I was a casual play money player (on Zynga poker, no less ) for a long time before I turned to real money games. I'm naturally pretty frugal and risk averse when it comes to money, and the idea of wagering REAL MONEY in a CARD GAME seemed daring and edgy and almost unthinkable at the time.
But I was beating the highest level play money SnGs (LOL Zyngaments), and eventually just started wondering if I could take on tiny stakes real money games as well. Because of my risk aversion I started reading up on real money online poker before I even made my first deposit, so I was at least somewhat clued into basic strategy, rakeback, what my options were with regards to poker sites
, what to expect as a complete newbie, etc. Studying and playing went hand in hand from day one.
It must have helped because I was able to run with my first deposit, and haven't needed to reload. I played like a moron in those early days, but I guess less so than the field on average.
It was amusing to return to Zynga a couple of weeks later, armed with my new insights into how to play SnGs somewhat properly, and come to realize how awful these players are; how truly awful I was back when I thought I was so good for being able to beat high stakes play money SnGs.
Uh, so, to summarize--start small, study as you play, grow gradually.