3 Pessimistic Philosophers Who Will Cheer You Up - Carlyn Beccia - Medium

Carlyn Beccia 9-11 minutes 4/28/2022

Let “The Messenger of Misery” brighten your day

Artwork: © Carlyn Beccia |

In 1961, philosopher Martin Heidegger was asked how to live a more authentic life. His reply was morose, albeit pithy — “we should spend more time in graveyards.”

It’s a sentiment more people should embrace. Graveyards are a modern memento mori that reminds us of the importance of a life well-lived. And I mean really lived. Not lived through a curated social media feed.

And while we are romping through graveyards, we should find our favorite plot of earth above the dead and curl up with the teachings of the following pessimistic philosophers.

Artwork: © Carlyn Beccia |

Arthur Schopenhauer (1788–1860)

Any study of pessimism has to begin with the man who earned the monikers — “The Messenger of Misery” and “The Sad Prince of Pessimism.”

Schopenhauer has long been accused of being the poster child for the grouchy philosopher, but that’s not entirely fair. He simply viewed happiness not as profound joy but as the absence of misery.

According to Schopenhauer, we can appreciate our happy moments only when life has dealt us a round of suffering. In other words, if you focus too much on the pursuit of pleasure, misery will find you. For many, pleasure becomes a thinly veiled mask to pain.

Instead, Schopenhauer recommended people embrace their sadness. He believed that we must understand the reasons for our unhappiness if we want to develop an exit plan from our sorrow. And if we don’t understand the root of our suffering, we will engage in meaningless sex or buy unnecessary creature comforts.

According to Schopenhauer, the fulcrum of happiness is to tame loneliness. He believed the problem with most unthinking people is they don’t make a distinction between solitude and loneliness. While loneliness is a desperate need to be around others, solitude is your choice to connect with your inner aspirations. And that capacity to connect with your more authentic self is the mark of an emotionally mature person.

Maya Angelou sums up a more modern interpretation of his philosophies, “You are only free when you realize you belong no place — you belong every place — no place at all.” In other words, you can only belong to others when you belong to yourself. Thus the less sociable we are, the more time we have to reflect. But only in those moments of solitude are we truly free.

Schopenhauer was definitely not Mr. Socialable. Perhaps that is why he died alone with his dog, content in the reasons for his misery.

Mostly it is loss which teaches us about the worth of things.” - Arthur Schopenhauer

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Søren Kierkegaard (1813–1855)

Danish writer Søren Kierkegaard is remembered today as the “father of existentialism” because he was the first celebrity philosopher to explore the problematic nature of authenticity.

Kierkegaard tussled with this tiger because he was a bit of an attention whore himself. Simply put, Kierkegaard’s ego caused him a boatload of suffering. But unlike modern-day celebrities, he was willing to stare that demon down. He tamed his ego with one sharp weapon — pessimism.

Pessimism was a trait baked into Kierkegaard at a young age. By the time he was twenty-five years old, he had lost his parents and five out of his six siblings. He was also physically frail and suffered from anxiety — a subject he wrote openly about.

His dad wasn’t so great at cheering him up. At one point, papa Kierkegaard informed his son that he wouldn’t live past thirty-four because that is when Christ died. Ah, ok. That is weirdly morose. But it’s no wonder that death and religion became a bit of an obsession for Kierkegaard.

When you read Kierkegaard, his distrust of others taints his words with cynicism. “The crowd is untruth,” he warns. At first blush, that advice might sound misanthropic, but it wasn’t humans that Kierkegaard avoided. It was humans coming together that were problematic. Kierkegaard believed that people lose their authenticity and moral responsibilities once they are part of a crowd.

Psychologists will agree with his philosophies. In the “bystander effect,” researchers have found that people are less likely to offer help to someone if they are in a crowd.

And not only are they less likely to help, but they are also more likely to go all Lord of the Flies on vulnerable individuals. In one famous study, Australian psychologist Leon Mann found that when someone was attempting suicide by jumping off a tall building in front of a large crowd, the people on the ground were more likely to scream “jump” if they were part of a large crowd.

Yeah, so people suck, and Kierkegaard got it.

Kierkegaard’s solution is clear — avoid mind-numbing crowds. (And that means you social media darlings.)

Most of Kierkegaard’s teachings center around this one tenet — the loss of the self is what leads to despair. And it's getting caught in crowds that causes this despair because it stymies choices. He called the inability to exercise choices wisely — “angest” — what we know today as angst.

Kierkegaard again had a solution — have a passion. He believed that those who have a passion also have a direction. He wrote, ‘Life can only be understood backward, but it must be lived forwards.’

“People settle for a level of despair they can tolerate and call it happiness.” — Søren Kierkegaard

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Michel de Montaigne (1533–1592)

If there is one philosopher that I could go back in time and get rip-roaring drunk and silly with…it is Montaigne.

Montaigne approached life with a raw candor that many people would find refreshing today. He abhorred small talk and preferred to discuss the visceral nature of bodies. He tackled everything from the smell of his own sweat to impotence — a subject most Renaissance philosophers wouldn’t dare touch. There’s a lot of philosophizing about farts in Montaigne’s work. He is often carnal, sometimes crass, and definitely clever.

He also thumbed his nose at intellectuals and their pretensions. “Kings and philosophers shit, and so do ladies,” reminds Montaigne.

Montaigne ran naked through the halls of academia, poking fun at the learned. He found Plato tiresome and believed the problem with most people is they think they are far more intelligent than they are. (Hello, Dunning Krueger effect.)

Montaigne found most pedantry irksome because it lacked the utilitarianism needed to impart meaning. He wrote, ‘If man were wise, he would gauge the true worth of anything by its usefulness and appropriateness to his life.’

Montaigne would have scoffed at the self-help industry, mostly because he found nobility in leading an ordinary life. In a society obsessed with being exceptional, it is advice we should heed — it’s ok to be mediocre. After 10,000 hours of Gladwell sweating practice, most of us will end there.

Part of why Montaigne is so refreshing to read is that he embraced the contradictory nature of humans. Introverts, extroverts, empaths, narcissists, thinking, feeling, rich, poor…no one is ever one thing at one time. At the very least, Montaigne preached we should know ourselves before we start to label others.

But his life attitudes were more than just empty solipsism. He also never feared death. And Montaigne had a lot to fear. During his life, the plague killed half of Bourdeaux. His brother was killed by a tennis ball. Only one of his six children survived. Death enveloped him.

When his best friend died, the grief made him feel like he had been “cut in half.” He needed a literary form to express himself, so he turned to the essay. He didn’t exactly invent the essay, but he gave it its name from the french essai meaning “to try or attempt.”

And try he did. He got up every day and tried to know himself by writing about himself. He writes about his ears, penis, kidney stones, sleep, friendship, sex, love, and had an oddly acerbic defense of cannibalism. He wrote about everything.

Montaigne is my inspiration to write about everything. Whenever writers ask me, “should I write in one niche?” I always advise them to read Montaigne. Montaigne will convince you that finding your niche is only running from yourself.

You won’t find a niche. It finds you.

“There were many terrible things in my life and most of them never happened.”― Michel de Montaigne

Recently, I have noticed attacks on “doomsday” writers. If more people read philosophy, these attacks would not exist.

The job of philosophers is to make you feel both dejected and inspired. If you feel only the inhumanity when reading their works, that is your self-projection. You are choosing to see the world from a slighted angle instead of changing your vantage point.

Philosophy does not carve out answers for you and hand them to you on a silver platter. You have to find those answers.

Graveyard romps are optional.

“To suffer without complaint is the only lesson we have to learn in this life” — Vincent van Gogh

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