There comes a time in every poker player's life when the wanderlust sets in. You grow tired of nickel and diming your friends at the kitchen table and want to explore the world of the rounders. Know thyself, caterpillar, before you spread your wings.
The number one identifier of your skill is money. It is, after all, how we keep score. Macro-consistency is everything. Marco meaning not micro. If you have a bad day, or an unprofitable week, it doesn't necessarily meaning you are a bad player. You want to play long enough to look at the big picture. Do you average a strong profit? What's you standard deviation? These are questions that can be, and need to be answered with good record keeping and a lengthy poker history.
There isn't much to learn in the short run. Wins and loses are subject to some luck day to day, but you can still assess your play by looking at how you won or loss. When I correctly read my opponent on a straight draw and bet the pot at him on the turn, I played well, regardless if he calls and catches on the river. Inversely, if I catch trips on the river against an aggressive two-pair, I know I misplayed the hand even though the poker gods were kind to me. I'd go so far to say, as your play on the turn is concerned, luck is inversely related to skill.
Before you make the jump to big money games, also look at the caliber of your normal opponents. You may be winning not only on your own merit, but also due to the lack of skill or seriousness of the rest of the table. Although this is just what you want in poker, it can be hard when gauging your play relative to Gus Hanson. Be sure to go up against more than just the same five guys to experience more styles and see if your consistent winning pattern holds up.
That's the long way of saying, if you are making money, go to the next level and make more of it. Give yourself a "raise." You can always go back to the drawing board if it doesn't work out. Don't rush, but don't be afraid to play to your potential either.