David, Welcome! Come on in, the water’s fine…
I remember lurking for over a year and a half before dipping a toe in for the first time myself. Everyone I’ve met has been so kind, thoughtful, supportive, and helpful that I now regret having let so much time pass before jumping in with both feet.
Since it looks like you’re playing in the WordPress world, feel free to drop into the #WordPress channel (or any of the others for that matter) anytime to ask questions, help others solve problems (we can always use help with UX/UI, and themes especially), talk about what itches you’re working on, or even just to say “hi”. If you haven’t yet, I’m sure you’ll enjoy meeting some of the WP regulars including pfefferle (Germany), GWG (New York), miklb (Florida), snarfed (San Francisco), jgmac1106 (Connecticut), jeremycherfas (Rome), and me: chrisaldrich (Los Angeles).
I hope that the most overwhelming part isn’t getting to know the community, but the sheer number of things that are becoming possible to do with one’s website that weren’t as easily possible just a few years ago. My biggest problem reading the chat logs usually comes in the form of saying, “That sounds/looks cool, I want that too!” about 8 times a day. My best advice for “eating the whole whale” is to do it one bite at a time.
I’ll also personally extend an invitation to the upcoming IndieWeb Summit in Portland at the end of the month. If you can’t make it in person, there should be enough support to allow a lot of direct participation via chat and live streaming video–it’s not quite as much fun as attending in person, but you can participate to a level higher than most conferences typically allow.