So I've been playing for maybe a year and a half while anchoring my pinky on the guitar. It doesn't hurt when I play this way and I'm able to play various things just fine but I have feeling playing un-anchored will greatly increase speed and flexibility.

My question is how long do you think it would take one to have to relearn this? and is it worth it in your opinion?
how long - depends on if you practice everything right, and for how long you really practice every day.

is it worth it - playing anchored definitely limits speed and flexibility, but it DOESN'T limit your ability to become a great guitarist. if you want to become the best guitarist you can possibly be, then it's worth it. if, however, you're a hobby player with absolutely no intention to study music to be a composer/scorer/arranger/etc., then it doesn't matter. that small limitation won't mean the difference between sucking and dropping some jaws.

really, only you yourself can determine what benefits re-learning can provide for you.
Anfangen ist leicht, Beharren eine Kunst.
I've actually never been able to anchor, my pinky on my picking hand just isn't long enough. It should only take a few weeks (thats how long it took for me to learn to use my pinky)
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