I'm male 16, living in Iran for clarification. (English is not my first language so sorry for any mistakes)
I have always struggled with my hair style and look, as I always cut my hair very short and uniform all around because of strict school dress code and policies.
But as I'm getting older I'm starting to want to improve myself and have better mental and physical health.
I've become self-conscious of face and looks after the pandemic specifically because I feel left out of many things compared to my peers. One of which is my hair style and cut.
I'm not sure how should I cut, style and maintain my hair. As I mentioned previously I always cut it short and uniform and I showered every 2-3 days, so I'd like to know how to maintain the hair.
But most importantly I don't know what to tell my barber?
Personally, I would try to realize others might respect you more for confident behavior like trying new hairstyles instead of ridicule you if the hairstyle isn't the best for a few weeks.
If I see someone I know (especially someone I know to have issues with self esteem) trying something like a new haircut, or asking a girl out or really anything that presents a social risk, I gain respect for them.
Heed some advice from Nelson Mandela:
I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.
Preface: I'm US based, I don't know how barbers work where you're from.
For me, finding a good barber includes having a conversation about what kind of things Im looking for. This can be as broad as "I don't really know what fits me" or "I'm looking to go a bit longer so I can style it like this picture of a person with similar hair".
After a couple of cuts, if I trust the barber can combine what I'm asking for with their skillset along with what they think looks good, I'll tell them something like "look, I trust your style. You can cut it however you think looks good". Their job is to cut your hair, but more importantly cut it in a way that makes you happy so that you keep coming back. A good barber will listen to you and get you a good haircut that gives you confidence :)