Oct 2016: Am currently in the process of shuffling these around to fit headers, so things might not make sense for a while.
What was the Peloponnesian war all about?
What was the American Civil War wall about?
What was the Asian Financial Crisis, really? What’s Bretton-Woods?
Simon Bolivar & the spanish colonies in Latin America.
Why are some people more addiction prone than others? 
What are the economics of sex? 
What was “Consider The Lobster” all about?
What is the history of roads? What’s the relationship between roads and humanity?
How should I spend the remainder of my life? How to think about death? Should I do hard things? Can I get smarter? Can I get stronger? Can I learn to cook? Should I learn to program? How to think about risk ?
What are the software bugs in my own head? How do I identify them? How do I fix them? What is an optimal information diet? How do I prioritize things? How do I live well in a world I will never fully understand? What are the things that powerfully influence the reality we inhabit? What of those things are systematically hidden from view? (Analogy: Everybody poops, but if you were an alien who weren’t allowed into toilets, you might not know.) What might I not know?
How can I overcome procrastination and become productive / Get Things Done? What’s stopping me from becoming better and more effective at work? What new skills do I need to learn? What things do I need to stop doing? What are some thinking tactics I should use?
How can I take better care of my body? What is the brain? [1, 2] What are the components of health? What are Circadian clocks ? What is sleep? How do I ensure that I am fit and healthy to a ripe old age? How do I stave off cancer, heart disease and the other major killers? How do I do squats?  What is cortisol [1, 2, 3, 4]? Testosterone? [1, 2] How much of hunger is psychological?  How do you whiten your teeth?  How does protein become muscle?  Why are people predominantly right-handed [1, 2]? What other things are like that, and phantom limbs? Why do people have foot fetishes ? Why is sugar bad?  What’s up with keto? 
How much water a day? Real effects of coffee, tea? Effect of coke? Beer? How many beers can I drink? How much whiskey can I drink? Cigarettes? Relationship between cigarettes and blood sugar? Effect of diet on mental clarity? Effect of exercise? How to run better, faster, longer distances? Effect of sleep deprivation?
What is the breath? How does it work? Is it conscious or unconscious? Why shallow breathing? How do animals and humans breathe differently? How do babies breathe? How do athletes breathe? How do smokers breathe differently?
How does ADHD work? How does depression work? How do you know if you’re depressed? What is bipolar disorder? What is autism? What is Down’s Syndrome? Was Freud on to anything? How do you be less hard on yourself? 
What are the list of objects in my house? Review of each object? How have things changed? Cats. How to think about different rooms in a house. How my home has changed over the years since I got it. How I thought about the house I grew up in. Neighbourhood, 3rd places.
What is human nature? Why do we abandon babies? How do we encourage people to touch more? How do we encourage cultural changes in attitudes towards things like working hours, exercise, exposure to sunlight, sitting, etc? What are some human rituals that are good for us, that we aren’t currently doing? How do we make people less selfish, greedy, apathetic? How do we encourage people to question their own assumptions? How do I encourage myself to do that? What am I wrong about?
What is social status? How is it defined, how is gained? How much is real, how much is imaginary? How much of it can you accrue just be shuffling things around? What’s the difference between cheap signals and costly signals? How much is dental? 
Why is it so satisfying to do DIY fixes and handiwork?
How do we identify great people BEFORE they become great people? What do great people have in common before becoming great? What percentage of people have the capacity or potential for greatness? How many people are limited because of circumstance, and how do we fix that?
How does humor work? What makes people laugh? What is charisma ? What is identity? How is identity constructed, how is identity performed?
Why are video games so addictive?  What is addiction, and how is it overcome? What are the things about smoking that make it so compelling, beyond being addictive? Why do people get stuck in dysfunctional or destructive relationships? What is so addictive about drama?
What is perversion, how common is it? What is “erotic”? What is the role of censorship? Why are people so eager to “protect the children”? Why are breasts still sexualized? Why are attitudes towards sex still so prudish? What is the basis of human attraction? 
How do we get people to open up to talk about painful and uncomfortable things? What is trust? How do we encourage people to be more trusting of one another? How do we design for trust?
How does prejudice (racism, sexism, outgroup-ism) actually work? How can we actually reduce it?
Why do people compare Malala to Kylie Jenner , and more broadly, why do we compare people to one another so much? Is it inescapable?
What is the artistic/cultural significance of Sanjay’s Super Team? Why does Indian culture venerate goddesses but still remain so misogynistic ? What was “Argumentative Indian” all about? What about “Can the Subaltern speak”? What was VGR’s understanding about how to write online in English as an authentic voice, about being read with a non-English name?
How does communication work? How do we make new friendships? How do we maintain existing friendships? How do we develop deeper, better relationships with people who’re already in our lives? How do we end or phase out unhealthy relationships?
If I could clone myself, what would I have my clones do? If I were to die tomorrow, what would I do? In a week? In a month? In a year? In 10 years? In 20 years? 30? 40? 80? 110? 200? 500? 1000? If I woke up tomorrow on an alternate version of Earth, where none of my friends and family existed or knew me, what would I do? If I had to quit my job, what would I do? If I were paralysed, what would I do? What would I do if I were not afraid? What would I do if money was not a concern? What other thought experiment should I consider?
Why are so many online communities so shitty?  Why do subreddits get spammed, and how is that problem to be dealt with? Who do people treat each other so badly? What’s up with internet advertising? 
What is search? How did it get so big? How has it changed the world? (Politics? Business? Art? Culture? War?) What is the future of search?
What is social? What is social shopping? What is the real future of social shopping going to look like?
What does it mean to be a man? What is masculinity? How have concepts of masculinity evolved over time, how do different cultures embody it? What are things that other cultures know or do that are drastically different from what I’m familiar with? What would shock me the most if I travelled the world? What is the history of family relations? What is the relationship between parent and child, around the world? What is the truth underlying child labor, prostitution, human trafficking, sex slavery, etc?
What is the history of love and marriage? How and why do marriages fail? Why is infidelity so common? Is marriage as an institution poorly designed? How do I ensure that my wife and I are happily married and learning and growing together for the rest of our lives? How do we decide when to have kids? How do we decide how to establish a family? Why is abortion such a thorny issue, and how do we navigate it?
Why are some accents sexier than others? Are men with larger penises happier? How do we solve racial discrimination? Why are people so bad at holding more than 1-2 ideas in their head at a given time?
What is physics ? What is electricity? What are computers [1, 2]? How are CPUs made?  How does the Internet work? [1, 2] What is TCP/IP? How does DNS work? Routers? Servers? Security? How does hacking happen? How is Wordpress put together, and how can I wrangle it to better suit my needs? How do its plugins work? What is AWS? How does CSS work? What about HTML? How What are sorting algorithms, how do they work, why do they matter [1, 2]? How is data written onto a CD?  What is Moore’s law? 
What is mathematics? What are some cool math facts ?
How does the economy work? What is money? How does it work? What is Bitcoin?  How does it work? How will it affect existing financial systems? What is the history of banking and finance? What was the Bretton Woods system all about? What was the gold standard, and why was it left? What were the different points of view of Keynes and Hayek? What if we had let the banks fail? 
Marketing. How does marketing work? How does word-of-mouth work? How do you build a great content team or media organization? What’s PR?  What is a brand? What are logos? How do brands sell building blocks of personal identity? What is the future of marketing? What is the future of content marketing? What have been the worst marketing fails in history? What are the most cringeworthy ads? How do you have a voice while meeting audience needs? How do you produce quality content? How do you effectively utilize content marketing? What is organic marketing and how does it work? How do you build a personal brand? How do you remove the guesswork from marketing? How do you market on reddit? (Questions people asked on Facebook – 1)
Is the self real?  How do I live well despite knowing that my life probably doesn’t matter in the grand scheme of things? What is a good life? How is a good life lived? How do we die well?
Which people should I be learning from? How is learning done?
What would I love to give a talk about?
What are the best hardware startups in the world?
What is the job of a blog? What is my job? Is the customer always right? Am I proud of my work? If no, why not? More examples? Better navigation? More evidence, more data, more incisive questioning? “Is this true? Why?” What do I want to be doing 10, 20, 30, 40, 50, 60 years from now?
What is the history of the media? Why do we trust journalists? If journalism had any predictive value why aren’t they all rich? Why don’t we surface false predictions more? Why isn’t news written with more historical context? Why isn’t everything imaginable explained with incredibly entertaining and engaging content?
history / geopolitics
Why did the Roman empire fall? What were the great lessons of history? When and how will the US decline into relative obscurity? What is the future of Singapore/Malaysia relations? What will happen to Singapore and Southeast Asia as China continues to develop? What will India’s role be in all of this? What does it mean to be an Indian outside of India in the modern world? What are the most important lessons from history? Why do people outside of the Middle East have such strong opinions on Israel/Palestine?
Why does war happen, and how do we mitigate it?
Why is sex education so bad around the world? How can it be better?
Why exactly did I have such a bad time at school? How can I help other people avoid experiencing the pain and discomfort that I did? How can we accelerate the future of education? Can we make learning fun ?
How soon will it be affordable to take a commercial spaceflight into orbit to enjoy the Overview Effect? How soon will we get to Mars? How will that change life here on Earth?
How do we provide clean water and basic literacy and an Internet connection to every human that wants it? How do we mend gender relations? Why are fathers so lacking?
Can we persuade people to care more about reducing less-sensational deaths instead of sensational deaths? Should we?
What are missing features from social media? Why isn’t it easier to schedule spontaneous meetups with friends?
How do we encourage clear thinking and writing? How do we discourage bullshit?
How have sports, UFC, etc evolved to take advantage of evolutionary psychology? (Flags, teams, competition, replays, analysis, attractive humans) What’s up with yoga?
Why are MPs (Michael Palmer), etc not allowed to have sex out of wedlock? Why is intercourse so special? Why is “sex for grades” such a big deal, and what if they did something else instead of sex? How does good art crack us open so well, how does it overcome the bandwidth problem?
Can social commentary ever make a difference? How do we improve the quality of the content that we read every day?