"Understanding that your job is to make something happen changes what you do all day." - Seth Godin in LinchpinThe answer is yes, Ridiculously Extraordinary Freedom is possible with a day job.
Here's why: Ridiculously Extraordinary Freedom means you are able to do what you want to do, but are not forced to do anything you don't want to do. If you want a day job, if that is Freedom to you, then it's all good.
A couple months ago I created a list on twitter: http://twitter.com/KarolGajda/only-person-id-work-for
It's the only list I've created thus far and it consists of exactly one person: Mark Cuban, owner of the Dallas Mavericks, HDNet, Landmark Theatres, blogger at BlogMaverick.com, and all around bad ass.
And when I mean I'd work for Mark Cuban, I mean if he wanted me to clean his house or scrub the floor of the American Airlines Center, as long as I had access to his brain in some way, I'd do it. (There's the rub!)
I know I would learn a lot from him. I know I could execute a lot of ideas for his businesses that others wouldn't be willing to try. And I also know it would be hard work, but fun as hell.
But let's get off that for a moment because, well, although I would accept if Mr. Cuban contacted me, I'm not looking to get my first job since the year 2000. :)
Where this is coming from: I'm currently working on the anti sales letter for How To Live Anywhere and it starts with a story of two of my friends.
One of them, who makes a very nice amount of money online in only a few hours (usually less than 10) per week (*ahem* thanks to my teachings), doesn't want to quit his job. I think that's awesome. He has the option, the Freedom, but he likes his job, so why quit?
It's almost the ultimate Freedom: knowing that the second he doesn't like his job he doesn't have to worry about what he'll do. He can move on.
When To Stay and When To Kill a Day JobIf you have a business that is generating enough cash to live on and you hate your job, you quit.
If you have a business that is not generating anything, and you hate your job, and you have no savings, you stay. And you get your ass in gear to start generating that cash!
If you have a business that is generating some cash, but if you worked on it harder you could ramp it up, and you hate your job, you quit. And you get your ass in gear to start generating more cash!
If you have a business that is generating some cash, but if you worked on it harder you could ramp it up, and you love your job, you stay ... and reevaluate that decision when your business is generating job replacing income.
Or if you're Dave Navarro, you wait until your business is rocking so hard you'd be crazy not to quit your high level management day job.