Practical Stoicism

In this episode, I'm talking about how to get over your ex, particularly when a relationship ends that you valued more than the other person did. Breakups can be especially difficult because, unlike losing someone to death, you have to watch someone you once shared a life with go on living theirs without you. Over time, the relationship can begin to feel like something that happened in another lifetime, and it's easy to get caught up in missing them, resenting them, or questioning what any of it meant.
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I approach getting over an ex through three steps grounded in Stoic philosophy, beginning with understanding where your actual value comes from.
For the Stoics, our worth isn't determined by our relationships, careers, wealth, or whether somebody wants to be with us. It resides in our rational faculty, the hegemonikon, which receives impressions, forms judgments, and directs our choices. This faculty makes us capable of acting as rational moral agents, and the character we develop through its exercise is what matters most.
From there, I ask you to examine what you're doing with that faculty. Are your thoughts and judgments helping you become someone you respect, or are you allowing resentment, longing, and frustration to shape your character? I use some admittedly ridiculous metaphors involving moral auras, coloured plastic, and keeping the inside of your mind from becoming a pigsty, but the point is serious: the quality of our inner lives affects how we show up in the world.
Finally, I explain why recognising your responsibility to develop good character changes how you think about your ex. You have something more important to attend to than a relationship that's ended: becoming a decent, rational, virtuous person, not just for your own sake but for the benefit of everyone who shares the cosmopolis with you.
The Stoic approach isn't to make your ex irrelevant by pretending the relationship never mattered. It's to recognise that your value was never theirs to give you or take away, and that your attention belongs to the person you're becoming rather than the relationship you've lost.
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This week, I’m answering a question I genuinely never expected to cover on Practical Stoicism: how do you stop masturbating? More specifically, what do you do when masturbation has stopped being an ordinary sexual behaviour and become something compulsive that you no longer feel reliably able to choose?
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I start by clearing up something important: there’s no particular reason to think the ancient Stoics regarded masturbation itself as morally problematic. Sexual pleasure isn’t the issue. The Stoic concern begins when our pursuit of pleasure starts overruling reason, self-command, our responsibilities, or our ability to live appropriately.
So this isn’t really an episode about how to stop masturbating. It’s about what to do when your relationship with masturbation has become compulsive enough to interfere with your life.
I work through seven practical steps: identifying the triggers that precede the behaviour, changing your environment around those triggers, developing replacement behaviours, addressing any emotional problems you may be using masturbation to regulate, seeking professional help when you repeatedly cannot regain control, considering reputable support groups, and measuring the problem by control and consequences rather than an arbitrary number of times per week.
I also talk about the difference between ordinary sexual behaviour and compulsive behaviour. The important question isn’t simply how often you masturbate. It’s whether you can reliably choose not to, whether you continue despite wanting to stop, and whether the behaviour is interfering with your work, relationships, responsibilities, health, or ordinary life.
There’s plenty of room for humour when talking about masturbation (and I certainly take advantage of it), but compulsive sexual behaviour can cause genuine distress, shame, isolation, and disruption. The Stoic response isn’t to treat sexuality as dirty or shameful. It’s to recognise when pleasure has begun governing us rather than remaining something we rationally choose.

In this episode, I’m challenging one of the most common assumptions in modern Stoicism: that journaling is somehow an inherently Stoic practice. Marcus Aurelius wasn’t keeping a daily diary, Epictetus wasn’t assigning journal entries to his students, and the kind of expressive writing we now associate with “Stoic journaling” is largely a modern self-improvement practice.
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That doesn’t mean journaling is useless. Regular reflection, planning your day, reviewing your behaviour, and expressive writing can all be helpful. But they’re no more uniquely Stoic than they are Christian, Buddhist, atheist, or useful to an anthropomorphised and literate potato.
So if we’re going to talk about “journaling like a Stoic,” I think we need to invent a better standard for what that actually means.
I break Stoic development into three parts: study, practice, and living. First, we learn the philosophy from people who know more than we do. Then we practise applying what we’ve learned until new patterns of thinking and behaviour become habituated. Finally, we put down the books and training aids and go out into the world to see whether any of it actually stuck.
That middle stage is where I think writing can be genuinely useful to a Stoic practice.
Rather than simply recording what happened during your day or writing about your feelings, I suggest explorative writing: take a difficult question or real-world situation and try to reason through it Stoically without reaching for a book, ChatGPT, or a cheat sheet. The purpose is to discover what you actually understand, where your reasoning falls apart, and what you need to return to your studies to learn.
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So, ironically, my advice for journaling like a Stoic is to stop journaling, at least in the conventional sense, and start using writing as a place to practise the philosophy instead.

In this episode, I take on the Lindsay Clancy case, but not to tell you what you should think about her. Instead, I use this extraordinarily difficult case to explore how a Stoic should think when confronted with terrible acts, mental illness, questions of responsibility, and our very human desire for punishment.
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I begin with the facts as I understand them and an important limitation: I don't know every detail of the case or trial. Clancy killed her three children and attempted to take her own life, but she had also sought extensive psychiatric help before the killings. The defence has argued that she was suffering from postpartum psychosis and that her condition had previously been misdiagnosed.
For Stoicism, that raises an important question. The acts were hers in the causal sense, but to what extent were they hers in the moral sense? Stoic ethics places enormous importance on our capacity for rational assent. If someone's rational faculty is profoundly impaired by psychosis, then determining their responsibility requires us to consider how capable they actually were of perceiving, judging, and responding to reality rationally.
That does not mean pretending the acts didn't happen, nor does compassion require us to ignore the safety of everyone else. If someone remains dangerous, restraint may be entirely appropriate. Justice has obligations both to the person who is ill and to the people who require protection from them.
Drawing on Seneca, I distinguish justice from vengeance. Restraint or punishment may be appropriate when it protects others, prevents further harm, or contributes to correction and treatment. Making someone suffer simply because their actions caused suffering is something else.
Ultimately, I suggest three things we should hold simultaneously: Clancy is a seriously mentally ill human being; she may require restraint for as long as she presents a danger; and where treatment and restoration are possible, justice should concern itself with those things too.
Stoicism should make our responses to cases like this slower, not faster. We should resist the satisfaction of immediate condemnation, examine the context carefully, ask what Justice actually requires, and only then decide how we ought to respond.

Most of my listeners are somewhere between 35 and 45, which means quite a few of us are reaching the age when mortality starts feeling a little less theoretical. In this episode, I explore one reason the idea of death can trouble us that has less to do with fear and more to do with something deeply human: the desire not to feel disposable.
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I begin with a conversation I recently had with a private coaching client about why believing in something after death can be comforting. My suggestion was that the comfort may not necessarily come from imagining rewards, avoiding punishment, or even continuing our conscious existence. It may come from believing that we remain important to something beyond ourselves, that we continue to have a place.
Stoicism offers an interesting answer to this without requiring a supernatural afterlife. The Stoics understood the Cosmos itself as God: the complete, contained system of Nature of which every one of us is presently a part.
Within that system, nothing simply disappears. The matter and energy that presently constitute us return to the Cosmos and continue participating in it. The individual person, with their name, memories, career, possessions, and personality, may not continue indefinitely, but that from which the individual is constituted remains part of the whole.
In that limited but meaningful sense, I suggest there is something resembling immortality available within the Stoic worldview. Stoicism doesn't promise a celestial city, an eternity spent with deceased relatives, or reincarnation as some other creature. Instead, it offers the idea that we were never separate from the Cosmos in the first place, and that what constitutes us continues to belong to and participate in that same whole.
If what troubles you about death is the thought of becoming irrelevant or disposable, perhaps there's some comfort in that. You aren't something the Cosmos eventually throws away. You are part of it now, and what constitutes you remains part of it after the particular arrangement presently called "you" is gone.