>I'm interested to hear stories from consultants about when they realized the time was right to go out on their own. What were the major factors in your decision? What would you have done differently? How did you approach it?

If you feel your skills are strong enough, and (very important) have a client lined up for a non-trivial gig, go for it! Then make absolutely sure you do a great job for them so they are referenceable. Then find a second gig. Repeat.

One caveat, and I'm sure you have heard this before, is to be realistic about what your income will be. Any benefits that aren't covered by your wife's job will come out of your pocket. And whatever you do, don't start multiplying an hourly rate by 40 hours a week and 50 weeks a year. Not only will there be gaps between jobs, both intentional and unintentional, you need to set some time aside for keeping your skills up to date, going to conferences, marketing, and the like.

User groups and other professional organizations are a great way to develop a network Network, network, network!

From what I can tell about you here, I don't think there's any question you can do this. You are knowledgeable and just by being here you show you aren't just mailing it in from 9 to 5. I'm also pretty sure you would rather be your own boss than have to do whatever someone tells you to. Which is great if you have the self-sufficiency and self-discipline to do it. Again, I bet you do.

Good luck!