New Year, New Guide: An Invitation to Inquiry

I am starting my philosophy practice again next week. I have opened slots for the year and looking forward to fostering long-term inquiry partners. If interested, you can schedule me in here:

Additional information can be found on the scheduling link above. If you have any questions, email me at thestoa at protonmail dot com or by replying to this newsletter.

I have seen recent mentions of "philosophical counseling" in mainstream publications—one in Oprah Magazine last October, then in The New Yorker a few weeks ago. Considering the rising interest in my philosophy practice over the years, I am beginning to believe there is a growing interest in philosophical-oriented inquiries. I sense this interest for a practical philosophy has these primary reasons: worldview, wisdom, and friendships of virtue. 

Many of my clients have tried therapy or coaching before and were left underwhelmed. I have also held space for many coaches and therapists who felt something was missing from their practice. A clue to the missing piece is located in a passage from The New Yorker article, quoting an individual who benefited more from philosophical counseling than therapy.

The therapists he saw wanted to help him become better adjusted given his current world view—but perhaps his world view was wrong. He wanted to examine how defensible his values were in the first place.

Therapy and coaching, the primary space-holding practices popular in modernity, are usually bounded by a theoretical framework for how to practice, which, from my experience, most therapists and coaches will not put into question during an inquiry. In fact, during my past exposure to therapy and coaching, practitioners often displayed sensitivity when their approach was respectfully challenged or questioned.

The best (or wisest) therapists and coaches are only therapists and coaches in name, embodying the spirit of a practical philosopher. Yet, many space holders today shy away from becoming intimate with someone's worldview, which is unfortunate because frequently, an individual's worldview and their understanding of reality and belief of what is true directly contribute to a sense of feeling stuck in life. 

To truly understand someone's worldview, you must also allow them to understand yours. Authentic philosophical engagement involves creating a space for mutual transformation. This level of intimacy is what we need to become comfortable with. It should be no news to readers of this newsletter that we are in a collective transition with the following bewildering symptoms:

• The accelerated technological changes we are experiencing are resulting in "future shock," the disorientation and anxiety that occurs from rapid change.

• The “restarting of history,”¹ with regional conflicts popping off worldwide.

• The collapse in trust in legacy institutions that validate truth coupled with the understandable rise in conspiracism. 

• The "great weirding" that is occurring. The once impossible now feels possible: slapping people at the Oscars, World War III, UFOs manned by interdimensional beings in cahoots with the US government², etc.

• A relentless onslaught of our worldviews is happening via the culture war or psyops.

To navigate the world today demands one's worldview to be examined, along with the axiomatic premises that undergird it. Moreover, a worldview-nimbleness is required (aka a "minimum viable philosophy"), and philosophical inquiry - with oneself via journaling or with a philosophical counselor - is the best practice that nurtures such nimbleness.

Now, "philosophers" have a bad rap, which I have written about previously in this newsletter. The philosophical inquiry the world needs now is not the theoretical kind detached from everyday concerns found in academic philosophy departments (See: "All Philosophers Are Charlatans"). Nor will it be found in the pseudo-psychology masked as "pop philosophy" in philosophy sections at big box bookstores. (See: "The Dildoification of Philosophy") What is needed is being aligned toward a more expansive value (or meta-value), namely wisdom. 

Besides being worldview-shy, coaches and therapists are usually guided by values such as "success" and "mental health," while academic philosophers by "truth" (in the theoretical sense) and pop philosophers by "entertainment." Each of these values has its appropriate moment and context. Sometimes, letting a single value guide an inquiry may be the wisest move. However, considering the complexity of the challenges we confront, embracing a range of values becomes essential.

Wisdom serves as the overarching value that allows for such diversity. To genuinely embrace a love of wisdom, a weaving of the values is needed, along with corresponding inquiry methods. If practical philosophy is to find its footing in culture, a return to the love of wisdom is required, and such love is best experienced between bodies that venture boldly towards wisdom together.

“Begin, be bold, and venture to be wise.” – Horace

The last reason I believe practical philosophy is becoming mainstream relates to what is missing in our social lives. Therapists, coaches, and philosophical counselors alike are placeholders for an absent societal role: friendships of virtue. Of course, I could be projecting, but one thing that resonates the most with my readers since I started writing online is writing about friends of virtue.

A friend of virtue is the highest form of friendship, in which Aristotle contrasted two lesser forms of friendship: utility and pleasure. A virtuous friend not only offers "unconditional positive regard" but also upholds their friend to a specific standard, holding them accountable for what matters most and course-correcting them towards the good, the true, and the beautiful when necessary.

Such friendships are extremely rare today. Most people are terrible at holding space, do not really listen, and are quick to covertly or overtly judge and shame another, even to those closest to them. The existential loneliness today is palpable, wide-spread, and arguably at the core of the “meta-crisis.” Philosophical inquiry is the practice of becoming skilled at being a friend of virtue.

***

Typically, the inquiry partners who gravitate towards my practice and with whom I often enjoy most demand a particular level of sophistication in their thinking. This fact is why I am compelled to outline the aforementioned reasons for considering engaging in philosophical inquiry.

However, occasionally, it's better to connect with the vibe of something through art. My friend and ritual artist

Rebecca Fox

drew the essence of my practice, which she executed flawlessly:

I love this illustration. It has everything: breaking through the spatial and temporal boundaries, the felt sense of being stuck in underworldly places, honoring that there are no straight paths or answers, and a hopeful pointing toward whatever spiritual north star is guiding an inquiry.

Additionally, this concise three-song playlist captures the spirit of what it's like to have an ongoing inquiry partnership with me:

This playlist has it all as well: the encouraging beginnings that come from finally being seen, the soul-suffering that comes from having the courage to change, and the-sun-is-slowly-emerging vibe that comes when one grounds their soul in “phronesis” (aka prudence or practical wisdom).

***

I'll keep my schedule open throughout the year and I will be available for one-off inquiries for those who need some help with their existential knots. I will also be having ongoing inquiries with select individuals. I have worked with hundreds of people over the last few years, and I have found I work well with the following:

• Those who succeed in career and family but are still experiencing a lack of meaning.  

• Those looking to build bespoke bridges to close the “vocation gap.”

• Those looking to cultivate long-term friendships of virtue.

• Rationalists with worldview fatigue regarding rationality or utilitarianism and rationalist-types working on projects related to AGI.

• CEOs and startup founders looking for a more meaningful “full-spectrum success” in life.

• Creatives that want to become more artful with their "second self" (digital persona).

• Anyone needing to navigate the culture war and needing to improve with wisdom-based social dynamics and power literacy.

• Younger men who struggle with discipline and have relationship challenges with the opposite sex.

• Advanced spiritual practitioners who sense something more is needed to complement their meditative practice.

I thrive with a variety of inquiry partners. Therefore, if you don't fit into one of the above categories but still feel drawn to engage in inquiry, please feel free to get in touch.

If you wish to engage in inquiry with me, additional details and booking options are available here:

If you believe someone you know would benefit from a philosophical inquiry, you can share this invitation with them.

Lastly, consider joining a wholesome group of self-inquirers at Collective Journalling, the place where I primarily write the majority of my Substack entries.

What is Collective Journalling? This communal practice happens via Zoom and is 90 mins, with check-ins in the chat at the beginning and an opportunity to connect with fellow journalers in breakout rooms at the end. You do not have to stay the whole time. If you are in an antisocial mood, you do not have to interact with anyone, yet you can still enjoy the coffee shop-esque communal vibe. The session concludes with an optional sharing of a passage in the chat. Most of the time is spent in silence together, individually inquiring about what matters most. A lovely group of people has formed around this practice. The practice occurs on weekdays @ 8 AM ET. RSVP link is behind the paywall.