Ask any guy on this site no matter what age they are and they will tell you that their only regret is they didnt shave their head sooner.
The plan should be to buzz it down right away and try it out. But ideally never let the new job see you with any form of longer hair. That way they accept and expect you to be buzzed down or shaved smooth, so no questions or hassle. Just take that first step and buzz it down yourself. Watch a youtube video since there are so many. It is such a popular look today. I see many guys your age with full heads of hair buzzed down to the skin. Do it and have fun !
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