Take Stoicism Into Your Practice With a Grain of Salt

It’s been almost a decade since Ryan Holiday published The Daily Stoic and yet the ancient philosophy of stoicism is still having it’s rebirth moment. Its presence feels especially dominant in the world of entrepreneurship where Stoic thought is constantly getting dropped into podcast episodes, newsletters like this one ;) and, some founders say, into their practice.

I received The Daily Stoic as a gift five years ago and read it religiously every single day for four years in a row. The insight on every page promised me a way to create a version of myself that could easily move on from disruptions that were out of my control, a version of myself that wisely chose what got my attention at any given moment. I loved it so much that after the first year I bought a copy for my brother, the following year I even bought Meditations, read a dozen pages and (honestly) gave up. Then, this year, on January 1st, I decided not to start the ritual again.

Why? I read Nietzsche and Schopenhauer. The more I read, the more I understood that Stoicism might not be as deep or life affirming as it seems and in many cases it takes away the “human” out of us.

Now before you Stoicism fans get upset, I’m not saying there is no merit in Stoicism - there absolutely is! All I’m saying is that it isn’t this end-all be-all to being adaptable that it’s often portrayed as. Let me explain…

Stoicism is a virtue ethics meaning that the Stoics believed that the universe has a rational, stable order (the logos). They also believed that if you live rationally and cultivate the four virtues (justice, courage, wisdom, temperance), you can eventually become aligned with that order. Thus, the Stoic sage is the ideal “finished product”: calm, consistent, virtuous, and in harmony with nature.

This view is teleological at its core: there’s a fixed goal and the purpose of life is to align yourself with it. Additionally, and really importantly for the rest of this newsletter, this view assumes there is a stable essence to the universe that can be modelled and followed.

source: https://pleated-jeans.com/2025/02/07/funny-stoic-memes/

1. Clinging to “rational order” makes you rigid; embracing becoming makes you anti-fragile.

Nietzsche was a philosopher in the 19th century who argued that the universe isn’t stable or rational at its core but is in constant flux, chaos, indifference and emergence.

Sounds familiar? cough - entrepreneurship - cough.

Unlike the Stoics, in Nietzsche’s view, there is no final state of harmony to “arrive at.” Instead, life is in perpetual transformation where improvisation, passion, creativity, and destruction are all interwoven. According to Nietzsche, the Stoic project of being virtuous is naïve because it imposes an artificial stability onto a world that is fundamentally dynamic. It’s like trying to freeze a flame into one permanent shape, since the very nature of fire is transformative, the moment you try to hold it still, it is no longer fire.

Similarly, I believe that entrepreneurship is about becoming, and oftentimes, if you try to build a company according to fixed virtues or rational frameworks (always calm, always rational, always disciplined), you may feel safe, but you might miss a deeper connection to the dynamic nature of your product’s market in the real world.

Imagine for example that you launch a startup with a beautiful five-year plan. During the five years you seek stability through disciplined processes, balanced budgets, calm decision-making until AI disrupts your industry overnight. If this scenario isn’t that hard to imagine it’s because you know that in the world of entrepreneurship, shit like this happens all the time! However, the Stoic buck stops there because the Stoic sage would sit in apathy when the news hit. Instead, successful founders tend to acknowledge the challenges, improvise, pivot, take risks, and transform, along with the changing demands.

2. Greatness emerges from intense passions

Stoicism teaches self-tyranny which basically means governing your passions until you’re calm and “virtuous.” For example, if you’re furious at your boss and quit on a whim to start your own company, a Stoic would say you failed to control your anger. On the other hand, Nietzsche would argue that passion was the spark of self-overcoming; therein, the messy fights, late nights, and emotional rollercoasters of building something new are not moral “failures” they’re the crucible that forges creativity. To numb those emotions would be to miss the energy that makes entrepreneurship possible.

Now I’m not saying that there isn’t value in this Stoic idea of creating space between yourself and external events that have the potential to mess up your day or that it’s a good idea to quit your job every time your feelings get hurt (realistically I don’t think you’d quit from just one-rough event, something like that would probably be a tipping point of accumulated tensions). What I am saying is that the Stoic would have us believe that we need to minimize the pleasure we get in life to minimize the pain we get, and minimize intense situations that could ultimately lead to growth.

3. Suffering = compassion and innovation

As you might have gathered in your contact points with it, a key underlying objective of Stoicism that makes it so attractive to entrepreneurship is the promise of inner peace of mind free from suffering. Basically, when Stoics came across suffering, they trained themselves to react with indifference.

However, another 19th century philosopher, Schopenhauer argued that this is a bit of a misinterpretation. Yes, Stoics are calm and tranquil but that’s not supposed to be the goal at all cost. The real goal of Stoicism is technically* adherence to the virtues, and if calmness is a by-product, thats just a matter of coincidence.

Schopenhauer claimed that if indeed the reduction of suffering is the true goal, then the Stoic virtues (such as courage, wisdom, etc.) become merely instrumental things used to achieve that inner peace. Basically, Schopenhauer was pointing out a paradox. Either you’re orienting yourself to fixed virtues and calmness is a by-product of that OR you’re just preaching ancient advice rather than practicing ethics.

Schopenhauer was especially critical of this because, for him, morality begins by internalizing suffering. Not only is suffering an inevitable part of life according to Schopenhauer, he considered it a really important teacher. In entrepreneurship, innovation often begins with suffering, our own or others’: solutions to reduce pain points. If we didn’t let ourselves feel those pain points we would never have thought of solutions for them because it wouldn’t be necessary.

Then, to deny suffering is to cut yourself off from the raw fuel of creativity and ultimately, moral action. Again, true morality, for Schopenhauer, begins in compassion - suffering with others, not suppressing your feelings so you stay calm. According to Schopenhauer, by only seeking only inner peace, Stoicism risks selfishly disconnecting us from reality and from others. Funny enough, he thought the Stoics don’t avoid suffering but rather suffer twice. First through the actual event and again through naturally suppressing emotions.

So, what is the grain of salt to take with Stoicism?

My interpretation of the appeal of Stoicism in the world of entrepreneurship is as a reminder to create space between individuals, their emotions and the external world. To me, this is more self-reflection than it is Stoicism.

Do I think there is value in letting go of what you can’t control? Absolutely.

Do we often wrap ourselves up so tightly into external events and the emotions that are born from it that we often cause our own suffering? Yes. Seneca himself said “A man is as miserable as he thinks he is."

Long story short, our thinking is absolutely the cause of our suffering (recommended reading: Don’t Believe Everything You Think) but I believe that our acceptance of these thoughts and trying to understand them for what they really are is the path. Nietzsche would tell us, face the messiness of life head on!

Similarly, Schopenhauer would say would say that we should sit in suffering, acknowledge it as a part of the journey, and find a way through it. He believed that if you want to deal with suffering you have to deal with constantly listening to the underlying will. This means taking notice of how we are constantly driven by forces (feelings, drives) to make choices, and practice being aware and more conscious of those forces. Practice compassion for others’ suffering. Practice a quieter mode of being. It’s an acceptance of rather than a suppression of.

The quick and dirty?

Stoicism may give you peace, but it alone will not solve your suffering. Heck, it might even make you suffer twice, once in the event and again trying to suppress your experience of it! Some philosophers argued that even if it could solve your suffering, we shouldn’t look to solve or ctrl-alt-del suffering because it’s an important part of life and often inspires innovation and morality. Lean into understanding the suffering, experience it and use it as fuel for innovation and evolution. Ultimately, Nietzsche and Schopenhauer don’t promise peace; they promise intensity. And in the arena we’re in, intensity is often the greater truth.