The eternal conflict between exploration and exploitation. Keeping your options is what keeps the good options within your reach, and prevents you from going too far in the blind alleys. But at the end, if you have walked through the whole shop and didn't buy anything, you leave empty-handed. At some point you gotta have a job (or other source of income) and people are going to pay you for something specific.

I think this is even more complicated when people are not explicitly aware of the skills they really have. They may feel like they don't specialize in anything, when in fact they do. For example I have a friend working in IT whose programming skills are not very impressive: he can do simple things in many systems, but is not very good at math, cannot write complicated algorithms, and is not really nerdy enough to spend evenings obsessing over some technical details. Yet somehow his career was at least as successful as mine. Because what he lacked in programming skills, he compensated by great communication and leadership skills. But he didn't realize this was his real strong point; he identified with being a programmer, because that's what most of his friends were. It took him a few years to fully realize that he is more fit for a role of a manager or consultant in an IT company, and that instead of trying to learn yet another programming language (he somehow believed that his lack of mathematical skills could be fixed by finding the "right" programming language; which is a delusion many bad programmers and IT managers seem to share), he should rather find a position where he gets paid explicitly for doing what he is good at. This more or less doubled his salary, and he is no longer worried about not sufficiently understanding some abstract things his nerdy friends debate about. -- So he actually was a specialist all the time, but in a skill he didn't think about as essential for his job.

Are most people entrepreneurs here or what?

I think entrepreneurs are a minority here, but still a larger fraction that in the general population. Also other types of people need motivation and efficiency while working relatively alone, for example PhD students.

I don't need better time management because I don't have enough tasks to fill out my workday and if I could I wouldn't as it would not result in a raise or promotion as they are generally not visible ones.

Do you have any goals outside of your work where being more productive could help you reach them better? My promotion options are also rather limited (and as far as they exist, this website seems more relevant than LW). But I also have other goals, where productivity helps. I am doing the productivity stuff for myself, not for my boss.

The planning fallacy happens to people who plan aggressively, but why the hell would people want to do that ... I just make a comfortable guess and multiply it by three to six

I most frequently think about planning fallacy when correcting the estimates of my colleagues at work. For example, last week: We had to do 3 critical things, each of them requiring the same resources for at least 1 day. So my colleague immediately sends an e-mail to the customer promising that it will be done in 3 days. Which in reality means 2.5 days, because then we have to travel to the customer, fill the paperwork, install the stuff, and hope that nothing goes wrong. And it assumes there will be no non-trivial bugs in a project that wasn't maintained for a month, doesn't have a proper documentation, and two programers who worked on it, including the previous team leader, have left the company during that month. And my colleague just doesn't care: she sends the promise to the customer, puts my e-mail in the copy, and the problem is "solved". She doesn't even tell me; if I would miss the e-mail, she would only tell me on the third day. So me and a few helpful coworkers voluntarily stayed at work for 12 hours a day, fix a few horrible bugs, completed the stuff in 3.5 days (that included waiting half day until a broken server was fixed), delivered the result to the customer... and the next day I am invited to the CEO where my colleague blames me for failing the customer and for "making her look stupid". (And the only thing that saved my ass was completely unrelated to my skills or work, it was a random office-politics advice from internet that I decided to test experimentally at work a few days ago, and luckily it worked.) -- Uhm, okay, this is not really about planning fallacy, but about a completely fucked up system. But planning fallacy apears here all the time. Pretty much all deadlines we have ever made were unrealistic, and all of them were done like this: "don't think about details, just make a very simplified model, imagine the best-case scenario for that model, and write it down as the official estimate".

I feel like somehow the methods are optimized for a very competitive, confident, driven, accomplishment-oriented approach. Probably it requires that you feel that you get rewarded for things you do. This was always missing for me, in my life experience in what you and what you get is really loosely related.

Heh, my work experience also suggests that what I do and what I get is loosely related, and I think this years-long experience also has contributed to my laziness. (It is hard to get motivated when your uncosciousness insists that what you do it completely unrelated to the outcome, and it is hard to make yourself think otherwise when you have a ton of experimental evidence supporting that.) But I think the life outside of the work doesn't have to be like this. If I decide to make a computer game in my free time, it is up to me. I do have a computer and a development environment, I know programming, I do have a few hours of free time every week... and it is my choice how to use them.