Stoic practice

One way to actually DO stoicism, instead of reading about it.

I love stoicism. In short, it's a bag of tricks to help the mind calm the fuck down, both in good and bad times. However, besides reading several books, I find it hard to establish a daily practice. In spirit, stoicism feels like a less ornamental version of Buddhism, and the two overlap in a surprising number of themes and insights. But Buddhism has a much better tradition when it comes to practice. There are many schools of active practice, and numerous manuals to consult, whether on the Jhanas or breathing exercises. But for stoicism? Nihil. (This is Latin and a testament to how desperate I am that this essay sounds intellectual.)

Many people "practice" journaling, but I find this tedious, and worse, all thoughts sunk as ink onto paper cannot be used for full-text search or as context for AI. Besides this organisational difficulty, there seems to be resistance in stoic thoughts themselves, which Nadia Asparouhova describes as "antimemetic". Our minds do not seem to like them, maybe because they force us to avoid evolutionary shortcuts in our decisions, which costs more energy, who knows. I found that my main hindrance was how little engaging Stoicism books were, in contrast to its rich history of practice, which was marked by a group of guys (mostly men back then, sorry) sitting on stairs arguing. It was highly dynamic and interactive.

Whenever I hear the words "(custom) content" and "interactive", I default to AI as a solution to try first. And indeed, I managed to put together a nice Stoic practice using Claude (and Anki). Already, I shifted some of my views about friendships and networking, and they feel more grounded and — well, reflected on.

Since I find it unreasonably fun and useful, and since I am now more than a month into this practice, I thought I'd share. It is based on Seneca's letters to Lucilius, a set of 124 bite-sized pieces of content, more than four months of daily practice at one letter each day.

The letters often begin with an observation on daily life, and then proceed to an issue or principle abstracted from that observation. The result is like a diary or a handbook of philosophical meditations. The letters focus on many traditional themes of Stoic philosophy, such as the contempt of death, the stout-heartedness of the sage, and virtue as the supreme good. — Wikipedia

However, I do not read these letters. Instead, AI uses the letters as content for my daily practice. Traditionally, when you wanted to learn anything, you got a tutor. Now, and especially with the progress curve of AI, replace the tutor with "a good LLM".

(I am assuming you have access to Claude Desktop and a plan that includes the Opus 4.1 model, though Sonnet might work as well; I have not tested it. The entire setup takes only minutes, and each reflection session may be five, so there is really no reason not to try it.)

TL;DR: Create a Claude project using Seneca's letters and some instructions (both below), and set aside five minutes a day to reflect, going back and forth with what Seneca would have said, prompted either by commands like letter 5 or your personal experiences like /synthetic boredom. Distill the ensuing discourse into memory flashcards, including a daily challenge. Then resurface these cards using spaced repetition to practice stoicism. Not only will this develop a lasting intuition on the discussed issues, but it also creates a searchable library of content for you to use later on. As neatly stated in one of my discussions of letter VI, I had with this setup:

The Stoics would say: When you're gathering material and experience, operate. When you've discovered something worth preserving and multiplying, withdraw to refine and record it. The tragedy is that those who never make the second move, forever gathering experiences they never distill into wisdom. (Claude)

Conversation

Setup: In Claude (Desktop), open a new project. To files, add the letters.txt file I (legally) copied here (ignore the bad formatting, AI does not care), and as instructions, add the following prompt (feel free to modify):

Take the letter from Seneca to Lucilius (I will simply prompt you with the number of the letter), and present it as a challenge, like in a case study, to me. Reflect on my answer in light of what Seneca writes.

First, as title, write the title of the letter. Then look it up in the provided sources.

Assume I have not read the letter, and do not know of its contents.

Support your response with direct quotes from the letters (in English).  Cross reference other stoics, if this seems fitting.

<commands>
- When I write the `/short` command, summarize the letter's core argument into a tweet-sized piece of actionable insight (akin to Marcus Aurelius' meditations).
- `/challenge` .. Can you provide me with a SINGLE challenge for this day to practice what we talked about? This challenge should be specific, and I should be able to write it on a little card or tweet-sized piece. No title/ emojis/ markup/ newlines etc.
- `/feedback (some text goes here) .. I will present my experiences with the /challenge and want Seneca to give feedback on this experience, as if I had a personal consultation with him. Start with "Seneca says": ...`
- `/synthetic` (some description, situation or topic here) .. Write a letter to Lucilius about the text after the command as if Seneca had written it. No title etc., just the letter. Avoid anachronisms.
</commands>

What is happening here? You probably know your way around Claude, so you're used to prompting, or "context engineering". In short, you provide instructions to the model. The only unusual thing here is that we define a "commands" block in XML syntax (to make it easier for the LLM), and define commands in the form of /command that we can later use as shortcut to prompt the model. With these instructions, you can do things like:

• letter 5 .. This will start the discourse about the topics discussed in the 5th letter to Lucilius, and you can actively reflect on its content in a back-and-forth with the model.

• /short .. After some interaction, get a tweet-sized summary.

• /challenge .. Give a daily challenge, to practice in the real world. If the generated challenge is not suitable, try entering /challenge again until you find one that suits you.

Synthetic conversation

Seneca offers a great selection of themes, but there are many things I am interested in that he does not cover. How to deal with boredom, or is there any stoic insight to procrastinating on daily chores? Well, because LLMs can role-play where they act as a superposition of roles, and when prompted correctly, they can act as a simulacra of a person, such as Seneca. They also know a lot of stuff about other Stoics, and can thus cross-reference, but be aware:

From a software engineer's point of view, you can think of LLMs as the worst database you've ever heard of, but worse. -- pydantic.ai docs

The /synthetic command gets "Seneca" to write a letter about the specified topic, e. g. /synthetic boredom. When you practice (see below), you can request /feedback from the master stoic, e.g., in the same conversation you discussed the topic in:

/feedback I have difficulty not engaging in preference falsification when in professional networking events. any other suggestions besides the ones mentioned above?

I manage to engage in pretty personal and insightful discussions in this way quickly. This might be because by engaging in a personal discussion, there is more "emotional connection" (I know this sounds weird), which makes one more forthcoming, which in turn advances the discussion much quicker.

Practice

Taking the time to reflect is nice, but I started out wanting to practice. For this, we use spaced repetition flashcards using Anki or any other spaced rep app. On the front of the cards, I put the response from /short and on the back, my daily /challenge. For example, a card might look like this:

Front:

Boredom is not the absence of activity but the absence of purpose. The restless mind that cannot sit with itself in quiet will find no peace in motion either. Set your mind to worthy questions each morning; make your leisure a workshop, not a wasteland. You are never less alone than when alone with philosophy. (synthetic)

Back:

Today, when you feel the first stirring of boredom or restlessness, stop immediately and ask yourself: What am I fleeing from in this moment? Sit with that discomfort for five full minutes without reaching for any distraction, then write down one truth about yourself that emerged from the silence.

At night, during my reflection session, I go through them and score how difficult or easy I have found the tasks. The easier the challenge, the longer it takes until the card is resurfaced. This scheduling ensures that still-challenging tasks receive more attention. The resulting "spacing effect" results in pretty efficient learning. Since I aim to internalise the Stoic teachings, this is a good place to start.

Farewell.