Question bank

The links are to Wikipedia lists of unsolved problems for the given domain. Way too many questions to copy over and list here, so I'll list the ones that are on my mind from each section. My commentary is indicated, and my questions relevant to the given topic are listed below a line separator.

I provide attributions and commentary accordingly after the question. They are in no particular order (yet). If there are no attributions, then the question comes from me (or more likely I think I came up with it, but I heard it somewhere).

• What is something that you believe to be true, that if you told people, they would not only disagree with you, but think you are totally crazy? From Peter Thiel. The context here is that if you have a definite answer to this question, there's a chance that you could turn this into a pretty good startup that "disrupts an industry" to use the optimistic lingo of the late 2010s.
• How can you achieve your ten year plan in six months? From Peter Thiel. I like to flip this one too and ask how you would achieve your six month plan in 10 years. Related to an article I wrote called "how to get fit in 20 years," whereby the context of losing weight and getting in shape often should be slow-tracked rather than the trap of "lose 30 pounds in 30 days" or whatever.
• What would I do if it were impossible for me to fail?
• What would I do if I knew I was going to fail? From Seth Godin, who flips the script on the more commonly asked question about what one would do if failure were impossible. It flips the focus from the outcome to the process? This resonates with me quite a bit.
• What is your felt sense on the topic? Attributable in part to Daniel Schmachtenberger, but also Focusing by Eugene Gendlin? Felt sense can be a vibe check, or it can be a physical sensation, like a pit in the stomach. These feelings are important at least in figuring out where you brain sits on a subject, and should be interrogated accordingly.
• Is this a finite or an infinite game? If its a finite game, how can we move it in the direction of an infinite game? From James Carse. For context, a finite game is a game in which the goal is to win, and an infinite game is a game in which the goal is to play the game again tomorrow. Working out is an infinite game. Pick-up basketball with regulars at a park has both finite and infinite elements to that. You want to win, but you also want your friends to want to play basketball again with you next time you show up, so you have to play nice.
• Where are people gaming the game? Also related to James Carse, but its something I've been asking recently. An example of a game that has been gamed is professional bodybuilding, which basically has anabolic steroid use as an entry requirement (not to strawman the rest of the sport).
• How can I solve a simpler but related problem? How can I simplify the problem? How can I generalize the problem? Related to Chaude Shannon, and this MIT lecture about his problem solving process. Often, you do this loop where you simplify and generalize and reformulate over and over until you get to something fundamental. Like perhaps a theory of information. If you don't listen to this lecture that I linked, note that this is different than you think. It's not the Einstein quote about making things as simple as possible but no simpler. It's actually about not being afraid to simplify beyond that, even if it takes you away from the problem you're solving.
• What kind of problem is it that I'm solving? (eg. a math problem, an optimization problem, etc). This might help cue up the right mental models.
• What is the inverse of the problem? From Charlie Munger's habit of inverting the problem. How could I totally mess this up? How could I make things maximally worse? How could I ensure that I would lose in the fewest possible steps? Alex Hormozi uses this a lot as well. I find it to be very effective.
• What are the biggest ideas in your field? Related to Charlie Munger, and his process of collecting so-called mental models. It's a question you ask an expert in something that you're not an expert in. I'd say its increasingly important as things get increasingly interdisciplinary (eg. talk to any cancer biologist about how many fields merge together for that one).
• What action could you do today that would make every other thing today irrelevant or trivial? Related to Tim Ferriss and I think Cal Newport. Think of it as the thing that would take down the other things like dominos.
• What are the most important things to get done this week (as opposed to shorter time scales). Cal Newport. You can move this out to month and year and even farther out. It at least gets your head in the right place. Related to the question of whether you're hunting antelope or field mice, by Tim Ferriss.
• What are the steelmanned versions of each of the perspectives around the topic/problem? What is the dialectic of each of these perspecives? Daniel Schmachtenberger's sensemaking process, which is increasingly important in a world of ingroup/outgroup polarization.
• Version 1: thing. Verion 2: different thing. Version 3: thing from version 1. Balaji Srinivasen. Not a question but more of a mental model for organizing a particular topic. Eg. Version 1: learning via conversations with experts. Version 2: learning via books and lectures. Version 3: learning via conversations with expert AI models.
• How can I do the thing without spending a penny? Jacob Lund Fisker. Related to his exercise of not spending a penny for X months. You start thinking in terms of growing your own food, learning new skills, and all of that, even if you do this as a thought experiment.
• For a given action, what are all the things that I am doing (you never do one thing, as per systems thinking)? Jacob Lund Fisker. For example, riding my bike to the gym as opposed to driving is also cardio, and "getting out into the world" and learning about necessary bike maintenance and repair, which could turn into a side gig, and so on. Lots of benefits there as opposed to driving to the gym in order to sit for 1 hour on an exercise bike.
• What is actually on your mind? Even if its toally politically incorrect and absurd? Indirectly related to Louis CK, whose humor often revolves around him saying things that a lot of people think about but don't outright say. This is not a question to get you to talk a certain way (especially in these times), but one to at least get you to be real with your thoughts and feelings, even if they remain private.
• What would X do? What would X say about this. A generalization of what would Jesus do. But also related to Charlie Munger's mental models. What would a chemist say about this? An economist? Joscha Bach? Whoever your intellectual heroes are. Family members and friends you trust and respect. And so on.
• What wisdom can I pull out of this person/thing/event? For example, my mom taught me how to be tough, in ways that often go beyond words I could put here.
• What are the levers here that I can pull? How could I max them out? An example: if a certain type of outreach is getting me clients, maybe I can just do more of that.
• What are the incentives behind this? Related to Charlie Munger "show me the incentive and I'll show you the outcome."
• What cognitive biases could be impacting this topic/problem? Related to Kahneman and Taversky, and also Eliezer Yudkowsky and the rationality movement? There are quite a number of them.
• Why do you THINK this is the case? Eliezer Yudkowsky on dissolving the question.
• Where are the leaky abstractions here? What are they pretending to be? What are they really? This is Gwern's article on the hacker mindset, as "seeing through and unseeing."
• Why? Can't forget the importance of chaining these together. Just don't fall into the trap of answering with words every time. This is similar to what is known as the "five whys" in business. But the devil in the details is knowing what specific "why" question to ask at least point. Why is not a line of inquiry. It is a tree of potential why branches that pretends to be a line in that you only really traverse one path when you do five whys.
• What are the relevant things here? This sounds like a trivial question, but as per John Vervaeke and his concept of relevance realization, there is a whole lot of "what is relevant" that happens sub-verbally. So this is actually getting you to pick up on the things that your brain finds to be relevant at any given time.
• What are the virtues that I am working on? What are the virtues that matter to me? This is Ben Franklin.
• What does my Jungian shadow want? Related to Carl Jung. The Jungian shadow is your so-called dark side.
• Am I oriented toward the greatest possible good? If not, how can I adjust my life such that I am? This is Jordan Peterson in terms of the specific wording (disclaimer: I don't necessarily agree with his political views), and it is a common religious theme. Daniel Schmachtenberger has similar questions around "who do you serve, and is that the higest possible thing you can serve."
• What makes you laugh? What makes you cry? Especially things that make you laugh and cry when no one else is doing so (which can be embarrassing)? What makes you laugh so hard that you're on the ground rolling around? What's the hardest you've laughed in recent memory? Same questions go for crying? Are there particular themes here?
• What fictional characters or situations in fiction do you most relate to and why?
• What would your 85 year old self tell you? Alex Hormozi asks this question. Related to the Solomon effect: everyone can give good advice, but its harder to give that advice to yourself.
• What Jungian archetypes (aka characters from fiction or wherever else) are guiding you day to day?
• What programs that gave you success earlier in life are no longer appropriate at this phase in life? From a conversation with a (very wise) collague named Chandra during a business trip.
• If aliens came to the planet and they were going to kill 99% of the population, and they were deciding whether or not they were going to kill you, what would be the case you state for them to keep you alive? This is a grad school interview question that Garry Nolan likes to ask.
• In the given situation, what are the things that you can change, and what are the things that you cannot? This is Epictetus, essentially from the start of the Enchiridion, though it is a theme throughout, and a common pillar of stoicism at large.
• If you knew you were going to die in six months, how would you spend the remaining time on this Earth? I'm pretty sure most people ask this question at some point. Maybe one of the "endgames" in life is to get to a point where you wouldn't change a thing.
• If you could start and run a project that would continue for 1000 years after you were dead, by competent people (and/or robots), what would that project be? Related to the Long Now.
• What do you see as the third attractor? What does it look like? What needs to be done to move us in that general direction? This is from Daniel Schmachtenberger, and the metacrisis.
• What kind of music really gets you going and why? What songs are you really into right now? Some times I find that there's some deeper meaning here.
• If you were suddenly on your deathbed, what would be your regrets? What would you be proud of?
• What good can come out of this? Related to how Jocko Willink says "good…" whenever something bad happens.
• What are the nth order effects, positive and negative, for the action that I am going to take? Lots of people ask this, but the ones that stand out in my corner of the world is Charlie Munger, and Jacob Lund Fisker. A pillar of systems thinking.
• What is the relationship between X and Y? Purposely a broad question. This comes from Whitehead, David Bohm, Forrest Landry…thinkers who focus less on the "nodes" and more on the "edges." Related to systems thinking.
• What are the attractors your actions (or the actions of whoever) are moving you towards? This is complex systems theory, but spoken by Daniel Schmachtenberger, in terms of where society is heading. The attractor of order (eg. police state, AI surveillance), and chaos (eg. anarchy of so-called failed states), and the third attractor, which is not really well defined except in terms of what it is not, and it is not the first two.
• What is/was this particular thing (part of me, habit, thought pattern, feeling) serving? From psychotherapist Dr. James Hollis.
• What is wanting to find expression through you? From psychotherapist Dr. James Hollis.
• (when faced with a decision) Does this path enlarge me, or diminish me? From psychotherapist Dr. James Hollis.
• If I was found to be naturally really bad at X (eg. a skill I'm trying to learn, marriage, etc), how would I do things differently? This question is one of the reasons I got good at computer science. I originally thought I was naturally bad at this type of discipline, so I treated myself as if I was really bad at it, which led me to devote extra time to it, review the fundamentals more often, etc.
• It's five years from now and X failed (where X is some sort of endeavor). Why did it fail? This is called pre-mortem, and I first came across it from Tim Ferriss. You can also do this with habits and everyday life as opposed to goals/endeavors. Eg. It's five years from now and I gained 100lb of fat, or I'm in a midlife crisis, and so on. Why? The pattern here is these types of questions are good ways to stimulate constructive self criticism around whatever you're doing right now.
• For a given future thing, what is it that you fear most? If that thing you fear happens, what is one thing you could do that would make the situation a little better? This is the concept of fear setting, from Tim Ferriss.
• What are the limits of the model? Can you use the model to reveal its own limits? This is often said by Daniel Schmachtenberger, with reference to Gödel's Incompleteness Theorems, as well as the first line of the Tao Te Ching (The Tao that can be told is not the eternal Tao). Every model has its limits, and it is important to know what those limits are when you use the model. This can range from a literal model in data analysis (eg. the limits of tools like UMAP, something I've talked a lot about), to lenses through which you see the world (eg. relating everything to computation by analogy, as people like Joscha Bach masterfully do).
• What is it about me (the things I can control) that has led to or catalyzed this outcome? From Dr. James Hollis, but can also be thought of as a generalization of pre-mortem.
• What is inevitable? This is a question that my former thesis advisor Garry Nolan asks.
• How do we taxonomize it? This is a question from Daniel Schmachtenberger. When he is discussing a problem in whatever domain, ultimately whatever is found needs to become a taxonomy. This is related to the MECE trees that consulting firms like McKinsey make. Which is also related to problem decomposition, which you learn how to do in your first computer science class. The outcome is the same. You've taken what you've got and put it into a tree form. Yes, it might be better represented as a mind map, but for some reason, the brain is better at thinking in taxonomies than mind maps (without the aid of pen and paper).
• What would a [characteristic X] person do? Eg. what would a healthy person do? This is from James Clear's Atomic Habits. It gets you to think in terms of the habits and systems you need to build to achieve a particular goal.
• What am I optimizing for? What games am I playing? This is from the Tim Ferriss podcast featuring James Clear.
• What would make this situation amazing? This is from Alex Hormozi on Modern Wisdom. He asks this question when something bad happens. Essentially how do you make the best of it? The concrete example discussed is when Chris Williamson (maker of the Modern Wisdom podcast) ruptured his Achilles tendon, which led him to spend more time on his podcast, which led to the podcast taking of and being the most successful thing he's done.
• What actions or behaviors does this thing change? This is from Alex Hormozi in the context of what learning actually is, and you can ask it in the context of books you read, podcasts you listen to, conversations you have, and so forth.
• What goal(s) is this action in service of? This is from me, but inspired by Jacob Lund Fisker, who thinks of every action in terms of a goal. In other words, even if you don't set goals explicitly, you are striving toward goals nonetheless. For example, you have the goal of "don't starve" even if it's not on your list of goals.