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To chop or not?

Since you've had both: do you feel that short hair is easier for you to style? I only ask because I've actually found that shorter hair is more high-maintenance on me. My hair is really thick (not course, but I just have a lot of it), so it poofs out more when it's short. Also, I always have the option of putting my long hair in a ponytail, which I really like.

That style is kind of cute, but I personally tend to prefer long hair. Of course, that doesn't really matter; it only matters what you like the most. When you close your eyes and picture yourself looking your best, do you have long hair or short hair? I think that you should go with what makes you feel most confident with.
 
Go for it. It is not all that different than what you already have, so why not?
 
i think u should cop it,so nice
 
Congrats on your new position! That's so exciting! I think that your hair is adorable now (though I might agree with cleaning up the ends a bit). It looks to me that the photos you posted of your "inspiration" look are just a bit shorter and more layered....if you can handle the grow out if you don't care for it, I say go for it!
 
It sounds like you really want to do it. If so, I'd definitely cut it, but since you had poor experience with bad haircuts before, take some time to find a really good stylist.
 
I like the inspiration photo with the shortest hair length.

You'll probably need to keep your hair moisturised and frizz free, maybe go a to a richer, darker colour. It'll look playful without being too cute.
 
I have very thick dark brown/black hair, and I am in a similar boat as you. I usually wear it just past my shoulders, or past my collar bone. For the latter, I have had it permanently straightened (Japanese Liscio product), and it's like a dream. I can shower, comb my hair, and it will dry straight and not be so poofy, and it is stick straight. I prefer it over shoulder length hair because straightened long hair is much lower maintenance, and I can wear it up.
 
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