in: Career & Wealth, Featured, Leadership

• Last updated: September 26, 2021

Work, Command, Create: Tips on Hustling, Leadership, and Hobbies from Winston Churchill

The Winston Churchill Header.

Note: In yesterday’s Churchill School of Adulthood lesson, we offered examples from Winston’s life as to how he embodied artist Constantin Brancuși’s maxim that to live a fulfilling, flourishing life, one must “Work like a slave; command like a king; create like a god.” Because the takeaways of that lesson were so numerous and important, we’ve given them a separate article. What you’ll find below encapsulates much of our best life advice, wedded with Churchill’s examples and insights – I think it’s really worth a read!

“Broadly speaking,” Winston Churchill mused, “human beings may be divided into three classes: those who are billed to death, those who are worried to death, and those who are bored to death.”

Certainly, many adults fit all too well into one or all of those categories. Growing older often means sliding into a monotonous career and giving up one’s interests and hobbies. The result is predictable, but tragic: boredom, restlessness, anxiety, and even depression.

Unfortunately, the solution commonly sought for this malaise produces exactly the opposite result, and tends to make us even more anxious and restless. Most adults think they have too much on their plate, so they long to unload some of their activities and have time to just veg out in front of their screen of choice. The problem, however, is not the quantity of activities, but the quality. Most people could in fact use more activity in their life, just the right kind of it: more enjoyable work, more satisfying responsibilities, more opportunities to create.

Work Like a Slave: Hustling and Finding Your Vocation

Winston Churchill Quote no use doing what you like.

Find work you enjoy (but not necessarily by navel gazing). Churchill believed that in addition to the three classes of people mentioned above, the “rational, industrious, useful” portion of the population could be divided into two groups:

“first, those whose work is work and whose pleasure is pleasure; and secondly, those whose work and pleasure are one. Of these, the former are the majority. They have their compensations. The long hours in the office or the factory bring with them their reward, not only the means of sustenance, but a keen appetite for pleasure even in its simplest and most modest forms. But Fortune’s favoured children belong to the second class. Their life is a natural harmony. For them the working hours are never long enough. Each day is a holiday, and ordinary holidays when they come are grudged as enforced interruptions in an absorbing vocation.”

There’s never been a time in history when young people have been so loathe to wind up in the first group, and so keen to join the ranks of the second. And yet the advice given on how to do so — to look within, find your passion, and then follow it no matter what — unfortunately consists largely of abject poppycock.

Churchill did indeed develop a deep love of the English language and of reading in his youth that might have portended his illustrious writing career. But in other ways such a path seemed an unlikely prospect — he struggled with most subjects in school, bombed his examinations, and attended a military college rather than an academic university.

In fact, his writing career didn’t start because he knew early on it was his true vocation, but rather because of the real love of his life: war. Churchill wanted to get to the frontlines of any conflict he could, and when he was denied permission to join a battle as a combatant, he’d get a newspaper to sponsor his participation as a correspondent. After his dispatches won a warm reception, he figured he’d write a book about one of his expeditions. In so doing, he saw both how much he enjoyed the process and how much more money he could make with his pen than his sword. It was only then that he decided to quit the military and give writing a real go. Thus, he found his calling as a writer not by directly trying to figure out what he was meant to do, but indirectly, by taking action and simply pursuing things that he enjoyed. Such a path has been the means by which many others have also stumbled upon their life’s work.

Churchill found his other calling in life – politics – using an even better method for finding one’s vocation: instead of looking within to discover his passion, he looked outside himself and found a problem that needed solving. In his case, the problem was the lack of honorable, visionary men in government – and he addressed the issue by running for office himself. That path is actually how I found my own vocation too: I saw a problem – the dearth of quality men’s magazines – and decided to take a crack at filling the void. It wasn’t that I had a pre-existing passion for reviving manliness, and then looked for a way to follow that passion; instead, I found a love for my work after I started trying to tackle a problem.

Pleasure in one’s work is less likely to precede the beginning of an adventure or career path, than it is to follow it. (And the nature of the path just may surprise you).

The world belongs to those who hustle. When you do work you enjoy, you often don’t mind toiling long hours. And that’s a good thing, since if you don’t work long hours, you’ll never get your dream off the ground!

Everywhere you turn, you can find lifestyle design gurus promising that if you figure out the right “hacks” and “secrets” to success, you’ll be able to earn a good income with minimal work. Passive income, baby! Is it possible to earn a few bucks using some kind of internet scheme? Sure. But is it possible to create something lasting and legacy-producing in just a few hours a week? Absolutely not. Anyone who tells you otherwise is a huckster selling you a bill of goods.

Getting any kind of worthwhile project or career off the ground will take a ton of work and long hours. If there aren’t times where you feel like your eyeballs are bleeding, you’re doing it wrong. For example, while many folks think you can start a successful blog by chinking in a little time now and then, in the early years of the site, Kate and I often worked 60 hours a week on it, each. And even today we work weekends, on vacation, and sometimes the whole night through.

In whatever endeavor you pursue, the world will always belong to those who hustle.

Enjoyable work still feels like work. There’s a misconception out there that if you’re passionate about your work, then every single day is going to feel like a fun, good time, and if it doesn’t, you’re in the wrong job. But that’s just not the case.

Even if you get a lot of pleasure from your work, that doesn’t mean it’s going to feel like you’re playing all the time. Churchill himself categorized work and play as two separate things. Enjoyable work still feels like…work. That means you’re not going to jump out of bed every day rearing to do it, and that sometimes it will be quite difficult. And that’s okay; pleasure and satisfaction aren’t found only in fun and play, but in embracing challenges as well.

Even when you love your job, sometimes you’ll still want to ditch it. Just because you love your job, doesn’t mean you won’t sometimes feel like calling it quits and trying something else.

Churchill sometimes found the task of writing absolutely exasperating. When he had writer’s block, he would descend into a terrible mood, exhibit a foul temper, and kick over wastebaskets. And when deadlines loomed, he could find the stress unbearable: “I am toiling double shifts,” he wrote Clementine during one arduous stretch. “It is laborious: and I resent it and the pressure.”

People consider being a blogger a highly desirable gig, but my job too is sometimes stressful, pressure-filled, and highly annoying (see: internet comments), and I dream of running away to become a barber in a quiet little town in Vermont where no one can find me. Doesn’t mean I don’t love my job, just means I’m a human being. Everybody wonders if the grass is greener somewhere else. Soldiers figure they’ll be happier as civilians, quit the military, and then wonder if they should join back up. Office workers think they’ll be happier as entrepreneurs, and entrepreneurs dream of being able to clock out entirely and leave their work behind each night.

The more your work is a good fit for you, the less you’ll experience such moments. But everybody, at one time or another, wants to stop the train they’re on and run for the hills.

Find opportunities in spare moments. If you’re currently in a job you hate (more of the time than not), and want to pursue a new career, get started by finding opportunities in spare moments.

Churchill wrote his first book during a 3-hour afternoon break he was given while stationed in India. The 23-year-old and his fellow cavalrymen typically used the time to nap and play cards. Churchill decided to instead sequester himself and spend those hours writing. The result launched his literary career.

The Art of Manliness similarly began as a moonlight for me in law school. I’d spend 9am to 9pm each day at law school, studying and working a part-time job. Then I’d come home at night and put in a few hours writing for the website and working on the manuscript for our first book: The Art of Manliness: Classic Skills and Manners for the Modern Man. It was only three years after I launched the site that I was finally able to do it full-time.

Keep a routine and schedule. As we’ve previously discussed, Churchill kept a unique, but quite strict daily routine. This helped his productivity enormously, and it will do the same for you – especially if you’re trying to get a side hustle off the ground. To get started, learn how to plan your week, and you’ll be one step closer to Churchillian productivity.

Focus. Churchill’s enormous productivity was not a result simply of the number of hours he worked, but how well he concentrated during those hours. Lt. General Ian Jacob was astounded by “the fury of his concentration. When his mind was occupied with a particular problem, however detailed, he focused upon it relentlessly. Nobody could turn him aside.”

Working long hours isn’t enough if you spend half the time surfing the internet. How you use your hours is also paramount — quality is just as important as quantity.

To improve your own attention span, try these 11 training exercises, along with one Churchill heartily endorsed himself – the daily nap.

Focus is also improved when you have a clear vision and objective. Don’t engage in activity for activity’s sake — know your aim. Churchill would often set a goal for himself, such as writing at least 1,000 words a day, in order to make a deadline. And during the war, Manchester writes, “His eyes were focused on Hitler to the exclusion of all else.”

Know your mission thoroughly, plan your strategy shrewdly, execute your battle plan tirelessly, and victory will be yours.

Command Like a King: Embracing the Role of Leadership

Winston Churchill Quote make a life by what you give.

The common wisdom these days on how to retain your youthful zeal into adulthood follows the line of avoiding commitments and responsibilities like the plague. Remain unattached; live only for yourself.

There’s only one problem with this approach — in seeking perpetual youth, it denies one of the strongest inclinations of childhood: being effective in the world.

When Gus was just emerging into toddlerhood, he just couldn’t get enough of flipping light switches and pressing buttons. The light goes on, the light goes off; the light goes on, the light goes off. This was truly one of his earliest delights: making something happen outside himself. He was just beginning to understand the innate power we have to change our world.

Though we often forget the depth of this satisfaction as we get older — sating it on trivialities than require us only to be spectators — the longing to be effective in the world remains. It is an itch that can only be scratched through the assumption of responsibility, for in responsibility there is power.

Those who spurn responsibility do remain as children, but in the least desirable of ways. They continue to endlessly flick the light switch up and down – an act now rendered in the form of clicking a mouse. That is the end of their power: the ability to impotently select from a predetermined menu of options. When said menu does not yield sufficient options to their liking, their only recourse is to whine.

To take on responsibility is to strap oneself into the driver’s seat rather than sit idly as a passenger. Studies have shown that military pilots experience less stress during flight than their navigators; those who have control, even when their burden of responsibility is greater, are more at peace than those who are simply along for the ride.

Thus, the vigor of youth is not found in responsibility avoidance, but in its embrace. The most miserable adults are those who complain about media, culture, politics, and everything else, and feel like they can’t do a damn thing about it. The happiest adults take on the extra burden of becoming leaders, because they enjoy the satisfaction of making a change – however small – in the world.

In becoming a leader — in your family, church, community, work, and culture — keep a few things in mind:

Winston Churchill quote withhold no sacrifice.

Be ever ready and prepare yourself to lead. In studying the lives of great men, I have been struck by the way many of them felt as though their opportunity to lead had passed them by, only to unexpectedly be called into service later in life.

In the 1930s, when Churchill was already approaching his 60s, the prevailing wisdom was that his chances of ever becoming prime minister were almost nil. When a British delegation of MPs led by Lady Astor traveled to the Soviet Union and met with Stalin in 1931, the Russian leader asked them about rising politicians back in England, and in particular about Churchill. “Churchill?” Astor exclaimed with a scornful laugh, “Oh, he’s finished.”

While most everyone else counted him out, Churchill kept himself ever ready to serve and did not give up on his dream of becoming the head of Her Majesty’s Government. By cultivating contacts who confidentially passed along information to him, he kept himself better informed than nearly anyone else about what was going on inside Germany during the 30s. And he never watered down his positions or softened his jeremiads to better align with the public mood. Instead of changing to match public opinion, he stood steady, and let the world slowly come around to his truth.

Thus when Churchill finally assumed the office of prime minister, he felt as if he was “walking with Destiny,” and that all of his “past life had been but a preparation” for the challenge ahead. By remaining true to his convictions, he had positioned himself to be a far more effective leader than he otherwise would have been: “My warnings over the last six years had been so numerous, so detailed, and were now so terribly vindicated, that no one could gainsay me. I could not be reproached either for making the war or with want of preparation for it.” And by staying keenly abreast of Germany’s preparations and strategy over the course of the previous decade, he could confidently say, “I knew a good deal about it all, and I was sure I would not fail.”

The time to prepare to lead is not in the midst of the storm, but in the calm before it. Things may be going great in your family and business right now, but if tough times come are you ready to step up and serve?

Have a command of language. Just because mere whining is childish and impotent, doesn’t mean words have no power. They have in fact a great deal of it – when they can be masterfully wielded. “This is stoopid,” will hardly win adherents to your cause, but evocatively worded, potently constructed, logically sound arguments can, and have, changed the world. Thus, Churchill argued, he who has a command of language:

“wields a power more durable than that of a great king. He is an independent force in the world. Abandoned by his party, betrayed by his friends, stripped of his offices, whoever can command this power is still formidable.”

It is partly for this reason that a strong case can be made for literacy being one of the fundamental traits of adulthood.

Example is king. Even greater than the force of words is the power of example. Churchill did not simply talk the talk; he walked the walk. The might of his moral code was unquestionable, and the strength of his character created an effect that was downright electric and magnetic. People wanted to follow him to the ends of the earth.

As fathers, coaches, and bosses, a good example is worth far more than a hundred sermons and diatribes. A leader who demonstrates sterling, purpose-driven manhood will hardly need to open his mouth to get others to expend themselves in his cause.

Winston Churchill you have Enemies good.

Prepare yourself for the fact that people will want to dethrone you. Whenever you find yourself in a position to enact real change, critics will take notice and try to tear you down. Just embrace these attacks as a sign you’re actually doing something in the world, and carry on.

Have the courage to face ingratitude. Just because you do great things, don’t expect to be forever fawned over with praise and thanks. People have a short memory, and a penchant for concentrating on the negative. After Churchill led his countrymen through almost six years of world war, they turned him out of office, desiring a different leader to govern them in peacetime. The blow made his friend Harold Nicholson “sick with human nature. Once the open sea is reached, we forget how we clung to the pilot in the storm.” But Churchill waved off such grousing about ingratitude. “Oh no,” he replied, “I wouldn’t call it that. They have had a very hard time.”

Churchill regretted that his service was cut shorter than he would have liked, but he had accomplished much of the mission he had set out to do, and that was enough.

Create Like a God: The Essential Nature of Hobbies

Winston Churchill Quote Ought to have Hobbies.

The secret behind Churchill’s herculean productivity may seem like a paradox: an equally productive use of his leisure time!

Churchill had found that it was only possible to do so many hours of effective work each day; after a certain point his output of writing and ideas became muddled. By turning to another activity – one that was different from his central work – he could return to his labor truly refreshed and start cranking out top-notch stuff once more.

Churchill believed that oscillating between different activities in this way actually provided superior rejuvenation to one’s mind than even a bout of full-on relaxation:

“It is no use saying to the tired ‘mental muscles’… ‘I will give you a good rest,’ ‘I will go for a long walk,’ or ‘I will lie down and think of nothing.’ The mind keeps busy just the same. If it has been weighing and measuring, it goes on weighing and measuring. If it has been worrying, it goes on worrying…It is useless to argue with the mind in this condition…A gifted American psychologist has said, ‘worry is a spasm of the emotion; the mind catches hold to something and will not let it go.’ One can only gently insinuate something else into its convulsive grasp. And if this something else is rightly chosen, if it is really attended by the illumination of another field of interest, gradually, and often quite swiftly, the old undue grip relaxes and the process of recuperation and repair begins.”

For this reason, Churchill recommended that everyone have a few hobbies. Within the cultivation of stimulating pastimes lay the antidote both to being “worried to death” and “bored to death.”

Choose your hobbies thoughtfully. Though Churchill felt that hobbies were an essential part of a fulfilled adulthood, he didn’t think one’s pastimes were something to be chosen willy-nilly:

“this is not a business that can be undertaken in a day or swiftly improvised by a mere command of the will. The growth of alternative mental interests is a long process. The seeds must be carefully chosen; they must fall on good ground; they must be sedulously tended, if the vivifying fruits are to be on hand when needed.”

Engaging in stimulating hobbies, Churchill believed, was equally essential both to “those whose work is work and whose pleasure is pleasure” and “those whose work and pleasure are one.” The most important factor in choosing a hobby, he posited, is to select a pastime that is sufficiently different from whatever work it is you perform in your day job:

“It is no use offering the manual labourer, tired out with a hard week’s sweat and effort, the chance of playing a game of football or baseball on Saturday afternoon. It is no use inviting the politician or the professional or business man, who has been working or worrying about serious things for six days, to work and worry about trifling things at the week-end.”

Churchill also noted that while reading is a popular pastime, engaging in that hobby alone is “too nearly akin to the ordinary daily round of the brain-worker to give that element of change and contrast essential to relief.”

Churchill further counseled that the hobbies that are most effective in restoring “psychic equilibrium” are those that “call into use those parts of the mind which direct both eye and hand,” and noted that “Many men have found great advantage in practising a handicraft for pleasure.” This bit of advice is particularly important for information workers; finding an activity outside of your job in which you can use your hands can bring needed balance to your life. Giving yourself the opportunity to create in a tangible way is truly important no matter what your job – especially if you don’t get to exercise your creativity during the workday.

Finally, Churchill warns against the impulse to want to dabble in a bunch of things simply to enjoy “a new pleasure, a new excitement.” Everyone knows how fun it is to run out and buy a new mountain bike or paint set…which then gathers dust once one’s initial burst of enthusiasm has worn off. As Churchill advises, “discipline in one form or another is the most hopeful path.”

To sum up: thoughtfully consider what kinds of hobbies might be the most interesting and rejuvenating for yourself, pick ones that involve an activity different than what you do for your day job, and then stick with them for an ample length of time to see if they might become a lifetime love.

Keep a quiver full of interests at the ready to prepare yourself to quickly break from boredom. “Boredom,” Manchester writes, was “an assault on [Churchill’s] equilibrium.” Winston saw boredom as a waste of his short existence, and whenever it struck, he would invariably make a “ruthless break” in pursuit of a more satisfying activity:

“The balm might take the form of dictating a letter, singing off-key renditions of Gilbert and Sullivan, perhaps wielding his trowel to lay bricks in the gardens at Chartwell…He always kept his quiver full of possible activities: read a novel, feed his goldfish, address his black swans, parse the newspapers, declaim on England’s glorious past.”

As his literary assistant William Deakin recalled, because Churchill always had alternate pastimes in mind, “He could switch off in a marvelously tidy way.”

Modern adults often get stuck in a tedious rut not only because they haven’t figured out other hobbies and activities they enjoy, but because they don’t even realize they’re bored! In every empty moment, it’s so easy to turn to fiddling with our phones and computers that we don’t realize we haven’t actually vanquished our boredom at all, but have simply distracted ourselves from it. I know I sometimes get caught in an endless, mindless cycle of web surfing, to the point where I almost need to slap myself to break the spell and realize, “@#$! Why I’m wasting my life away on this!”

To make time for hobbies, learning the art of the ruthless break is truly key!

Outsource when you can. Churchill’s supernatural productivity wasn’t of course 100% due to his enthusiasm and focus; he also had a team of servants and hired help that took care of his basic functions and freed up time in his schedule (though it should also be noted that millions of men have had as much or more money, and just as many servants, and yet accomplished little to nothing with their lives). Churchill didn’t clean his own house, cook his own meals, or make his own purchases.

I used to think that personal outsourcing like this was an unmitigated bad – a practice that sapped a man of the DIY ethic so central to character. Yet as I studied the lives of great men, I discovered that nearly of all them were, like Churchill, consummate outsourcers. And it seemed to me that they achieved their greatness not despite this tactic, but in some ways because of it. Which is to say, it’s hard to argue that Churchill, and the world, would have been better served had he spent his Saturday mornings raking leaves, rather than writing speeches.

Outsourcing not only allowed history’s eminent men to focus on legacy-producing work, but also allowed them time to pursue stimulating hobbies…which as we just learned, ultimately benefited the quality of their work!

These men were of course significantly wealthier than the vast majority of us. But in some ways outsourcing has become more accessible than ever before; you can hire people to do most anything these days, often for a reasonable price. To free up a little extra time, you don’t need to hire a team of manservants; instead, look at your budget and pick even just one undesirable chore you’d like to excise. It may be something to consider when making bigger financial decisions as well: would you rather live in a larger house, where you have to spend all your time cleaning and maintaining it, or, buy a smaller house, and use the money saved to get someone to clean it for you? If a housekeeper saves you just two hours of cleaning each week, then over the course of 30 years, you’ll open up 3,120 hours for yourself you wouldn’t have had otherwise. That’s a lot of time for woodworking, fishing, gardening, biking, blacksmithing, hunting, beer brewing, tinkering, painting…

Conclusion: Make a Ruthless Break With a Boring Adulthood

Winston Churchill Walking down street with Briefcase.

Many adults today are bored, restless, anxious, and depressed. Churchill himself was prone to bouts of melancholy, but his ceaseless engagement in satisfying work, meaningful responsibilities, and stimulating hobbies, kept his “black dog” at bay.

In order to stave off the dark moods that accompanied idleness and boredom, Churchill would make one of his famous “ruthless breaks.” As the bodyguard tasked with keeping track of him lamented, “He will move at a moment’s notice. He will move without notice!” If his dinner guests were stuffy and dull, he’d try to act civilly and bear with them for awhile, but then he’d simply give up and leave the table. If a movie he was watching turned out to be a snooze, he wouldn’t make himself see how it ended, but would get up and walk out – even if his theater companions were Mr. and Mrs. Franklin Roosevelt!

While we should all try to be gentlemen, and we all have aspects of our lives we must sometimes put up with and push through, there does come a time when one must make a ruthless break with a mundane, spiritless, humdrum adulthood. Our work, responsibilities, and leisure time can be difficult, stressful, and challenging, but they need not be totally dull. You’re already going to die once; don’t let boredom take you before you’ve even reached the grave!

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 #6: Don’t Be Afraid to Start a Family
Lesson #7: Work Like a Slave; Command Like a King; Create Like a God
Conclusion: Thought + Action = An Awesome Adulthood



The Last Lion Trilogy by William Manchester

Painting as a Pastime” by Winston Churchill

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