Note: I have acquired enough slack to resume writing, but cannot guarantee that it will be consistent.
Sometimes, it makes sense to view your life from a narrative lens - to pretend that you're the main character in a book of your favorite genre. From there, you can try and make guesses at what the plot might be. For some of you, there will actually be a plot - an ambition/mission/purpose that shines through you. For others, such a plot will be less obvious, and that's ok; remember, "not all those who wander are lost."
However, given that your life has a plot, you should take a moment to remember that you don't actually live in a book; there's no real reason why the plot can't just end at chapter two. This is a different problem - one that is tackled by other techniques.
The goal of Hamming questions is to figure out what the heart of your plot is - to find the biggest problems in your life, so you know which problems you need to solve.
By ancient literary tradition, all great magics require an equally great sacrifice. The power of hamming questions is to rapidly accelerate the course of your life, identifying key milestones and obstacles for you to confront. The cost is unique to each individual, but might include the pain of an accurate self-assessment, uncomfortable and difficult conversations, and the possibility of catastrophic failure.
This isn't a light warning. There are people who will have net-worse lives if they try to seriously answer certain hamming questions. If you find it extremely difficult to think of an answer, that's a sign you should stop looking - most of the time, people can't think certain thoughts for very good reasons.
The rule is that you should be able to do things that you're slightly uncomfortable with, but to not force yourself to do things you don't want to do. Be kind to your parts. Don't avoid all pain, but there is some threshold of pain that you should definitely avoid.
There's some meta-hazard where people might think that not being able/ready to answer hamming questions is a sign of weakness and then try to force themselves to answer. I'm not sure pointing out the meta-hazard resolves it, but I don't think it makes it worse.
Sometimes, all of the problems in someone's life revolve around a single nexus. Sometimes, this is extremely obvious. Hence the first question: what's the biggest problem in your life? Why aren't you trying to solve it?
This problem might already be on your bugs list and you haven't realized it yet. There's a failure mode in which people treat "solving life problems" as the same, despite the vast differences in benefit from solving various problems.
For some people, this question is all there is. They have an answer, and now they know. Others must soldier onwards.
Perfection is achieved
Imagine that your life is perfect - that you're living in your personal utopia. Compare this to your current life. What can you do in your utopia that you can't do now? What do you have that you don't have now? What do you feel that you don't feel now?
Usually, this doesn't produce a clear problem. But it generally points at a class of possible problems. Adjusting the scale of how "good" your utopia is can allow you to pinpoint more precisely, as sometimes imagining a perfect life can make it difficult to identify what exactly you're currently missing because the only real answer is "everything."
The opposite problem also occurs - sometimes people's utopias are too shallow. If you think you might be one of these people, you should imagine that your life is beyond perfect - that you're as omniscient and omnipotent and omnibenevolent as you desire.
As the saying goes, "meta is betta" quote me, right now. If there's no object level problem that immediately identifies itself, hop to a higher level. What's the reason why you can't instantly solve all your life problems? What resource on you most constrained on"
In chemistry, there are steps of a reaction that are rate limiting - the entire reaction proceeds at the speed of this step. What are the rate limiting steps in your life? How can you make these steps go faster?
Most resources can be traded for each other (usually with money as a lubricant). Can you sacrifice in areas that aren't rate limiting to speed up areas that are?
There are things my friends think are obvious about me that I utterly failed to see in myself. The easiest move is to literally go and answer your closest friends/mentors/advisors what they think are the biggest problems in your life. This is a good strategy if you're interested in figuring out what your biggest problems are. On the meta level, the skill you might actually want to train is the ability to identify the biggest problems in your life, in which case you might want to try to figure it out yourself before you ask.
Simulate copies of your closest friends/advisors/mentors and ask them about yourself. What do they think the biggest problems in your life are?
(Yes, this is very silly in the sense that it's still your brain that's doing the simulation, which means you shouldn't be able to get new knowledge from just simulating. Brains are weird.)
Are there any obvious problems in what external observers would see if they observed your life? There's a failure mode in which people always have good explanations for why they're doing what they're doing, but if you actually observed their life, they're just spending 8 hours a day playing video games. Sometimes you're just rationalizing (but sometimes there actually are good reasons, like being a professional video game player).
People who are iron deficient sometimes eat a lot of ice. This is called pica. The lesson we learn from this is that brains are bad at propagating needs into actions.
Do you notice anything confusing about your own behavior? Do you sometimes do things, ask yourself why, then give explanations that seem a little forced?
Somes humans act in confusing ways - not all "weird" behaviors are garbled needs. Don't psychoanalyze yourself (too much). However, it's worth considering whether or not behaviors your taking are pica-esque.
The focusing check is to say "everything in my life is fine" outloud. Sometimes, there will be a part of you that sticks. This feeling might point to a part of your life that is not fine. This part of your life might be an important problem.
If you're brain is particularly helpful, you'll think about saying "everything in my life is fine" outloud and it'll respond with "NOPE you don't have X or Y or Z". Sometimes, however, you'll have problems that won't cause any sticking sensations. There are many hamming questions because they work for different types of people.
Timothy Ferris writes that "the opposite of happiness is boredom". By analogy, if not by exact argument, the opposite of the opposite is the thing itself, so we infer that happiness is equivalent to excitement.
If you want to know what your life's purpose is, it's not that useful to ask yourself what makes you happy. When I ask myself this, my mind conjures images of serenity, moments that I enjoyed in the past. However, when I ask myself what makes me excited, I get images of achievement and triumph (the fact that there are no specific details is perhaps a bit troubling).
What sparkles in your life? What makes you excited? What makes your heart pound and your pulse thrum?
(Only to be done if it does more good than harm)
Set aside 20 minutes, get a non-brain thought recording device, and seriously try to answer each of the questions.