/fa/ - Fashion

How do I get past the "awkward stage" on the way to long hair?

I have fine, straight, blond hair. I've tried lots of different cuts and product to give myself volume but just can't get my hair to comply. So for most of my adult life I've done short undercuts because it's all I can do to fit my face that works for fine hair.

I want to try growing it out long because although it's fine it's silky smooth. The problem is I always reach the "awkward phase" and abort mission. The length starts to look dorky and for me specifically I get these wiry/scraggly and curly hairs on my sideburns and side head hair when it grows past a certain length.

How do I make the most out of that phase or skip it entirely on the way to gorgeous long hair?

Pic unrelated and I'm a guy if that isn't clear