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Hi friends 👋,

Happy Wednesday!

I’ve been spending a lot of time thinking about the Big Question I’m trying to answer in my work and life. This essay, like many, isn’t meant to provide an answer, but to share how I’m thinking through it in real-time.

As more knowledge workers spend their days prompting LLMs, it’s become popular to argue that asking good questions is becoming more valuable. What is less obvious but I think more interesting is that it will expose how little we actually care about answers, and in turn, what makes questions so valuable in the first place.

Let’s get to it.

Long Questions/Short Answers

Writers all know a secret that I want to share with you, because whether you consider yourself a writer or not, you’re writing a story, too:

Questions reshape your reality.

We all think what we want is answers. We don’t, actually. Answers are dead things. Questions are animating. What we want is great questions.

By the time a question gets its answer, all of the juice has been squeezed. The answer is the pulp and pith. Answers are static things. Questions are kinetic. I like watching the NBA Draft more than I like watching any single NBA game. The Draft creates questions. Games are answers.

Actually, fuck answers, the more I think about it. The best questions don’t have answers. The point of the question isn’t to find an answer. The best questions are organizing principles, magnets, ways of seeing.

Writers know this. Staring at a blank page with no question to answer is felt proof of Sartre’s observation: “Humans are condemned to be free.” (Maybe it had to be a writer who made that observation.) Fire up a blank page with a question in mind, however, and the world becomes grownup Blue’s Clues. You’re reading something or talking to someone and it’s almost as if you see a blue paw print and hear little kids shouting “A clue! A clue!” whenever something you might be able to use appears.

What’s true in writing, I’m arguing, is true (maybe increasingly so) with life.

The most important question you can ask yourself, if you don’t know your question already, is “What question am I trying to answer?” Like with your life. This one actually should have, if not an answer, at least a working hypothesis. But since the answer is a question, we’ll let it slide.

Writers get to do this over and over again, each time we work on a new piece, in silico. If I am writing an essay on networking, my brain tingles every time I come across some bit of information that might be useful to explaining networking. It is unbelievable to experience the first few times; tidbits I would have skimmed right over suppressing a yawn in normal times become engrossing when they help answer my question.

For a writer, though, each essay is a specific question in service, hopefully, of a larger question, and it’s that larger question that is relevant to even those of you who don’t consider yourself writers, because it’s about how you write the story of your life. This is the question that shapes you in vivo. The one that animates you.

This kind of question is like a mission, but with infinite paths – equally driving but endlessly explorable. A mission is almost too much like an answer, after which you autopilot in pursuit. A question branches. A mission is a wonderful thing, but more people have questions (and more of them).

Over the past few months, I’ve been obsessed with becoming a better writer. That is not my main question - How can I become a better writer? - but exists in service of it. Sub-questions are important, too, like side quests, and are made pointier by the existence of your Big Question. So I’ve tried to read a lot of great essays and profiles – David Foster Wallace’s David Lynch Keeps His Head and Roger Federer as a Religious Experience, and Guy Talese’s Frank Sinatra Has a Cold, and Tad Friend’s The Mind of Marc Andreessen and Sam Altman’s Manifest Destiny – and I’ve read some books on writing by the greats in the particular literary nonfiction form in which I want to write: John McPhee’s Draft No. 4 and Robert Caro’s Working among them, the latter in which Caro, who you might recognize from The Power Broker and The Years of Lyndon Johnson, writes:

One of the reasons I believed I had become an author in the first place was to find out how things really worked and to explain those workings, and, as my focus had narrowed to politics, that reason had become to explain how political power really worked. And during the few years I had been a reporter I had convinced myself, in part because of the easy gratifications that go with the journalist’s life–the bylines; the gratitude or the wary respect or fear that the subjects of your articles had for you; the awareness of friends or neighbors of what you were doing; the feeling that you were at the center of the action–that I was succeeding in doing what I had set out to do.

But the more I thought about Robert Moses’ career, the more I understood that I had been deluding myself.

That is a question-haver right there. Extrinsic praise crumbles in the face of the question.

Caro’s question is: How does political power really work in America?

Once he asks it, it takes the wheel. Caro is willing to go broke to answer it.

For example: one day in the 1960s, his wife Ina sold their home so that he wouldn’t have to, because it was obvious to both of them that they needed to. And despite being warned by those around Robert Moses, the subject the only book that Caro wrote while broke, unknown, and powerless, that no one over whom Moses held any power (which was a lot of people) would speak with him about the book, and certainly Moses himself would not, Caro just spoke with whoever he could, even four layers removed from the man, until, eventually, Moses caved, impressed by the younger Robert’s doggedness: “ [Sidney M. Shapiro, Moses’ aide] had said that ‘RM,’ learning of my stubbornness despite his strictures, had concluded that at last someone had come along who was going to write the book whether he cooperated or not.” The book became The Power Broker.

Caro asks plenty of specific questions, ones with specific answers, in The Power Broker. Exactly how much did Moses build? How did he physically shape New York City? How did Moses use Authorities as his source of power? What was his impact on people who lived in his way?

Each of these, though, was in service of the larger question of how political power really works. It’s this question that drove him to ask all of the others, even at great personal cost.

This question literally shaped his life, how he spent it during the months that turned into years writing The Power Broker, and how he would spend it afterwards, when he’d won a Pulitzer and could write about whatever he wanted. Caro had been planning on writing a biography on New York City Mayor Fiorello LaGuardia – Caro lived in New York, and after writing about Moses, he knew New York – but he realized that if he really wanted to answer the question How does political power really work in America? he would need to study someone who shaped America on the national level. So he chose Lyndon B. Johnson, and he has been writing about power through the LBJ lens for over a half century since.

Do you see what I mean? The question shaped everything about him – where he and his wife Ina lived, what they read, who they spoke with, and the words he wrote.

Nothing in Caro’s life would have been the same if he’d asked a different question.

There is nothing unique, from that perspective at least, about Robert Caro. What is perhaps unique is that he found a question so powerful to him that he allowed it to fully shape his life. Had he chosen another question he cared about less, he presumably would not have let it dictate where he lived or how he’s spent every day for fifty-one years (and counting). He also wouldn’t be Robert Caro; I certainly wouldn’t be writing about him right now.

But I think that for most of us there exists a question that could impact each of us similarly, and I know that most of us have not spent nearly enough time asking what that question is.

Let’s test that: what’s your question?

—

Often, almost as a way of catching my breath, I’ll feed what I’ve written to Claude and ask for feedback. I just did just that. After some specific suggestions, Claude wrote, “The piece is developing a compelling argument about how the right question can generate almost supernatural persistence.”

That is funny. I will explain why.

—

It’s Saturday morning (as I write this). I’ve been noodling this piece for a few days, and I put fingers to keys on it for the first time yesterday (Friday) afternoon. I went fingers up at around 5pm in order to get back and meet Puja and the kids for dinner near our house. It was a sharply cold but clear and beautiful afternoon, so I got off of the N at Atlantic and instead of transferring to the R for the last leg, I walked the 13 minutes to the restaurant. Since listening to The Telepathy Tapes, I have been meditating every day, as I shared in The Return of Magic. Since getting into meditation, I’ve started appreciating light, planes, and clouds more than I have in the past. So on my walk yesterday, looking up at the light, planes, and clouds, I asked the universe for a sign. This wasn’t nearly as weird or dramatic as it sounds, it was almost a throwaway thought as I was walking sans headphones with mental time to kill, and the dream scenario would have been a glowing orb or something but I didn’t actually expect that (or anything) to happen. But then I looked up and to my right and I saw this:

That looks like a question mark, right? While I’m in the middle of writing a piece about questions? Weird, at least. You gotta give me that.

To be fair, that is most likely a coincidence, potentially a hallucination, and only possibly a synchronicity – a meaningful coincidence that suggests an underlying pattern or connection beyond normal causality. Carl Jung first coined the term.

I wrote about synchronicities in The Return of Magic, too. About how one Friday night, I was watching the Jesse Michels’ American Alchemy interview with Riz Virk in which they talk about simulation theory, Philip K. Dick, simulacrum, and glitches in the Matrix, and then I asked the “simulators” to help me pick a book. My eyes went to a book I forgot I owned: The Simulacra by Philip K. Dick. Weird, at least. You gotta give me that.

So last night, another Friday night, this question of how to write about questions – about how questions are like more flexible missions – bumping around in my brain, I decided to shut my brain off and watch the new American Alchemy, this one with Communion author Whitley Strieber. Then two hours in, this exchange happens:

Whitley: Stanton was the most driven human being I've ever known. He would go anywhere, he would do anything, he would not stop... And he was very coy about whether or not he had been activated - you see a UFO up close or you have a close encounter experience, you're activated. Most people that happens to… a lot of people don't remember, a lot of people blow it off, but there are certain people who just will not stop. They will not stop.

Jesse: So the UFO almost installs in them some sort of drive or mission to disclosure or an insatiable curiosity.

Whitley: It installs in them a burning question, and they just cannot let it go.

Come on. That is the thesis of this essay: burning questions as motivating force and organizing principle. Remove the UFOs and Whitley is describing Robert Caro.

Does that seem like a synchronicity to you? At least a coincidence, right?

I mean, even if you’re skeptical, even if you think I’m fooling myself because I want to believe and that I just noticed “burning question” because I’m in the middle of asking questions about questions… AHA! Well that’s exactly the point I’m trying to make.

The questions we ask reshape our reality.

If I were not asking myself a question about questions, there is no way that, 2:04:20 into an interview at 9:45pm on a Friday - past my bedtime - I would have even registered that sentence. But since I was asking myself about questions, that sentence jumped right into my brain and, from there, sent tingles down my spine. A clue! A clue!

This is what questions do: they pull the right stuff into your brain. The late, great strategy professor Clayton Christensen apparently told Jason Fried (lightly paraphrased by Fried, emphasis mine):

Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question — you have to want to know — in order to open up the space for the answer to fit.¹

Your mind can’t fit everything. Questions filter out the things you don’t care to fit and find a place for the things you do. So having a question becomes more important in proportion to the amount of information available to you, which these days is way too much. A question keeps you from getting sucked into the algorithmic noise, and surfaces some signal at least when you inevitably occasionally do. Algorithms are braindamaging btw because they shoot at you a stream of answers you never asked for, answers with no right place to fit, like a wetware DDoS attack.

But questions do more than just filter; filtering is too passive a thing. Questions attract, drive, and distinguish.

We talked a little bit about attracting. This is what happens to me when I’m writing a piece. Suddenly, I discover useful tidbits without even looking for them.

We talked about their driving, too. Asking a question doesn’t just make information appear. It pushes you to seek out any information that might help you get closer (asymptotically, never really getting there, because that’s when the fun ends) to an answer. This is the story of Robert Caro. This is why he waded through piss and feces in East Tremont and why he and Ina moved to Hill Country. Having a question that you truly want to answer gives you what Graham Duncan calls a “hungry mind,” which he says, correctly, is very hard to fake. Questions are what send you in search of old out of print niche publications instead of scrolling the same garbage everyone else is. They’re what push you to uncover informational alpha – to call the person who knew the person who knew the person, in case they might have a nugget. We say curiosity is one of the most important traits in a person; questions are curiosity made tangible.

We haven’t really talked about distinguishing, but having a question does that too.

I told you that in trying to become a better writer, I’ve been studying Caro, McPhee, and DFW. All three are masters of literary nonfiction, even if DFW would have identified more with his fiction. The three are entirely, completely different writers in a way that I never bothered to appreciate until I asked myself the question “How can I become a better writer?” in service of a bigger question I can feel but am still trying to pin down concretely. They are different writers because they ask different questions.

Caro asks: How does political power really work in America? and attempts to answer by studying just two Americans who wielded power most impactfully. Really, since 1965, sixty years ago, he’s written two books (one over four, soon to be five, volumes).

McPhee asks something entirely different! On the surface, it might look like he’s asking, “How do humans interact with and shape the natural world, and how does it shape us?" or something. But I think he’s really asking "How can words capture the full depth, structure, and texture of reality?"

Asking an entirely different question has created an entirely different life! Where Caro has produced two stories, McPhee has published 34 books and written more than 100 articles for The New Yorker. That is the output of someone who is working on the craft itself. What’s more, McPhee has been teaching writing at Princeton University since 1975.

Caro uses writing in service of his subject. McPhee uses subjects in service of his writing.

DFW asked a much different and more personally urgent question: “How can we live a meaningful, non-bullshitty life in a world increasingly full of irony, entertainment, and distraction?”

His novels, like Infinite Jest and The Pale King, are long (long) explorations of the question; his profiles, like David Lynch Keeps His Head to Roger Federer as a Religious Experience, examine rare individuals, whose strangeness and mastery, respectively, suggest an answer.

Incidentally, in both of those essays, two of my favorites, DFW explicitly names the sub-question he plans to pursue in order to handle the particular subject in a way that others – others with different Big Questions than DFW, or with no Big Questions at all – would not.

In D.L.K.H.H., he writes:

So the obvious "Hollywood insider"-type question w/r/t Lost Highway is whether the movie will rehabilitate Lynch's reputation. For me, though, a more interesting question ended up being whether David Lynch really gives a shit about whether his reputation is rehabilitated or not. The impression I get from rewatching his movies and from hanging around his latest production is that he really doesn't. This attitude-like Lynch himself, like his work-seems to me to be both grandly admirable and sort of nuts.

In R.F.A.A.R.E., he actually names the idea we talked about earlier about answers not being that interesting…

Journalistically speaking, there is no hot news to offer you about Roger Federer. He is, at 25, the best tennis player currently alive. Maybe the best ever. Bios and profiles abound. “60 Minutes” did a feature on him just last year. Anything you want to know about Mr. Roger N.M.I. Federer — his background, his home town of Basel, Switzerland, his parents’ sane and unexploitative support of his talent, his junior tennis career, his early problems with fragility and temper, his beloved junior coach, how that coach’s accidental death in 2002 both shattered and annealed Federer and helped make him what he now is, Federer’s 39 career singles titles, his eight Grand Slams, his unusually steady and mature commitment to the girlfriend who travels with him (which on the men’s tour is rare) and handles his affairs (which on the men’s tour is unheard of), his old-school stoicism and mental toughness and good sportsmanship and evident overall decency and thoughtfulness and charitable largess — it’s all just a Google search away. Knock yourself out.

…before writing that what he wanted to write about was the transcendent experience of watching Federer play:

This present article is more about a spectator’s experience of Federer, and its context. The specific thesis here is that if you’ve never seen the young man play live, and then do, in person, on the sacred grass of Wimbledon, through the literally withering heat and then wind and rain of the ’06 fortnight, then you are apt to have what one of the tournament’s press bus drivers describes as a “bloody near-religious experience.” It may be tempting, at first, to hear a phrase like this as just one more of the overheated tropes that people resort to to describe the feeling of Federer Moments. But the driver’s phrase turns out to be true — literally, for an instant ecstatically — though it takes some time and serious watching to see this truth emerge.

Understanding DFW’s Big Question, do you see why he asks the specific sub-questions he does in each of these profiles?

I guess the point here being that do you see what I mean w/r/t answers just not being that interesting and the questions you ask shaping your reality? No one else would write Federer like DFW did. McPhee, writing about a tennis match in one of his most famous essays, Levels of the Game, writes an entirely different piece! It’s analytical and structured where DFW’s is subjective and ecstatic. They are both excellent. They both answer entirely different questions.

In a New Yorker profile on Wallace a year after his death by suicide, D.T. Max describes the particular tragedy of losing a genius mid-question:

The sadness over Wallace’s death was also connected to a feeling that, for all his outpouring of words, he died with his work incomplete. Wallace, at least, never felt that he had hit his target. His goal had been to show readers how to live a fulfilled, meaningful life. “Fiction’s about what it is to be a fucking human being,” he once said.

I don’t know. One of the things it is to be a human being is to pursue a question so Big that you could pursue it for a Bryan Johnson Lifetime and never get your answer.

How many total lives have been spent questioning the meaning of life? Are we closer to an answer? Is there an answer?

Most of us spend most of our working lives trying to find specific answers to other peoples’ questions. No two ways about it: that skill is becoming commoditized.

There has never been a better time, however, to be someone with a burning question to answer.

Pinning down your question isn’t easy – I’m still wrestling with mine – but it’s worth every second you can give to it. It will shape everything else you do.

Take some time this weekend – better yet, play hooky, take a snow day or a sick day – and just think about the question you’d be happy spending a decade or six trying to answer. It’ll light up your world more than any answer could.

Long questions, short answers.

Thanks to Claude for editing and to Vanta for supporting Not Boring. Go support them so I can keep asking questions.

That’s all for today. We’ll be back in your inbox on Friday with the Weekly Dose.

Thanks for reading,

Packy

1

I was going to take the piece in a different direction from here because I thought the string of connections from Christensen to Rumelt to Graham Duncan was clever, but now that I’m trying to be a better writer, I decided to cut it. It didn’t earn its word count. Having read too much DFW, however, I decided to put it here IYI.

Christensen was in the right place to make that observation. As a professor, he must have seen thousands of kids fumble the opportunity to learn from THE CLAYTON CHRISTENSEN because they were there to get a degree, not answer a question. One of my great regrets is not having had the questions I have now when I went to school, a magical place designed to let you explore all of them. One of my great joys is that my son Dev wants to build worlds and approaches almost everything through the lens of “Will this help me build a world?” I can see the question opening up places in his mind. My job now is to protect that question-led curiosity at all costs. But Christensen doubtlessly saw so many kids whose driving question was “Will this be on the test?” that the question-as-place insight became obvious.

As a strategy professor, he would have experienced the opposite: the value of asking the right question. A friend of Richard Rumelt, my other favorite strategy professor, once observed to him that “it looks to me as if there is really only one question you’re asking in each case: What’s going on here?” Rumelt writes that the observation was “instantly and obviously correct. A great deal of strategy work is trying to figure out what is going on. Not just deciding what to do, but the more fundamental problem of comprehending the situation.” Not just getting the answer, but the more fundamental problem of asking the right question.

I came across that Rumelt anecdote in Graham Duncan’s essay, What’s going on here, with this human?, which I re-read after listening to Graham’s fantastic conversation with Patrick O’Shaughnessy.

Graham Duncan - Talent Whisperer - [Invest Like the Best, EP.409] Colossus | Investing & Business Podcasts Episode

Patrick named the episode “The Talent Whisperer,” and what becomes clear throughout the conversation is that Graham has crafted a successful career and life by asking the question: “How do you see someone, including yourself, clearly?”

Graham has made an art of understanding people – Patrick introduced him by saying that his “reputation was as the most discerning people picker on Wall Street” – and in his essay, he writes that one of the best ways to do that is to see what kinds of questions they ask:

It also helps to have the candidate you’re trying to see clearly ask you questions. Questions have very high signal value compared to most anything else you can get from a candidate… I write down each question and sometimes respond with “I’ll answer, but first I’m curious, why did you ask that?” I’m looking for the felt sense of a “hungry mind” based on the way their questions flow. That’s very hard to fake.

I am picturing myself, many moons ago, in the last few minutes of many Wall Street interviews, the portion when they ask, “So what questions do you have for me?”, asking dumb questions like “What’s your favorite part about the culture at Deutsche Bank?” or something equally stupid because I didn’t actually care enough. I left finance a few years later when I realized that I had friends who loved finance, and that they would always beat me.

Another way of putting that, in the context of questions, is that they actually wanted to answer the question, “How do you pull money from the markets when so many other smart people are competing to do the same thing?” So when they got put in a room with someone who did that professionally, they asked hungrier specific questions in order to better answer their big question. As Graham wrote, it is very hard to fake what your mind is hungry for.

This is why it is so important to figure out the big question you’re trying to answer. Putting yourself in situations that feed your mind what it’s hungry for lets you outwork everyone else without even realizing you’re working. You’re just trying to answer your question!

Each person’s mind is hungry for different things (different nutritious things, at least), and each person’s big question will be different. There are things that I find absolutely fascinating that possibly only 37 people in the world would care about. Like when I was interviewing Anil and Sunil for the Deep Dive on Meter, I was ravenous for more information on how they chose which architecture to bet on and why they “selfishly” replace all of their hardware whenever they release new hardware. That was so much fun for me, because one of my sub-questions is, “How can Vertical Integrators beat incumbents by building better, faster, cheaper products?” and there were two of the best I’d ever met at doing just that willing to spend their time to help me answer it.