This reminds me a lot about a blog post I wrote some weeks ago:
http://blog.opportunitycloud.com/2010/05/07/the-cloud-or-the...
The cloud or the ladder, it's two different ways to view your career or even your life. I think most people on HN are clouders.
That is an interesting post. Your idea of an opportunity cloud is something I've spent a lot of time thinking about. I even made a decision recently to stay at my current job instead of taking a somewhat better job, because I believe the opportunity potential is higher if I keep with what I am doing for a while longer.