I want to have meaningful conversations. It is a notion I think many of us have. We want to raise the conversational bar with our friends and peers. We want to reach above the noise.

The problem is that these kind of aspirations are left as aspirations. The demand to have meaningful conversation is crippling. When I demand so much out of myself I am left not trying at all. I fear sounding like a pompous ass if I ask about the meaning of life at a cocktail party.

Why not start smaller? Why not find rules that could immediately be put into practice? Maybe all we need are little nudges towards meaning. Perhaps our goal is to collect and utilize heuristics that can help us slowly develop into better conversationalists. It might be more important to develop this sort of compass rather than a step by step roadmap. If that is the case, then we better get started.

The first one I have found use for in my life is from Soren Kierkegaard’s The Present Age:

“If we could suppose for a moment that there was a law which did not forbid people talking, but simply ordered that everything which was spoken should be treated as though it had happened fifty years ago, the gossips would be done for, they would be in despair. On the other hand, it would not really interfere with any one who could really talk. That an actor should have mispronounced a word could only be interesting if there was something interesting in the mispronunciation itself, in which case the fifty years make no difference…”

Kierkegaard’s rule is echoed in Jeff Bezos’ advice to focus on what does not change. If we can focus on what would not erode after fifty years then we can reach conclusions and questions about human nature and meaning that transcend otherwise petty “He said, She said’s”.

Keep finding more and using them. I sure need to develop the toolkit. If there are any that prove useful for you then please feel free to share. Much obliged.


A year into the Revolutionary War, the city of Philadelphia was captured by the British. It served as the closest thing to a capital city for the burgeoning nation fighting for independence. As someone ignorant about the specifics of the Revolutionary War, I had no idea this happened so early in the conflict.

As someone even more ignorant about military strategy, I thought this kind of move would signal end-game. The capital city taken? Game over.

Far from the case.

Members of the Continental Congress, America’s proto-government, retreated further north. What’s more, Washington and his Continental Army were still on the loose. Washington acknowledged the capture of Philadelphia but realized the conflict was far from over.

“By this point”, Ron Chernow notes, “Washington knew he was engaged in a war of attrition and that holding towns was less important in this mobile style of warfare.” Washington stated similar sentiments in a letter around the time of Philadelphia’s capture. “The possession of our towns, while we have an army in the field, will avail [the British] little”, Washington wrote. “It is our arms, not defenseless towns, they have to subdue.”

There are defeats that seem dramatic, signaling the end. Having the capital captured by the enemy is one of those demoralizing events. There will especially be events in life that signal a similar rupture.

But the important thing to realize is that these kind of events are only symbolic of defeat. They are not defeat itself.  It is you that needs to be subdued, not a relative or job. Surrendering your entire being truly signals the end. 

As long as the army continues moving, there’s still a chance. Even in those demoralizing moments, our internal army makes it out. If we consistently remind ourselves of that we can churn through strategies and approaches to continue fighting.

There’s still a chance.

Do we reach for low hanging fruit when it comes to our heroes? Can we reach higher? Take this passage from an essay by writer and college professor Mark Edmundson:

“Not long ago, I asked my Freud class a question that, however hoary, never fails to solicit intriguing responses: Who are your heroes? Whom do you admire? After one remarkable answer featuring T.S. Eliot as a hero, a series of generic replies rolled in, one gray wave after the next: my father, my best friend, a doctor who lives in our town, my high school history teacher. Virtually all the heroes were people my students had known personally, people who had done something local, specific, and practical, and had done it for them.”

Is Edmundson knocking a father off his well-earned pedestal? Does he have it out for your high school history teacher? I don’t think Edmundson is berating the admiration of family members or local influences. Let’s unpack his thoughts. To do so we need to enlist a military theorist, BH Liddell-Hart.

In the beginning of Strategy, Liddell-Hart introduces the concept of practical experience by using a line from Bismarck: “Fools say that they learn by experience, I prefer to profit by others’ experience.” This quote lays out two forms of practical experience – direct and indirect. Direct experience is learning by your own experience, indirect from others’ experience.

The heroes of Edmundson’s students fit within direct experience. These people were doing something local, specific, and practical, and had done it for them. Within military strategy, relying solely on direct experience proves to be a crippling detriment. “Direct experience” Liddell-Hart mentions, “is inherently too limited to form an adequate foundation either for theory or for application. At the best it produces an atmosphere that is of value in drying and hardening the structure of thought.” 

This ossified state of mind should be emphasized. Nothing can seep through that isn’t in the immediate lifetime. Even if you are the most interesting person in the world, going to exotic places and meeting new people, your direct experience will still be limited. Liddell-Hart says the same of a military life: “Even in the most active career, especially a soldier’s career, the scope and possibilities of direct experience are extremely limited.” This leaves us in what Cicero called the tyranny of the present. How can one break through it?

Indirect experience. 

“[O]f the two”, Liddell-Hart writes, “indirect…experience may be the more valuable because [it is] infinitely wider.” History is a neighborhood that dwarves my own. It contains more teachers than my high school, more townsfolk than the population of my home town. 

Now let’s state the obvious: we cannot interact with these people in the same way we interact with people in our schools or towns. I cannot ask George Washington a question, let alone hang out with him on Friday nights. While George Washington cannot be my next-door neighbor, he can be my hero. I can take the qualities Washington embodied and use them centuries earlier as points of emulation. Adding indirect heroes creates access to a larger swath of good qualities to nurture.

It turns out the present is not a tyranny when the past is added to it.

In the beginning of the Revolutionary War, disaster seemed imminent for George Washington. The Continental Army was short in supply and disciplined soldiers. From resorting to supplying his soldiers with spears to dealing with inexperienced officers, Washington started out with a severe disadvantage. This deprivation rang true in the disastrous New York defense, leaving Washington licking his wounds. 

“In short,” Washington wrote to Lund Washington in the aftermath, “such is my situation that if I were to wish the bitterest curse to an enemy on this side of the grave, I should put him in my stead with my feelings…In confidence I tell you that I never was in such an unhappy, divided state since I was born.”

In another letter he bluntly expressed, “I am wearied almost to death with the retrograde motion of things.” Was this exhaustion and frustration expressed to everyone around him? Contrary to his written sentiments, Washington kept the stolid appearance at the helm of command.

During their retreat after the New York campaign, James Monroe noticed Washington “…at the head of a small band, or rather in its rear, for he was always near the enemy, and his countenance and manner made an impression on me which I can never efface. A deportment so firm, so dignified, but yet so modest and composed, I have never seen in any other person.”

Monroe was not the only member of the Continental Army to express the outward resolve of their commander-in-chief. Washington lead by example, instilling courage through his own display. However this may be, it is important to realize that this was not Washington’s natural mode of operation. He had doubts and frustrations throughout the war. His choice was to hide most of them in privacy. “The means used to conceal my weakness from the enemy”, Washington confided to John Hancock, “conceals it also from our friends and adds to their wonder.”

That wonder exists to this day. We primarily look at Washington through the stoic self he crafted, so much so that we forget the melancholy that also entered into him. It is just that he hid his emotions so well, confiding to a select few.

I think Washington’s conduct contrasts our modern yearning for authenticity, for a ‘true self’. Living artificially, David Brooks writes in The Road to Character, “with a gap between your inner nature and your outer conduct, is to be deceptive, cunning, and false.” In contrast, Washington reveals to us a noble sense of crafting the self.

“This code”, Brooks continues, “held that artifice is man’s nature. We start out with raw material, some good, some bad, and this nature has to be pruned, girdled, formed, repressed, molded, and often restrained, rather than paraded in public. A personality is a product of cultivation. The truth self is what you have built from your nature, not just what your nature started out with.”

This does not mean that inner wrestling is nonexistent. Washington even expressed that he waged a “secret warfare in my mind.” Envy brews, frustrations fester, and hatred creeps upon us. What matters is how we wage this warfare in our minds. Do we control these feelings, giving them a safe outlet for their eventual defeat, or do we let them conquer our dispositions? The choice is ours. 


Take life advice from a man who lived in a tub: Diogenes the Cynic

“Lose yourself.”

This phrase usually pops up as a positive sentiment. If you are focused on a craft, losing yourself follows suit. Everything disappears while writing, performing, or creating a business. This type of dedication usually signals any kind of success. Who could argue against Picasso losing himself in his art or Kerouac in his writing? It would be hard to.

And yet it would be even more difficult to argue against losing yourself in any worthwhile endeavor. How can you without being thought of as egotistical, curmudgeonly, and even a bit envious?

Enter Diogenes the Cynic.

I am reminded of a passage in Montaigne’s “On schoolmasters’ learning” where he references the Greek philosopher. Diogenes “used to laugh at the professors of grammar who did research into the bad qualities of Ulysses yet knew nothing of their own; at musicians whose flutes were harmonious but not their morals; at orators whose studies led to talking about justice, not to being just.”

That passage floored me.

At the time I was immersed in graduate school for music with a classical guitar performance focus. Intense practice regiments were expected if you wanted to excel. I lost myself in the study. But upon arriving at this passage in Montaigne, I thought of myself: I wondered whether my morals were as harmonious as the music I was striving to perform. Did I think about my character as often as the pieces of music I played? Was the discipline needed for hours of daily practice expanding to other aspects of my life?

These weren’t questions I asked myself before. It alarmed me that my priorities could be out of line. Music’s effects were opposite of what I thought. Instead of enriching my mental, moral, and spiritual state, music was heightening my ignorance concerning them.

The questions I now asked myself helped me resist ignoring my ignorance. I now saw that I was losing myself at the expense of myself. What could be worse? It gave me a new spin to the passage in Matthew: “For what shall it profit a man if he shall gain the whole world, and lose his own soul?” Far from dealing with accumulation of wealth, it now meant any endeavor that made one lose a sense of his soul. 

Let us be clear: you can still become a fantastic writer or musician without losing yourself in the process. Your character can be as mighty as your corpus. I would argue that such an aspiration is more ambitious than solely wanting to be a successful entrepreneur or artist. For it is one thing to say that this or that person is a great artist.

But to also add that she is genuinely a good person? That should be the priority first and foremost.

“Don’t talk unless you can improve the silence.”

This saying of Argentinian writer Jorge Luis Borges sticks with me. I think it is in part due to the quote’s universality. It translates to so many other things than conversation.

Is not every creative endeavor, from writing and music to architecture and painting, a way to improve the silence? When I think of people who have made an impact in my life by their work or example, they are those who have dramatically improved my own silence. What I mean by silence is the time spent with my own thoughts. We all have time in-between the flotsam and jetsam of life where we are alone in silence.

So if someone can make me contemplate beauty on a walk, cultivate a sense of character as I drive, make me wrestle with truth as I wait in line- then that is improving the silence.

If we get down to it, it seems like a good part of our business in life is attempting to improve the silence of ourselves and others.  

Biographies allow us a near infinite grab bag of ‘what if’ scenarios. We can ask ourselves, “What would I do in this situation?” Most of the time, if you’re like me, I find myself succumbing to baser tendencies or left in baffling indecision.

A recent scenario I entertained came from Ron Chernow’s Washington. 

So imagine you receive an intercepted letter from one of your associates intended for another. This letter contains content where both men are damning your competency to lead and shows that they are flagrantly disobeying your orders on purpose.

How would you respond?

This is the exact scenario that befell George Washington when he received a letter from Charles Lee intended for Joseph Reed. Both generals under Washington, they did not mince their words about Washington’s leadership. The criticism especially incriminated Reed because, in the letter, Lee quoted his venomous remarks from a previous letter.

So take that in mind. Washington is the one clearly wronged here. He had a right to ask about the letter’s content, to ask why they were being subordinate, why they would betray his trust. That is at least what I would have done. It seems like a universal response.

But Washington’s response is nothing like that. Here is Washington’s letter to Reed (know that he also attached a copy of Lee’s letter with it):

“Dear Sir: The enclosed was put into my hands by an express from the White Plains. Having no idea of its being a private letter, much less suspecting the tendency of the correspondence, I opened it, as I had done all other letters to you…upon the business of your office…This, as it is the truth, must be my excuse for seeing the contents of a letter which neither inclination, or intention would have prompted me to, I thank you for the trouble and fatigue you have undergone in your journey to Burlington and sincerely wish that your labors may be crowned with the desired success. My best respects to Mrs. Reed.”

I admire this letter but find it hard to write commentary about it. All I know is that it works on me – makes me think how my response would be nothing like it, rewires my brain to different modes of operating, forces me to consider nobler ways of living.

May this little letter work on you in a similar fashion.