I'm ambivalent to boundaries. Rigid rules can make me feel oppressed if I don't see a good reason for them and especially if I see reasons I strongly disapprove of, which tends to happen a lot because governments support capitalism and inequality so much instead of supporting the communities and people they're supposed to serve.
On the other hand, without clear boundaries I tend to flounder. When I quit my job, I wasn't expecting it to be all wonderful, but only because I thought it might be too late for me. Having worked for bosses for decades I figured I might not lose my habit of anxiety about being at the mercy of people who didn't care how I suffered as long as their profits were maximised. Indeed I still have some of that anxiety, which has transferred to authority figures in general, but I now think there's more to it. When there's nothing particularly important to do, and no obvious threats from the tinpots, I feel lost, unable to organise myself, and although I can well afford to be as lazy as I like, I never feel right about it. I came to the conclusion that in some way I have too much freedom and that I don't know how to put it to good use. Part of it is probably an internalised work ethic (which I'm ashamed of), but I think another part of it is that I need people to set me some boundaries and to organise me. My own brain can't do it all.
But if it's ever going to work, it'll have to be totally egalitarian and light-touch. No life coach or therapist with even a hint of a guru trip or anything else dodgy about them is going to cut it. Forget the armed forces, I'd last about 5 seconds. I think my best chance is with my partner, but we're so nice to each other that it's hard to know what boundaries she'd set if she didn't feel so averse to hurting my feelings. Of course there are a lot of implicit rules that I obey for (what I imagine to be) her sake, and I should be careful what I wish for. I think most relationships are rather like that though - a lot of the things a couple do for each other are never asked for in so many words, and (especially with women I think) there's often a feeling that to have to ask or demand things somehow makes them less satisfying in a rather fundamental way. Boundaries are social things, so it's probably not surprising that an Aspie hermit wouldn't find it easy to make their own.
It seems to parallel socialist / anarchist thinking - that the working class are kept in an undeveloped state, never being allowed to flex their muscles or become confident, and that they have the potential to mature and take their lives back into their own (collective) hands. We've all become so used to relative powerlessness that we see responsibility as something to lay at the door of the ruling class instead of taking it on for ourselves. So maybe in time I'll mature and prove myself worthy of the autonomy and freedom I've lately managed to acquire. It's quite a challenge, I don't think I realised that at all not so long ago, but I think it's the right road for me. It's too easy to sit around waiting for somebody else to tell me what to do.