Where exactly is this 'leap' you're talking about??
You're talking about GROWING your hair out ... and if it's really short now, that might take months to get to the length you're talking about.
And why are you doing anything with your hair because of what others think? Cut your hair to what YOU want and screw anyone else that doesn't like it.
I keep my hair cut short. Not for anyone else but because it's a hell of a lot easier to wash, dry, and manage it when it's short. No other reason.
We're men ... we're not supposed to screw around with our hair. Go with whatever style you like and leave it at that. TBH - women shouldn't be f_cking with their hair all the time either. Too many women have some gaggy looking dried-out destroyed hair from all the f_cking with it they do - dying it, burning it, etc.
If you want HEALTHY hair, then cut it at whatever length fits your schedule / lifestyle, don't screw around with it, and use shampoos and conditioners that are good for your SCALP. (Remember, hair is DEAD. Dead cells. That's all it is.) If you want good healthy hair, use products that take care of the part that is still alive - your scalp.