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Meditation and Philosophy with Caleb Ontiveros




This month I talk with Caleb Ontiveros, creator of the highly-recommended Stoa app, about the relationship between Stoicism and meditation. Caleb is a software engineer and former philosophy Ph.D. student. You can learn more about Stoa here or see more of Caleb's thoughts on his personal website or Medium page.



Brittany: It's great to talk with you, Caleb! Could you tell us more about your pre-coding background in philosophy? What did you study, and what drew you to the study of philosophy and Stoicism in the first place?

Caleb: I became interested in philosophy in high school, because I wanted to know whether God exists. Whatever the answer to the question is if God exists that should make a large difference to how one lives. It turns out there’s a whole field and tradition devoted to rigorously answering questions like this.

That’s the aspect of philosophy that most engaged me. It’s focused on big questions that matter. Ultimately, how to live.

The Stoics and other ancient philosophers exemplify that style of philosophy, so it was only a matter of time before I was drawn to them.

I read Epictetus’s handbook in undergrad. It didn’t strike me then. Later, I read Nassim Taleb’s Antifragile. He talks about Seneca. It was then that I understood how relevant and insightful the Stoics were.


Brittany: In your highly successful Stoa app, you’ve managed to bring together your passion for Stoic philosophy with your tech skills. Do you see these two skill sets (philosophy and coding) as informing or complementing each other? You offer one way of answering this in your piece Programming as Metaphysics, but I would be interested in hearing more. So does philosophy make you a better coder, and does coding make you a better philosopher?

Caleb: That’s a good question.

As you say, there are conceptual similarities between good code design and philosophy that I explore in Programming as Metaphysics. In that sense philosophy can help programming. Apart from that, to program well one must be precise in communication – with humans and computers. If you’re not, your program may break and, in the best case, you’ll know rather quickly. Having quick access to feedback from the world forces you to be honest and as accurate as possible. Two valuable traits in philosophy.


Brittany: One theme that I notice in your work (e.g., On Reality-centeredness) is the importance of getting outside oneself to see things as they really are. Your term for this is “reality-centeredness,” which you define as “the ability to look at the world as a whole while identifying with and being motivated to promote the good. Seeing the world through all the seers, not merely one's own vantage point.” Can you explain more about reality-centeredness and why it’s important for those of us who wish to live a philosophical life?


Caleb: When one is ego-centered or self-centered, our view on the world is narrow. It’s narrow in temporal, spatial, and personal ways. We think on short time scales, don’t take into account the bigger picture, and don’t act with others in mind.

Being reality-centered is all about transcending this self-centered view. It’s about viewing the world with the big picture in mind. We’re only one animal in a sea of trillions. Many have come before us and there will be many after us.

One can get a sense of what this feels like, with view from above exercises. Some forms of fiction and intellectual work can also help. From this wider vantage point, it’s easier to see what is actually important. With deep time and space in mind, the trivial can fall away. There’s a risk of becoming too detached and distant. I see reality-centeredness as falling in between the mean ego-centeredness and complete detachment.

Brittany: You’ve been practicing mindfulness meditation for about a decade, and you developed the Stoa app because you wanted to combine Stoicism with mindfulness meditation. In the Stoic context, is mindfulness meditation mainly about developing our ability to notice and then consciously manipulate our emotional reactions? Would you equate this to the ancient concept of prosoche?


Caleb: Jon Kabat-Zinn defines mindfulness as nonjudgmental awareness. That’s a useful definition.

One can think of it as objective representation. Marcus Aurelius talks about seeing wine as fermented grape juice, royal robes as sheep's wool dyed in the blood of a shellfish – he decomposes things into their parts to clean them of his usual narratives. Elsewhere he says:

“Don’t tell yourself anything more than what your primary representations tell you. If you’ve been told, “so-and-so has been talking behind your back”, then this is what you’ve been told. You have not however been told that “Somebody has done a wrong to you”.”

This is nonjudgmental awareness – seeing things as they are without making unnecessary or false value judgements.

That’s the nonjudgment aspect, the awareness part is also emphasized by the ancient Stoics. Especially by Epictetus.

I wouldn’t say that modern mindfulness and prosoche are the exact same. Massimo Pigliucci, Gregory Sadler, Pierre Hadot and others have good pieces on that technical point.

What matters here is the emphasis on cultivating attention and reducing unnecessary value judgments. The Stoics thought these were important. Mindfulness meditation is one tool for getting better at both.

Brittany: In a post for Modern Stoicism called Meditation for Stoics, you make the case that mindfulness meditation is a type of non-cognitive or non-conceptual practice that can complement the traditional cognitive Stoic meditative practices. Do you see this practice as similar to other types of spiritual exercises (as identified by Pierre Hadot)? Why do we need non-conceptual practices in addition to cognitive practices?


Caleb: Yes, one can practice the view from above or contemplation of the sage in non-cognitive ways as well.

When contemplating the sage, one can visualize the sage taking your place and acting virtuously. Doing this in a detailed and visual way is non-cognitive. It’s like an athlete imagining their ideal performance.

As you say, non-conceptual practices and cognitive practices are both useful. There’s empirical support for both. The non-conceptual involves implicit, intuitive, image-based ways of thinking. We cannot ignore it, since conceptual and non-conceptual creatures.

Although the ancient Stoics often emphasize the explicit, conceptual, and rational part of human nature, they do talk about the intuitive and implicit. Marcus Aurelius especially.


Brittany: Lately I’ve become interested in the idea that certain types of meditation, such as tonglen or metta meditation, could help us cultivate what the Stoics call the good emotions, or propatheiai. The good emotions include good intent (eunoia), goodwill (eumeneia), and enjoyment (terpsis).

Do you practice tonglen or other types of meditation in addition to mindfulness meditation? If so, what benefits do you notice? Do you see a space within Stoic meditative practice for cultivating the good emotions such as joy, goodwill, and kindliness toward others?


Caleb: Personally, I don’t practice loving-kindness meditation. I’d rather spend time doing kind things for others than cultivating feelings of compassion. Feelings aren’t necessary for acting well.


That said, some people have found loving-kindness meditations useful for cultivating self-love or prosocial emotions for others.


Related exercises that can be useful are gratitude meditations and the contemplation of the sage. During gratitude meditations, one can bring to mind who has been kind recently and remember to thank and serve them. With a contemplation of a sage exercise, one can consider how a role model would treat others – visualizing that in detail is a way of generating ideas for kindness.


With a lot of these exercises, it varies by person. Loving-kindness meditations may be worth trying. If you and those around you notice positive effects, then it’s working. One needs to be an empiricist about this kind of thing.




Brittany: Are there any other practices or ideas you find useful in living a philosophical life?


Caleb: One idea I like I’ve called the tilde strategy, after the logical symbol. Whenever one reads advice, consider the negation of the very same advice.

Another idea that’s currently underrated is the notion of ideological Turing tests.

A Turing test is a test one gives to an AI. The AI passes if a human can't tell the difference between the AI and a human. An ideological Turing test is given to a person. They're given an ideology, say Marxism. The person passes if another can't tell the difference between them and an actual Marxist.

One can think of it as cognitive empathy. The idea is to understand others' ideas as much as they do. To put their position in the words they would. Whether I’m thinking about abstract political debates or concrete disagreements with my partner, this is an indispensable idea.


Brittany: What projects are next on the horizon for you?

Caleb: I’m continuing to work on Stoa. I have nothing else to announce yet. Stay tuned!


Brittany: Is there anything else you’d like to share with readers of Living in Agreement?

Caleb: Don’t hesitate to get in touch if I can help with anything.




Brittany: Caleb, thank you so much for taking the time to answer a few of my questions! We’ve done a couple of previous interviews for your Stoa app, but this is the first time I’ve gotten to turn the tables and ask you the questions. I really enjoyed getting your perspective on Stoicism as a way of life, including how a Stoic might meditate. Thanks again!