You may be correct that when looking for a "cog" job that the specialist has a leg up. For the startup though, it pays to be diversified because you end up having to do many things yourself for awhile. For example, I have to be my own pc hardware support. I have to be my own SVN repository maintainer and also maintain my linux boxes. If I develop a rich internet application, most larger companies hire different team members to do the server side and client side development. I have to be able to do both.

Personally, I find the "always learn new skills/broaden your experience" suggestion very encouraging. I think personality-wise I'm more of the "jack of all trades" (I'm INTP, for those familiar with the MBTI). But the latter-half of that expression is "master of none", and when competing for a job, the jack will often get beaten by the master. I think that's generally true for "cog" jobs, but probably matters less with startups, independent contractors, freelancers, etc.

Another consideration: the specialist, depending on how unique the skill is, has the opportunity to make a lot of money. The person will probably have to look longer and harder and/or relocate to find someone willing to pay for that specialist knowledge, but when they do, they ought to be able to name their price. Like the financial analyst above: yes, finance is a bad place to go looking for a job now, but there still is some demand for them. And if this person is truly a specialist, i.e. top-tier 0.1% of all financial analysts, someone somewhere will pay top dollar for that skillset. (On the other hand, "financial analyst" is a pretty vague title, and in the given example, probably isn't a specific-enough skillset to as marketable as I'm suggesting. The catch is being the master of a unique or maybe even niche skill.)

Just some rambling thoughts to avoid work at my cog job…

I don't think FT was security, but rather an easy out of having to deal with the whole sales of you as an independent contractor. Prior to the Valley, I was a no one (and to most, I still am LOL). I know that trying to be an independent contractor would've been too hard for me and would've caused a lot of unnneeded stress in my life.

As for being cogs, I don't mind that either if you're okay with being a cog. John and I had this discussion once. Some people just like the safety of a FT job, where they do the same thing everyday for years on end. Sadly, I think a lot of people feel the way to escape being a cog is to climb the corporate management ladder. I told eBay management once, "Look, I don't want to climb the management ranks, so can we devise an employee progress plan that does NOT have a goal of management?" It came as a great shock to them.