Discovering Wisdom

Tomorrow’s events:

  • Collective Journaling w/ Peter Limberg and Co-Hosts. Daily @ 8:00 AM ET. Patreon event. 90 mins.

  • Stoic Breath w/ Steve Beattie. Every Sunday @ 10:00 AM ET. RSVP here. 60 mins.


July 17th, 2021

Socrates had no system to teach. Throughout, his philosophy was a spiritual exercise, an invitation to a new way of life, active reflection, and living consciousness.

That is Pierre Hadot writing about our spiritual homeboy in Philosophy as a Way of Life. I like Socrates so much I named my cat after him. That was probably a pretentious thing to do but whatever, my little furry guy is living up to his namesake. He is a gadfly, and does these hit and runs on me, where he hides and pounces, then runs away, usually when I am unexaminedly in doxa mode. He must know!

Here is another quote from Hadot: 

Ancient philosophy proposed to mankind an art of living. By contrast, modern philosophy appears above all as the construction of a technical jargon reserved for specialists.

Yeah. This is that beautiful distinction between “artists of life” and “artists of reason” that Hadot writes about, and I am going to discuss how to do the former today. So, how do we do philosophy as a way of life, and become artists of life?

I do not really know, and as I will get to later on in this entry, not knowing is the first aspect of doing philosophy. The last three entries were building up to this one, and I do not know where this one is going to take me, but there is a destination in front of me, which is the second aspect of doing philosophy.

Perhaps a brief recap of the last three entries before I begin today’s destination: 

In the framework I presented, there are at least three heavenly paths of life transformation: wisdom, awakening, and love, or put another way: navigating reality, witnessing reality, and loving reality. And there are three hellish paths of life transformation: doxa, power, and chaos, or in other words: following others’ reality, controlling reality, and destroying reality. 

When in doubt the Path of Wisdom is the wisest path to walk down, I argue, because it is the path that affords you to walk down the other two heavenly paths, or to pursue beneficial aspects of the three hellish ones, when wise to do so. 

The Path of Wisdom, it seems to me, has at least three claimants today: philosophy, life coaching or self-help more generally, and psychotherapy. I explored the latter two yesterday, and argued that while they are valuable and needed, they both are overextended in their reach, and serve as “existential placeholders” for something that wants to emerge.

I would say another existential placeholder for philosophy as a way of life is the applied rationality movement. As I argued before, rationality is different from reasoning, and the former is meant to set up the latter. The rationality movement presents really good psychotechnology for clearing up our inherent irrational cobwebs, but focusing on becoming rational beyond a certain point has diminishing returns. It is one of those skills you learn and then move on from, so that you can start really philosophizing as a way of life.

Life coaching or self-help, psychotherapy, and applied rationality are needed on the Path of Wisdom, but they are not the main things. As I have been suggesting, philosophy could be the main thing. Reasoning is indeed important for philosophy, but being in the right relationship with reason is what separates one from being an artist of life versus an artist of reason.

I wrote eight journal entries in May about reasoning, concluding in an entry called So, How Does One Actually Reason Well Anyway? I sense the reason why I was going on about reasoning so much was because I often see two trends with really smart people: overplaying the importance of reason and underplaying the importance of reason. I want to approach reason in a way where a healthy balance is found, and a middle way is discovered between those who are overplaying and underplaying with reason.

I still agree with the prerequisites, constraints, conditions, and containers I introduced in that concluding entry, but I sense more nuance can be added to help distinguish the difference between artists of life (aka philosophy as a way of life) and artists of reason (aka academic philosophers), and how each one relates to reason.

A good distinction to add here is the distinction of “practical reasoning” and “speculative reasoning,” or praxis and theoria. The former is about using reasoning that results in action, and the latter is using reasoning to figure out what is true. Now, it is tempting to make a move where we say that artists of life are concerned with practical reasoning, and artists of reason are concerned with speculative reasoning.

I do think the latter is definitely true, at least in their professional roles, as I argued when I previously dunked on academic philosophers, but I do not think it is correct to say that artists of life are only focused on practical reasoning. I would say that life coaching and self-help are strictly focused on practical reasoning for personally getting more of something. Most psychotherapy, especially cognitive psychotherapy, uses practical reasoning to personally get less of something.

Artists of life do both practical and speculative reasoning, so perhaps an intermediary phrase is needed here. I like the “wise reasoning” phrase that the folks who designed the “Situated Wise Reasoning Scale” use. They claim that wise reasoning consists of three things: epistemic humility, accounting for context, and integrating different perspectives.

So much yes to that. I do want to repurpose this phrase for the artists of life though, and add the following aspect: artists of life engage in wise reasoning, which is a reasoning that allows them to engage in both the practical and speculative, with a readiness to switch between the two. Both types of reasoning are needed to navigate reality, and it becomes problematic when a heavy bias is placed on one or the other.

I would say another important aspect of wise reasoning is reasoning from a place that is “existentially salient” (oh, hello there daemon). This place, which is hard to lock down in the realm of propositions, is perhaps the axis mundi for philosophy as a way of life.

John Vervaeke and the folks involved in the “dialogos conversations” are actively talking about all of this stuff, which is fucking awesome, but my concerns with those conversations are A) they are happening mainly in the hyperconversation on the clearnet, B) they are happening between people who have a talent for high abstraction, C) what is most existentially salient for them usually falls in the realm of speculative reasoning, and D) the conversations often shy away from what is deeply personal, and for good reason, as they are being broadcast to the world.

Now, I think all of this is perfectly fine for the context, but my concern is that this might turn philia sophia into a spectator sport, making people both awestruck and intimidated at the verbal prowess and knowledge asymmetry that those engaging in the public dialogos conversations have. The likes of John Vervaeke, Gregg Henriques, and Christopher Mastropietro are incredibly intelligent individuals with a super high verbal intelligence, and a ridiculous knowledge base.

People who see only this might think, A) I cannot play this game, or B) to play this game I need to play it in the way I see it being played. Overall, I do sense it is a good thing that more people are listening to philosophy than to culture war noise (philia nikia), and as Alex Ebert has often said to me, philosophy is ripe to become the next cool thing.

It is actually motivating me to create a parallel attractor to these public dialogos conversations, something that is in deep alliance with them, and is more inviting to those who think engaging in philosophy is out of their reach. I sense what is key is having a safely unsafe container where what is existentially salient can fully breathe, as what is most existentially salient for most are the things that are deeply personal.

Philosophers, in the artist of life way, need to get back some sacred real estate from the life coaches and psychotherapists, and engage in practical reasoning about “planting seeds and pulling weeds,” while also engaging in speculative reasoning to explore the main branches of philosophy in an accessible way. These include ethics, epistemology, aesthetics, and metaphysics: aka the good, true, and beautiful, along with reality/God.

Andrew and I are in the active planning of launching something called “Discovering Wisdom,” hopefully in October or November. We are looking for another name other than a course to call this thing, and we are considering calling it a “philosophical venture,” which feels philosophically coherent with what we want to do, and what we want to do is something really fucking beautiful. 

While reason is important, the venture is not going to directly discuss or teach reasoning, as the focus is going to be on philosophical inquiry, which does incorporate wise reasoning. In our philosophical venture, an updated version of Andrew’s lovely little e-book, The Art of Inquiry, will be included. From the e-book:

An inquiry is an unrehearsed genre whose principal aims are, first, to reveal to us what we don’t know but thought we did and, second, to bring us a greater sense of clarity than we could have possibly imagined.

As mentioned at the beginning of this entry, there are two aspects here, and the first one is coming from a place of unknowingness, which is the place “the question” is asked...

How do we fucking live our lives?

Or as articulated more beautifully by Andrew:

One end of a philosophical inquiry, by contrast, is to draw our life into question. There is no sense in which this drawing into question can take place unless we are able to lose our footing, come to stutter, get muddled by what we mean, flail about in confusionunless, in short, we come to know that we do not know what we thought we did, that we do not grasp what we had for so long taken for granted.

And on the other end of a philosophical inquiry:

There is something we want to say but do not know yet; there is somewhere we want to head but this somewhere remains elusive; there is something missing we want to find but the discovery has, as of yet, remained hidden. The conclusion to an inquiry, accordingly, is like poetic naming: a new destination, a novel discovery, a long-sought-after homeland.

I am excited about this venture. It would be deeply foolish for me to figure out how to walk down the Path of Wisdom alone, via solo journalling. It is wiser to figure this out with a committed community of practice, community of inquiry, and community of purpose. I am tempted to replace the word “purpose” with “daemon,” but that is probably a given to the regular readers here. 

While we are still in the process of designing this venture, I can say a few things about it now. It will have opportunities to practice and get better at philosophically inquiring with oneself (journalling), with another (I-Thou), and with others (we-space), about what is most existentially salient, which could be about what is alive with oneself (first-person epistemics, or intrasubjective), what is alive with being together with others (second-person epistemics, or intersubjective), and what is alive with what is True between all (third-person epistemics, or objective).

I am excited about all of this because I love creating lifeworks while going on adventures, and I get to do both here. I do not know if my current philosophy as a way of life will remain intact after this venture though. I am currently a Stoic, or more accurately, a maybe Stoic, as I have journaled about last year in an entry called Being a Stoic

I was originally drawn to Stoicism temperamentally, and I stayed with the philosophy because I think it is the cleverest virtue ethics out there, as it affords the best of Aristotelianism and Cynicism, aka you can still pursue Aristotelian external goods with thumos, while giving zero fucks if you do not achieve them like a good Cynic.

It also affords a lot of philosophical entrepreneurialism, if you approach the philosophy as a “live player.” A lot of the original Stoic texts went missing, hence I see an openness for “boundary play” to happen with the philosophy, instead of just “boundary work,” which is what both the advocates and critics of Stoicism engage in. 

But yeah, during this venture I may Stoically become Unstoic in front of you, and I am actually very excited by this prospect. Not because I do not like Stoicism, as I fucking love Stoicism, but I love wisdom more than any particular philosophical configuration in logical space. I sense it would be good to close this entry with a few distinctions:

Having a philosophy,

Adopting a philosophy,

Doing philosophy,

I will define “a philosophy” as a worldview that provides you enough sense of what is and what ought to be. I would say philosophers and non-philosophers alike have a philosophy, some have a conscious philosophy that is examined, but most have an unconscious philosophy that is not examined. If the philosophy is examined, that does not always mean one is congruent with their philosophy, as their reasons and actions are not always coherent.

Adopting a philosophy happens when you are born into a philosophy and never question it, like a lot of those on the Path of Doxa. You can also adopt one through getting “red pilled” or “woke” by some memetic tribe in the culture war, or perhaps be persuaded by a good book, or the impressiveness of some autodidact galaxy brain. Most people who call themselves a Stoic adopted the philosophy, and are more historians of it than practitioners; they do not really question how the philosophy could be understood differently.

On the other hand, doing philosophy in the right way is different from having a philosophy or adopting one. It is about wise reasoning during wise opportunities to reason, and going on an inquiry with yourself, another, and others, all of whom have a “wisdom readiness”: a readiness that invites unknowingness, and a new destination.

So yeah, this concludes my roundabout inquiry, and I still do not know what I am going to call my “coaching” practice, but I am so fucking ready to do philosophy. If you are called to do philosophy with me, then stick around, as doing philosophy together is the destination this maybe Stoic is going towards.


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