I teach you to embrace living wisdom. 

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Why Self-Examination?

You first come to examine your life when you’re ready to ask the most burning questions of human existence.

Such questions may arise at any time, often when you no longer see the world as self-explanatory but as puzzling, perplexing, even terrifying. These questions urge themselves upon you, inviting and entreating you to consider them in the hope of understanding them as well as yourself. Philosophy is the activity that enables us to find answers we can hold fast to, embrace, and–above all–live out.

How Does Self-examination Begin? 

Two of my favorite lines offer clues to where you’re likely at right now. The first comes from the movie Fight Club: “You met me at a very strange time in my life.” And the second, regarded as an apocryphal Chinese curse, reads: “May you live in interesting times.” Put them together–you’ve now entered an especially strange period in your life, one that’s nested within an astonishingly bewildering moment in modern history–and you get a first handle on how practical philosophy takes off.

What Are Existential Questions?

After finishing a Ph.D. in 2009, I completed training with the American Philosophical Practitioners Association (APPA) in philosophical practice. Over the past 15 years, I’ve spent roughly 12,000 hours philosophizing with individuals–executives, tech founders, and finance professionals–who are keen not just to explore but also to embrace the most basic questions of human existence.

Existential questions appear once an “existential opening” has occurred: precipitating events like a sudden loss or a great swerve in your life turn you, the questioner, back on yourself, inviting you to turn inward–perhaps for the first time. These questions–broad, and at first especially vague–sound like this:

What does it all mean?

What am I doing here? 

What is life all about? 

Where am I going?

The Aim: Living Wisdom

If the beginning of practical philosophy is a certain feeling of being brought into a time of strangeness and confusion, then its aim is living wisdom–both a wisdom that is attuned to, and thus in step with, our time and the actually living out of a wise life on a daily basis. That is, thanks to philosophical inquiry, you’re bearing the fruits of an examined life in the very awake and vibrant life you’re now leading. In practical philosophy, the rubber must, and does, meet the road.

Readiness for Philosophical Inquiry

Undertaking philosophical inquiry does not require any specialized training in professional philosophy. It requires only that you be alive and receptive to the basic questions of existence.

Individuals open to inquiring into their lives tend to be high-functioning weirdos committed to thinking things through. Many are in their 30s through 60s, most have become financially successful in their chosen professions, and yet all sense that something significant is missing in their lives. Something is strangely off, something mysterious, vague, seemingly indefinable. They seem to be searching for something without knowing what it is and without knowing how to find it. They long to find out.

Philosophical Conversation

The basic unit of my philosophy practice is a philosophical conversation. Each philosophical conversation consists of one or more philosophical inquiries, the aim of the latter being a kind of existential clarity that, at the outset, is completely unimaginable.

Typically held over Zoom, philosophical conversations may last 1 ½ to 2 hours and often occur every 3 to 5 weeks. The duration of any conversation is based on the length of time it takes for us to arrive at good answers to the inquiries we’ve begun. The ultimate goal is not just to think but to live the right understanding.

Zooming Out: Your Life In Our Time

What’s unique to practical philosophy is that it zooms out from the concrete concerns that surface in your daily life in order, from a broader point of view, to get to the existential core of the matter at hand. In lieu of fixating on a particular preoccupation, we widen, broaden, and deepen our inquiry. From this higher point of view, it becomes clear that to make sense of your life is also, and at once, to make sense of our time.

This basic claim, in fact, goes one step further: practical philosophy seeks to reconcile us to the nature of our time. For the philosopher Charles Taylor, the distinctive character of the modern world is that it offers us the opportunity to “affirm ordinary life.” For more than a decade, topics pertaining to the well-led ordinary life that have regularly been taken up in philosophical conversations include:

• Good Work: What is good work, and what role does it play in a well-led life? Which ends does it serve? Why does it matter?
• Wholehearted Love: What is love? Whom do I love? And why can’t I seem to love these individuals or those people? 
• Beautiful Home: What is home, truly, and where is it? With whom do I belong? To whom or to what am I committed? 
• World-historical Themes: For instance:
  • Does a good life require having a lifelong partner, or can one be happy on one’s own? 
  • Given the plummeting birth rate in the West, does it matter whether my partner and I have kids? Do we have a responsibility to do so?
  • Is the intergenerational, biological family in the midst of a slow-motion collapse and, if so, what kind of response is wise?
  • What does work in an emergent age of AI look like? Is there reason for anxiety or, on the contrary, for optimism?
  • Is the recent uptick of interest in longevity and healthspan a positive development or one engendered by the fear of death?  
  • Is home really a concrete place involving mutually enmeshing commitments, is it simply a state of mind, or is it something deep and elusive within?
  • Is religion a thing of the past, or is the return to religion today vitally necessary?

Finding A Good Fit

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