your preferred form may change as you get older and enter different seasons of your life. Churchill thought war represented the pinnacle of adventure, but as he aged, he found ample excitement in writing, politics, and travel as well. The kind of adventure you most enjoy will be personal to you, and you should discover what it is – without paying too much mind to what others think it “should” be.

For example, I’ve never had much of the travel bug at all, and no burning desire to see the world. In our peaceful, prosperous times, travel seems to have become the end-all, be-all of adventure, so perhaps this inclination marks me as an uncosmopolitan dolt. So be it. What I am inclined towards is spending time in the great outdoors, and seeing a bunch of different national parks is on my bucket list. So too, this year I’ve made it a goal to learn how to rock climb. I also find that entrepreneurship, and even family life can oftentimes feel like an adventure. These are the activities that give me a sense of excitement and challenge. Find what endeavors do it for you.

Take risks in the direction of your goals. Churchill mused that youth seeks “adventure for adventure’s sake.” Invigorating your own excitement is not an unworthy goal, but as you mature, you should shift some of your adventurous impulses towards more productive ends – endeavors that benefit not only you, but others as well.

As you get older, and have more people relying on you, you’ll begin to have more to lose than gain from taking dangerous risks. So be judicious with your risk-taking, and take ones that are aligned with your greater goals. Churchill’s transcontinental flights not only gave him a thrill, but furthered the war effort. Starting your own business can not only be a satisfying personal adventure, but also allow you to be home more with your kids.

Winston Churchill looking at war map with general.

Pick a job with adventure. The greater your craving for adventure, the more important it is to choose a job that comes with a degree of adventure built-in. As you get older, you’ll likely have more and more responsibilities, and taking off on spontaneous adventures-for-adventure’s-sake will become more difficult to do. In having an adventurous job, you ensure that one of those responsibilities not only doesn’t impede your sense of adventure, but requires it. Churchill, for example, was able to satisfy his penchant for risk and excitement through choosing to become a politician, a role that required making high-stakes decisions and crisscrossing the globe. If you need a high level of adventure in your life, choose to become a soldier, firefighter, war correspondent, pilot, etc., rather than becoming an accountant.

Bring more adventure to whatever you do. In any situation, you can make moves to add a greater element of adventurousness. The best example of this is your yearly vacation. Most people get at least two weeks a year of paid time off. What do you do with yours?

A cruise ship vacation is completely relaxing and just what the doctor ordered sometimes. But it’s also tightly scheduled, structured, and predictable. A backpacking trip, on the other hand, will be more open-ended, more apt to challenge you, and much more likely to feel like an adventure.

As a traveler, Manchester writes, “Winston disliked sightseeing, and he loathed being part of a tour group which would pause, in this gallery or that museum, while a guide explained what the tourists should appreciate and why.” He wanted to be off on his own, making his own discoveries. In all areas of our lives, we should likewise shun the approach of the tourist, and adopt the mantle of the explorer.

See the world though romantic eyes. Even when you can’t changes the circumstances you’re in, you can still perceive an experience as more adventurous, simply by shifting your perspective on it.

While Churchill’s adventures involved intrinsically colorful scenarios, his romantic perspective heightened their mystery and excitement all the more. Flying in a cold, uncomfortable B-24 or living in a muddy trench would give many men an excuse to feel miserable, but Churchill could find excitement and enjoyment where others would only see hardship.

As we discussed in our class about romanticism, simply shifting your perspective on something can bring even mundane situations to life. And experiences that are already enjoyable can become even more so when you choose to view them with excited and curious eyes, and allow yourself to experience a little wonder. Think about when you were a kid; walking in a patch of woods a few hundred feet from your house or riding your bike to school felt like a grand escapade. If you strip yourself of excessive cynicism, you can experience everything from your relationships to a Disney World vacation to your morning run as more of an adventure.

Say yes whenever you can and overcome the inertia of rigmarole. One of the greatest impediments to adventure as an adult is the number of your responsibilities, and how said responsibilities sap your willpower. Psychologists have shown that we have a limited supply of willpower each day, that if we use it for one thing, we have less it for another, and that when our willpower runs low, our default answer to everything becomes “no.”

That’s why when you’re a grownup faced with the opportunity to have an adventure, even a small one, your inclination is often to turn it down. I know when I get an invitation to something like the Vanguard, my first thought is something like, “Sounds cool, but man I’m already behind in my work, and I’ve got this other thing going on that week, and blah, blah, blah.” Thinking about buying tickets and packing and the other things I’ll need to do to go away makes me want to default to “no.” And even when I say yes, as the time for the event approaches, I think, “Why did I agree to this? I’ve got so much going on. It’s probably going to be a waste of time.”

Of course, such things almost always turn out to be great experiences. Even the perceived rigmarole of making it happen ends up being less than you thought. It’s almost always better to say yes to something that might turn out to be an adventure (of the kind you enjoy!), so accept opportunities when they come up, and don’t let the boogeyman of grown-up rigmarole keep you stuck at home.

The wonderful thing about saying yes to adventure, is that every adventure holds within it the seeds of possibilities for even more adventures. In having the courage to open up doors in your relationships, work, and leisure time, you’ll find more interesting and exciting journeys awaiting. Where they’ll lead, you never can tell!

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 #6: Don’t Be Afraid to Start a Family
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

My Early Life by Winston Churchill

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