For me, the first step was simple...attend a day at Gen Con for the first time. I've been a gamer for 30 years, lived in Indianapolis longer than Gen Con has been here, yet I never involved myself at all. This year that changed, and now I'm on a quest to prep myself to have the time of my life next year. I've been out of tabletop gaming for 10 years, and even threw a lot of my stuff out. I've had problems with being overly obsessed with MMO's I've had to overcome. I've got a roommate that doesn't approve of my geeky ways at all. Still, I plan on being at Gen Con 2011 for the full event, and I'm going to take this year to slowly plan my time and learn/relearn enough games to have a lot of fun.
That journey will be chronicled here :).