Now we're getting somewhere significant. Thanks for the opportunity to have this very meaningful conversation, guys!
Maddy, I completely agree with you about the vague undercurrent of hellish wrongness that permeates modern life. We aspire to accumulate more, to constantly expand our leisure time, to reduce the societal shackles we're told society places upon us, but those of us who get closer to achieving these aims seem no happier than anyone else--often less so, in fact.
I think the problem is that "self-actualization" is defined in our culture to be total freedom to express yourself with no barriers or limitation on action; it's a completely liberal, individualistic notion. There's this idea that once people are freed from the bondage of work and social conventions, they'll become artisans, painters, sculptors, musicians, whatever.
The self-actualization concept still works if you acknowledge what true fulfillment looks like to most people, and has looked like since the dawn of human history: it looks like doing useful work that benefits members of your community whom you know and like; it means being a valued element of the social organism you are a member of. This is why men lose meaning in their lives when they can't find a job. It's not really about the money; it's about feeling socially useless. This is common among men, but a similar thing happens to a lot of women after their children leave home.
Now what? How can I continue to contribute? Why am I still here? What's the point? There's even a term for it: "empty nest."
Our highly atomized society gives us little doses of that all the time. Many jobs feel either useless or wrong, giving their workers the sense that nothing of value is being created for others, or that the thing being created is a mere facsimile of value, that people are being tricked into consuming what you are producing, that you're making things that are really frivolities or trivialities that will being no lasting value to your community. This is definitely what I feel, and it's probably why I have 9,000 posts on this forum, most of them written during business hours. In my experience, it's not at all an uncommon sentiment in the worlds of tech and non-infrastructural engineering. So much of what we do seems, well,
unnecessary. Why bother? Is the new version of the software really any better than the last one? Does anybody really want or need it?
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I think it's tempting, for people who feel this, to want to escape entirely and fabricate a life that demands constant useful work. I wanted to do this myself for several years, and came very chose to purchasing 40 acres of land in rural Nevada with my wife, the goal being to create a little Tatooine-like self-sufficient desert homestead. Constant useful work required, right!?

The deal fell through, but the feelings that made it seem desirable never abated. Later on, we moved into an RV briefly, but that wasn't meaningful either because it was a never-ending vehicle maintenance chore which, despite being clearly useful, felt ultimately like a pointless and avoidable treadmill. Most recently, three years ago we moved to suburban New Mexico and bought a modest fixer-upper house on a large plot of land. Never-ending maintenance and repair! I've re-done bathrooms, installed new hardwood flooring and windows, fixed plumbing, done significant electrical work, planted ten trees, you name it. I've plowed through these very physical tasks, and learned an enormous amount of constructions skills, but none of this really brought me more meaning, which was puzzling. I sincerely thought that more directly useful physical work would make me feel energized.
Eventually I realized what probably every four year-old knows: that I feel best when I'm around my family, friends, and neighbors in a social context, and when my work can be seen to directly benefit
them and people near to them. The home improvement projects I've felt best about have been the ones that my wife was exited about. The stuff that she didn't care about didn't seem as socially useful, so
I didn't end up getting as much out of it, either. The gardening I do with my son ranks very highly, too.
So the key, I think, is to be doing work that seems meaningful to the people you care about--your family, friends, neighbors, and members of your community.
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This is why I think the traditional city model has the potential to be so successful. With no cars needed for day-to-day tasks, people will actual see and interact with their fellow residents on a daily basis. A sense of community will return--something so absent from American cities and suburbs where we all bundle individually into our cars and hurry off to distant destinations, 20 feet apart from other people who we never meet or know. Many people in these new traditional cities will be working in small, street-level shops and firms frequented by pedestrian traffic. You'd be directly selling to members of your own community, and the barriers to entry would be incredibly low because of the low cost of very small commercial real estate and low government regulation and taxation (a man can dream, right?

).
Do you feel un-fulfilled in your big law firm or engineering job? Open up a teeny corner store or something. Easy as pie in that setting. Sell healthy food or something to your neighbors and fellow residents. And with everything having a human scale, there would be an increased desire for beauty and ornamentation in building, decorating, architecture that is so absent today when most places are experienced at a distance, through the window of a car. You could produce artisan furniture or carve stone gargoyles or make public-sized statues or something in your corner shop and people would actually want to buy them! A far cry from the self-actualization model where you make art for your own sake, totally disconnected from anyone else.