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More often than not it is likely due to lack of investment in new software/hardware/or research & development that leads to unsatisfaction. That or employees may be hearing the plotter printing very loudly all day!!!
Companies that appreciate their GIS employees are more likely to invest whereas companies that don't think spatially are slow to change. For example, Excel has been around forever! But GIS software and capabilities change rapidly. I never even used ArcGIS lower than 9.0 (except when they forced us to in grad school). Yet there are still ArcView 3 organizations out there.
Right now I don't consider myself a web developer or desktop developer but I have gotten involved in some projects and school work involving these tasks and my advice for younger (below my 24 years) GIS folks would be to concentrate on one of these two routes.
For example, check out this job description...
http://blog.davebouwman.net/2008/02/05/LookingForAChangeWereHiring.aspx
Oh yeah, as I look for different beer ingredient stores online I'm beginning to learn that there is a hops shortage supposedly due to an increase in investment in biofuels. If anyone has any useful links or anecdotes from this dilemma please let me know!