I don't think I ever explicitly recommended this essay before, but here it is: Jo Freeman's "The Tyranny Of Structurelessness". Go read it first, then circle back here.
When I was younger, I had what I've now come to call a "confused radical utopian" worldview. Radical utopian in the sense that I wanted to see everything removed and replaced with something better, a viewpoint that in the end is about as profound as saying that things should be good and not bad. Confused in the sense that no matter how much I thrashed around between political philosophies — anarcho-syndicalism, cypherpunk [sic], what have you — I couldn't get any closer. I ended up with the sense that any effective changes have to be made from whatever position you are currently in, that being a decent human being to those around you is never a bad stance to take, and that voting is as much a chess move as it is a valentine (to use someone else's lovely turn of phrase).
Some of the utopianisms I still carry around with me are like broken-off pencil points in the callused heel of a hand: they linger with me, but they don't do much more than that. They occasionally goad me in the direction of longing for better things, but I don't let them run the show if I can help it. One of those ideas was, and is, the notion of leaderlessness — that the world should be structured to allow power to emerge organically, and to dissipate just as organically, to arise when needed and dispel itself when not.
Such things only seem possible amongst very small groups of people — single digits at most — and seem only to work when there is a high degree of existing trust between everyone in question. They don't scale, for the same reason intense friendships don't scale: you simply can't make something that deep between more than a few people at a time without it becoming diffuse-to-counterproductive.
This is why reading Jo's essay hit home for me so hard: she was pointing out that even amongst people who in theory are embedded in a web of trust with each other, it's far too easy to become exploitive and asymmetrical in one's use of power. The problem with leaderlessness is that the power structures that emerge spontaneously between people become invisible and thus unaccountable, and if you try to point that out you get dogpiled. Worse, the people exploiting the whole arrangement aren't always conscious of it; sometimes they're just behaving in bad ways that would also be rewarded in a less idealistic setting. (All this and more is touched on in Jo's essay.)
The problem with power isn't so much power as it is things like lack of accountability and unearned authority. I don't have a problem with someone having power over me as long as both of us know clearly what the limits of that power are, where they apply, and how they can be questioned. Abolishing power entirely is not only unrealistic but outright counterproductive, because there are some very large scale problems faced by human societies — e.g., an impending meteor strike — that simply cannot be solved by way of decentralized little communes.
It's not a bad thing to want a life that tilts in the direction of less uneeded coercion. Note the way it's framed: not a life without coercion, but a life with less of it. And less of it only to the point where you're not starving yourself of power that may be badly needed to keep greater harms from arising. Leszek Kołakowski described it as a three-way tension between freedom, equality, and efficiency, where the dominance of any one of those leads to tyrannies anew, and where no magic formula exists to automatically put those three tensions in perpetual harmony without also wrecking the dynamism needed in human society to thrive.
Still, I have my utopian streak, and I give it life and breath in my fiction. I come back again and again to the idea of a little circle of people who come together because there's no other place for them, who realize they only have themselves and each other, and use that as best they can to make an improvement. A guy's gotta have his dreams somewhere.
New York City
Other Lives Of The Mind