[cross-posted here]
This post is a recap of some naturalism studies I did a few months back. At the outset, I didn’t know where the studies would take me. Now, I believe they taught me about how to do the “real” version of the thing you’re trying to do, where “real” tries to point at things like “the territory” and “what actually matters”.
To  communicate my idea, I will rely on two central examples and offer two  frames of interpretation. I want to offer people several, slightly  different footholds, such that, if one example or one frame clicks for  you while the others don’t, you can run with the one that did. I end the  post with some thoughts on how to respond to the problem I’m  outlining. 
Outline
Examples
“Ideal solutions”
“Being helpful”
Interpretative Frames
Maps of maps
Empty expectations
What to do in response?
Let’s go!
Examples
“Ideal solutions”
Some  time ago, I was working on an important work project. I cared about  doing it well. Initially, things went well but soon I started to feel  stuck and grew increasingly averse to working on the project. Whenever I  would turn to thinking about the project, I had an experience of my  mind “cramping” or “tensing up”, and a veil of fog settling over my  mind, preventing me from thinking clearly and making progress. I’d start  to feel increasingly frustrated, self-judgemental, and averse to  working on the project. 
A central part of the phenomenology of  this experience is a sense of “trying really hard”, but failing to  really get a grip on the problem. It’s a chain of trigger-action patterns  where, when I notice I get stuck in this way (trigger), my mind reacts  by “trying harder” (action), which in turn makes my mind tense up more. This  creates more of the mind-fog preventing me from being able to think  clearly, meaning I’m even less able to make progress (trigger), causing  my mind to want to try even harder (action), etc. The resulting  experience is one of “drifting away from” rather than “towards” a clear  understanding of the task/problem. 
When I first ran into this  problem, I didn’t understand what was going on. So, I started studying  this tensing-up experience, which eventually led me to an insight that  was central to my making progress on this problem.
I realized that I was holding the subconscious belief that there existed, somewhere, an ideal,  a perfect solution to my project. I didn’t have access to this “ideal  solution”, nor did my belief about its existence contain any details on  what it looked like. And yet, part of me was convinced that this perfect  solution existed.
As a result of this belief - and until that  point unnoticed to myself - my orientation to the project had shifted.  What I was trying to do when working on it had moved away from “thinking  about and solving the problem” towards “finding and replicating the  ideal solution”. Anything I did in fact produce - necessarily -  fell short of its perfection, thus harbouring frustration, a sense of  insufficiency, and further pulling my attention away from the  object-level of actually solving the problem. 
I’m inclined to call the “ideal solution” a construct of my social cognition. It was created out of beliefs about how I was supposed to  carry out my project, and out of comparisons with how others would do  it. It wasn’t that the project itself was unbelievably hard, so much so  that I couldn’t have made meaningful progress on it. Rather, linked to  my desire to do it well - to live up to some high, yet ill-defined  standards, as well as my desire to be seen as doing so - my thinking had  become tangled up with a lot of thoughts, only some of which still had  to do with the plain task of making progress my project.
Once I  noticed that, in some sense, I had ceased to plainly try to solve the  problem, combined with some additional hacks that helped me get back on  track with doing just that (described in more detail below),  my frustration and sense of stuckness with regards to the project  started to melt away successively. With my mind clear (instead of fogged  up) and able to sustain a gentle focus (instead of cramping), I would  return to thinking clearly, which allowed me to regain traction and soon  be reconnected to the joyful creativity of genuine problem- solving. 
“Being helpful”
Some  time ago, I helped a friend debug a problem of theirs. They wanted to  support their partner, who was going through an intense couple of  months. The problem was that my friend's attempts of helping their  partner weren’t always as successful as one would hope. 
We had  talked about this problem before, but this time my friend came to me  with a specific new insight - one that proved to be particularly juicy  with respect to making progress on their problem. 
“I realize  that, sometimes, when my partner asks me to do something for them, I  switch into the mode of ‘trying to be helpful’ or ‘trying to be seen as  helpful’, instead of ‘trying to solve the problem they asked me to solve  for them’.” 
We went on deconstructing this dynamic further. It  looked like “being seen as helpful” served two distinct purposes. For  one, my friend wanted to be the sort of person who is a supportive  partner. This was, in essence, a need that they themselves had. Second,   they wanted to signal to their partner that they “had their back”.  Importantly, this desire to offer emotional support was genuine and did  serve an important purpose (which their partner recognized and valued).  They could signal their commitment by, for example, adjusting their body  posture, engaging in certain verbal patterns, being generous in what  resources they were willing to spend on solving the problem. 
However,  their kind intention alone wasn’t solving the problems their partner  had asked them for their help with. In optimizing for “being a  supportive/helpful partner”, they would give up on some things that  normally made them more efficient at solving problems. For example, in  discussing with their partner what solutions were most appropriate, they  felt disinclined to disagree with their partner and clarify where the  disagreement (or confusion) came from. Voicing disagreement felt like it  was going against their goal of making their partner feel supported.  However, it also decreased their ability to fully understand what it was  their partner cared about. 
Just like myself in the earlier  example, my friend got trapped in - tangled up with - a behaviour that  was optimizing for something other than “solving the actual problem”.  Given that my friend genuinely cared about “solving the actual problem”,  their strategies for achieving this goal was non-ideal. This is not to  say that the other things their behaviour was optimizing for might not also be valuable in its own regards. By gaining clarity on what was going on, and acknowledging that they did in fact care about several things  in this situation, my friend found a way to satisfice each of them  separately. As a result, the tension they used to feel when trying to  help their partner reduced, and they became more effective at actually  helping them. 
Interpretive Frames
I now want to offer two complementary ways in which one can interpret and draw lessons from the above two case studies. 
Maps of maps
The two examples are trying to point at a way of orienting to reality - namely, engaging in a sort of “guessing the teacher’s password”  move, rather than trying to solve the real problem - that comes with  detrimental effects on one’s cognitive/epistemic processes. Let me  unpack:
In “rationalist lingo”, I would describe the shift from  “trying to solve the problem” to “trying to replicate the ideal  solution” as follows: Instead of trying to create my own map of the territory, I was trying to create a map of someone else’s map of the territory. 
However, whenever the problem that you’re trying to solve resides in reality,  the epistemic process of “trying to create a map of someone else’s map  of reality” is inherently misguided and likely to lead you astray. One  of the most important aspects of this, in my experience, is that you  cannot interact with someone else’s map of the territory in the same way you can interact with - say, run experiments on - territory. 
Two caveats on what I just said seem appropriate:
First,  this is not to say that you cannot (or that you should not) interact  with and learn from other people’s maps of the territory. In fact, other  people’s maps are a great source of information, and I’m all in favour  of downloading and adequately integrating parts of their maps into your  own. What I am trying to point at, however, is that the type of  relationship between you and someone else’s map is importantly distinct  from the relationship between you and the territory. There is a  difference between a) treating someone else’s beliefs as evidence about  the territory, and integrating that evidence into your own overall view,  and, and b) confusing someone else’s map of the territory for the territory itself, forgetting that there is an actual territory and that the way your actions cash out depend on the territory, not the other person’s map. 
Second,  things become a bit more complicated in cases where the problem you  care about does in fact reside in someone else’s map of reality, and the  evidence you’re looking for is evidence about their map, not the  territory per se. These types of problems exist, and in these cases,  you are correct in trying to build a model of the other person’s model.  What does remain valid, however, is the importance of tracking what  level it is you actually care about, and what level it is you’re  currently on.
In my experience, one of the  simplest-while-still-robustly-useful ways for (re-)orienting is to  pause, take a (mental or actual) step back and ask “Soo.. what is it  that that I’m actually interested in/trying to do here?” 
This is another way of saying, the “maps of maps” problem is a type of Goodhart’s problem:  you tried to solve a problem, you picked (consciously or nor) a metric  that was at some point correlated with the thing you actually cared  about, but eventually, once you optimized enough for that metric, it  ceases to capture the thing you actually care about. (For example: goal -  helping; metric - being seen as helpful.) Asking “what’s the thing I actually care  about is here” helps you re-calibrate where you’ve come since you last  asked this question, and what looks like the right direction to be  moving in now. 
“Empty expectations”
Here’s  another way of describing what is going on in the above examples. It  revolves around the cognitive move/phenomenon of “having expectations”.  In the first example, say, I had expectations about what the ideal  solution looks like. But, as I will argue in a bit, something was off  about my expectations - it was empty.
First, let us do some ground work. Expectations come in different types. There is a type of expectations that works like predictions.  Prediction-type expectations are great because they contain a lot of  useful information. Assume I write a post. As I re-read it, I have some  sense of the current draft “falling short of my expectations”. I can now  use my inner-sim to poke at this sense of “not quite right”, and it will tell me things about how exactly I  am falling short, and what a better version of the post would look  like. Maybe I need to add an example, or maybe this sentence is too  wordy, etc.
There is another kind of expectation. To understand  how it works, let’s take the “ideal solutions” example from earlier.  There, the expectation I (subconsciously) held (about the existence of a  perfect solution) was empty, non-specified. All it had to say  was that whatever I had produced so far “surely wasn’t perfect”. But my  expectation had nothing at all to say about how my current draft  solution was falling short, or in what direction I should be travelling  in. I call this type of expectation an “empty expectation”. 
Note  that, sometimes, a prediction-type expectation might reside somewhere in  the blackbox-y parts of your mind that, at first sight, it looks like  an empty expectation. However, just because it is difficult to  succinctly verbalize how what you are seeing falls short of the expectation - let’s say the expectation is preverbal  - that doesn’t yet mean it is empty. The preverbal expectation does  still clearly carry information about where I ought to look or what I  ought to do next, even if it would be hard for me to explain that to  someone else. An empty expectation doesn’t have that. It might require  some extra attention to correctly distinguish preverbal from empty  expectations in practice. In my own experience, however, once I look  more closely, the distinction quickly becomes evident. 
Since  giving this phenomenon of empty expectations a name, it has become even  more salient to me just how widespread it is. Any of the following  sounds familiar to you?
You think about [starting a project], but then you think: “Nah, I'm not good enough. I couldn't possibly do that."
You have been working hard on [a project], but you keep thinking to yourself: “I’m not doing enough. I’m not doing it right. I have to do more. I have to do better.”
These  aren’t always cases of empty expectations. To check whether they are,  you can ask yourself some of the following questions: 
Does the thought have anything specific to say about in what way you’re not currently up for the tasks, what you’re lacking, or what, concretely, it would look like for you to be? Is there any bit of evidence that could cause you to think that you were up for it? If no, that’s an empty expectation.
Does the thought have anything realistic to say about what it would look like for you to do enough or will it continue to ask for ‘more’ indefinitely? If there is no realistic and concrete answer to that, that’s an empty expectation.
And here’s a bonus question: What if you swapped out “you” for some other person in the same scenario. Do you get the same or a different answer? If different, why does one answer not apply to the other case (and vice versa)?
In the “ideal solutions”, it was important for me to  internalize that the “ideal solution” I had been trying to replicate  doesn’t exist the way I was conceiving of it, and that I could stop  trying to look for it. This also meant I could give myself the  permission to think for myself a bit more recklessly, and come up with my own solutions, a bit more desperately. 
***
So  far, I’ve been talking about what happens if we shift away from ”trying  to solve the actual problem”, towards some other, more convoluted way  of orienting to reality. We might describe this convoluted orientation  as not noticing that you’re building maps of maps, instead of maps of  reality; or as being fooled by empty expectations. 
Conversely, we might wonder what it is that happens if I orient back to “trying to solve the actual problem”. What is the mode that I am advocating for here? 
I believe the best way to answer this question is to try it out yourself. What does happen when you ask yourself what you’re actually trying to do, and then do that; when you - nothing but - genuinely try to do the thing you’re trying to do? 
Beyond that, all I have are pointers. What I find when trying to orient to reality in this way is related to original seeing, to the mode of orienting to the world that is a constant undercurrent of the Replacing Guilt series, to “the thing” that (according to me at least) most deserves to be called “research” or “truth-seeking” or “sensemaking”. 
What to do in response
Having  worked through some examples and interpretative frames, let me now  share some observations about what might help - what helped me - when  you notice yourself getting tangled up in things other than what lets  you do the “real” version of the thing you’re trying to do.
Noticing
Learning to notice when the situation occurs (e.g. noticing the tensing-up experience from example one, or noticing the experience of “trying to be helpful” in example two) is extremely helpful in terms of gaining surface area with this specific way of getting stuck.
Initially, I would only notice the experience after having been struggling along for maybe an hour or so. Over time, I learnt to notice the experience sooner; maybe after 20 minutes, then 10, then after 2. Eventually, I wasn’t so much noticing the experience itself, but rather a "precursor experience" (which is to say, the thoughts and mental moves responsible for the experience themselves). This process of becoming better at noticing can dramatically increase your ability to do something about the problem. (More about what to do about it below).
Replacing TAPs
In example one, my default reaction to the tensing-up experience was to “try harder”, causing a detrimental and self-reinforcing cycle to kick in. Understanding this allowed me to replace this natural trigger-action-pattern with a more conducive behaviour/mental move (such as asking myself what I was actually trying to do, or “letting go”/”backing up”; see below).
Asking yourself “What am I actually trying to do?”
Somehow, those “empty expectations” don’t exist in the space where I’m genuinely connected to what truly matters in what I’m trying to do. Again, this mental move can be turned into a TAP which is a great way for learning to track the “real thing”/the territory more reliably.
“What am I actually trying to do?” is the version of this question that has been most robustly useful to me. However, depending on the situation, you might want to play around with, tweak and customize what exact question(s) you’re asking. For example:
What am I doing right now? Why am I doing what I'm doing? What problem/thing am I trying to solve/achieve?
According to my behaviour, what am I trying to achieve (on top of my explicit goal)? Or in other words, what is my current behaviour buying me? Is the way I currently try to achieve all of these goals the best way to do it? If not, can I separate out these processes, so that they cease to interfere with each other?
What can I gather (from the world, from my interlocutor, ..) that tells me about what’s actually valuable here?
Am I trying to be [helpful]? Is this still worth doing X if it's not seen as [helpful]? If no one else seemed to care, what would I still care about there?
etc.
Ways of “letting go”/”backing up”
A lot of mental moves that proved helpful to me are in essence about shifting from “trying harder” to “not applying force”. These things overlap a lot with what I would do to get more grounded, such as engaging/focusing on my sensory experiences (e.g. looking at some natural structure, reading poetry, observing my breath, checking what my body feels like, drawing something, ...). All of these moves involve observing reality directly. When I look at a tree or feel my own body, there's little chance I’ll accidentally try to look at someone else's model of a tree. Speculative, this might help by reminding myself of how to make maps, rather than maps of maps.
Something that initially was very helpful for me was to “de-prime” my mind from the “the stuckness” and frustration that I felt around my project. Successfully de-priming my mind would mean that I could go back to working on the project without immediately falling back into the same cognitive pattern, but instead being able to maintain my newly gained orientation. Doing the groundedness exercises and breaking the above-mentioned trigger-action-chain were helpful with that.
Notes on Actually Trying also contains some pointers at how to back up and properly reorient to a task/project.
Noticing picas or bucket errors
In all generality, we get derailed from tracking reality directly for reasons. Usually, these reasons are valid in their own rights (such as my friend's desire to provide emotional support to their partner), even if the way we currently pursue them interferes with other things we also care about (e.g. solving the actual problem). The fact that they interfere with each other is often not an inherent problem but emerges because we might be committing a bucket error (e.g. disagreeing with my partner means that I’m not being supportive), or we might be pursuing what we care about in a convoluted way (e.g. the act of obsessively worrying about something in our minds is like the “ice” we eat to address our “iron deficiency”, say, our wish for the project to go well). When we can understand these dynamics, we can often find ways to serve all of the different goals through alternative, separate actions.
Beware social cognition, and drop it wherever it doesn’t serve you
Social cognition refers to the set of mental processes that are concerned with the social world; they aim to perceive, make sense of, remember or attend to other people and our relationship with them. Social cognition is powerful and critically useful to a lot of aspects of human life. However, spending social cognition on, say, solving a math problem is rarely helpful. It might make you ask questions like: “How quickly do I think Anne solved this problem? What will Bob think of me if they learn that I got the answer wrong for all of my first three attempts? If I don’t manage to solve this problem, what will this mean about me?” Again, I am not saying these types of thoughts are never useful for anything. I am saying that they are barely useful to actually solving things like math problems.
So, what can you do? First, observe your thoughts for a few moments. How many of your thoughts are exclusively about what you’re working on, and how much of them are social cognition? If you have a lot of social cognition going on, ask what work this is doing for you, what needs it might be addressing? In all generality, we do things for reasons, even if the way we pursue them might not be the most effective. Now, either take care of these needs right away, or credibly commit (to yourself) to taking care of them at some later point in time. Often, the crux is in creating enough internal emotional safety such that, at this point, you can simply drop whatever social cognition that isn’t serving you and return back to the object level of what you’re working on. (Be sure though to come back to these needs if you committed to doing so. Trust (including self-trust) is a precious thing.)
Maintaining a healthy distrust in labels
If you want to maintain a pure orientation towards what actually matters about the thing you’re working on, it is often important to be careful with labels, i.e. your choices about how to carve up the problem space into relevant entities/concepts (ontology) and the act of naming and refining these concepts (labelling)).
Practically speaking, it is often useful to come up with short and condensed descriptions of what you’re doing (e.g. “I am a teacher”, “I am working on our annual impact evaluation”, “I’m writing a strategy document”, etc.). However, in my experience, these labels (e.g. “teacher”, “impact evaluation”, “strategy”) can become increasingly obstructive to my sense-making/problem-solving process - as if the label itself prevented me from seeing clearly what is actually there and what matters. For example, it becomes easier to move towards optimizing for a neatly formatted strategy doc, as opposed to working out relevant considerations about what your medium- and long-term plans should look like.
Especially in the earlier phases of a process, your S1 is often better at understanding the most relevant aspects of your problem compared to what an initial, S2-generated ontology will be able to capture. If you unambiguously run with this initial ontology, you risk running off in the wrong direction. My guess is that this is related to (something like) verbal overshadowing, i.e. the fact that preverbal, S1-based intuitions can be fragile and easily overwritten by the more “forceful”, verbal, top-down S2 processes. In order to avoid overwriting what your S1 might know, you can start by maintaining a decent amount of distrust in any of the concepts and labels you initially come up with (or avoiding them altogether). Later, once your S1-understanding of the problem space has become sufficiently nuanced and robust, you can start eliciting better labels that will (hopefully) carve reality (more) at its joints.
 
Thanks  to Logan Strohl for developing and coaching me in the methodology of  naturalism. If you want to learn more about it, this is a good place to start.
Thanks to various other people for helpful discussions and  comments on this post.