I like color photos with dark, rich colors and I adjust them so in PP.

When I convert to black and white and try different settings I just can’t make it look as good as other people’s black and white even when I look at YouTube videos and use presets. I just really don’t like black and white but some people can do it really well and it’s acceptable.

Same thing for that light and airy look. Sometimes I think it looks good for weddings. I try that in camera and in PP and it looks like s**t. It just looks overexposed when I do it. Although I saw one person’ light and airy that was so overexposed you could barely tell there was an image in the photo and I felt it was way over done.

And about half the time everyone else’s photography looks better than mine. Even when I get a lot of compliments from my clients and friends.

It’s like I’m my own worst critic. Every so often I create a shot that I’m really proud of.

Does anyone else have these feelings?

Ditto on the "light and airy" look. I cannot stand to see that "expression"--I really think it is due to folks that don't know how to adjust the background shutter speed and overexpose it. There is absolutely no reason why the background highlights should blow out with a skilled photographer. The "point and shooters" or the "smwac" are the ones that do this and I detest those images. arrrrrgh.....

Regarding the b/w conversion, try playing with the color filter options in LR (or Nik Silver Efex). Back in the film days, whenever we shot b/w film, we would always slap a yellow filter on the lens to darken the sky. You can adjust these sliders to give you the best gradations between blacks and whites so that the entire image is not gray.

Perhaps you are trying to do, rather than researching How to do. Monochrome is a genre of Photography with both a history and a modern following. As you say some people 'can do this' very well. Perhaps you need to re-look at tutorials and 'actually follow them' rather than trying to remember 'how'. Certain subjects lend themselves to Black and White - The Mill towns in the UK or perhaps Inner City US. Talk to Graham on UHH he can get a cafe shot to work. Investigate why you are not satisfied.
High Key and Low Key again is a technique not simply a case of merely altering the F stop. The right lens and the right light - not necessarily a bright back light. Read up and practice till you feel confident (again).

One of the problems with Photography is that it often is a solitary pursuit. You can be confident in 50 - 60% of situations and then BANG.....nothing works because you are into a whole different situation. So you move on and look for something safe to Photograph.

Whist I agree that creating your own style is important....it is not an excuse to stop 'researching and trying different things'. The internet has a wide range of tutorials -written and video, that can re-introduce you to the techniques (and Kit) to do 'anything'.

I can show my friends and family really crap images and they say 'that's nice'. But they don't really understand what makes a great image.....plus they are polite. Some on UHH complain that they get a whole list of negative feedback - is it always undeserved? Negative feedback is a positive area of research and re learning.

Working on your own is difficult - especially when you have no 'reason' to stretch yourself. No critical editor, no critical workload, no set agenda etc.

A wedding Photographer for example not only has to work to a set group of images BUT also add 'something unique'. The fashion of wedding images constantly changes, so new techniques need to be mastered rather than 'tried'. The demands are increasing as 'joe public' now owns a camera!!! So easy for a hobbyist to stick with 'what they know'.

Have I said anything NICE yet?