I love playing pool but quite frankly it's such a niche sport that I can never really find people to play with, my friends enjoy pool and will play me if I ask but they don't own tables and the only time I play them is at my house so I typically will always beat them

There is a local bowling alley/pool hall that typically always has players at its table and soon I want to approach a player and ask if they would like to play for some cash but I don't want my success against my inexperienced friends to blind me into thinking I'm good

At what point is it ready to hit the next level? When you clear a whole rack in one opportunity? When your able to knock down 3 wall shots? When you pocket 90%? Or am I over analyzing and putting a number on something that shouldn't?