Five Big Ideas
Golum's Whispers | Fixed-Point Futures | Conceptual Ancestors | Voice | Magical Charisma
I. How Dr. Pippa Malmgren Learned to Beware Gollum’s Whispers
“Frodo gave a cry, and there was, fallen upon his knees at the chasm’s edge. But Gollum, dancing like a mad thing, held aloft the ring, a finger still thrust within its circle.”
— J.R.R. Tolkien; The Lord of the Rings
Working in The White House taught Dr. Pippa Malmgren () how someone in power asking your opinion is “both the moment you’ve trained for and a dangerous moment in your life.”
There, she saw the corrupting influence that proximity to power can hold. There, she realized J.R.R. Tolkien had taught her more about the true nature of power than J.M Keynes or any other political or economic theorist ever could.
In no uncertain terms, a senior executive had been complaining to Dr. Pippa about the catastrophic impact of the administration’s policies.
Seeing that this problem needed solving, Dr. Pippa suggested they meet the President so the executive could have it out with him directly.
Upon arrival in the Oval Office, the fire and brimstone of the chief executive’s anti-presidential proclamations gave way to humble deference. He lost his ability to speak truth to power.
Just as Golum will do anything to maintain access to the Ring, so will proximity to power lead the ambitious to do anything to remain in its orbit:
“As I sat in that room watching this, I realized, ‘Oh, my gosh. The Oval Office is round and this is the ring and Gollum lives above the door of the Oval Office, and he jumps on your shoulder when you walk in that room and says, 'Don't say what you think. Say what you think he wants to hear.’ Most people, they succumb to this because they're ambitious and they want to be on Air Force One, and it takes quite a force of character to walk in there and say what you actually think. So this is, again, Gollum lives above the door of the Oval Office. That's where he lives.”
Power often corrupts, but proximity to power corrupts equally.
For honesty to flourish, those close to power must courageously speak the truth, unswayed by fear or ambition. Responsibility for this lies with both the power holder and the power-proximate.
When confronting power, resist the seductive whispers of Gollum. If you wield power, remain vigilant, as Gollum might lurk on the shoulders of those before you.
II. How Venkatesh Rao Escaped Nihilism
“The cynic knows the price of everything and the value of nothing.”
— Oscar Wilde
Venkatesh Rao’s () house-purchasing experience risked becoming a nihilist nightmare:
“You can make up a spreadsheet about buying houses with all sorts of attributes about property values, income taxes, property taxes, blah blah, blah. And you can lose yourself in this optimization problem of a million variables, and sort of get everlastingly trapped in this hell of trying to decide what your utility function is.”
Struggling to stay afloat in a sea of spreadsheets, it was the embrace of arbitrariness that provided a liferaft:
“But on the other hand, you can pick something arbitrary that is going to break you out of that. So for example, my wife is arbitrarily attached to the idea that she must have beautiful view, where either of the ocean or mountains or something like that.”
“Another similar one for me is, I like amateur astronomy. So it's like I want to live in a place where the skies are relatively clear, at least part of the year, and I can look up at the sky with my telescope. It's an arbitrary variable to toss into the problem.”
These arbitrary aims (which Venkatesh labels “fixed-point futures”) infused the process with a newfound purpose. What could have been an endless stream of abstract variables now had something tangible to coalesce around. No matter what happened, those fixed points were going to become true. A nihilistic set of calculations became laden with meaning:
“But at the same time, it also does this little philosophical sleight of hand trick of turning a nihilism process into a meaning-making process. It's like now you've decided no matter what happens to the rest of the world and whether we are all doomed to die in a zombie apocalypse, you are going to make one thing true about the future.”
Rationality is a terrible guide to a meaningful life.
By breaking everything down into a series of weighted and quantified variables, we reduce life to an optimization problem.
We become cold, calculating automatons, laser-focused on problem-solving at the cost of a meaningful existence.
When feeling trapped by the optimization obsession, the answer isn’t more rationality. It’s less.
III. How Billy Oppenheimer Learned to Choose His Conceptual Ancestors
“Prospero [is] a great ‘white magician’ who is the conceptual ancestor of more modern wizards such as Gandalf in Lord of the Rings and Dumbledore in Harry Potter.”
—Dr. Nancy Andreasen; The Creative Brain
Billy once asked his mentor, Ryan Holiday, about developing his distinct writing style.
He shares Ryan’s response in his newsletter:
“‘The key is that no one has the same combination of influences,’ he [Ryan] said. ‘It feels like me because I’m the only person to combine my interests in my way.’ (More recently, he said about the success of his books, ‘I learned it all from Robert Greene.’) It feels like him because he’s the only person to combine his conceptual ancestors in his way. Which is a wonderful technique for being yourself.”
True originality is a mirage. Everything is a remix; each idea a descendant of another.
Magic lies not in the originality of creation but in the alchemy of your influences.
Unlike your biological heritage, you get to choose your conceptual ancestors. Make this choice with intention. Select wisely, select widely, and you’ll produce work that, while echoing its origins, becomes distinctly yours.
IV. How Morning Brew Found Its Voice
“A pen transmits the voice of the soul”
— Fennel Hudson
Morning Brew was growing.
What had started as Alex Lieberman’s college side hustle now had a small but dedicated core of readers, a team of young, hungry writers, and a talented chief editor.
But with this growth came new forms of risk.
When Alex was the sole writer, the newsletter’s tone - conversational, funny, quick-witted - came naturally. It was a natural extension of his personality, as effortless as his accent. With the expansion of the writing team, this voice risked being diluted.
Without its voice, Morning Brew was as good as dead. Recognizing this, Alex and his co-founder Austin successfully implemented two changes:
They hired a voice editor: “So Austin and I literally created a job description of voice editor that was the name of the job. And we went to Michigan and we found the one guy who could add voice to any story. And it was a guy who was a double, or he majored in business, but he also was in the improv troop at Michigan. And he basically would take every finished story for our newsletter for a year and a half straight, and he would add voice to it.”
They codified their voice: “We literally described if Morning Brew was a person, how old are they? What are their interests? What do they do on weekends? What's their go-to cocktail? What are things they say versus don't say?”
Morning Brew has since become one of the largest daily newsletters in the world.
Dead writing speaks with no voice.
Nurture your voice with the same dedication you give to structure, grammar, and ideas.
To survive in the Age of Content, your writing must be instantly recognizable as yours and yours alone.
V. Why Dr. Julie Gurner Thinks That Charisma is a Form of Magic
“ First there is the setup, in which the nature of what might be attempted at is hinted at, or suggested, or explained. The apparatus is seen. Volunteers from the audience sometimes participate in preparation. As the trick is being setup, the magician will make use of every possible use of misdirection.”
— Christopher Priest; The Prestige
Master magicians (like Jim ‘Houdini’ O’Shaughnessy) often say that the essence of a great magic trick is misdirection - drawing your attention to one thing while the real trick unfolds elsewhere.) has noticed that a charismatic individual can deploy misdirection just as effectively as any magician:
“Charismatic people are often, they are masters of how they direct attention, the attention of others. So, you are no exception to that, and they are going to attempt to direct your attention as well. They will do it like a magician who is working a slight of hand and sometimes the slight of hand has no mal-intent, and other times they're really hiding the important element in something that you're not able to see.”
Charisma can be dangerously misleading in certain situations, such as investment decisions.
When confronted by overwhelming charisma, Dr. Julie recommends being “very, very clear about what you're evaluating for, not allowing them to take you off the trail into something else, and making sure that you have a sometimes physical list so that you don't get taken away on the train of the charismatic personality.”
Beware of the charismatic’s allure.
Through a well-placed compliment, a carefully deployed joke, or the sheer magnetism of their energy, the charismatic can wrench control of an interaction and, like a rabbit from a hat, pull any conclusion they want you to reach from thin air.
By focusing on the things that matter, your job is to spoil the trick.