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I hold hour-long individual checkins every week with everyone on my team.
This week, one of my teammates remarked: “You ask us a lot of questions during these sit-downs. You take notes and you more often than not act on our feedback. But why don’t you ever tell us what we should be working on?”
This essay is an attempt to answer that question.
The Hippie School of Management
I’ve learned the hard way, in several different domains of experience, that people contain all the answers to their own questions. Modern society is a hammer that only sees nails. When we see problems, our impulse is to search frantically for quick, temporary solutions rather than to seek deeper understanding.
And so I spend these hours with my teammates asking them questions, the same ones, over and over again, until their understanding of my questions becomes more clear and my understanding of them sharpens.
“What did you struggle with this past week?”
“Where do you see yourself in six months?”
“What is missing?”
“What can I do to help you?”
“What do you want to be getting better at every day?”
By asking these types of questions, I subconsciously ask them of myself, and my teammate and I unwittingly meditate over the same query. Through repetition, we begin to understand the words we use to describe certain sensations and phenomena. We hopefully begin to occupy a shared space of being.
Some weeks, these conversations are duds -- one or both of us aren’t in the mood, and so we just go for a walk around town and get some coffee. Other weeks, we lose track of time and work together to map out a vision for how we as individuals and as a team can grow.
I’m still learning, but it’s been a pretty fascinating experience so far.
What Is Understanding?
In the process, I’ve come to realize that to understand a person is to understand the way she experiences the world. And to even begin understanding another soul requires much self-understanding. Such a pursuit is an asymptote, as you’ll never actually understand someone else -- perhaps not even yourself.
That sounds pretty obvious. But as most important things go, what appears simple very quickly becomes complex and bewildering the more you inspect.
For instance, I’ve used the word “understand” assuming you know what it means. Yet I struggle myself to find a definition for it that isn’t circular. To understand is to “perceive the intended meaning of.” Yet do you ever really know what you’re trying to say?
Does any speaker really know what he intends to mean when he says anything that doesn’t take the form of “Look at x. If we both can agree it is there, please bring x to me.” Understanding is the pursuit of approximating more precisely the difference between what is stated and what is intended.
Immensely Manifold Connections
My brother introduced me to the philosophy of Ludwig Wittgenstein, who I am growing to believe is one of the most important thinkers in human history. He devoted his life to “understanding” these types of problems. Wittgenstein lamented that philosophical problems emerge from confusion over language.
“The limits of my language mean the limits of my world” is the quip he’s most commonly cited for.
Another one: “People are deeply imbedded in philosophical, i.e., grammatical confusions. And to free them presupposes pulling them out of the immensely manifold connections they are caught up in.”
These “immensely manifold connections” constitute how we each represent the world in our heads. They are the reason for most conflicts between us. Many mystical traditions have broached this topic in the past. My mysticism of choice is Sufism, so I’ll share a Sufi fable that illustrates this quite well.
Four men were in search of nourishment.
"I want to buy angur,” said the Persian.
“I want uzum,” said the Turk.
“I want inab,” said the Arab.
“No!” said the Greek, "we should buy stafil.“
Another traveller passing, a linguist, said, "Give the coin to me. I undertake to satisfy the desires of all of you.”
The traveller bought them four small bunches of grapes.
Understanding is a process of untangling. And what it has taken me twenty-eight years to even begin to untangle is that untangling is not a goal, but an activity. What more, it is largely an internal activity that manifests itself externally.
I cannot sit down and say “Today, I am going to untangle this computer program” or “Today, I am going to untangle this disagreement I have with my friend.” It will just happen as an emergent property of the process of seeking understanding.
I will ask questions of my code or to my friend, which will hopefully lead to more precise and meaningful questions, and then the untangling will merely reveal itself. This is very much akin to the programming pearl of “Choose the right data structure and the problem will solve itself.”
Conclusion: My Damned Headphones
My headphones frequently get tangled in my pockets. In the past, I used two approaches.
The first approach was brute force desperation -- I’d shake the headphones and command them to untangle themselves. They would not and I myself then would become tangled.
The second approach was careful surgery -- I’d find the “source” of the tangle and slowly unbraid the wires.
Now, I trust that lightly shaking the headphones will awaken some ancient Braided Logic that will reveal to the headphones, through seemingly randomized stressors, a path out of its tangled existence.
The less tangled I am on a given day, the more likely I am to choose option two or three.
I read somewhere recently that in the modern world, we experience more external stimuli in one day than our ancestors did in an entire lifetime.
This creates the possibility of multiple lifetimes of tangled states of mind existing in one person. The tangled web of manifold connections this creates makes us short of attention, impulsive, disagreeable, and unhappy.
This also creates the possibility of an incredible untangling of our words, thoughts, and intentions. The constantly untangling web makes us more aware, focused, and attuned to the world happening around us. And maybe then we begin to understand ourselves.
Hope you enjoyed reading! Maybe this week's essay brings more confusion than clarity. I'm still grappling with "untangling" this one. Happy Saturday and until next time.