Are Jobs Obsolete?

My response to Douglas Rushkoff’s article “Are Jobs Obsolete” that has provoked a bit of discussion.
Rushkoff is an acquired taste. Really, it’s very hard to write as much as he does and make sense the entire time, and he does it pretty well by throwing some big ideas out there and provoking thought.  But sometimes a bit indelicately.
In this piece, I think it’s a great point.  As someone who hasn’t had a proper “job” for about 10 years (for better or for worse), I do feel pretty much unemployable some days.  Yet, the problem isn’t my skillset, it’s that I my experience doesn’t fit neatly into a category.  Hiring companies are given specs for jobs and they need to tick the boxes and fulfil them. Whether or not that’s good or useful doesn’t matter, so much as they need to tick those boxes because *there must be measurable performance goals*.
It’s amazing to see the under-qualified people who work at many jobs but keep on going because of career momentum.  The ones I’ve spoken with (especially in finance) really understand this, that they are specialized in a career that don’t enjoy but don’t have time to gain the skills to grow out of.  It’s a trap for them, where they are jsut qualified enough to do their job and make a living, but also trapped because of their specialization in something that has almost no general application outside of their current position.  I fully agree with Rushkoff that employment only serves those at the top – read the management theorist Weber from the turn of the 20th century and his observation that bureaucracy is inherently un-democratic.
If you have a job, you work for someone.  We’re moving towards a contractor-based society, where contractors are their own bosses, except we’re still stuck in a paradyne where contractors are not fully independent but almost worse than employees due to lack of rights.  They’re people who often have jobs that are sub-jobs of other jobs, temporary positions that give power to the employer and have little inherent benefits (health care, etc).
If the contractors could mobilize, and use the new information tools available to negotiate their own positions as truly independent actors, they could revolutionize what work is, and whom is subservient to whom.  Read Art Kleiner’s “Age of Heretics” and you’ll see that the most productive management structures (as unexpectedly proven by some very large companies, such as Proctor and Gamble) are based more on the collective-agency model of production and design than a “command-and-control,” centralized planning approach.
Of course, as Art pointed out, there is a paradox that enlightened group production usually has some sort of small power structure, some non-democratic bureaucracy of management layered on top like the sweet sticky caramel top of a Crème brûlée.   Will we figure out a way around this, or is this the only way humans can operate collectively, with a small group at the top dictating policy in the end?  And along the way, can we achieve some sort of open source, transparent, collective society that is both post-socialist and post-capitalist, in the true spirit of Adam Smith’s enlightened individuals pursuing their own happiness and also contributing to the group’s common good?  These are the questions of the time, and its exciting to be able to ask them and have a chance at experimenting with potentially viable solutions.