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Stoicism And The Art Of Happiness – 5 Gruesome Facts


Photo by Nadine Shaabana on Unsplash

When it comes to personal development, life coaches, counsellors, and therapists like to find solutions mostly in behavioural, cognitive, and social psychology. But we often forget there’s a wealth of practical wisdom to be found in ancient and contemporary philosophy.

Indeed, when it comes to useful life lessons, it’s the Stoics of ancient Greece and Rome who win pants down. Or tunics up rather.

Although less well-known than the latter, there are striking similarities between Stoicism and Buddhism. For example, both philosophies stress how important it is to be accepting of all things that happen in life – the good and the bad. Like Buddhists, Stoics also believe the best approach to pain and suffering is to take on a more cheerful and humorous approach to life. 

It’s therefore a little unfortunate that when we hear the words ‘stoic’ or ‘stoical’, we immediately assume a lack of emotion, thus ignoring that many Stoics had a dark sense of humour and were masters of dry wit. 

Take Chrysippus for example – a famous Stoic philosopher who literally died from belly laughing. What was so funny, you wonder? He was watching a donkey eating a fig in his garden one evening. 

It must have been a really fat ass...

Before I go into some of the more gruesome aspects of Stoicism, let me set out one of its core principles first. Stoics believe you can achieve happiness by making the best of the only two things you have real control over – your actions and your judgements.

Only once you accept that happiness is purely internal and can’t be found in external sources, will you stop being a puppet to the ups and downs of life.  

Stoic philosophy is enjoying a bit of a cultural revival. Think Mark Manson’s negative self-help or Oliver Burkeman’s Happiness for people who can’t stand positive thinking. I’m happy about that because it’s the perfect antidote to the shallow positivity we’re being subjected to – a lot of which is doing more harm than good.

Besides, “Life sucks and then you die” provides a more solid foundation to build a meaningful life on than any of the unicorn quotes you find on Instagram.

Here are five gruesome but helpful truths to help you frame and navigate your day-to-day challenges in life.

1)    Memento mori – Remember you’ll die one day

“Think of yourself as dead. You’ve lived your life. Now take what’s left and live it properly.” – Marcus Aurelius

Of all the gruesome truths, this one’s my favourite. The legend goes that after each battle, prominent generals would walk triumphantly through ancient Rome being cheered on by a star-struck crowd. A slave would walk side-by-side with them constantly repeating the words ‘Memento Mori – which translates as ‘Remember you are mortal’.  

Think about that for a second. How different would life be if every time we were told how kick-ass we’d been in a sales pitch, someone else would whisper ‘you’re going to die’? Or when counting the likes on our Instagram selfies? Or when being awarded a long-overdue promotion? How much humbler and more graceful would we not walk through life if we regularly remind ourselves of our own mortality?

Let me be the one who delivers you that mortal reminder today. I'm telling you that your number might be up soon. You may kick the bucket and die tomorrow. Or today even. 

Truth be told, I might post this article and then kick that same bucket immediately after. I’d be disappointed, but I’d respect the universe for its comical timing.

For many of us, the idea that we might die soon is pretty depressing. It makes us angry at our humanity. But instead of thinking that life’s too short, listen to the words of Seneca, one of the fathers of Stoicism, who said:

“Life is long if you know how to use it.”

The Stoics knew that coming to terms with mortality rather than being defined by it, is an essential path to happiness. We should use our imminent death as the guiding principle for living a more meaningful and productive life, one that gives it a sense of purpose and priority.  

And if you’re still worried about dying, remember you were dead a long time before you were born. That wasn’t all that bad, was it?

2)    Amor Fati – Love your fate

“Not merely to bear what is necessary, but to love it.” – Nietzsche

One of the things I love about Stoicism is that it reminds us of how little control we really have over the events that rule our lives.

Amor fati conveys the idea that whatever happens – regardless of whether we perceive it as good or bad – we just need to accept it as it is.

Similar to Buddhism, Stoicism teaches us that while we often can’t control external circumstances, how we choose to respond to those circumstances is entirely up to us.

There's no way for us to avoid adversity. Indeed, we have little power over the vast majority of things that upset us in life – the idiot blocking traffic in our lane or a doctor diagnosis. And that powerlessness can drive us nuts.

There’s a famous story that illustrates an impressively Stoical approach to these kinds of life dramas. One December evening in 1914, Thomas Edison’s factory went up in flames. By then he was already one of the world’s most celebrated inventors. Seeing the fires rage, he famously called out to his son: “Go get your mother and her friends. They’ll never see a fire like this again.”

Legend has it that when his son told him he was mad, he calmly responded: “It’s all right. We’ve just got rid of a lot of rubbish.” 

You might assume that Edison was well-insured – he wasn't. He could have chosen hatred and anger as a response to seeing his life's work destroyed, but he did the opposite. By witnessing the fire objectively for what it really was – an event outside of his control. Doing so, he was able to make the best of it. And be glad he did or we'd still be using gas lights and messenger pigeons. 

Amor fati makes us look at life through a wider lens. Rather than identifying a situation as good or bad, we ask ourselves how we can make it helpful. We try and understand the valuable lessons that are hidden in every setback and how we can grow from them.

Stoicism teaches us that our internal response is the only thing we truly have control over. Everything in the external world is highly uncertain. We may not feel good about what happens to us. But it’s through our subsequent thoughts and actions that we decide whether a mishap either breaks us or helps us transcend as individuals.

3)    Premeditatio Malorum – Hope for the best, prepare for the worst

What catches us by surprise hurts us double. – Seneca.

If you hate ‘The Secret’ and other Law of Attraction nonsense as much as I do, you might want to tattoo this one on your forearm.

Lazily putting things ‘out to the universe’ while waiting for abundance to flow into your bank account is hugely disempowering. Premeditatio Malorum turns that idea on its head. Loosely translated as ‘prepare for all evils’, it encourages you to always look out for what can go wrong. It’s a negative visualisation exercise that forces you to consider everything that could go south. It’s an excellent mental tool that prepares you for the many uncertainties in life.

You may be thinking ‘Alright then, enough with the doom and gloom now’. I hear you. But to truly live a good life and become successful – whatever your definition of success is – you can’t close yourself off from what might be perceived as bad outcomes.  

And although preparing for the worst won’t do anything to change the outcome, it does train your resilience. When challenging circumstances do occur, you’ll be much better equipped to deal with them. Instead of being blown off course by events, Premeditatio Malorum allows you to hold your nerve because you already decided beforehand how you were going to respond.

And yes, life will still kick you in the balls, but at least you’ll be wearing a nice jockstrap.  

This idea of preparing for the worst may ring a bell with those of you familiar with cognitive behavioural therapy (CBT). Indeed, as part of a technique called emotional habituation, CBT therapists often ask their clients repeatedly to visualise fearful events as if they've already happened. By training them to confront these events in a controlled manner, clients become more effective at managing their anxiety and worrying less about the future.

A word of warning though. Simply hoping for the best might be delusional, but so is catastrophising. A Stoical approach to loving your fate forces you to look at events and outcomes from all angles – the good and the bad. The overall position then becomes one of neutrality.  

Ryan Holiday puts it nicely:

“Expect to have a pleasant and successful day. Just be ready in case it isn’t.”

4)    Impedimentum Ducit Viam – The obstacle is the way

Stoicism teaches us to welcome adversity and respond to it with lightness and even cheerfulness.

Despite their morbid touch, Stoics are actually a pretty optimistic bunch. Turning the idea of Premeditatio Malorum on its head, they believe that every negative has an equal and opposite. Indeed, every negative is a positive.

According to Stoic teachings, we should welcome obstacles. We ought to view them as opportunities to practise the Stoic virtues of Charity, Fairness, Faith, Fortitude, Hope, Prudence and – God forbid – Temperance. 

They encourage us to view every drama as a chance to thrive – not in spite of what's in front of us, but because of it. 

In the words of Mark Manson:

"Yes kids, you too can get your shit together and live a more satisfying and meaningful life by pursuing less, by letting go of all the stupid assumptions you've accumulated throughout your self-absorbed life, by forgetting about happiness and accepting that everything meaningful in this world requires struggle and sacrifice. So you might as well start picking out the scars you want for your birthday, kiddos because we're all going to get them anyway."


Listen, I know we're only human. So, even when we do try to show up as our best selves, there are plenty of irrational emotions that will play havoc with our decision-making. But the only way to counter this is by keeping our emotions in check and by staying steady. 

That doesn’t mean pushing away or ignoring bad thoughts and feelings. On the contrary. Our emotions are a fundamental part of who we are, and we don’t want to become apathetic or lose our ability to feel things.

Stoics encourage equanimity instead – a calmness and composure that allows you to steady yourself and not panic. It’s a sense of poise that stops you from being carried away by passion. Instead of getting swept up by the storm, you drop your anchor and become grounded. You then ask yourself: “At this moment, does freaking out add anything constructive to this situation?”  

Historian Ada Palmer talks about building an inner fortress:

“When I find myself dwelling on something that's upsetting me, and I have a sort of triage of responses. I ask myself (A) can I find an actionable solution to the problem? If not (B), can I get myself to stop worrying about the problem and let go? Can I laugh at the problem? Can I ask myself whether this will really matter in a year or five years?”

5) Ego Inimicus – Ego is the enemy

It’s impossible to learn that which one thinks they already know. – Epictetus

I’d love to say that humility is the key to success, but you don’t have to look far to notice that plenty of arrogant people often do pretty well in life too.

Think politicians with egos big enough to destabilise entire regions. Or influencers whose humble brags and inspirational stories ignore that we're only interested in seeing them naked. Or colleagues so eager for validation they'll gladly push you under an oncoming stationary delivery truck.

Ego can be a powerful driver for success, but it’s a pretty unreliable one. On a good day, it’ll stroke your nipples and tell you're better than everybody else. On a bad day, it’ll kick you in the groin, calling you a worthless piece of shit wearing a ridiculous jockstrap.

Stoicism accepts that a big ego can be helpful when it comes to being successful. But it also acknowledges you pay a price as it slowly ruins your character and soul.

Similar to Buddhists, Stoics believe that ego shows itself as an inflated sense of self-importance. It prevents us from having the humility to accept that we only know a tiny proportion of what there is to know. It stops us from learning.

This is what all of us divas and buffoons know deep down but find hard to admit. That we're not quite as amazing as we think we are. We congratulate ourselves on being the smartest person in the room. Instead, we should probably be asking why we were afraid to surround ourselves with more intelligent people in the first place.

Ryan Holiday puts it nicely in his excellent book Ego is the Enemy:

“Ego is the enemy of what you want and of what you have: Of mastering a craft. Of real creative insight. Of working well with others. Of building loyalty and support. Of longevity. Of repeating and retaining your success. It repulses advantages and opportunities. It’s a magnet for enemies and errors.”

Or in the words of Atomic Habits author James Clear:

“The surest way to prevent yourself from learning a topic is to believe you already know it.”

Conclusion – Stoic philosophy rocks

Stoicism gets rid of the fluff and teaches you to look at life in practical, humble and steady ways.

It teaches us that the path to happiness is purely internal and that how we interpret outside events is entirely up to us.

As a reminder, the five core truths of Stoicism are:

1) Use your mortality as a compass for prioritising your life

2) Accept everything that life throws at you

3) Hope for the best, but prepare for the worst

4) Any obstacle is an opportunity to practise virtue

5) Ego is the enemy of learning and growth.

There are several easy-to-read books on Stoicism. I owe a considerable debt to Ryan Holiday and The Daily Stoic blog for helping me gain some initial insights into Stoicism. I owe an even bigger debt to the original Greek and Roman Stoic philosophers – Zeno, Seneca, Epictetus, Marcus Aurelius and many others – but I figure they’ll be less likely to sue me for plagiarism.

For those interested in digging in a little deeper, here are some excellent resources.

·      The Daily Stoic

·      Ryan Holiday ­– The Obstacle is the Way

·      Ryan Holiday – Ego is the Enemy

·      Marcus Aurelius – Meditations

Also, here’s an excellent article that combs through the incredible similarities between Stoicism and Buddhism.

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I send out one short email at the end of each month with a few practical tips on how to develop a more meaningful and exciting life and career.

You'll also be the first to find out about my next group coaching programme and upcoming retreats.