A couple of observations/thoughts/resonating recognitions all whisked together this time, Tupp. As you write things down, get it out of your head... I can see them better. Doesn't mean I'm "right" about what I see; but some of it may be useful to you.
Primary connection
I believe (rightly/wrongly) that for most of us, we grow our connection to ourselves via the connection we have with our primary caregivers. I kinda suspect that our foremothers knew this instinctively and that explains the tradition of moms being practically still physically attached to their infants for the first months of their lives. Think papooses, and how comforting it must've been to still be carried by mom, while making the transition to consciousness of the world around the babe.
I believe our ability to trust ourselves and have a measure of self-confidence also derives from that early imprinting. Attachment theory has a lot to say about that, so I won't expound. But doing the work you're doing now, it might be a valuable research project to you. The operative relationship that transfers being totally cared for and protected by the caregiver - to an internalized sense of "being OK" within oneself, come what may - is called "mirroring". Mom reflects back to babe, what BABE is and feels; corrects things that Babe can't fix for him/herself yet; and slowly lets go the responsibility for that over the toddler years as Babe begins to be able to physically operate the world around them.
Imagine how proud babe is of herself, the first time she can pick up a piece of food herself or finds she can throw snack all over herself, the chair and the floor! Later, she learns - oh, that doesn't get the food where I want it > in my face!!
Now, imagine how babe feels if she is screamed at, or hit, or "punished" by being removed from the food, the companionship of caregiver, and is told she is "bad" - over & over for years as she fumbles her first attempts at developmental achievements.
Imagine what happens to babe, if she's never "seen" as being a separate person from mom - with Babe's own feelings, thoughts, habits, personality - and is constantly told she's "just like - mom, when she's "good" and dad, when she displeases "mom". Babe never has the important "mirror" feedback of WHO SHE REALLY IS and that IT'S OKAY to be HER.
If she's lucky, she finds someone else later in life, who can be a clear mirror for who she is and doesn't complicate things, with their own internal crap. (Yes, probably just like I'm doing right now - but you're smart enough to separate the "me" parts out.)
Should is double-edged sword
There are shoulds that come with consequences attached. "I should pay my bills today" comes with the kicker, if the bills are late or simply unpaid. I try to follow those, but I also have to watch that I'm not making them more important than they really are in the general scheme of things.
But all the other shoulds are negotiable; and I ask myself: do I really WANT to do that? (regardless of what other people think is important - and that includes the so-called "balance" in my life; what works and is important to others isn't always on my "need" chart right now) I no longer worry about if I'm "normal", because I'm seeing that I'm enjoying how people are different from each other, way more than how we're alike. Sometimes it works that we want to spend time together; sometimes it doesn't. That doesn't necessarily imply that it's impossible to have a relationship with that person or that circumstances might not alter how we both feel at some other time. Just means it's not going to fit the recipe we've been told (conditioned to expect) "should be" what is.
There are some consequences attached to the 2nd type of shoulds. If I choose not to invite someone over... and maybe Holly's feeling social or restless or has an obligation to someone else... I can find myself alone. But that doesn't mean I'm lonely. I might put off doing certain jobs because I'm a bit anxious about tackling it on my own. (I'm trying hard not to hurt myself, and learn my physical limits.) Or I might be bored, with silence... or not being engaged with other people. But "lonely" only comes to visit me occasionally. I'm just weird that way, I guess.
And even when I don't feel I have any energy at all - I CAN still read and learn something new. Or re-arrange some corner of the room, to allow room for new impressions of the space, etc. (Sometimes, I have to move things back, though... LOL.)
It's amazing to me, some days, how comfortable I am with my self now. I used to find being alone the worst kind of torture and deep down believed I was going to go stark raving mad - a drooling idjit - if forced to be alone for any length of time. Then, I started working with actually drawing boundaries between "times I wanted to be alone" and "times I wanted to socialize" - and that was awkward too. I'd just get comfy one way or the other and the shift would be intense.
Having Holly here - and her spontaneaity and her generation's established "hang out" culture - I've adjusted to a smoother transition between both solitude and groups of people. It might just be having the practice, you know? It takes 5000 repetitions before something new feels "normal" to you; before it's internalized; before it's just what you do... and are becoming.
I'm using me as an example... of the choices; not as an example to emulate. I don't know how to talk about things like this a different way. It's just like Hops & I have different goals in mind in online dating. A lot of our experiences and observations overlap; but we're both going to a different kind of solution that works just for us.
PS, I edited the typos more than once. I find I'm skipping words a lot now when I type. Brain's moving too fast these days.