The questions that haunt me at 3 in the morning

I think that everyone has unanswered questions that bug them. Recently though, I’ve been making a point of jotting them down. I’ve begun to realize how many of these thoughts are reoccurring, and that these constellations of questions define my mental life almost as much as my beliefs.

You may think that you know the answer to some of these questions- you may well be right. You may think that the answers to some of these questions are obvious. Here I would have to disagree with you. There are times in my life when I would have agreed with that about some of them, but I’ve became less and less confident of them over time.

Regardless, let me know what you think.

The Questions


  • To what degree are people motivated by sadism in everyday and political life?
  • Is self report a reasonable measure for variables like personality and happiness?
  • What is the optimal amount of caffeine to ingest? How does this vary by life you are trying to live.
  • Sovereign citizens believe both A) That the legal system is run by incredibly evil people entrenched in power B) That if they can just say the right sequences of words, those people will be compelled by the rightness of their arguments to let them off various crimes, civil liabilities etc. Obviously this combination of beliefs is irrational- that’s not in dispute- but what about it makes it so compelling? Shouldn’t the factors that make you feel the legal system is incredibly evil also make you feel like you’re not going to be able to sway them just by making a strong argument? Why is this seemingly contradictory combination of beliefs such a potent attractor?
  • Would the Milligram & Stanford Prison experiments replicate if ran properly today?
  • What the hell is going on with the replication crisis? A lot of the failures to replicate are in really simple experimental designs. How much of it is outright fraud? How much of it is pure chance and the file drawer effect? How much is ad hoc analysis and statistical fishing? How much is participants giving the experimenters the “expected result”?
  • How can we make trying to replicate experiments an honourable and attractive path given the structural incentives of academia?


  • What percentage of convicted incarcerated people are innocent?
  • What would be an acceptable false positive rate in a just criminal law system? How does this apply to crimes which can be extremely destructive, but which are often by their nature extremely difficult to prove “beyond reasonable doubt”.
  • Under what conditions -if any at all-, and in what ways -if any at all-, should society informally punish people for whom a criminal conviction is likely impossible?
  • Are people who have done horrific things (rape, premeditated murder) generally all round bad people? Or is human character contradictory in such a way as to allow at least a significant minority of such people to be, despite it all, good or at least average or not far below in most other areas of life? This may sound absurd to some readers, but a lot of anecdotal evidence tends to suggest it might be true. What is going on here? To what degree do people have consistent moral character?

Misc human sciences

  • To what degree are there political or social ideas which, even now, if someone dreamed them up and went to some modest effort to promulgate them would transform the world? Are such remaining unthought ideas relatively few, and their effects mostly modest? Relatively many, and quite a few with great effect? Some other combination? The real underlying question here- to what extent is theorizing about political and social issues an effective strategy for changing the world?
  • What would be the social effects of a working lie detector?
  • Similar to the question about a lie detector. A wizard waves a wand. From that point onward, no one can lie. Does society A) collapse B) get much worse on net but continue C) continue with surprisingly little change D) get much better on net E) become a utopia?
  • Is it possible to throw down the tyrant irony and return sincerity to her rightful throne?


  • Our period is defined by greater political divergence on the basis of age than ever before seen since we started taking polls on this sort of thing. Preliminary evidence suggests so far that this is a cohort effect not an age effect auguring that the younger generations will not age out of their opinions as they get older- at least not automatically. Will this trend continue?
  • To what extent are people who make comically bad takes about politics acting in bad faith- versus stupid or self deceiving? Especially those with the expertise in politics to know better? Let me give examples from both sides of politics. I recently saw a senator complaining about raising the minimum wage to 15 dollars partly on the grounds that when he was young he was paid only 6 dollars. Adjusting for inflation , this turns out to be 24 dollars in today’s money. On the other side of politics, I recently saw a news station try to insinuate that privilege is the reason we are paying for the lawyers of many of the Capitol Hill rioters. In cases like this- awesomely stupid takes by people with adequate education to know better- are people A) Lying B) Bullshitting in Frankfurter’s sense or C) engaged in feats of incredible self deception or D) apocalyptically stupid This might sound more like a complaint than a question, but I mean it sincerely as a question- what is typically going on here?
  • Why the aren’t democratic politics more effective? There are certain issues on which the average member of the public disagrees greatly with the average politician, and yet there is very little movement. Obviously money in politics has something to do with it, but how does money exert its influence exactly? It’s easy to get blase about this replacing incredulity with a faux wise cynicism, but if you stop and think, it’s weird that 70% of the public can strongly support something, yet it be considered a fringe position among politicians. How much of it is caused by monopoly power wielded by political parties due to existing voting systems? How much of it is due to rational or irrational voter ignorance? How much of it is caused by voters deceiving themselves about what they believe? How much of it is due to the action of the media? What forms of action by the media (and other ideological apparatus) count here?
  • What on earth happened sometime in the mid seventies? The wage stagnation, the incarceration spike, the union membership decline…
  • Is neoliberalism a useful concept for understanding this phase of economic and political life that began sometime in the mid 70’s? Was it ever useful and is it still useful?


  • In philosophy and several other disciplines it seems like people were having more “big ideas” before about 1970. The period from Frege to the tail end of logical positivism and ordinary language philosophy – or maybe even till 1980- seems to have been very fecund. Is this an illusion of hindsight? Or is it possible that we’ve exhausted the “low hanging fruit” in certain disciplines, and the remaining brilliant theories and questions are harder to find?
  • What the hell are qualia? How do they fit into the world?
  • There are many positions which I think are good “in an aspirational sense”- as organizing myths and sources of inspiration- but would not work in practice- at least with the current level of technology. These include communism, prison abolition, and to a certain extent, in some moods, anarchism. Is this meaningful in anyway, or is it just a glorified way of saying “I wish things were different”- a vacuous waste of energy?
  • Is there a compact definition of what it means for a person’s life to go well for them which doesn’t imply that we should do something absurd- like tile the universe with people enjoying their best moment over and over again?
  • A lot of questions in philosophy seem like semantic wrangling. Often undergraduates will claim that this or that topic is just semantic wrangling. Why is it so rare for professional philosophers openly embrace the view that a lot of philosophy is semantic wrangling,? One could then argue that’s nothing to be ashamed of because some sorts of semantic wrangling and surveys of the semantic landscape are important.
  • Is consequentalism self-effacing? Would we consequentialists be well advised not to hope that consequentalism becomes widely appreciated common-sense because this might have various bad consequences (undermining integrity, inspiring a certain callousness, allowing people to rationalize their preferred course of action)?


  • Most actual businesses don’t face rising marginal costs- instead marginal costs are typically either falling or constant. How should neoclassical economics be transformed in light of this?
  • What lies at the bottom of the Cambridge Capital Controversy well?
  • Why don’t we talk more about the above two questions?


  • An argument can be made that poetry was once the most important of the arts, yet now it is effectively dead!??!! Is it because poets became too focused on avant gardeism and not enough on classical technique (esp rhyme & meter)? Is it because singing -when done well- is strictly superior to poetry for most people, and technological advances make high quality and/or catchy singing always available? I tend to favour the second explanation, because the first explanation implies that poets are just “”leaving free money on the ground” by not returning to classical technique. Nevertheless, this is a great artistic and cultural mystery. Even the fact that there is not more discussion of the disappearance of poetry is a mystery in itself.
  • Why is so little fantasy and science fiction writing literary in the capital L sense? Why has no one written Love in the Time of Cholera except with fae? Ulysses with familiar spirits? Obviously there’s magical realism, but I’m surprised more people haven’t tried a blend of literary writing and genre fantasy. Maybe fantasy writers are too smart to fall into that trap?

Sufjan Stevens

  • In the song “The Mystery of Love” the narrator says that they are “like Hephaestion who died, Alexander’s lover”, but it seems they are actually the opposite of Hephaestion, who, after all, died still the beloved of Alexander. In what sense are they “like Hephaestion”.
  • What does Gideon, the biblical judge, have to do with a breakup?
  • Why Ursa Major?
  • What sense to make of “The Ascension” the title track of the eponymous album? Who is Cordelia? What is a chariot hallucination?
  • How to understand the dialectic of a singer whose songs are very personal and whose life is very private.

AI safety related

  • How much smarter than a human would you have to be to trigger a singularity?
  • Imagine a person started off in good health in a first world country with an apartment, internet access and $5000. How much smarter than a human would they have to be to take over the world in one year?


  • It seems like we should be able to greatly reduce the length of time it takes to become a medical specialist. Indeed the length of time required smacks of industry protectionism & regulatory capture- especially when one considers that the various colleges self-regulate who can and can’t access the relevant titles. Yet these lengths of time seem pretty consistent around the world. Is there anyway we could safely slash these times by a third or even a half (e.g. six years to become a psychiatrist out of high-school)? Is the specialty structure itself, where everyone learns to become a doctor and then specializes, the best way to handle medicine?
  • Linked to the above- medicine generally has been more resistant to proletarianisation than any of the other professions (law in particular has been smashed, pharmacy even more so). Could medicine be proletarianised and doctors made just another type of worker? Should it be?


  • How can I live an authentic life, true to what I actually think, without being wildly ineffective and getting people offside? Presumably the answer is a compromise where I try to keep the lion’s share of both my effectiveness and authenticity by sacrificing a bit of both, but isn’t sacrificing a bit of one’s authenticity for strategic reasons massively inauthentic?


  • How close are we to the ceiling of performance in chess?
  • Consider a being that can see all possible game trees in chess, and in particular knows for each move whether it keeps the current game state, (win for white with best play, win for black with best play, draw with best play) or pushes it into a worse game state for its side. It is playing against a superb human grandmaster. Presumably the starting position of the game is a draw with best play. The being then picks from those moves which don’t “slip” the game state into something worse for it. Is there a relatively simple way to describe an excellent strategy for this chess super being to increase the likelihood of its human opponent slipping up and making a move which throws the game into a win state for the chess super being? of such a chess super being, E.g. one option, although I think it doesn’t work, is “choose those actions which increase the total number of losing options for my opponent, even if she picks the shortest path to a draw”.

Want more de Pony Sum content? You can join our email list via Substack here:  and join our subreddit here: 

Here's How You Can Overcome Insomnia – Health Essentials from Cleveland  Clinic

3 thoughts on “The questions that haunt me at 3 in the morning

  1. In all strategy games where I believe myself to be much better than my opponent, but they don’t make mistakes, of all the moves that don’t change state, I’ll take the most complex one.

    So pick complexity to take advantage of superior ability


      1. I can try

        By complexity I mean a combination of
        making it hard to brute force analyze all the relevant options to know which is best, and making more different options for both players so both sides are more likely to miss something

        This often translates into making slightly ‘suboptimal’ moves that create situations that most players are unfamiliar with.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s