Seeing as I'll be passing my 15th anniversary in this whole sysadmin thingy as of this December, this is kind of relevant. As it happens, I am facing the choice to exfiltrate to Management or stay in tech and potentially dead-end myself. I narrowly missed dead-ending myself at my last job, which is a big part of why I left it.

Like Ned Harvey, I also have seen most job openings looking for the 5-7 year mark, with very few looking for more then that. The few I saw had very specific requirements; prominent in all of them was high level project-management experience for mid-size teams, a skill I lacked due to the small team I was on at OldJob.

And yeah, there are times to admit the specific technologies you worked on 10+ years ago, and times to just mention highest-level duties without reference to WHAT you're working. Or if what you were working on is something of a pariah technology, which can be a problem if the pariah was a major job-duty until really recently (like that large NetWare migration project in 2008, 8+ years after everyone thought NetWare was dead).

Being aware of what your resume looks like in light of the overall job-market is a big thing. Of course, if you've planted roots and don't plan to move because you're happy where you are, then you can happily ignore that. I left my old job because my resume looked like it was from 2005. Since I really didn't want to be a lifer at that job, I left for something that'll HELP my resume instead.

15 years is enough to have lived through two major technology cycles. By now it's "embrace change, anything else is just drifting."

My current employer is decidedly buzzword compliant, and it's great. I'm now living in 2012, not 2005. I'm working on technologies that will actually help me find a job should I suddenly not have this one, which is a pleasent change. They're even better about CE, thought not by much (only get it in good quarters).

It also means I'm climbing 7 years of hill to get up to speed, and it's a slog. I'm learning lots (a nice change), and so is the dev-team I'm working with. It's great.

However...

This is a very young company. I'm one of the oldest people in the company and I've yet to hit 40, and I'm the oldest person in the Engineering department (we lump Software and Systems engineers into one department). A good half of our software engineers are ex-interns we've hired after graduation. The corporate culture reflects this fresh-faced population, with hey-whatever hours that tend to add up to somewhat more than 40 hours a week and beer-heavy company parties. I'm finding an actual age difference here in attitudes towards life-balance that is hard to overcome; I can't challenge it since I won't be seen as a team player, and attempting to go all-in is infeasable due to home stuff.

This is what the mid-career challenge looks like for me. The temptation to go into Management is rather present. But not yet.

--
Law of Probable Dispersal:
     Whatever it is that hits the fan will not be evenly distributed.
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