I always feel like there's a whole rule-book of "how to Do Life" that I didn't get, for this easing-into-the-upper-middle-class and/or doing-serious-business-stuff shit, that other people
just know, because of who their families are and who they grew up hanging out with.
I gather the version of that I did get was the middle-class version—which some others didn't get and have a similar "wait, that's just normal?" reaction as I do to the upper-middle stuff. Like 90% of that's basically credit-related—how credit cards work and how to use them, how to build credit, how to buy a house (generally with a mortgage, so, still basically a credit-related thing), that kind of stuff.
I've noticed similar things when it comes to paying others to do stuff for me. Having a house cleaner come in for the first time was fucking weird. Still is, really. I can't relax, feel like I ought to be helping. Or paying someone to do work on my house that I could do—tiling, drywalling, some light electrical, plumbing, most general home-improvement stuff. It feels gross—I don't think it does for those who grew up with that stuff being normal. I suspect it's a barrier to advancing in business, because those attitudes carry over. Delegation is weird to me. Being someone's boss is horribly uncomfortable. The notion of starting a business and hiring employees to take over stuff I've been doing feels icky and wrong, and no amount of one part of my brain telling another part to knock it off makes that go away.