An Understanding Of Understanding: Three Features Of Wisdom

Let wisdom, for my purposes anyway, be defined as right conduct directly flowing from right understanding. Then we can ask: how shall we enhance and enrich our understanding to the point at which it could be that from which we act?

Consider but three features of wisdom: perceptiveness, considerateness, and thoughtfulness.

To be very perceptive is to pick up on things–salient facts otherwise overlooked, shifts in the temperature of a room, minor or dramatic changes in people’s moods, and so on–that are very significant to our overall understanding of what is actually going on here. Perceptiveness is an observational virtue. With a quiet mind and attuned senses, the perceptive person notices much more than she can possibly say (or need to say), with this “noticing more” figuring prominently in her overall understanding.

Next, being considerate–that is, giving oneself over to considering a matter–is rather like taking a stone or pebble and turning it over time and again in one’s fingers. The more one turns it over and the more one passes the stone from one finger to the next, the more one is able to assimilate relevant complexity or to come to pristine simplicity. One has not simply touched the soil; one has turned the soil over and over until its richness sings. Being filled with genuine considerations is rather like both of these things.

And next but not finally (for there are surely other features of wisdom), being all filled up with thoughtfulness means seeing something through to the very end. One’s thoughts seem to reach out toward their implications and, in turn, toward those implications until thought, in virtue of its having ranged from the initial proposal to all the foreseeable things that follow therefrom, is sated. Thoughtful people seem to keep asking, “Whence?” and “Where does this go?” They are soberly drunk on depth.

It still remains to be seen how one acts on one’s understanding rather than willy nilly, on impulse, or whatever. I don’t yet know the answer to that question. Yet just given the discussion above, it’s already clear that our understanding of understanding needs to go much further than it has hitherto, and our understandings thereby need to be much profounder than they have been to date.

For as we become more perceptive and as this perceptive begins to inform our considerateness and as this considerateness begins to inform our thoughtfulness, we are already on the path to making our understanding, now vaster and completer, into something we can trust. And that trusted understanding may now be primed and cued for not just informing but transforming at least some of our conduct and, in time, saturating more and more of it.

The Entrepreneur’s And The Founder’s Conundrum

I speak with a good number of founders, entrepreneurs, and executives who are involved in the same kind of conundrum. How a countercultural philosopher like me came to speak with such individuals–well, that’s a story for another day. Today I’d like to tell you about that conundrum.

Let me begin with an analogy from Robert Wright’s book Why Buddhism is True. Suppose, Wright says, that someone prone to neuroticism is told that there is a snake in the bush so that every time this person comes close to that bush he is on his guard. Suppose, further, that, say, 99 times out of a 100 there is no snake in the bush–but one time there is. Wright’s lesson? Evolution has ‘designed’ human beings so that we’re ‘primed’ to be neurotic because evolution ‘wants’ us to pass our genes on to the next generation. The unfortunate consequence, however, is that we must sacrifice our happiness to ensure our survival. In other words, our lives are one big trade-off: our negative thoughts may save us from harm but not without causing us to sacrifice the prospect of genuine happiness.

I don’t know whether Wright is actually correct here about the conundrum faced by homo sapiens (I don’t know that he’s wrong either), but I do think that his anecdote sheds some light on a style of thinking that, because of my long acquaintance with certain conversation partners, I’ve come to be quite familiar with.

Their version runs: I should think about every possible scenario, most especially the worst case for fear that not doing so could lead me to be blindsided, to miss an opportunity, or to be forced to grapple with an existential threat to my business. Therefore, I must always be on my guard since, owing to accident or ill-preparedness, I may otherwise fail to foresee something especially significant.

The faux-meditation mantra or Zen Lite piece of advice–“Be in the present”–just won’t do. So far as I can tell, they’re right to believe that thorough deliberative thought is called for. And yet, I don’t believe that such thorough deliberative thought must entail the loss of happiness.

Ergo, what might be a way of having our caking and eating it too?

Some napkin suggestions:

  • First, we need to examine the ways that our identities are unnecessarily tied up with existential threats to some such entities (here, startups, companies, etc.). Can I be willing to let this thing die without thinking that it spells my symbolic death also?
  • Second, we need to be able to be more like mathematicians, as it were. Can we dispassionately, methodically, and inquisitively deliberate upon sundry scenarios, looking at things from different perspectives in the hope of being as thorough as possible? I underscore the dispassion here. The kind of mathematician I have in mind is animated by inquisitiveness, not by the fear of symbolic death. She genuinely wants to think something through to the very end.
  • Third, after we’ve thought something through to the end, can we lay it–and also, therefore, the mind–to rest? You might tell me that, ah ha, something new may always come up and that something new may change the considerations or the conclusion arrived at. Fair enough. Yet if we’ve really turned over almost every possible, hypothetical, and actual stone (so to speak), then this new piece of information could very well be folded into our prior considerations and our conclusions.
  • Sometimes, to be sure, something new and monumental does come up, yet, according to the understanding proffered here, we should reserve our uber-alertness or our alarm bells just for those cases where, yes, the case merits our vigilance.

How persuasive is what I’ve written above? I don’t know; try it out and see whether you can square dispassionate, methodical deliberations with peace of mind. It seems to me a matter of training–indeed, a training in concentration. So used is our mind to flying off of the handle that it may take some gentle suasion, and some time, to bring the mind back to dispassionate deliberation. I see no reason why meditation and philosophy can’t be twinned.

The Trailhead Of The Path To Wisdom

Suppose that you’ve been knocked off your horse. Yesterday I call this an “existential opening.” Good.

Why good? Because (I argue) you cannot possibly be wise if you’ve never been knocked off your horse. The latter, if you let it, can set the search in motion.

Suppose after you got knocked off your horse that you thought, “I want to know myself.” Also pretty damn good.

Suppose, further, that you intuited that knowing thyself was somehow connected to knowing reality. Now we’re talkin’! Methinks we’re on a roll!

Then you might ask, “How does an inquiry into wisdom ever get underway?” Hey, I like your style. Let’s keep it up!

Immediately or soon enough, you’d bump into two figures standing at the trailhead of the path to wisdom. Their names? Self-deception and Intellectual Humility.

Keenly would you see that we human beings, yourself and myself included, have a propensity to deceive ourselves. We overlook our shortcomings, neglect our peccadillos, pass over our misunderstandings, all the while assuming that we know what it is that we’re talking about. Deception, here, is a broad category that covers lies, blindness, and bullshit. Therefore, the one seeking to step foot onto the path of wisdom would, of necessity I think, have to confront his or her own forms of self-deception, not to mention all the pain bodies (Eckhart Tolle) and shadows (Jung) that appear along the way. To even possibly know thyself, then, one must be intimately acquainted with what one is not but yet what one thought one was (neti neti: cf. Nisargadatta).

And that other figure again? Ah, yes, Intellectual Humility. Deep in your heart you must understand that all too often you haven’t the foggiest about something you used to think you knew all too well. You’re clueless. For, indeed, someone or some being may know much better than you, and this ought to be profoundly, also painfully humbling. Remember Elizabeth Bennett who, in Austen’s Pride and Prejudice, upon realizing that she had misunderstood Darcy due to prejudice exclaims: “Till now I never knew myself.” Or remember Proverbs: “Fear of the Lord is the beginning of wisdom.”

Once these two lessons begin to sink in–voila!–the trailhead suddenly appears, and the path to wisdom begins to open up before you.

The Blessing Called Getting Knocked Off Your Horse

For the longest time, perhaps as long as you can remember, you’ve been riding along on your horse, heading in this direction or in that one, going toward this place or that place. All without a hitch.

Yes, sometimes you’ve crossed some scrub grass or clanked down on some hard pebbles or almost lost your trot on some loose sand, but each time your horse and you nimbly adjusted and went on as if nothing much had happened. Had someone asked you afterward whether there had been any incident along the way, you might have forgotten to mention it.

You know how this story is going to go, don’t you? Likely you do and you don’t. Well, one day out of the blue you get knocked of your horse.

Perhaps your horse gets up quickly and, spooked, runs off without you. Or perhaps you show some preternatural strength of the kind you didn’t you know you had and, restraining yourself, you refuse to get back on the horse. Something tells you not to and this time you listen. Either way, you’re horseless, ergo directionless, ergo also placeless.

This moment I call an “existential opening,” also an “uncanny blessing,” a moment, that is, that is the condition of possibility for being truly available to a matter of ultimate concern. Now everything may change for you.


What does “just going along on your horse” mean? Nothing but unexaminedly and therefore unconsciously following some script or other: going to school after school, taking job after job, taking up career after career, presuming calling after calling, pursuing relationship after relationship, raising child after child, tasting pleasure after pleasure, engaging in activity after activity. The mystic Gurdjieff would describe this as the life of an “automaton.” He would say that you cannot yet be and that you cannot yet do.

Yet something almost inexplicably marvelous happens when, having been knocked sideways off our horse, you do not get right back on it. And what is that? A painful crack in your being opens like a sinewy thread and out come ultimate questions that may first transfix you before, should you stay with them while nurturing them, they’re able to transform you.

That’s what.

Jobs Suck

For the life of me, I don’t know why people have been talking up jobs. All the jobs I’ve had have pretty much sucked.

If you can believe it, I was a security guard for the Chicago Bears back when their summer training camp used to be held in my hometown. Next summer I was a bilingual verifications agent, someone who confirmed that, yes, Jane did want to switch to AOL’s long distance calling plan or, es verdadMaria quiere cambiar su servicio de telefono (It’s true (or that’s right): Maria does want to change her telephone service).

I worked at Abercrombie & Fitch right around when it was thought to be the hip thing to do: to get paid $6 an hour to wear flip-flops and cargo shorts and to be a “brand rep” following the “style guide” to a T. I was a surprisingly mediocre server at a Marriott, almost dropping glasses of wine as I traversed the thick carpet from the bar back to the restaurant. Oh, and I was an temporary executive assistant at a place that built engine turbines: I entered data into spreadsheets, took calls and wrote post-it notes, and ordered more supplies. So impressed by me or rather because their permanent executive assistant ultimately quit, they asked me to stay on at the end of the summer and I was like no thanks.

After college, I could only find a job–a real blow to my ego–at a mobile home park where I mowed grass until (not my fault, I swear) the mower broke and I was relegated to weed whacking duty, which involved whacking weeds on blacktop and which, therefore, really sucked because when you whack weeds on blacktop, the threads wear down super-quickly and, in consequence, you need to stop this industrial beast, pull out more thread, and start it up again. And then repeat. And repeat. And repeat.

In grad school, I taught disaffected students and we pretended that they gave a shit about Kant or Hume; all semester long we half-winked at one another, knowing why we were there (hint: payment (me) and requirement for graduation (them)). After grad school, for a couple of semesters I taught business writing (again, if you can believe it) at a purportedly liberal arts college that was also purportedly Catholic. It got paid a pittance, and the place felt more like a crappy public high school, one with a super-long commute alllllll the way up to the Bronx by subway. (For those of you who care, that’s the very last stop on the 1 Train.) The name of the school? Manhattan College. Now that’s branding for ya!

Gigging and being enterprising were almost always more enjoyable partially or largely because they were free of pretense and bullshit. Over the years, I got paid (in no apparent order) to plant trees, to move library books from one library to another, to do grunt work around a house. I can’t even remember all the things I need. In each case, we met, I did the work to the best of my ability, they paid me, and that was that. Usually a handshake agreement bound us together. And in time, I became more enterprising and found that I was good at it: among many other things, I set up a successful tutoring business, I personally trained people, I taught people how to rock climb, and so on. I made up stuff that people were willing to pay me for. We came to an agreement. It was usually a pretty good thing.

OK, I suppose you’d say that I never made the transition from jobs to career (nor to the Promised Land of “meaningful work” or to that of “the calling”), and that’s certainly biographically true. I leaped, rather, from crappy jobs to being a solopreneur, that is, to being a practical philosopher who, with others, considers matters of ultimate concern. Yet that would be to miss the larger point: careerism, by my lights, is just a repackaging of jobism in that the former provides a fancier-sounding justification for the latter. It is the abdication of freedom by intellectual means.

Let’s get real. Regardless of how good certain jobs are, they still have something about them that really, inherently sucks. I don’t care if you’re an AI researcher doing cool shit at Google. Is your time your own? Can you come and go as you please? Do you not have obligations to fulfill and responsibilities to meet that you think aren’t patently silly? What about all those pointless meetings? Do you choose to be around these colleagues? How about that commute to the Bay Area, huh? What about where you live–is that up to you? Just tell me: are you a free person?

Jobs may not make us into slaves, but they don’t make us free.

*  *  *

This, of course, is a literary piece. If you like, you can read more sophisticated anti-job and anti-careerist pieces at Quartz

And on a personal note: my wife Alexandra and I will be a meditation retreat from Oct. 13-21. After that, I’ll be giving a talk on wisdom as well as taking part in a panel discussion of AI at Global Solutions Forum in Vail, Colorado. For these reasons, I won’t be blogging again until after October 25th. You can expect to receive 6 posts a week around that time.