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Oliver Wendell Holmes Jr. believed in hard work and knowledge. He remarked, “most things in this world, half their terrors vanish when you walk up and tackle them.” The anxious thoughts about what “might” happen were often worse than the actual situation. Once “you lay hold of the lion’s skin it comes off and the same old donkey is underneath.”

As he edged toward turning ninety, he wrote:

My old formula is that a man should be an enthusiast in the front of his head and a sceptic in the back. Do his damndest without believing that the cosmos would collapse if he failed. One should have the same courage for failure that many have for death.

When Chief Justice Melville Fuller delayed in getting the cases assigned to Holmes over to him, Holmes wrote him a note:

Will you let me know as soon as convenient the cases you assign to me. I worry until I know. Nil actum reputans dum quid superesset agendum.

The Latin was a quote from Lucanus’s poem about Caesar: “He believed nothing done, so long as anything remained undone.”

Holmes had an unbelievable work ethic. In total, he wrote 873 opinions, a Supreme Court record. “He brought that same zest for duty to everything,” Budiansky wrote. “In 1865, at age twenty-one, he began keeping a list of every book he read, noting them down in tiny handwriting in a small leather…book, known to his secretaries as the ‘Black Book.’ By the time of his death the list exceeded four thousand, which worked out to more than a book a week for seventy years. The range was extraordinary: law, philosophy, sociology, literature, religion, history, economics, murder mysteries, poetry, science.”


In his opinions, Holmes rarely used legal jargon. The quality of his prose demonstrated clear thinking. Learned Hand praised in Holmes’s opinions his “deadly eye” for “question-begging words” that disguised shallow thinking. “To Holmes, the act of writing was above all the act of thinking. Finding the right words was not rhetorical ornamentation: it was the very essence of his work of thinking though complex legal jargon.”

Note: What people mean by writing is thinking. It forces you to come up with words that describe what’s in your head. The mismatch between the words you use and the thoughts in your head is the actual process of your thinking being refined. You’re being forced to put a thought which contains many words and many meanings into a few words that each just have one meaning. That is thinking.


Boston in the 1800s was a town full of pompous, educated men and women seeking to make their mark on the world through their words and books. Pretty much everyone was Unitarian. “Unitarianisms’s fundamental tenet was that God had given man a rational nature and a moral conscience, and expected him to use them. Salvation was no longer to be found in outward conformity to rigid doctrine or unquestioning obedience to an unknowable God, but lay rather within each man’s own conscience.”

This philosophy “now channeled into a faith that made self-improvement, the cultivation of virtue, and social conscience the ultimate expression of God’s will.”

Edward Everett Hale put it best: “There was the real impression that the kingdom of heaven was to be brought in…if we only knew enough”

This was the culture Oliver Wendell Holmes, Jr. was born into, and came to love.


From a young age, Holmes showed an act for words and conversing. His report card at age six said, “Talk’s too much.” His brother Edward explained, “Wendell ends every sentence with a ‘but’ so as to hold the floor till he can think of something else to say.”


Holmes understood the importance of focus. He wrote in a letter about his father:

If he [his father] had the patience to concentrate all his energy on a single subject, which perhaps is saying if he had been a different man, he would have been less popular, but he might have produced a great work. I often am struck by his insight in things that he lightly touched. But, as I said, it is the last five percent that makes the difference between the great and the clever.


As a boy, Holmes had a “futile shrinking from new things” that kept him from learning to ride or drive a horse or ice skate. But this was not a “physical timidity; it was rather that he already had a sense of what it took to truly master a subject, and an inkling of the dissatisfactions of half-knowledge.”


Holmes did not value academics. In 1913, he warned Felix Frankfurter that academic life is…

a withdrawl from the fight in order to utter smart things that cost you nothing except thinking them from a cloister…Business in the world is unhappy, often seems mean, and always challenges your power to idealize the brute fact but it hardens the fibre and I think is likely to make more of a man of one who turns it to success


For Holmes, the war taught him “early on to face with courage and calmness the inevitable hardships of life.” In 1917, he told Harold Laski “I am converting misfortune into a source of satisfaction.” The author explains, “His limitless capacity for work was undoubtedly an emotional escape but it was also a need that he shared with many who had been through the intense experiences of war: civilian life just did not seem that exciting by comparison.” “Repose,” Holmes wrote, “is not the destiny of man.” “Life is a struggle,” the author observes, “and it is the struggle that gives it meaning. The only thing to do was to give one’s all, and leave the consequences to fate.”


In a great quote about opportunity costs, Holmes said, “Remember, my friend, that every good costs something. Don’t forget that to have anything means to go without something else. Even to be a person, to be this means to be not that.”


During his first year of law school, a professor said he “had never known of anyone in the law who studied anything like as hard as Wendell.” “From the start,” the author wrote, “he took heart in the belief that mastery of a subject, and thorough professional expertise, was the only way to accomplish anything significant in life. A year and a half after receiving his degree, and still thoroughly immersed in a now self-directed program of voluminous readings in the law, he wrote William James of his ‘ever increasing conviction that law as well as any other series of facts in this world may be approached in the interests of science and may be studied, yes, and practiced, with the preservation of one’s ideals. I should even say that they grew robust under the regimen.'”

Holmes’ father’s dilettantism worked out well for Holmes, because it showed him what not to do. He wrote:

Since I wrote in December I have worked at nothing but the law. Philosophy has hibernated in torpid slumber, and I have lain “slutishly soaking and gurgling in the devil’s pickle,” as Carlye says. It has been necessary,—if a man chooses a profession he cannot forever content himself in picking out the plums with fastidious dilettantism and give the rest of the loaf to the poor, but must easy his way manfully through crust and crumb—soft, unpleasant inner parts which, within one, swell, causing discomfort in the bowels.


Holmes became friends with both William and Henry James. William, while Holmes and he were close, was in a deep depression about the nature of the universe. In a world without a God, why did anything matter, James explained. Holmes, ever the realist, didn’t understand. He advised William (with words that a lot of us should take into account today re: politics and the “world” and everyone having an opinion on everything): “It seems to me that the only promising activity is to make my universe coherent and livable, not to babble about the universe.” This quote revealed Holmes’ philosophy about life: it doesn’t care about you, so get on with it and do your duty! (Or, rather, that’s my interpretation.)


One night after working late in the law library, Holmes and a younger lawyer, George Upham, walked home together. Recounting their conversation sixty years later, Upham said Holmes:

told me he had a theory that anyone could accomplish anything he wished, if only he wished it hard enough, continuously, morning, noon, and night, and perhaps subconsciously while sleeping

A half century after that conversation, Holmes told John Wu that to achieve anything of importance “takes time, the capacity to want something fiercely and want it all the time, and sticking to the rugged course.”

Holmes followed his own advice.

While editing a new edition of Kent’s Commentaries, Holmes became utterly absorbed in the work. “I have as you know given up all my time to Kent’s Commentaries and during the past year especially have hardly touched any other business,” he wrote in July 1872.

He kept his manuscript in a green back, and he took it everywhere with him. After dining one night with Henry James’s mother, she wrote a letter to Henry:

Wendell Holmes dined with us a few days ago. His whole life, soul and body, is utterly absorbed in his last work upon his Kent. He carries about his manuscript in his green bag and never loses sight of it for a moment. He started to go to Will’s room to wash his hands, but came back for his bag, and when we went to dinner, Will said, “Don’t you want to take your bag with you?” He said, “Yes, I always do so at home.”

This “green bag” was so precious to him that, once a month, he conducted fire drills with the servants and staff of his house and ensured they knew their first mission if flames were to ensue: rescue the green bag.

Chief Justice Charles Evan Hughes thought Holmes’ work on Kent is what allowed him to draft opinions faster than everyone else. The time Holmes spent in total immersion of the law “had given him an unusual and complete mastery of common law decisions and history. The effect of this in his habit as [a] judge was that, where others would be compelled to devote an enormous amount of time to the rediscovery of law, Holmes needed to make no re-examination—the law was at his fingertips.”

This is a great example of Dead Time and Alive Time.

The time in-between jobs he studied a ton, so that when he finally did get a court appointment, he was better prepared and smarter than everyone else. Such is how one should spend their days “waiting.” [[Notes/Active Patience|Active Patience]]

The author writes, “Success to Holmes above all meant accomplishing something original and of intellectual merit.” I relate to that strongly.


On the bench, Holmes had little patience for lawyers, remarking that they take 5 to ten minutes to say things that could easily be said in one. To pass the time, he wrote letters while lawyers were presenting their cases. This gave him the reputation of attentiveness, because, naturally, people thought he was taking notes on the case.


On writing, Holmes said, “One has to strike the jugular and let the rest go.”


2024-04-28

One of my old bosses was a genius.

He knew how to influence people in meetings, pitch ideas to decision-makers, and inspire his direct reports to get things done.

But more often than not, there were situations where he gave us vague directions about a project and then disappeared. Being good employees, we followed his directions as best as possible and hoped we were doing it right. (Our follow-up questions never received a response.)

Yet inevitably, when he circled back with us and saw our progress, it was always wrong. Rarely was our work not good; rather, what he imagined the project would look like was different from what we created.

The directions he gave were not enough to communicate what he had in his head. So, when he saw what we made, he could say, “No, not that. This.”

This was incredibly frustrating and wasted so many hours of productivity.

I was thinking about this yesterday when I asked my wife if she could buy a gift for an event we were attending. My text was, “Hey, can you buy a gift for the baby shower?” She said, “Yes.”

When I got home that night, she showed me what she bought. It was all great gifts, but it was not what I had in mind for this close friend, and I got a bit frustrated. But then I realized this was completely my fault. My directions were vague: buy a gift. My wife, being the great executor that she is, went out and did that. She had no reason to ask follow-up questions about whether or not there was something specific that I wanted. She just bought something.

It made me realize that in life—and business—you either need to give specific directions of how you want something done or simply be okay with it being done differently than you would have done it. Giving vague directions to employees and then making them change their work because it’s not what you “pictured” is a great way to waste time and make your employees resent you.

This “vague direction giving” is one reason people work long hours. They spend a whole week working 9-5 on their boss’ project, only for the boss to, at noon on Friday, check-in and say, “Oh, I meant this.”

Give specific directions, or shut up and be glad it got done.

2024-04-27

Someone asked on Twitter, “does anyone have any useful sentences that will change my life immediately upon being read?” I saw a few of the responses on my feed and thought they were great. Maybe a bit cheesy, but helpful.

Here are some of the ones I liked the most.


Do it scared.


“You know what you need to do to improve your life. You’re just waiting for someone else to tell you because our minds are trained to take instructions rather than create its own path.”

Source


“If you don’t pick a day to rest, your body will pick it for you.”

Source


The time will pass anyway. (One of my favorite ideas.)

“I don’t want to go back to school. It will take four years!”

“Yes. But the time will pass anyway.”


“Man I think it depends.”

Yes. Few things are black and white.

2024-04-16

I used to like the phrase, “How you do anything is how you do everything.”

Doing the little things right is important. But there’s not enough time in the world to do everything well. Some things just need to be done.

You don’t approach buying groceries the same way you approach creating and preparing for a big presentation at work. You shouldn’t approach those things the same way. No matter how “well” you get your groceries, at the end of the day, if the groceries are in your pantry, you did your job.

Paying bills is like this, too. Sure, there are ways to be efficient and strategic in paying your bills, but all that matters is if your bills got paid. How they got paid doesn’t matter.

I once read that a good measure of one’s maturity is how organized their sock drawer was. Because people don’t expect anyone to look at their sock drawer, having it organized shows they have integrity and care about doing the small things well. When I first learned that, I thought it was genius. But now I think it just means you spend too much time organizing your sock drawer.

Some things need to be done well, but a lot of things just need to be done. Don’t confuse the two.

2024-04-13

It was the easiest shot of the day.

A short chip to a back pin sitting at the bottom of a ridge put me in a great spot for birdie. I just had to get the ball on top of the hill and let it trickle down toward the hole.

I took a few practice swings, got my stance, and swung.

The ball sailed over the back of the green and into the woods behind the hole. I bladed it…and I was not happy.

Having shots like that on the golf course is embarrassing, especially when you’ve practiced them and are trying to prove you know how to play. But the only way to have fewer shots like that on the golf course is to put yourself in a position where you have more.

Here’s why.

My philosophy with golf used to be that I had to work on my swing at the driving rage more often than I played. This strategy worked initially, but once I learned the mechanics of the swing, practicing at the range more than playing hurt my progress.

The usual situation went like this: practice for a few weeks at my local course and then go play a round with friends or my dad. Even though my swing felt great at the range, when I finally went out on the course, it was like I forgot what golf was. I don’t mean just a few shots pulled here and there, but swinging and missing off the tee or topping a 7-iron from the fairway; total beginner stuff. That performance made me think I had to just practice more before I played again, so that’s what I did.

Even though I got invites to play, I’d deny them because I didn’t feel prepared or like I had worked hard enough at the range since my last round. And I said no, not because I was afraid of playing poorly—if I was the only one out there, I wouldn’t care—but because I was afraid of embarrassing myself by playing poorly in front of other people. I didn’t want to look like a fool. I didn’t want to fail.

But that exact mindset kept me from getting better.

Playing on the course is radically different from hitting balls at the range. Even if you’re out playing for fun, there’s a certain amount of pressure added that’s impossible to replicate at the driving range. This doesn’t only mess with your head, it messes with your swing too. It’s not that I forgot how to swing; it’s that hitting balls on the range doesn’t have the same amount of pressure as hitting a 7-iron into a green after an impeccable tee shot. You want to make the tee shot pay off, so you put pressure on yourself. Maybe you’re a bit nervous because the person you got paired up with is staring you down, waiting so they can hit, too.

Those are obstacles you have to overcome in your mind and body to swing well that you don’t face on the range. So, the only way to get used to that pressure is to be out on the actual golf course facing that pressure more. By nature, that will mean more chunked chip shots, topped irons, and maybe a few swings and a miss off the tee box with the driver. But to be great eventually, you have to be okay with being bad for a while. To get better, I had to be willing to look like a fool. I had to be willing to fail.

As Seth Godin says, “Learning is serial incompetence on our way to getting better.” Anyone who is now great at something was once bad. Even if they were born with an innate gift, they had to practice and cultivate their skill. They had to fail before they became great; they had to look like fools until they weren’t. You and I are no different. Don’t let the embarrassment of messing up keep you from getting better. Be okay with looking like a fool…until you don’t.

To write clean code, you have to first be okay with writing sloppy code.

To run a fast marathon, you have to first be okay with running slow.

To learn Spanish, you have to first be okay not knowing words in a conversation.

To have creative ideas, you have to first be okay with having lots of bad ideas.

I can’t expect to perform better on the golf course if I never get out on the golf course. I have to fail, and fail, and fail some more; it’s the only way to improve.

If you want to be successful, you have to be okay with looking like a fool. Failure at first leads to mastery at last. Mastery follows foolishness.

Embarrassment is the cost of entry.

If you aren’t willing to look like a foolish beginner, you’ll never become a graceful master.

– ​Ed Latimore​

2024-04-11