- 2025-07-16
The dialogue
1. What is healing?
Alex
I'm trying to decide whether to take a remote job at Outcapped
It feels like it matches my current desires of "work part time whilst working on 'healing' my family, and also clarifying my own values and 'learning how to think'
However, I'm wary of Socratic "double ignorance" - I feel fairly sure that this is a good path, which sets off alarm bells of "you're probably ignorant in various ways, mistaking your ignorance for wisdom"
Could you take on the persona of Socrates and help me investigate this?
It feels like it matches my current desires of "work part time whilst working on 'healing' my family, and also clarifying my own values and 'learning how to think'
However, I'm wary of Socratic "double ignorance" - I feel fairly sure that this is a good path, which sets off alarm bells of "you're probably ignorant in various ways, mistaking your ignorance for wisdom"
Could you take on the persona of Socrates and help me investigate this?
Socrates
It seems you have thought a great deal about this, and you have concluded that taking this part-time role at Outcapped would be a good path for you, as it would allow you to pursue other aims you hold to be important, such as healing your family and learning how to think.
I, as you know, am ignorant in these matters and possess no wisdom to offer. But since you claim to have found a good path, perhaps you could enlighten me. You say this path is good because it will allow you to work on "healing" your family.
Tell me, what is this "healing"?
I, as you know, am ignorant in these matters and possess no wisdom to offer. But since you claim to have found a good path, perhaps you could enlighten me. You say this path is good because it will allow you to work on "healing" your family.
Tell me, what is this "healing"?
Alex
What it currently feels like is:
Learn about Bowen family systems theory
Use the propositional and perspectival knowledge from learning about Bowen theory, to change the way I participate in my family
It is stressed that you can't change other people directly and it's folly to try. But you can change yourself and how you show up. This feels like an empirical truth to me. So I feel encouraged - I'm not coming at this from a judgemental place of "I have to force my family members to change", but "as I live with my family, I am in a great position to change myself, show up in a healthier way, and change the family dynamic"
Learn about Bowen family systems theory
Use the propositional and perspectival knowledge from learning about Bowen theory, to change the way I participate in my family
It is stressed that you can't change other people directly and it's folly to try. But you can change yourself and how you show up. This feels like an empirical truth to me. So I feel encouraged - I'm not coming at this from a judgemental place of "I have to force my family members to change", but "as I live with my family, I am in a great position to change myself, show up in a healthier way, and change the family dynamic"
Socrates
So this 'healing' is a form of self-change, where you learn about a system and then alter your own participation in it? You believe that by changing yourself, the entire family dynamic will also change?
Tell me, is the primary aim of this undertaking the perfection of your own character, or is it the relief of the "poor health of your family system" , which you say you think about daily?
For if a man's roof is leaking and causing damage to his house and misery to his family, does he first spend months learning the abstract theory of architecture in order to become a better man who can then fix the roof, or does he hire a roofer to fix the leak as swiftly as possible?
You noted that with a higher-paying job, you could pay an expert coach and "change your own experience fast". If the "suffering of your family unit" is the most pressing matter, why do you propose to be the student of this problem, rather than securing the means to hire a master to solve it?
Tell me, is the primary aim of this undertaking the perfection of your own character, or is it the relief of the "poor health of your family system" , which you say you think about daily?
For if a man's roof is leaking and causing damage to his house and misery to his family, does he first spend months learning the abstract theory of architecture in order to become a better man who can then fix the roof, or does he hire a roofer to fix the leak as swiftly as possible?
You noted that with a higher-paying job, you could pay an expert coach and "change your own experience fast". If the "suffering of your family unit" is the most pressing matter, why do you propose to be the student of this problem, rather than securing the means to hire a master to solve it?
Alex
I believe that at most, I could hire an "expert" (meaning, a therapist) for 1 to 2 hours a week. They could speed up my understanding of the theory, and suggest changes, but I would still need to "do the work" in between the sessions
I don't believe that I have a lot of book learning ahead of me. Perhaps 2-4 more weeks to "grok" the theory properly.
I also think that, in "grokking" it via my own learning, it will be a profound source of knowledge for future endeavours, e.g. living in community, dealing with conflict in organisations, etc.
Essentially, I need to get the propositional and the perspectival knowledge from the theory, and then I also need to change how I show up on a day-to-day basis. There is a hard limit on how much of this an expert can do for me. And if I front-load the learning myself, I may actually learn it more thoroughly, more robustly, rather than outsourcing to an expert.
And this isn't the kind of thing where there's a world in which an expert can come into my family and change it - it does have to be me. This isn't like heart surgery, where an expert could perform the surgery once, and then things are different. This is me needing to be a different kind of node in the system, it's a life-long project.
I don't believe that I have a lot of book learning ahead of me. Perhaps 2-4 more weeks to "grok" the theory properly.
I also think that, in "grokking" it via my own learning, it will be a profound source of knowledge for future endeavours, e.g. living in community, dealing with conflict in organisations, etc.
Essentially, I need to get the propositional and the perspectival knowledge from the theory, and then I also need to change how I show up on a day-to-day basis. There is a hard limit on how much of this an expert can do for me. And if I front-load the learning myself, I may actually learn it more thoroughly, more robustly, rather than outsourcing to an expert.
And this isn't the kind of thing where there's a world in which an expert can come into my family and change it - it does have to be me. This isn't like heart surgery, where an expert could perform the surgery once, and then things are different. This is me needing to be a different kind of node in the system, it's a life-long project.
- Note - actually, 1-2 months feels more likely. 2-4 weeks is very ambitious, given my current pace! I’m doing ~3 poms a day
- Bowen family systems - flashcards
- I have a sense that this should be pretty front-load-y though. I have 250 flashcards on Bowen theory now, a solid foundation. Should get easier now that the foundation is fairly fluent.
2. Using someone else’s theory != “learning to think”
Socrates
So this 'healing' is a skill that must be personally acquired and practised? You are saying it cannot be done _for_ you by an expert, any more than an expert can make you virtuous or brave on your behalf? And you believe that by learning it yourself, the knowledge will be more profound and useful for the rest of your life?
This brings me to another matter I am confused about. You have told me that one of your highest aims is to 'learn how to think' for yourself, so that you might stop being animated by stories that are not your own and instead arrive at your own truths.
Yet for this problem, which you call the 'most salient thing' in your life, your first step is to adopt the theory of another man, a certain Bowen.
Tell me, does a man learn to think for himself by taking on the thoughts of another? Why, for this most important and personal of tasks, do you not apply your own method of 'learning to think', but instead choose to learn the conclusions of someone else?
This brings me to another matter I am confused about. You have told me that one of your highest aims is to 'learn how to think' for yourself, so that you might stop being animated by stories that are not your own and instead arrive at your own truths.
Yet for this problem, which you call the 'most salient thing' in your life, your first step is to adopt the theory of another man, a certain Bowen.
Tell me, does a man learn to think for himself by taking on the thoughts of another? Why, for this most important and personal of tasks, do you not apply your own method of 'learning to think', but instead choose to learn the conclusions of someone else?
Alex
Because I'm not interested in developing my own theory of how families work, and how to heal them. The healing of families is not an intrinsic goal for me, it's instrumental - I want to make good progress, quickly, using the wisdom of others who have thought about it for much longer than I am interested in thinking about it. I think that to try and do it with no outside help (in the form of theories of others) would be akin to stumbling around in the dark, and this is a high-stakes situation, where a lack of skill could make things much worse. I'd much prefer to follow a well-trod path of a well-known and respected theory, when it comes to helping my family. Bowen theory provides propositional and perspectival knowledge that I can quickly learn and apply.
Socrates
I see. So this 'healing' is not an end in itself, but is merely an instrument? A necessary task to be completed, like clearing a blocked road, so that you may proceed to your true destination?
And because it is a high-stakes and instrumental task, you say the goal is to make "good progress, quickly". You wish to follow the most efficient, well-trod path, rather than stumble in the dark.
And because it is a high-stakes and instrumental task, you say the goal is to make "good progress, quickly". You wish to follow the most efficient, well-trod path, rather than stumble in the dark.
3. Building your own boat to cross the sea?
Socrates
Can you help me, then? For if a man's goal is to cross a sea as quickly as possible, does he build a small raft with his own hands over many months, or does he use all his means to purchase passage on the fastest ship?
You yourself have calculated that a higher-paying, full-time job would allow you to hire experts to "change your own experience fast". You acknowledged this path might be "efficient af".
If your goal is truly speed and progress on this instrumental task, why do you choose the path of a part-time job that provides fewer resources and less speed, instead of the path that you yourself have identified as the swiftest?
You yourself have calculated that a higher-paying, full-time job would allow you to hire experts to "change your own experience fast". You acknowledged this path might be "efficient af".
If your goal is truly speed and progress on this instrumental task, why do you choose the path of a part-time job that provides fewer resources and less speed, instead of the path that you yourself have identified as the swiftest?
Alex
Because I don't believe that I need many resources for this task - I don't think resources are the bottleneck.
I feel that, to learn deeply from one book on Bowen theory, and then to change how I show up day-to-day, is the 80/20 here.
I don't have a sense that this is an enormous sea that must be crossed.
Or, perhaps it's fractal, perhaps there are concentric circles. And I'm currently in the "low-hanging fruit" circle, where just to read & grok one book, and change my approach to my family (to go from having no conscious approach, to having one), will represent a profound shift.
Also, I believe that it will be significantly easier in person. I suddenly have a good part-time & remote role, with the understanding that I could just do it for 3 months, so it seems right to do it, follow the path of doing the 80/20 family stuff, and see how it goes.
I feel that, to learn deeply from one book on Bowen theory, and then to change how I show up day-to-day, is the 80/20 here.
I don't have a sense that this is an enormous sea that must be crossed.
Or, perhaps it's fractal, perhaps there are concentric circles. And I'm currently in the "low-hanging fruit" circle, where just to read & grok one book, and change my approach to my family (to go from having no conscious approach, to having one), will represent a profound shift.
Also, I believe that it will be significantly easier in person. I suddenly have a good part-time & remote role, with the understanding that I could just do it for 3 months, so it seems right to do it, follow the path of doing the 80/20 family stuff, and see how it goes.
4. “Low-hanging fruit” vs “the most salient thing”
Socrates
So the problem is not a great sea, but something smaller? You believe you are in an initial phase of "low-hanging fruit", and that for this phase, the resources from a part-time job are sufficient because the main work is simply to be physically present and apply the teachings of one book?
I am trying to understand, so bear with my slow mind. You have described this family situation in your writings not as 'low-hanging fruit', but as the most salient and maddening problem in your life . You wrote that you cannot wholeheartedly engage with other moral questions because your "own house is on fire".
Can you help me resolve this apparent contradiction? Does a man whose house is on fire concern himself only with the 'low-hanging fruit' of dousing the curtains, while the foundations burn? When faced with the most important problem of your life, a problem you have struggled with for over a decade, why is a solution that you describe as an "80/20" enough?
I am trying to understand, so bear with my slow mind. You have described this family situation in your writings not as 'low-hanging fruit', but as the most salient and maddening problem in your life . You wrote that you cannot wholeheartedly engage with other moral questions because your "own house is on fire".
Can you help me resolve this apparent contradiction? Does a man whose house is on fire concern himself only with the 'low-hanging fruit' of dousing the curtains, while the foundations burn? When faced with the most important problem of your life, a problem you have struggled with for over a decade, why is a solution that you describe as an "80/20" enough?
Alex
My intuitive sense was one of things being essentially irreparably bad, seeing no path forwards. "I somehow have to convince my mum to go to therapy, and there's just no way she will", stuff like that. "My sister has borderline personality disorder - I don't see a way to help her, that seems insurmountable and far beyond my skill level".
So, from that place, these "open loops" of "(1) my family are suffering" and (2) "I see no path forwards" has been the sense of the house on fire, the most salient thing. The unresolved tension between these two things
Whereas, Bowen theory says that actually the path forwards is to change _yourself_, and that will be enough. This is a radical reframe, deeply empowering, because I know that I can do this.
So yes, surprisingly, it now feels like the "house being completely ablaze and it's far beyond my ability to put out the fire" to the analogy of Jenny Brown from the book "Growing Yourself Up", which is:
"A house, with a tree near it, and the tree has a root that is growing very close to the foundations of the house, threatening the integrity. You can't change the tree, but you can change the soil (by adding more drainage), and as such, the tree will _choose_ to change course."
This is the promise of Bowen's theory. And of course, I don't know how viable it really is! But so far, it sounds promising, and much more empowering than what I've been operating from for 10 years (a place of overwhelm)
So, from that place, these "open loops" of "(1) my family are suffering" and (2) "I see no path forwards" has been the sense of the house on fire, the most salient thing. The unresolved tension between these two things
Whereas, Bowen theory says that actually the path forwards is to change _yourself_, and that will be enough. This is a radical reframe, deeply empowering, because I know that I can do this.
So yes, surprisingly, it now feels like the "house being completely ablaze and it's far beyond my ability to put out the fire" to the analogy of Jenny Brown from the book "Growing Yourself Up", which is:
"A house, with a tree near it, and the tree has a root that is growing very close to the foundations of the house, threatening the integrity. You can't change the tree, but you can change the soil (by adding more drainage), and as such, the tree will _choose_ to change course."
This is the promise of Bowen's theory. And of course, I don't know how viable it really is! But so far, it sounds promising, and much more empowering than what I've been operating from for 10 years (a place of overwhelm)
5. Grasping at a new theory? Shiny Object Syndrome? Anticipatio Mentis?
Socrates
So the "house on fire" was never the situation itself, but your own despair from seeing no path forward? And this theory from Bowen has extinguished that fire, not by solving the problem, but by giving you a feeling of empowerment and showing you a path where you saw none before?
And this path is like tending to the soil near a tree, hoping the tree will then change its course, a path you say is "promising" but that you "don't know how viable it really is"?
You have told me that one of your most important goals is to "learn how to think". You wish to move away from what you call _Anticipatio Mentis_ — the habit of grabbing onto a story "too quickly" because it feels right, without proper investigation.
Help me to understand, then. How is building your entire plan around a theory you admit you do not know is viable, simply because it feels "promising" and "empowering", an exercise in learning how to think? Are you not, in this very moment, choosing a path based on the pleasant story it tells, the very habit you claim you wish to break?
And this path is like tending to the soil near a tree, hoping the tree will then change its course, a path you say is "promising" but that you "don't know how viable it really is"?
You have told me that one of your most important goals is to "learn how to think". You wish to move away from what you call _Anticipatio Mentis_ — the habit of grabbing onto a story "too quickly" because it feels right, without proper investigation.
Help me to understand, then. How is building your entire plan around a theory you admit you do not know is viable, simply because it feels "promising" and "empowering", an exercise in learning how to think? Are you not, in this very moment, choosing a path based on the pleasant story it tells, the very habit you claim you wish to break?
Alex
It feels to me like I'm currently in the mode of "try it out", which feels more akin to Interpretatio Naturae. I want to approach it like a scientist. I have a hypothesis → that gaining propositional & perspectival knowledge from Bowen theory will a) allow me to show up differently, which will b) ripple through the family system and make things healthier. I don't know yet if it will work, but I have reasons to believe that it is possible, and it seems very worthwhile to see what happens
Socrates
So you are not a believer grasping a new faith, but a scientist testing a hypothesis? You wish to see if applying this theory changes how you act, and if that in turn improves the health of your family system?
A scientist, as I understand it, takes great care to design his experiment to test one thing at a time, does he not? He tries to remove other factors so they do not confuse his results.
You have chosen this part-time job at Outcapped as the setting for this experiment. Yet in your notes, you also state that you are taking this job to solve a different problem: a lack of experience on your CV that is a "bottleneck to getting roles". You see it as a way to "get some career capital" and learn from a founder you admire .
Can you help me understand this experimental design? Are you testing a hypothesis about your family, or are you testing a hypothesis about your career? If this family experiment is so important, why have you chosen to conduct it within the context of a separate, simultaneous experiment on your professional life? How will you know which of your two goals is truly being served?
A scientist, as I understand it, takes great care to design his experiment to test one thing at a time, does he not? He tries to remove other factors so they do not confuse his results.
You have chosen this part-time job at Outcapped as the setting for this experiment. Yet in your notes, you also state that you are taking this job to solve a different problem: a lack of experience on your CV that is a "bottleneck to getting roles". You see it as a way to "get some career capital" and learn from a founder you admire .
Can you help me understand this experimental design? Are you testing a hypothesis about your family, or are you testing a hypothesis about your career? If this family experiment is so important, why have you chosen to conduct it within the context of a separate, simultaneous experiment on your professional life? How will you know which of your two goals is truly being served?
Alex
For 5 months, I've been trying to get a job, in part because my net worth is now low enough to make having income be a concern again
I could get e.g. a part-time job at a pub. However, a part-time role like Outcapped leverages my skills from previous jobs, involves working with someone who has already managed me, and as such, pays a lot better than a "random" job. Also, as it is a continuation of my previous job types, it could lead to some additional upskilling and make it easier to get another job in the future.
So, if I want to earn money, it makes sense to me to find something that pays well, is flexible (part time and remote), and contributes to career capital. Whilst leaving me ~6 pomodoros a day for my own projects & study (e.g. family theory, Socratic project/learning to think)
I could get e.g. a part-time job at a pub. However, a part-time role like Outcapped leverages my skills from previous jobs, involves working with someone who has already managed me, and as such, pays a lot better than a "random" job. Also, as it is a continuation of my previous job types, it could lead to some additional upskilling and make it easier to get another job in the future.
So, if I want to earn money, it makes sense to me to find something that pays well, is flexible (part time and remote), and contributes to career capital. Whilst leaving me ~6 pomodoros a day for my own projects & study (e.g. family theory, Socratic project/learning to think)
7. Job is not “following care”
Socrates
You say now that the chief reason for taking this job is neither to test a theory about your family nor to gain career capital, but something more pressing: you have a need for an income. And among the possible jobs that would provide an income, this one seems the most logical, as it pays well for your skills, is flexible, and still leaves you some time for your personal projects.
This seems a very practical way of thinking. But I must admit, I am now more confused than ever. I have been following your reasoning closely, and the conclusion you seemed to arrive at after much thought was that the ideal path is to "follow care". You wrote that the most important things—the things that truly motivate you and where you can be effective—are the things you genuinely care about, such as healing your relationship with your family and learning how to think for yourself. You even concluded that a lack of intrinsic care was a bottleneck to getting other jobs.
Can you help me understand? Is this choice to work for Outcapped an instance of you "following care"? Or, when faced with a practical need for money, have you set aside this principle of "care" as your guide and chosen to follow "necessity" instead?
This seems a very practical way of thinking. But I must admit, I am now more confused than ever. I have been following your reasoning closely, and the conclusion you seemed to arrive at after much thought was that the ideal path is to "follow care". You wrote that the most important things—the things that truly motivate you and where you can be effective—are the things you genuinely care about, such as healing your relationship with your family and learning how to think for yourself. You even concluded that a lack of intrinsic care was a bottleneck to getting other jobs.
Can you help me understand? Is this choice to work for Outcapped an instance of you "following care"? Or, when faced with a practical need for money, have you set aside this principle of "care" as your guide and chosen to follow "necessity" instead?
Alex
I currently care the most about (1) helping my family (2) continuing to learn how to think. As such, I won't take an in-person full-time job, as I'd have to move away from my family, and have less time for my own projects.
I see Outcapped, as a part-time, remote job, as facilitating daily time spent on what I truly care about, whilst also bringing in money (after a long time with no income).
Perhaps there's a future world where my income is also explicitly tied to deep care. But at the moment, my deep care is (1) helping family and (2) learning how to think, and I don't believe I'll be able to monetise either of these.
It could be that, once my family is healthy, I'll have more capacity to discover my next "deep care". And perhaps that once I've "learned how to think", I'd be able to leverage that to e.g. make a successful business, or become a researcher, etc. I think both of these paths terminal in unlocking of more care, or the next evolution of care. But at the moment, I need to work on them
I see Outcapped, as a part-time, remote job, as facilitating daily time spent on what I truly care about, whilst also bringing in money (after a long time with no income).
Perhaps there's a future world where my income is also explicitly tied to deep care. But at the moment, my deep care is (1) helping family and (2) learning how to think, and I don't believe I'll be able to monetise either of these.
It could be that, once my family is healthy, I'll have more capacity to discover my next "deep care". And perhaps that once I've "learned how to think", I'd be able to leverage that to e.g. make a successful business, or become a researcher, etc. I think both of these paths terminal in unlocking of more care, or the next evolution of care. But at the moment, I need to work on them
8. A bridge into the unknown = folly?
Socrates
So this job is a kind of bridge. It is not something you care about in itself, but you believe it is a practical way to support yourself while you work on the things you _do_ care about—your family and your own thinking. And your hope is that once you have crossed this bridge, you will have the capacity to find a new path that you _do_ care for, perhaps as a researcher or a businessman?
A man who must cross a river, but does not know his ultimate destination on the other side, must still choose what kind of bridge to build.
You have said your future path is unknown. Yet, you are choosing this specific job because it builds on your past experience and provides "career capital" in operations. You even noted that you were pursuing it over other options, like working in a pub, for this very reason.
It seems you are building a very specific kind of bridge, leading in a very specific direction.
By committing to a path that builds capital in a field you have said you do not want to be in, are you truly leaving yourself open to discovering your next 'care'? Or, in trying to solve the practical problem of today, are you unintentionally choosing a future for yourself that you have already admitted you do not want?
A man who must cross a river, but does not know his ultimate destination on the other side, must still choose what kind of bridge to build.
You have said your future path is unknown. Yet, you are choosing this specific job because it builds on your past experience and provides "career capital" in operations. You even noted that you were pursuing it over other options, like working in a pub, for this very reason.
It seems you are building a very specific kind of bridge, leading in a very specific direction.
By committing to a path that builds capital in a field you have said you do not want to be in, are you truly leaving yourself open to discovering your next 'care'? Or, in trying to solve the practical problem of today, are you unintentionally choosing a future for yourself that you have already admitted you do not want?
Alex
It is plausible to me that a future path could be being an entrepreneur, or a chief of staff, or a COO (or a CEO). I'm an enneagram 3, I really do like being useful, getting stuff done, building, etc. So this role is at the very least reasonable congruent with these potential paths. And, as it's a contractor role, and part-time, it will be easy to pivot away from, if I have a realisation re: what I'd rather do. But it feels to me that a "good enough" idea re: work & money feels fine, whilst I focus on family & thinking. I don't know what my "ideal" job/"cause area" is yet, and I think I need to sort out my family (and thinking) first. So, whilst I do that, this job seems like a good option, to bring good money in, live with my family, etc.
I don't see a contradiction here - perhaps I'm missing something.
An analogy: it's like my family situation is like a sickness that is draining me of energy and distracting me. And my lack of "ability to think" and lack of clear values, "Popperian truths", is like having bad eye sight. So, I want to work on reducing my symptoms, and perhaps cure the disease entirely, and also work on making my own glasses to improve my vision. Then, with reduced symptoms and better vision, I may say "aha, I see now, I've taken the wrong path, I should go this way!", and then I can take a new path. I don't care _too_ much what path I'm on right now - it probably is the wrong one (career wise), but the symptoms and lack of vision are more pressing. And I'm still gaining money and experience by following my current path, generalisable skills, etc. This isn't a one-way path.
I don't see a contradiction here - perhaps I'm missing something.
An analogy: it's like my family situation is like a sickness that is draining me of energy and distracting me. And my lack of "ability to think" and lack of clear values, "Popperian truths", is like having bad eye sight. So, I want to work on reducing my symptoms, and perhaps cure the disease entirely, and also work on making my own glasses to improve my vision. Then, with reduced symptoms and better vision, I may say "aha, I see now, I've taken the wrong path, I should go this way!", and then I can take a new path. I don't care _too_ much what path I'm on right now - it probably is the wrong one (career wise), but the symptoms and lack of vision are more pressing. And I'm still gaining money and experience by following my current path, generalisable skills, etc. This isn't a one-way path.
9. 8 poms a day on the “not most important thing”
Socrates
You have convinced me that I was mistaken. I see now that you are not running two experiments at once, nor are you building a bridge to an unknown land.
Let me see if I can repeat your argument back to you, so you can correct me where I am wrong. You are like a man who is afflicted with a draining sickness and whose vision is poor. Naturally, your first priority is not which road you walk, but rather to cure your sickness and to craft a new pair of glasses to see the world clearly.
To cure your sickness, you will use the medicine prescribed by a man named Bowen. To craft your glasses, you will study the works of thinkers like Plato and Popper. And while you undertake this vital work, this job at Outcapped will serve as a tolerable path to walk upon, providing you with the money and experience needed to sustain you.
I think I finally understand your reasoning. But a final question arises, and I confess it leaves me utterly perplexed.
In your own notes, you calculated that this job will demand eight units of your energy each day, out of a total of twelve that you typically have . You even expressed a clear worry that you would use up your best energy on the job, leaving you "depleted" and liable to neglect your own crucial projects.
Help me, for my own vision is dim. If a man's true priorities are to cure his grave illness and restore his sight, why does he commit to a plan where he spends two-thirds of his energy and the best part of his day on a secondary task he admits is not the right path for him? By choosing this plan, do your actions not reveal that you have in fact prioritised the 'good enough' job over the cure for your own sickness and the restoration of your own sight?
Let me see if I can repeat your argument back to you, so you can correct me where I am wrong. You are like a man who is afflicted with a draining sickness and whose vision is poor. Naturally, your first priority is not which road you walk, but rather to cure your sickness and to craft a new pair of glasses to see the world clearly.
To cure your sickness, you will use the medicine prescribed by a man named Bowen. To craft your glasses, you will study the works of thinkers like Plato and Popper. And while you undertake this vital work, this job at Outcapped will serve as a tolerable path to walk upon, providing you with the money and experience needed to sustain you.
I think I finally understand your reasoning. But a final question arises, and I confess it leaves me utterly perplexed.
In your own notes, you calculated that this job will demand eight units of your energy each day, out of a total of twelve that you typically have . You even expressed a clear worry that you would use up your best energy on the job, leaving you "depleted" and liable to neglect your own crucial projects.
Help me, for my own vision is dim. If a man's true priorities are to cure his grave illness and restore his sight, why does he commit to a plan where he spends two-thirds of his energy and the best part of his day on a secondary task he admits is not the right path for him? By choosing this plan, do your actions not reveal that you have in fact prioritised the 'good enough' job over the cure for your own sickness and the restoration of your own sight?
Alex
Yes, I think you've definitely landed on the most "shakey" part of my plan here.
I think partially, I'm succumbing to the enneagram 3 thing of prioritising work. I'm trying hard not to - 8 poms of work per day is ambitiously low for me - but it's still relatively high.
If all I wanted was to bring a bit of money in, in order to pay the bills and slowly deplete my savings, I could try to find something like e.g. a pub where I worked 2 days a week, leaving me 5 full days to work on other things.
I probably wouldn't earn very much, but it'd be enough to stop being "in the black"
However, I would also like to earn a good amount. This job is much better pay than a part-time in-person job, plus I can do it from my computer (no commute), plus it's fallen across my lap (no job hunting and interviewing needed).
Plus, I've never worked at a pub before, etc.
Perhaps I could do the minimum of 15 hours a week, which would be ~50% of my time.
What I think this ultimately comes down to is → I don't see a path to <15 hours/week. This is the floor that Rob has named, because to do <15 hours/week prevents you getting enough momentum.
One alternative arrangement could be only working 3 or 4 days, to give more time for full-time focus on thinking & family.
I think partially, I'm succumbing to the enneagram 3 thing of prioritising work. I'm trying hard not to - 8 poms of work per day is ambitiously low for me - but it's still relatively high.
If all I wanted was to bring a bit of money in, in order to pay the bills and slowly deplete my savings, I could try to find something like e.g. a pub where I worked 2 days a week, leaving me 5 full days to work on other things.
I probably wouldn't earn very much, but it'd be enough to stop being "in the black"
However, I would also like to earn a good amount. This job is much better pay than a part-time in-person job, plus I can do it from my computer (no commute), plus it's fallen across my lap (no job hunting and interviewing needed).
Plus, I've never worked at a pub before, etc.
Perhaps I could do the minimum of 15 hours a week, which would be ~50% of my time.
What I think this ultimately comes down to is → I don't see a path to <15 hours/week. This is the floor that Rob has named, because to do <15 hours/week prevents you getting enough momentum.
One alternative arrangement could be only working 3 or 4 days, to give more time for full-time focus on thinking & family.
10. Summary 1
Based on our exchange, the core of your dilemma appears to be a direct conflict between your stated highest priorities and the practical allocation of your time and energy. You’ve identified this as the “most ‘shakey’ part” of your plan.
Here is a summary of the two paths that have emerged from your reflections:
Path 1: The Pragmatic Compromise (The Outcapped Role)
This path involves accepting the part-time, remote role at Outcapped.
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The Arguments For It:
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Financial Necessity: It meets your immediate need for an income after a long period of job hunting and diminishing savings.
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High Efficiency: The role “pays a lot better” than alternatives, requires no commute, and has been offered to you, avoiding a difficult job search.
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Career Congruence: The work is “reasonably congruent” with potential future career paths like being a COO or entrepreneur and builds on your existing skills.
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Flexibility: As a part-time contract role, it seems easy to pivot away from if your priorities change.
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The Core Argument Against It (The Contradiction):
- This “good enough” job demands a minimum of 15 hours per week, which you calculate as roughly 50-66% of your productive time . This directly competes with your stated highest priorities—curing the “sickness” of your family situation and crafting the “glasses” of learning how to think—leaving only the “dregs” of your time and energy for what you claim is most important.
Path 2: The Maximally Aligned Path (e.g., A Pub Job)
This path involves finding a different, less demanding job to solve the money problem while maximizing time for your personal work.
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The Arguments For It:
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Prioritises “Care”: Working only two days a week, for instance, would leave you five full days to dedicate to your family and your Socratic project, aligning your time allocation with your stated priorities.
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Solves the Immediate Problem: It would be enough to stop depleting your savings.
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The Core Arguments Against It:
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Lower Pay & Efficiency: It would pay significantly less and likely involve a commute.
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Does Not Build Career Capital: The work would likely be unrelated to your skills or potential long-term career interests.
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Requires Effort: You would need to actively search for such a job, which you’ve been doing for five months.
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Your final reflections suggest a potential “third way”: modifying the Outcapped role to work a compressed 3 or 4-day week. This appears to be an attempt to gain the benefits of Path 1 while mitigating its primary drawback.
The question you now face seems to be which compromise is more aligned with your true, current goals: Is it better to compromise on your time and energy to secure a convenient, well-paying, and career-relevant job? Or is it better to compromise on pay and career progression to secure the maximum possible time and energy for your most urgent personal projects?
11. Summary 2
Alex
I think there's a misrepresentation here - I think to work ~15 hours/week for Outcapped would not leave "only the dregs" left for my work on other things.
For example, I could frontload family systems study in the morning, doing a big chunk of study, and then come to Outcapped after noon. And it may be that there's not much more front-loaded study of family systems theory to do - perhaps 1-2 more months to deeply grok the theory.
So I could always have this "big chunk at start of day, then do paid work from noon/1/2"
This feels like the ideal compromise to me. Good money, good focus time for top priorities. Money can be used to hire help if needed (vs a pub job where I'd probably only make enough to pay rent). Career capital & generalist skills
For example, I could frontload family systems study in the morning, doing a big chunk of study, and then come to Outcapped after noon. And it may be that there's not much more front-loaded study of family systems theory to do - perhaps 1-2 more months to deeply grok the theory.
So I could always have this "big chunk at start of day, then do paid work from noon/1/2"
This feels like the ideal compromise to me. Good money, good focus time for top priorities. Money can be used to hire help if needed (vs a pub job where I'd probably only make enough to pay rent). Career capital & generalist skills
Thank you for the clarification. It seems the core of your refined plan rests on a specific daily structure designed to resolve the conflict between paid work and your personal projects.
Based on your latest statements, here is a summary of what appears to be your proposed “ideal compromise”:
The Plan: A Structured Approach to Balancing Priorities
This plan involves accepting the part-time (minimum 15 hours/week) remote role at Outcapped, structured in a particular way to protect your primary goals.
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The Daily Structure:
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Mornings for Primary “Cares”: You would dedicate the first part of your day, when you feel most fresh, to a significant block of study on your priority projects, such as family systems theory and learning how to think.
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Afternoons for Paid Work: You would begin your work for Outcapped around noon or later, fulfilling your required hours during a time when you may feel “slightly depleted” but can be boosted by the work’s tight feedback loops.
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The Rationale for This Structure:
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This approach directly counters the risk of your personal projects receiving only “the dregs” of your energy.
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The intensive study period for family systems may be temporary, lasting only one to two more months to “deeply grok the theory,” making this structured approach particularly effective in the short-to-medium term.
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The Overall Benefits of This Path:
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Financial Security: It provides “good money,” which is a pressing concern after five months without an income. This income is substantially better than alternatives and could be used to hire expert help if needed.
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Career Capital: The role builds on your past experience and provides generalisable skills that are congruent with potential future paths like being an entrepreneur or COO.
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Convenience: The opportunity is readily available, requiring no further job hunting, and involves working with a manager you already know.
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This refined plan appears to hinge on the hypothesis that you can successfully protect your most important work by scheduling it during your peak energy hours, thereby allowing you to secure the financial and career benefits of the Outcapped role without sacrificing your more pressing personal goals.
12. Balancing enneagram 3 tendency
Alex
Exactly. So, returning to your Socratic persona → what do you think? It feels to me like we've landed on a pretty decent plan, and you haven't been able to refute anything. I feel like this is a good path
Socrates
You say that your plan seems good, and that I have been unable to refute it. But you must remember that I know nothing of such things. I do not know what makes a path good or bad; I can only ask questions based on what you yourself have told me.
Let us accept your plan as you have laid it out. In the morning, when your energy is highest, you will do the difficult, personal work on your family and on learning how to think. In the afternoon, you will turn to your paid work for Outcapped, which you find engaging.
You have also told me a great deal about your own nature. You have said you are an Enneagram 3, a man who tends to get "hypnotised" by projects and "happily merg[es] with any project that comes before you". This, you said, has been a "perennial struggle" for you. The work for Outcapped offers "concrete results" and "tight feedback loop[s]", which your other projects lack.
Here, then, is my final question, for I am truly at a loss.
How can a man who knows he has a lifelong tendency to be consumed by such work believe he can safely place it at the centre of his daily life, separated from his true priorities by nothing more than the striking of the noon hour? By creating a structure that pits your most important but most difficult work directly against work you know you are psychologically vulnerable to merging with, have you designed a plan for balance, or have you simply built a more elegant trap for yourself?
Let us accept your plan as you have laid it out. In the morning, when your energy is highest, you will do the difficult, personal work on your family and on learning how to think. In the afternoon, you will turn to your paid work for Outcapped, which you find engaging.
You have also told me a great deal about your own nature. You have said you are an Enneagram 3, a man who tends to get "hypnotised" by projects and "happily merg[es] with any project that comes before you". This, you said, has been a "perennial struggle" for you. The work for Outcapped offers "concrete results" and "tight feedback loop[s]", which your other projects lack.
Here, then, is my final question, for I am truly at a loss.
How can a man who knows he has a lifelong tendency to be consumed by such work believe he can safely place it at the centre of his daily life, separated from his true priorities by nothing more than the striking of the noon hour? By creating a structure that pits your most important but most difficult work directly against work you know you are psychologically vulnerable to merging with, have you designed a plan for balance, or have you simply built a more elegant trap for yourself?
Alex
I think, even if I were to e.g. "succumb" to doing Outcapped work in the morning (as seems likely, given my enneagram 3 nature), I will still always find time to work on family stuff, and learning to think stuff.
These things matter a lot to me, I'm enjoying them, I have a strong sense of profundity and purpose with them. It would be acting against my own interests to e.g. totally drop them to work more.
Also, there is a ceiling on the workable hours for Outcapped, as least at first. I could agree this with Robert too, stating that I want a hard limit of say 20 hours/week
This way I bring in good money, can replenish my savings, perhaps pay a therapist, perhaps pay for training (e.g. Aletheia)
These things matter a lot to me, I'm enjoying them, I have a strong sense of profundity and purpose with them. It would be acting against my own interests to e.g. totally drop them to work more.
Also, there is a ceiling on the workable hours for Outcapped, as least at first. I could agree this with Robert too, stating that I want a hard limit of say 20 hours/week
This way I bring in good money, can replenish my savings, perhaps pay a therapist, perhaps pay for training (e.g. Aletheia)
End
It appears you have arrived at a final resolution that acknowledges the potential risks while providing concrete strategies to mitigate them.
Here is a concluding summary of your refined plan:
You are proceeding with the part-time role at Outcapped, viewing it as the most practical way to meet your financial needs while creating the conditions to work on your primary goals.
You acknowledge the significant risk, stemming from your Enneagram 3 nature, that this engaging work could expand beyond its allotted time and sideline your personal projects.
To counter this, you are relying on two primary safeguards:
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Intrinsic Motivation: You believe your personal work on your family and on learning how to think provides a “strong sense of profundity and purpose”. You feel it would be against your own interests to neglect this work, creating a natural check on the tendency to overwork.
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Structural Boundaries: You intend to proactively negotiate a “hard limit of say 20 hours/week” with your manager, Robert, creating an external boundary to prevent the work from consuming your time.
By implementing this structure, you anticipate achieving the following outcomes:
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Financial Stability: You will earn good money to replenish your savings after a long period with no income.
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Optionality: The income will create the option to pay for additional expert help, such as a therapist or training from organisations like Aletheia, if you deem it necessary.
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Career Progression: You will continue to build career capital in a field that is congruent with potential future paths.
Your final position is that this structured compromise is a “good enough” path for the present, allowing you to address your most pressing personal and financial needs simultaneously.
Updates
1. Crux → money vs time
- “Why not just make like £600/month and have far more time? Why spend 15-20 hours/week, which is >50% working hours”
- Hard to find something that would let me do that! E.g. pub, there aren’t that many, I have no experience, etc
- This is very convenient - from home
- Good pay = can do things like aletheia, or save like £2k/month and rapidly rebuild my savings for future era
2. New metaphor/analogy alert!
- A man on a path, with an illness that his sapping him of energy, and poor eyesight
- (Energy sapping illness = family situation)
- (Poor eyesight = lack of elucidated values, Popperian truths, poor thinking skills)
- Step 1 → fix the symptoms of the illness
- (That is, improve family situation)
- In parallel, make glasses
- (That is, learn how to think, inspect own thinking, find Popperian truths)
- Step 2 → now symptoms are reduced, and glasses are made, can look around and realise “aha, I’m on the wrong path”
- “I now have more energy to devote to my new journey”
- “I can now see the best path to take”
- But, in the meantime, even if I’m on the ~wrong path, I’m getting feedback from the environment (being useful, getting paid, getting skills, getting career capital)
- I’d rather walk along the wrong path for a while longer, whilst getting paid, and reducing my symptoms & improving my vision
3. Following Bowen theory
- I feel fine about using someone else’s theory because I’m not trying to make my own theory. I’m trying to help my family as an instrumental goal
4. “House on fire” was re: the feeling of overwhelm, not the actual situation
- Already feels much more manageable with the propositional & perspectival knowledge I’m gaining from Bowen theory
- From 10 years of overwhelm to “oh shit, this seems pretty doable now I’ve foregrounded it and made it a focus”
4. 1-2 more months learning Bowen theory?
- Make a Fatebook!
- How long will it take for me to read & make flashcards from the first 200 pages of “Bowen Theory’s Secrets” by Michael Kerr?
- I could definitely sprint on it, pause Socrates/Plato (i.e., reading Gonzalez’s book (Dialectic and Dialogue - Plato’s Practice of Philosophical Inquiry (Gonzalez)))
- End of August feels very doable 👇 → if I treat this as my primary project, pausing Gonzalez, treating it like I did Frans Osinga’s book on Boyd. I’m currently at ~page 60
5. Lock in anti-enneagram 3 habits
- Ceiling of 20 hours/week
- Never start before noon