[jrumbut]

One thing to think about, it terms of deep experience, is that in a product role you'll often only be using part of a stack. If, for instance, you are making a CMS you won't touch the numerical parts of the language. In consulting you may get to choose between using more of what's available in a stack or branching out to other technologies.

The entrepreneur thing is true too, I went from an employee to running my own operation and nothing was really surprising. I'm not sure how many other jobs you can make that transition so easily.

[throwanem]

Even if you just go self-employed as a consultant, it's a great springboard. A few years at a good small firm can give you everything you need except a decent accountant.