I struggle with this all the time. My hair currently is to my waist. It's sort of wavy and even if I do say so myself, it's pretty. It's sort of a light golden brown color and has reddish highlights in the sun. I've always been complimented on it. But the problem is, I always, always have it up in either a ponytail or a bun. I've literally done jack shit else with it for the past...well, forever, except for a couple of times I tried to wear it down or half-up, but it got annoying and I put it back up. And I can't just 'put it up'...it has to be fucking perfect. No strand out of place, everything right how I want it, or I will spend the rest of the damn day until I get it right. I recently (within the past year) figured out how to put it up in a bun where it will stay for a few days, even through sleeping and all. That made me super fucking happy because then I didn't have to face doing my hair in the morning. But I think I am developing tension alopecia from wearing it up and tight all the time. I have a couple of thin spots on my hairline that I do. not. like. I know if I wore it down more often, that would probably go away, but wearing it down as it is now is a no-go. I did cut my hair suuuuper fucking short one time about six or so years ago. Hated it with a passion. I looked stupid as hell. I thought maybe I'd like it shoulder-length, but that was still long and I still put it up all the damn time. I saw some women with chin-length hair that had beachy waves/loose curls and I loved the look. But they were thin and pretty and I'm...well, decidedly not. I have a very full face (read: fat). I'm working on losing weight, but it is really damn hard and I'm not seeing any difference in my face at all. I guess what I'm asking is if I should get my hair cut and permed so that it's chin-length and has loose curls/beachy waves. I am indecisive af and can never decide on anything. I'm so afraid I'm going to hate it. I've hated every other cut I've had. But I am so goddamn sick of putting this mess up all the time. If I had it cut like I'm thinking, I could get up, comb it, and go. Maybe pin it to the side once in a while. I should mention I'm fucking terrible at doing pretty, girly things with my hair. Putting a clip on the side is about as far as I'm capable.
Ughhhhh, Subetaaaaaa, what do I doooooo??
This is Brad Mondo's fault, btw. I've been watching his stupid videos on YouTube and he got me thinking that maybe I should just fucking do it. I should film myself getting it cut and maybe he'd see it, lmao. He would tell me to do it, I know he would.
First, do you feel safe getting a haircut in your area right now? I got one once the salons in my city were reopened and I was very pleased by the safety protocols in place. Look up how the salon is dealing with the pandemic on their website, or ask if/when you call to make an appointment.
I will say shorter hair means more maintenance in the form of more frequent haircuts. Do you know what kind of perm you want? I get digital perms (hot perms) rather than traditional cold perms. Have you gotten a perm before? They do require their own kind of products and styling methods.
I think wavy bobs are really cute! Jennifer Lawrence has a round, fuller face and she made the style trendy at one point. When my hair was at its longest during my city’s shutdown, I just wore it braided most of the time. Is that a style you like if you hold off on cutting it? A trim might be good anyway and talking things over with a professional. Good luck!

There's a salon at the mall that I've already picked out. They seems as safe as anything can be right now. They're a little more expensive than something like Great Clips, but I think for a big change, it's worth it. I've had a perm before, years ago. I had about the same length I have now and did a spiral. I loved it, but with that length it was a ton of work. I don't mind more frequent haircuts if I find a style I like. I can just go to a cheaper place for trims. I can't really do braids because I don't like the loose feel. I'm going to see if there's someone from the salon I can FaceTime with to see what they have to say.
Does your hair grow quickly? The consolation to a haircut you’re not happy with is that at least it will grow out. I hope you’ll like the one you’re planning on though! It sounds nice. I cut 5 inches off in June and it was so good getting rid of all that weight. I’ve started wearing scarves as headbands too, using just regular scarves or one from Heritage & Bloom to keep my hair out of my face.

Hey! Have you finally cut it or not? I recently went from tailbone- to collarbone-lenght and I have no regrets. :D (Even though I still keep my braid in a wardrobe and wonder whether I want to sell it, donate it or ocassionally pin back to my head). I love my natural colour and my hair is straight and not too dense, so it didn't cause much trouble even when it was so long, but I also just wore a bun and didn't do anything fancy. I looked nice and classy with some outfits, but the hair itself didn't do much good to my face (which is a bit round). So, one day, I watched Brad Mondo's guide to cutting your own hair (although in my case it wasn't his fault; anyway, he's great) and just cut it. :D I guess it was better for me this way, at least I knew if I mess things up, it would be my fault, not some silly hairdresser. And sometimes I miss the bun, I guess I'll let my hair grow back, but for now I feel good and I know I'm going to finally experiment with some hairstyles soon – for now the hair is a bit too short for that.
I can't tell someone else what is the best to do. I can only tell my positieve experience when I have shaved my head bald. If I'm bald I can do much more female things to do with my head, than when I have got hair. I have no alopecia but I have never liked my stupid natural kurls and I can do nothing fun with it. It was very boring to have. With a bald head I can paint my head and make it nice with all kind of little tuff I can stick on my bald head. I feel so much better with no hair. But as I said it's personal and I believe my bald look as a woman is not so usual. (Still not).
Maybe bald can looks great too by you even if you have got a round face. Round faces seems nicer with a bald head than long bony skinny faces with a bald head, if I'm honest. A collarbonelength or a lenght until your chin could be great too, especially when your face is round. Maybe your face will be seems thinner on an optical way if you have cut of your hair on a chin-length. A diogonal cut-line foreward kan make your face smaller too.