If I were to come up with a Clever Title for some of this, I might call it The Trap of the Local Maxima. 

I did childcare and disability care in college, because it was a better option than being a cashier or something. Then I graduated and it was a recession, but I could use my childcare experience to get nanny jobs. And so on, and so on. 

Now I have about 15 years of childcare experience. It is REALLY EASY for me to get GOOD PAYING nanny jobs. I can literally go on to a website, send out 5-10 applications to what I think are the best jobs there, and be working within a week. 

Every now and then I try to do something else, but it is harder to find other types of jobs given my resume, and when I do the job is usually harder than nannying, and pays less. (I was recently an Office Manager, which had expectations I couldn't live up to, and paid less than nannying. Now I do some Virtual Assistant work that is mostly writing / social media which is nice and easy, and a similar amount of pay per hour, but not as many hours per day)

I don't even LIKE being a nanny. I never CHOSE it as a career. I don't PARTICULARLY like children (not in the way most people who choose childcare do). Kids are easy, but my people-skills are mediocre when dealing with e.g. parents or other nannies. 

I tell myself someday I will semi-retire and be a dog walker.

I have some areas of artistic expertise where everyone around me is kind of like a level 10 and I'm a level 80. When I try skills near to it, I'm immediately a level 25, and so I actually feel pretty good exploring them. Note that these are not the core skills that my reputation and social status rest on.

I can think of many examples where I think this sort of dynamic happened in the world. I feel some impulse to not name them all because it's psychologizing others a bit. But I'll say one that I thought of lately was wondering why Nate Silver didn't do any forecasting around the pandemic, and this sort of answer was what I settled on.

You say you resolved to live life like a failure, which I like. I have something like this, but those words don't quite resonate with me. Paul Graham says to try to feel like a noob often, and he has the great line "the more of a noob you are locally, the less of a noob you are globally", which I also like.

This reminds me of Seneca.

Your modern parables give a better frame for some of his advises:

"Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I feared?”"

All of this would have made a teenager hate the idea of success altogether. I was not a teenager anymore, so I formulated a slightly more sophisticated answer: Regardless of how successful I become, I resolve to live like a failure.

I strong upvoted for this line

One of my role models is Bob Dylan. As I grew up, I learned the lyrics to all his songs and watched him never stand still. If you look at the artists, if they get really good, it always occurs to them at some point that they can do this one thing for the rest of their lives, and they can be really successful to the outside world but not really be successful to themselves. That's the moment that an artist really decides who he or she is. If they keep on risking failure, they're still artists. Dylan and Picasso were always risking failure.

-Steve Jobs, 1998

There's a lot of attention paid these days to accommodating the personal needs of students. For example, a student with PTSD may need at least one light on in the classroom at all times. Schools are starting to create mechanisms by which a student with this need can have it met more easily.

Our ability to do this depends on a lot of prior work. The mental health community had to establish PTSD as a diagnosis; the school had to create a bureaucratic mechanism to normalize accommodations of this kind; and the student had to spend a significant amount of time figuring out what accommodations alleviated their PTSD symptoms and how to get them addressed through the school's bureaucracy.

This points in a direction of something like "transitions research," an attempt to identify and economically address the specific barriers that skew individuals toward immediate modest-productivity strategies and away from long-term high-productivity strategies.

Imagine if there was a well-known "diagnosis" of "status-loss anxiety," in which a person who's achieved some professional success notices themselves avoiding situations that would be likely to enhance their growth, yet come with a threat of loss of status. It's like the depressed person who resists mental health unseling because it implies there's something wrong with them. Being able to identify that precise reaction, label it, raise awareness of it, and find means and messages to address it would be helpful to overcome a barrier to mental health treatment.

In economics jargon, what's going on here is not so much the sunk cost fallacy as a combination of aging, opportunity cost and diminishing returns. Learning takes time, aging us, and this means we have less time to profit off a new long-term investment in skill-building. Increased skill raises the opportunity cost of learning new skills. Diminishing returns means that, if we learn a skill that increases our profit from A + B to A + 2B, that this is less intrinsically valuable to us than when we increased our profit from A to A + B. All these forces together, along with status considerations, coordination issues, and misaligned incentives, conspire to work against learning and investment.

I don't know if "loss of freedom" is quite the most apt frame, though it's not inappropriate. I think the central point is that success and pressure go hand in hand. The more successful you are, the more others want to make use of your skillset, and the greater the stakes are for doing your job right. You become more aware of the problems you could solve, if you only had more time and energy, if you had fewer other obligations or one more skill. And you may become anxious about placing yourself in situations where you look incompetent, lest others make the assumption that your lack of skill in the new area somehow reflects a lack of competence in your previous area of expertise - a perversion of the idea of Gell-Mann amnesia.

As overwhelming as these problems can be, I like the idea that a simple personal practice of beginner's mind can take us a long way towards overcoming these barriers. Just because the problem is big and complex doesn't mean that the solution can't be small and simple.

Relevant quote from Paul Graham's recent essay What I Worked On:

One day in 2010, when he was visiting California for interviews, Robert Morris did something astonishing: he offered me unsolicited advice. I can only remember him doing that once before. One day at Viaweb, when I was bent over double from a kidney stone, he suggested that it would be a good idea for him to take me to the hospital. That was what it took for Rtm to offer unsolicited advice. So I remember his exact words very clearly. "You know," he said, "you should make sure Y Combinator isn't the last cool thing you do."

At the time I didn't understand what he meant, but gradually it dawned on me that he was saying I should quit. This seemed strange advice, because YC was doing great. But if there was one thing rarer than Rtm offering advice, it was Rtm being wrong. So this set me thinking. It was true that on my current trajectory, YC would be the last thing I did, because it was only taking up more of my attention. It had already eaten Arc, and was in the process of eating essays too. Either YC was my life's work or I'd have to leave eventually. And it wasn't, so I would.

I am not sure if this would solve the issue for you, but I try to make passive income towards not being dependent on work, so that I have the freedom to do what I want. But I am really not sure this would solve it because I think you pointed out that even wealth can be a limitation. It depends how much time you spend to maintain in it and how successful you are with it

The contrast between this post and lsusr's rejoinder reminds me of the Objectivist idea that success within the system always corrupts (to put it in LW terminology, you can't feed Moloch without feeding Moloch), and of Moral Mazes:

Its thesis is that this is the result of a vicious cycle arising from competitive pressures among those competing for their own organizational advancement. Over time, those who focus more on and more value such competitions win them, gain power and further spread their values, unless they are actively and continuously opposed.

Once things get bad in an organization they tend to only get worse, but things in general get better because such organizations then decay and are replaced by new ones. Unfortunately, our society now slows or prevents that process, with these same organizations and their values increasingly running the show. 

Investment and flexibility become impossible. Even appearing to care about anything except the competition itself costs you your allies. Thus things inevitably decay and then collapse, flexibility returns, cycle repeats.

Involvement with such patterns is far more destructive to humans than is commonly known.

This reminds me of the book "Four Thousand Weeks". The core idea is that if you become productive at doing something, then society will want you to do more of that thing. For example, if you were good at responding to email, always prompt, and never missing an email, society would send you more emails because you had built a reputation of being good at responding to email.

Curated. This is an idea I've thought about a little before, but this post says everything so cleanly and clearly, and helped me think about it in ways I had not before. The idea carries with me stronger for reading this post.

And the writing is great. I normally emphasize readability in curation notices, but here I feel like I also want to call it 'poetic'. Whatever.

(And yep, I see the irony in curating it, but the irony does not seem to me worth it to avoid. If Alkjash disagrees I will obey his preferences of course.)

Brian Josephson is an interesting example, his discovery of the Josephson effect at the age of 22 won him a Nobel physics prize. At about the same time that the physics prizes started to pour in for his discovery he switched hard into studying telekinesis, meditation and psychic powers (https://en.wikipedia.org/wiki/Brian_Josephson)

Now, specifically in his case it is tempting to reason as follows: If he spent the rest of his career working in physics he would always be primarily known for that thing he did right at the beginning. If he wanted his new work to match the success of the old he had to go for the high-risk high-reward stuff. Telekinesis probably doesn't exist, but if it does... This is my interpretation of his strange change in direction. Other people might instead suppose that the early success gave him the space to work on more-or-less whatever he wanted at a university, and what he wanted was the new age stuff.

This resonated a lot with me! (And I'm far from as successful as I would 'like' to be - or would I??? :angst:)

Speculative and fuzzy comparison-drawing

I was reminded, I'm not sure exactly why, of this interesting entry I recently came across (I recall I was led there by a link buried in a comment in Slate Star Codex somewhere...) https://plato.stanford.edu/entries/capability-approach/

While I wouldn't necessarily endorse all of it, it's an interesting read. As I understand it, the capability approach advocates a certain way of drawing lines in practical policy-making. Its emphases are on

• ‘functionings’ ('beings' and 'doings')

  various states of human beings and activities that a person can undertake

  example beings: ...being well-nourished, being undernourished, being housed in a pleasantly warm but not excessively hot house, being educated, being illiterate, being part of a supportive social network, being part of a criminal network, and being depressed

  example doings: ...travelling, caring for a child, voting in an election, taking part in a debate, taking drugs, killing animals, eating animals, consuming lots of fuel in order to heat one's house, and donating money to charity

• 'capabilities'

  a person's real freedoms or opportunities to achieve functionings

Here's a passage which we can hold alongside the premise of the original post

The ends of well-being freedom, justice, and development should be conceptualized in terms of people's capabilities. Moreover, what is relevant is not only which opportunities are open to me each by themselves, hence in a piecemeal way, but rather which combinations or sets of potential functionings are open to me.

For example, suppose I am a low-skilled poor single parent who lives in a society without decent social provisions. Take the following functionings: (1) to hold a job...to properly feed myself and my family; (2) to care for my children at home and give them all the attention, care and supervision they need. ... (1) and (2) are opportunities open to me, but they are not both together open to me... forced to make some hard, perhaps even tragic choices between two functionings which both reflect basic needs and basic moral duties?

[emphases in source]

Although that summary of the approach and the excerpt I've copied don't articulate this 'success as enemy of freedom' idea, I wonder if it would be helpful to consider the idea with the lens of the capability approach? There's a certain paradoxical symmetry of the examples, which I think is what the OP is drawing attention to. The challenge would be to draw out whether the mechanism is societal or part of human nature or some combination thereof or (...) and what measures we might take (individually or collectively) to mitigate it!

I relate very much to your old roommate who commented on your studying Go and attributing it to your intelligence. While I have always imagined myself living in a small wooden cottage with plenty of time to pursue my interests, I find it very difficult to evaluate a freedom/success trade-off while still in university. Even though I could make the case that I will most likely live more-than-comfortably as a data-scientist no matter how well I perform at the next examination, I still can't shake the feeling that I should be pushing myself to the limit. I feel as if the "fog-of-war" for determining future freedom is too thick, but I realize that I haven't actually tried to make a plan.

So here's the first outline of a "wooden cottage" plan:

1. Graduate with a masters degree to ensure employability
2. Acquire units of purchasing power in local currency
3. Pay off debts, build a heap of gold coins under a mountain
4. Scare off dwarves and a hobbit
5. ??? 

I'll figure the rest out later, but thank you for planting the seed in my mind.

I don't really agree with the concepts used here, nor with the conclusion.

The basic idea behind this article is that an increase in responsibility & standards in one field limits one to that field, this is simply untrue, or at least often not true.

For example, an academic might indeed get piegenholed into studying the niche they got good at, but that is only true until tenure.

A financial advisor might indeed be stuck doing boring backhanded deals and attending highhigh-class class NY bars to get access to the best dark polls, but that's only until they have enough money to quit working.

***

In part, the problems you outline are ones regarding how people put less value on freedom as they progress through life. But this is only natural and happens regardless of success levels.

However, given a change in value is possible, transitioning from a field to another should be easier, not harder, with success.

***

So the conclusion of putting on baby wheels when learning something new is not one I'd agree with. Indeed, I'd rather push myself much harder than I would push young me, since my previous experience and knowledge is likely to give me a better starting point for many endevours, at least for most of those I could potentially find interesting.

Even if it wouldn't, the "don't push yourself too hard" is simply a counter-biasing tool, useful only for saying "Hey, remember that X thing you are really good at, well, Y is completely unrelated to that, so expect to be mediocre at Y and take it slow".

I have changed occupations thrice - from a PhD student (dropped out) to lab technician (in a different lab, for children), from LT to bookshop cashier/..., from BC to the-one-who-proofreads-articles-and-stuff in a lesser research journal. I kind of expect to switch at least once more, to a librarian or postman.

All of it revolves around the need to be home for the kid, and around hating some aspects of the job. (The lack of science; the late hours; the cold; and currently, the need to be reputation-wise.) And there was freedom in every thing I've done, although not exactly freedom to do what I wanted to do. Just - freedom to see the world. I think it should not be underestimated.

Valleys of bad rationality and Reason as memetic immune disorder come to mind after reading this. I think framing it these ways is useful.

Pursuing success is... well... good, we can say. But there are some serious dangers along that road. It makes me think that mental health maintenance/self-care should be an important component of the art of rationality.