I have experienced a lot of the lack of progress indicator angst you mention. I'm nowhere near rich and it isn't that important of a goal to me in itself, but since leaving college at 19 (I'm nearly 26 now), I haven't had a 9-5 job. I played online poker professionally for 4-5 years and I've been a developer for the last 2. My development work has either been a set my own hours/work from home arrangement or contract work. I'd say the struggle to live with some kind of structure while also maintaining the high level of freedom and flexibility that I can't stand to be without has been the defining challenge of my life so far.
I'm very glad that I've been able to get out of the box and do my own thing, but it's also made life a lot more difficult in many ways. It's been harder to develop consistent social circles since these tend to center around college and work. Even though I'm pretty good at making friends, at least for a fairly introverted person, I rarely feel like I really fit with whatever groups I fall in with--I tend to go back and forth between feeling insecure and being bored and annoyed by others' seeming conformity and lack of imagination. A bit of social anxiety is involved as well.
I've also never been able to maintain a consistent circadian rhythm. At this point I've just given up on worrying about it and regularly stay up for 30+ hour stretches when I'm not tired or have a lot to do. I've found it easier to just go with it than trying to force myself into the 'normal' way. This also contributes to feeling weird or different from others though--just feels like I'm on another wavelength a lot of the time.
Not sure why I decided to share this exactly. I can definitely imagine having a lot of the same issues as a billionaire. I suppose that's why it doesn't seem a particularly worthwhile goal to pursue. I'd rather focus on finding a good creative writing group or learning to meditate or finding a place/way to live that helps me find more balance and belonging. Things that would have a tangible impact on my day to day being. Making a lot of money seems beyond a point to get in the way if anything.
I don't know if there's anything in particular to blame, but our society is quite exclusionary in many ways toward folks who go off the beaten path, even if they are otherwise kind and productive people with plenty to offer. Generally reasonable people can be very judgmental about things like not having a college degree or a normal job or typical sleep patterns. I've learned to take it in stride for the most part, but it leaves sort of a bad taste in my mouth. I suppose wealthy people may have to face some irrational prejudice from others as well.
I think the best way around this is to join a team sport. You can quickly get a social circle without a lot of time commitments. At the same time you get to feel what success is like when there is a real risk of failure. If you can find something with a reasonable exercise component you can also relapse a lot of boring workouts with something far more fun.
However, as much as people might dislike them the most accessible team sport is Raiding in an MMO. People get addicted because they fill some basic human needs that the average modern life does not.
Well, it sounds like you know the problem (you haven't found a community you like yet) and have ideas about how to solve it (finding a good creative writing group; I would also try science fiction conventions, hacker dojos, a Unitarian church and your local Less Wrong meetup). I can't think of much else to say - if you know where your problems are coming from, you know how to solve them better than I do.
Thank you, it's encouraging to get the sense I'm on the right track. Those all sound like good ideas. I think living near a hacker space would be ideal as a way to work independently but still be part of something. Some of my relatives are Unitarians and I've always admired the philosophy--it's like religion distilled down to the good parts. I haven't heard of Less Wrong but I'll check it out.
I'm going to move soon, most likely to SF or Oakland, where I don't have any real friends or contacts to speak of. I'm very excited at having the chance to fully restructure my life, but the wimpy worrier in me is worried that being alone will cause me to freeze up. Ah well, suppose all I can do is try :)
I'm very glad that I've been able to get out of the box and do my own thing, but it's also made life a lot more difficult in many ways. It's been harder to develop consistent social circles since these tend to center around college and work. Even though I'm pretty good at making friends, at least for a fairly introverted person, I rarely feel like I really fit with whatever groups I fall in with--I tend to go back and forth between feeling insecure and being bored and annoyed by others' seeming conformity and lack of imagination. A bit of social anxiety is involved as well.
I've also never been able to maintain a consistent circadian rhythm. At this point I've just given up on worrying about it and regularly stay up for 30+ hour stretches when I'm not tired or have a lot to do. I've found it easier to just go with it than trying to force myself into the 'normal' way. This also contributes to feeling weird or different from others though--just feels like I'm on another wavelength a lot of the time.
Not sure why I decided to share this exactly. I can definitely imagine having a lot of the same issues as a billionaire. I suppose that's why it doesn't seem a particularly worthwhile goal to pursue. I'd rather focus on finding a good creative writing group or learning to meditate or finding a place/way to live that helps me find more balance and belonging. Things that would have a tangible impact on my day to day being. Making a lot of money seems beyond a point to get in the way if anything.
I don't know if there's anything in particular to blame, but our society is quite exclusionary in many ways toward folks who go off the beaten path, even if they are otherwise kind and productive people with plenty to offer. Generally reasonable people can be very judgmental about things like not having a college degree or a normal job or typical sleep patterns. I've learned to take it in stride for the most part, but it leaves sort of a bad taste in my mouth. I suppose wealthy people may have to face some irrational prejudice from others as well.