I think you have more internalized technical skill than you give yourself credit for. For me (and other more skilled amateurs that I talked to) there was a need to consciously think about what images are possible versus not. Otherwise I would spend all my time thinking about bad or impossible photos.

For example, I'm on a balcony right now, and I might notice a detail of a cloud behind a corner of a building three blocks away that would make an interesting composition if I had a telephoto lens with me. That's a waste of attention (and frustration) if the only camera I have with me is my iPhone. Or I might see an interesting building and see in my mind the dramatic photo that I'd get if I walked right up to it with a wide-angle lens, but if I don't have a wide angle lens with me, it's not going to happen. I might even have in mind an image that can't be captured at all, because I'm not yet a master of the equipment. As I got better at using the equipment, I learned to focus on the images that could be captured with my current skills and what I was carrying, and let everything else go.

Separate from the question of what's possible is what's good. I might see a photo, take the photo, and discover later that it has no impact, because I haven't learned the skill of knowing how the static image will feel when every other aspect of the experience has been removed. In photography, the golden hour is an oppressive reality. When I'm out backpacking, I can be thrilled and overwhelmed by an amazing vista any time of day, but no matter how amazing it is to see in person, if the light isn't right, the pictures are going to be boring. A more experienced friend tried to explain this to me, but I wasted hundreds of shots trying to prove him wrong before I gave up and followed his example. Well, I follow his example of not bothering shooting landscapes during the middle of the day, not his example of waking up at 4:30am so he can hike to the best position and set up to take advantage of the morning light.

It’s funny to me how Instagram has popularized my way of experiencing the world, but in a social context. I spent half my life doing what these Instagrammers are doing and never felt bad for a second.

That's a comparison that I've thought a lot about, in the context of Facebook. Communicating a person's experience is a core conceit of Facebook, just like my initial misconception of photography. Just like photography, when you try to get good at it, you find that the opportunity to create a post that communicates a certain experience coincides with actually having that experience much less often than you would expect. You can be having a great time and realize there's no way to share it in a way that makes sense to others. Likewise, you can be in a boring or unpleasant place and happen to find a perfect backdrop and some props for a selfie that makes it look like you're having a blast somewhere very chic. So that's what you do.

You would think that with over a billion active users of Facebook, many of them sincere people who find it hard to present themselves on Facebook, there would be guidance out there for people hoping to communicate authentically on social media. But if you look for tips on social media, you instead find advice for people trying to succeed at social media, either financially or according to the metrics of the medium. Like photography, if you take it seriously, you have to give up any naive notions of authenticity. If the situation is conducive to making a funny and relatable post about feeling a certain way, that's the post you make, no matter how you actually feel. If there's no funny and relatable thing to post, then you don't, no matter how much you long for people to understand how you feel in that moment, just like if the light isn't right you don't even bother looking through the viewfinder, no matter how much you're struck by the beauty of the scene in front of you.

Instagram seems to be a mix now of people using it to present themselves as represented by their lifestyles and people using it to present interesting photographs, often but not always of things that were designed to have visual interest in themselves, such as art, design, fashion, and architecture. Of course there's inherently an element of the former in the latter. I suppose I must sound very cynical saying that, but it's something I can't stop noticing, and I don't know how to feel about it.