I can pretty honestly say that the bulk of my real life social life exists because of the Web. All of my best friends today I met in one way or another because of the Intertubes. Even Diana came by way of eHarmony. The surprising side effect, one I've never thought much about, is that the richness of those relationships can probably be attributed to the fact that via online community, you have a much larger pool of people from which to interact, and the people you most hit it off with are actually easier to find.
A large subset of friends I know because of CoasterBuzz, PointBuzz and CampusFish. Of the three, the only one to get any serious attention in terms of improvement is PointBuzz (after three and a half years), and I think the motivating factor there was that I co-own it with Walt. So on one hand, these things I created are responsible for many of my friendships, but on the other hand, I don't understand the responsibility my friendships have on those properties.
I've had a lot of conversations that go along the lines of, "It'd be cool if you could do this with that site." Sometimes I agree, sometimes I don't, but regardless, people close to me still have feelings for those sites. There are two problems. The first is that I'm not always sure that I have the same feelings for the sites. The other problem is that, dammit, there aren't enough hours in the day to work on those sites as long as I'm working a day job.
I love our little mini-community at CampusFish. I struggle with it every day because stuff is limited in how it works, it's based on .NET 1.1 code and the damn moblogging gets hosed up constantly. On one hand I feel personal motivation to re-build it because I love it, but on the other hand it isn't something that would pay the bills in the event it was part of my stay-at-home day job.
CoasterBuzz is more tricky, because I don't feel like coaster enthusiasm is what it used to be. We've talked about that in the podcast and in the member-only forum at length. It's still a place people meet, and the club membership number has remained relatively constant for years despite relative neglect. Those couple hundred people are really important to me though, and I feel like I owe them.
Time feels like my enemy. Those six hours every night seem destined for slacking because I need to balance out the previous eight (plus commute) or go nuts. I want to give Diana attention. I want to play with my cats, and play video games. It's hard to come home to work my "other" job.
Of course, the obvious remedy is to make this stuff my full-time job, and in short stints, that has worked for me in the past. But when you go down that route, you essentially burn a bridge. If I decided it wasn't working, it's not like I could go back to ICOM. Not that I couldn't go elsewhere, but would it be as good of a job? I'm too risk averse lately, and I have no idea how I got that way. I'm still trying to get my arms around what that damage is so I can fix it.
The heart wants to pursue what I see as real obligations, but the reality of needing to balance out my time outside of work gets in the way. It's something I've been thinking about quite a bit lately, and I hope I arrive at some useful conclusions very soon. My happiness hangs in the balance.
"I'm too risk averse lately, and I have no idea how I got that way. I'm still trying to get my arms around what that damage is so I can fix it."
Sounds to me like you answer your own question with your comment above. I think our risk aversion becomes greater as we get older because we have the maturity and experience to know what could happen.
I would say there are at least two factors that are true when you consider the risk involved with leaving your current job to pursue your own endeavors:
1) You know what it feels like to not know exactly where your next pay check is coming from and in return how your bills are going to get paid. It wasn't a good feeling and a part of you never wants to feel that way again.
2) You know what it feels like to be financially comfortable and have the freedom to spend money on the things you enjoy most. That is an excellent feeling that you wouldn't want to part with for anything less than the most beneficial of circumstances.
Just some thoughts.
Indeed you did, which is why I would guess you are drawn to exploring the idea again. But there is surviving and then there is living within the means you have grown accustomed to lately. I mean there had to be a reason you sought out the day job you have now in the first place right?
I guess the best thing you can do is find out where your price point lies. Is the satisfaction you gain from exploring your own interests full-time worth the sacrifice of not going to Orlando? How about not getting Blue Man tickets? How about not living debt-free? How about not having as large of a nest egg at retirement?
Only you can decide what these potentially great opportunties mean to you and subsequently how much you are willing to sacrifice in order to achieve them.