Finding my way to $1 million

I have been struggling for some time now with how to cope with my finances. This has been hard for me because I can't talk about it with friends and family: My problem is that my finances are going too well and I am not prepared for the next steps. Ironically, it would be easier to talk about things going poorly, but an improving net worth is positively in poor taste as dinner table conversation.

Then in surfing tonight I found some really nice personal finance blogs. How neat that the anonymity of the internet allows honesty about finances in a way that isn't possible except perhaps with your accountant. So I've decided to give this a try as a way to put my thoughts in writing, explore the issues and hopefully reach some conclusions. I called myself The Money Diva not because I am but because I would like to be. I have more questions than answers right now and I perceive a long path ahead of me. But I think that by writing it out and possibly with input from the net community, I will find my way.

As a beginning, I would like to set out my goals:
1. Reach $1 million net worth
2. Generate passive income sufficient to stop working
3. Have a sensible asset allocation with appropriate risk level
4. Do this in a way that does not require microscopic monitoring or multiple advances degrees to understand

I plan on refining my goals as I revisit my situation and my vision to add timelines, details and perhaps even change direction. But these general ideas will start as a pointer in the basic direction.