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Sometimes a solution is so secure it becomes insecure.  The primary example of this is requirements for passwords that are so complex that people write them on a note and stick them under their keyboard.

I have several times been locked into a corporate network where the possibility to cooperate with the outside has made my work more complex and expensive.
Limited email storage and chat protocols that don’t make it through the router are things that might hinder my work all the way to effectively stopping it.  A limit of 100 megs of email storage makes it impossible to send large emails without risking filling the mail box of a colleague.  Without chat my communication with competence peers is severed.

A slow internet connection makes every search take longer time or give less thorough result.

Then there are hinderances like forbidden FTP, an email washer that stops binaries and source code, or the stopping of youtube in the firewall.

I live in a world, a community, and we communicate.  A big part of my work is to gather information and spread it to interested parties.  Too many times the rules of a corporation network limits this.  Hence workarounds that don’t always play well with security but makes my customer happy.  And that is what it is all about, helping your Customer.

Wired has an article http://howto.wired.com/wiki/Traverse_Corporate_Firewalls that explains some workarounds from the dead simple to way more complex.