When I came back to skating I realized I couldnt really be serious about skating street for much longer in my life, considering I will be 45 soon. I'd never really skated tranny before, so I took lessons.
I worked in skating and was totally ingrained in skateboarding culture non-stop for a long time, and the idea of taking lessons was so fucking weird to me. But I swallowed my pride and did it, because I knew the only way I could pro-long my skate life-span was to learn how to skate tranny better, best part of all is that I did it with my (then 11 year old) son. It was such a foreign idea, it definitely took some pride swallowing and felt cringey AF.
The bottom line: It's just about the person you pick and how open you are to the experience. If you get the first one right and stay open minded to what's possible, it can make a big fucking difference. It accelerated my learning curve in a tight 5' bowl and gave me the confidence to buy my own mini ramp and start learning tricks.
Without this I would have definitely gotten discouraged and been a bit aimless. I will be 45 in May, I dont really have time for that. I am not doing any lessons right now. I did them for 3-4 months, once per week, and stopped once snowboarding season picked up and I was traveling a lot. Starting next week I am gonna work with someone new to learn some specific building block tricks on my mini and help get over some fears. Just doing four sessions and I will take it from there.
I should note, the lessons I took were at a private bowl, private facility, 1v1. No interference at the park. No showing off shit, just doing the work.
Maybe one of the best decisions I've ever made in skateboarding (and as a Dad).