Every resource, every person, every project, every machine you have to manage comes with an ongoing cost. This is just as true of servers as is it is of people who work on projects that you're in charge of or have some responsibility for, and while servers and teammates present very different kinds of management challenges, working effectively and managing management costs across contexts is (I would propose) similar. Or at least similar enough to merit some synthetic discussion.
There's basically only one approach to managing "systems administration costs," and that's to avoid it as much as possible. This isn't to say that sys admins avoid admining, but rather we work very hard to ensure that systems don't need administration. We write operating systems that administer themselves, we script procedures to automate most tasks as much as possible (the Perl programing language was developed and popularized for use of easing the administration of UNIX systems,) and we use tools manage larger systems more effectively.
People, time, and other resources cannot be so easily automated, and I think in response there are two major approaches (if we can create a somewhat false dichotomy for a moment:)
On the one hand there's the school of thought that says "admit and assess management costs early, and pay them up front." This is the corporate model in many ways. Have (layers upon layers of) resources dedicated to managing management costs, and then let this "middle management" make sure that things get done in spite of the management burden. On servers this is spending a lot of time choosing tools, configuring the base system, organizing the file system proactively, and constructing a healthy collection of "best practices."
By contrast, the other perspective suggests that management costs should only be paid when absolutely necessary. make things, get something working and extant and then if something needs to be managed later, do it then and only as you need. On some level this is inspiring philsophy behind the frequent value of favoring "working code" over "great ideas" in the open source world.  Though I think they phrase it differently, this is the basic approach that many hacker-oriented start ups have taken, and it seems to work for them. On the server, this approach is the "get it working," approach, and these administrators aren't bothered by having to go in every so often to "redo" how things are configured, and I think on some level this kind of approach to "management overhead" grows out of the agile world and the avoidance of "premature optimizations."
But like all "somewhat false dichotomies," there are flaws in the above formulation. Mostly the "late management" camp is able to delay management most effectively by anticipating their future needs (either by smarts or by dumb luck) early and planning around that. And the "early management" camp has to delay some management needs or else you'd be drowned in overhead before you started: and besides, the MBA union isn't that strong.
We might even cast the "early management" approach as being "top down," and the "late management" camp as being "bottom up." If you know, we were into that kind of thing. It's always, particularly in the contemporary moment to look at the bottom-up approach and say "that's really innovative and awesome, that's better," and view "top-down" organizations as "stodgy and old world," when neither does a very good job of explaining what's going on and there isn't inherent radicalism or stodginess in either organization. But it is interesting. At least mildly.
Thoughts? Onward and Upward!
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