6 Powerful Lessons Photographers Can Learn from Winston Churchill

The wall loomed – a rough-hewn barrier of stone and mortar, standing between him and the open. Climbing it was a gamble, the risk of being spotted high, but he had no choice. Hauling himself up, muscles screaming, he dropped onto the other side, landing in a cloud of dust. His escape had begun. He had to reach the train yard.
 
Luck, it seemed, was on his side. A freight train, shrouded in the pre-dawn gloom, sat idling on the tracks. He slipped into an empty boxcar, the metallic tang of coal dust filling his nostrils. Hours crawled by, punctuated by the rhythmic clatter of the wheels and the ever-present fear of discovery. But the train was not going far enough.
 
Forced to disembark, he found himself in a mining town. Desperate for refuge, he sought shelter in the dark, echoing depths of a disused coal mine. The air was thick with the smell of damp earth and decay. He spent days in the mine, avoiding people. It was damp, cold and he had a sense of hopelessness.
 
Finally, a chance encounter with a sympathetic local led him to the next leg of his journey: a train bound for Portuguese East Africa (Mozambique). Hidden amongst the cargo, he endured the long, arduous journey, each mile carrying him closer to freedom. The man who orchestrated this daring escape, a man who would later shape the course of history, was the young, audacious Winston Churchill.
 
What would be the results if you collected the wisdom from one of the most complex and fascinating characters in history? I decided to find out. 
 
Soldier, parliamentarian, prime minister, orator, painter, writer, husband, and leader all combine to make Winston Churchill one of the most studied humans ever. Most leaders and historians are guaranteed to have at least one book on Churchill, but how many photographers have? 
 
Expect to learn why self-pity has no utility, how to rise from failure and succeed, Churchill’s secret life as a successful artist, 3 essentials for photography success and more. 
 
Since reading this book my dedication to photography has increased even more. Learning from Churchill has helped my art and life in many ways. More on that later. 
 
 
POWER OF READING
 
When Churchill was a young soldier in India, “he was conscious of his ignorance and begged his mother to send him big, important books. She did… He read everything of value he could get his hands on and forgot nothing he read. But there were always gaps, he felt, in his knowledge which he eagerly filled when vital books were recommended to him.”
 
Churchill, like all outliers in all fields including photography, knew the power of reading. Although he was mediocre academically, his drive for self-education replenished his intellectual insufficiency. 
 
Outlier photographers read countless books. Whether it’s photo books, photography-history books, or biographies of the best photographers, they all read and have a drive to learn and improve. 
 
Churchill had a white-belt mentality when it came to knowledge. He knew there was so much to learn, and the best way to learn was to take action and read. Congratulations, you’re reading right now. By the end of the episode, there will also be actions you can take to improve your craft. 
 
 
EMBRACE YOUR UNLIKELY TALENTS
 
During WW1, he was blamed for the Dardanelles disaster—a failed naval operation in Turkey that resulted in huge casualties. He was dismissed from government.
‘This was the lowest time in Churchill’s life.’ His wife ‘thought he would die of grief.’
 
During this period Churchill took up painting by chance. He loved it: “he discovered that painting is not only the best of hobbies but a sure refuge in time of trouble, for while you are painting you can think of nothing else.”
 
All kinds of activities that give you peace of mind are key to unlocking success. For me, photography, reading and the gym have this effect.
 
For Churchill, “Painting, after politics and family, became his chief passion, and he painted for the rest of his life.”
 
He even ended up winning an anonymously submitted art competition; judges included Joseph Duveen, one of history’s greatest art dealers. Duveen ‘found it hard to believe the painter was an amateur’. 
 
The reason Churchill became a successful painter was because he enjoyed it! To be a successful photographer, you have to enjoy photography. All outliers do things that feel like play to them but look like work to others. If don’t enjoy what you do, you won’t stay in the game long enough to become an outlier. You’ll quit without the fuel of passion driving you. 
 
Passion is a necessity for success. 
 
 
IMPORTANCE OF LIGHT
 
Out all the memorable lines in this book, there’s one simple quote that sticks in my mind…
 
“Light is life.’
 
This is the case for our photos but also our existence. Light is needed to create images—it’s the blood of our art. It supplies the rest of the image by illuminating it—giving it life. Sunlight also gives us serotonin, a brain chemical which makes us feel good. 
 
Use light effectively when making images. The outlier photographer knows where to position himself in relation to the light. For me, that’s shooting against the light, either side of the sun. This creates dramatic backlighting. I love it.

If I didn’t shoot towards the sun in my print, Silver Rain, the raindrops wouldn’t have been visible. A layer of depth would’ve been lost.  
​https://www.jacobwatsonhowland.com/silver-rain.html
 
Without light there is nothing...
 
BUILD ALLIES
 
When he was chancellor: “he formed a habit, early each morning, of going from his own house, 11 Downing Street, through the connecting inner door to number 10, and having a chat with (prime minister) Baldwin before each began work. They became very close and like-minded and never had a dispute.”
 
What’s repeated in every successful person’s story is the power of building allies, and the futility of burning bridges. To succeed we must build relationships. Relationships bring access, friendship and opportunities with like-minded people you wouldn’t get without it.
 
WATCH YOUR COSTS
 
Wall Street crash caused Churchill to lose all his wealth. His advisor had been ‘investing his funds on margin (something Churchill did not understand), so he not only lost all his money but had to buy himself out of the mess.”
 
But he was resourceful and used his strength: writing. “His earnings rose to £40,000 a year, an immense income in those days.”
 
If financial advisors were so good, they’d already be rich and wouldn’t need to use your money. All photographers need to watch their costs. The best understand before they invest. The photographer who doesn’t watch their costs is doomed for failure. Frugality is key if you want to turn your art into profit.
 
After the crash, Churchill was hit by a car “he was lucky to be alive”. “He told his wife: I have now in the last two years had three heavy blows, the financial crash, loss of my political position, and now this terrible injury.” He was afraid he would never recover from these blows.”
 
Churchill suffered many downs in his career, but there’s always one common theme. Despite depression and uncertainty in the moment, he always managed to stand back up on his two feet, brush himself off, and begin walking towards victory again. This often occurred through positive reframing.
 
He wrote an article which said “Live dangerously, take things as they come. Fear naught, all will be well”.
 
Success rebounded fast: “he got £600 for world rights [for the article], the largest sum he had ever received for a single piece. It was printed everywhere. Then he went back to the fray, shaken but calm, to live more dangerously than ever before, but to fear even less.”
 
He acted, despite fear. Outlier photographers do this. They persist through financial, physical, mental and creative trouble. They reframe the negative and make it positive. They endure the tough and rough. Get bruised, and come out the other end stronger, wiser and even more determined than before to succeed. That’s what it takes to win.
 
THE IMPORTANCE WHERE YOU LIVE, WHAT YOU DO, AND WHO YOU’RE WITH.
 
Churchill chose to do what he loved (politics, writing and painting). He chose to be with whom he loved “he was lucky to have an adoring (but wise and sometimes critical) wife and a growing family of children who were his warmest supporters.” He chose to live where he loved, too “Lucky to have Chartwell, a burgeoning paradise where he could lick his many, and often serious, wounds”
 
What you do, who you’re with and where you live are the three most important things choices in life. All outliers follow their gut instincts and decide to choose all 3 wisely. 
 
They ignore what others might believe to achieve success in these 3 fields. To have control over these 3 things is to have control of your life. For successful photographers, they are sure to spend time planning these three pillars of life effectively. The best do what they love. The best live where they love. They spend time with those they love. They also avoid negative actions, people and places that don’t align with goals.
 
 
CLARITY IS KEY 
 
After a decade in the political wilderness (just like Steve Jobs' decade of wilderness years between his two stints at Apple), he returned to politics as prime minister of the UK. World War 2 had already begun as Germany invaded France.
 
Churchill’s “courage was high, he recorded:
 
I was conscious of a profound sense of relief. At last, I had the authority to give directions to the whole scene. I felt as if I were walking with destiny, and all my past life had been but a preparation for this hour and for this trial. Ten years in political wilderness had freed me from ordinary party antagonisms. My warnings over the past 6 years had been so numerous, so detailed and were now so terribly vindicated, that no one could gainsay me…
 
I was sure I would not fail. Therefore, impatient for the morning, I slept soundly and had no need for cheering dreams. Facts are better than dreams.”... 
 
France surrender. Now as leader of the last neighbouring nation to defy Germany’s power, every order he made was of life and death importance. 
 
“All his orders, without exception, were in writing and were absolutely clear”
 
This helped Churchill win the war, and it can help photographers succeed too. Writing complements our work well, we can use it to create stories about our images and help viewers resonate with our work more. To achieve this, clarity is key. Short, simple narratives and sentences can be a superpower when explaining/promoting your work. Use clarity as a tool for your success.
 
Clarity of thoughts, speech and goals are important. Churchill’s goal was ‘simple and clear: Victory at all costs, victory in spite of all terror, victory, however long and hard the road may be; for without victory there is no survival’
 
Outlier photographers have a clear mission. Clarity helps focus. Having a clear goal makes it easier to stick to the goal, and therefore to succeed.
 
 
SMALL STEPS FEROCIOUSLY
 
After successfully escaping the jaws of the Germans in Dunkirk people felt, now Churchill was in charge, that the country was ‘moving upward, if only an inch at a time’.
At the time, this slow upward movement may’ve seemed futile. In hindsight of victory, we now know these small relentless successes throughout World War 2 are what compounded to result in the Allies’ win.
 
Big things start small. Outlier photographers aren’t born the best. They become the best through small wins, repeatedly over a long time. In the micro, the wins look futile. Outliers may doubt themselves and ask, “Is this worth it?” But in the macro, after a long period of repetitions, they’ll look back and realise all the small wins compounded into a huge win. Success isn’t the big win. It’s the small victories every day that get us one inch closer to our specific goals. As Jeff Bezos says, ‘Small steps, relentlessly’.
 
BE AN ESSENTIALIST
 
Churchill persuaded the USA to join WW2, a major turning point in the war. “Churchill had an uncanny gift for getting priorities right.” Like many outliers, Churchill was what the author of Essentialism Greg McKeown would call a true essentialist.
 
“Churchill’s greatest intellectual gift was for picking on essentials and concentrating on them.” 
 
Concentrating is an important word. Picking the essential actions is one thing. Concentrating on them by ignoring all else is what separates the average artists from the outliers.
 
What is essential for photographers? I think it boils down to 3 things: preparation, creation and sales.
 
Preparation involves researching, practising and learning photography. This involves analysing inspiring images, planning a big photo project to focus on, reading books on great photographers and practising making photographs, every day.
 
Creation comes after preparation. It’s the climax of all the previous hours spent researching, learning and practising. It involves making the image you spent 6 months planning, editing the image in post-production until it’s what you envisioned and creating countless prints of the image until you are satisfied that it matches what you visualised.
 
Sales is the final step in the process, but the most overlooked by photographers. Preparation and Sales separate the outlier from the average amateur. Sales is advertising your work. It’s showing it to people. It’s sending press release emails to journalists after a career milestone. It’s using social media as leverage to gain an audience and make yourself a brand. It’s pitching your work to big-city gallery dealers or brands. It can be as simple as posting your photo on Instagram.
 
Outlier photographers create great work and advertise it. The more people who see your work, the more leverage you have. The more leverage you have, the more influence and wealth you have. The more of that you have, the more you will be able at create photos you love for a living.
 
Reading the book Essentialism has helped me realise this. Future episode on Essentialism (Greg McKeown) amzn.to/41ED5R6 coming soon. I will get Greg McKeown onto the podcast soon!
 
AVOID SELF PITY
 
“I will never give way to self-pity”. I live by that. As the wise vice-chairman of Berkshire Hathaway, Charlie Munger said “Self-pity has no utility”. These were the words of a man who watched his young son slowly die of leukaemia. 
 
Even in Churchill’s darkest hours, in which he had many, he never favoured falling into self-pity.
 
After unsuccessful shoots, ideas that seem to be failing or short-term misfortune that seems so permanent but can easily evaporate, the average amateur will loathe self-pity. That’s human instinct. The outlier knows that self-pity has no utility. Like Churchill and Munger, they brush themselves off and endure. They continue to iterate because they know the power of compounding. They don’t give up after one failed to shoot. They return every day until they succeed.
 
Avoiding self-pity is an antidote to misfortune.
 
6 Things Photographers Can Learn from Churchill

1. Aim higher.
2. Work harder.
3. Don’t hate.
4. Waste no time.
5. Enjoy the company of others.
6. Rise from failure.

 
That is where I’ll leave it. I highly recommend Churchill by Paul Johnson for any photographer or professional who is serious about their craft and wants to become an outlier.
 
If you buy the book using the link below, you’ll be supporting the show at no extra cost to you.
 
Churchill (Paul Johnson) amzn.to/3CYeJbu
 
Thank you for reading and I’ll see you again next week.
 
Jacob J. Watson-Howland

​Every week, learn photography secrets from history's greatest minds. Enjoy new podcasts and blog episodes 12 hours before anyone else. Plus, unlock my exclusive reading list, packed with life-changing books. Get it all now, for free!

 
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