How to make IT lemonade from obsoleteist/ageist career lemons
July 27, 2021 4:35 PM   Subscribe

I'm an IT generalist, mostly a sysadmin but I was once a coder. Closer to the end of my career than the beginning. I've given up on getting hired as an FTE and I want to put together an IT contracting practice in a more current niche than sysadmin. If you were in my situation, I'd like to hear from you about how you found yourself there and what you specifically did to pivot to success.

I'm an IT generalist, mostly a sysadmin but I was once a coder. I had to leave employment for a couple of years for personal reasons, and now that I'm back looking for work, I see the IT world has greatly changed. My contact network all bugged out into retirement the moment they heard the words devops and Kubernetes at their respective companies, so I'm now totally on the outside looking in. Doesn't help that my 60th is visible on the horizon, either.

I've given up on getting hired as an FTE and I want to put together an IT contracting practice. I can set up and run a small business, but I've never had to fight for work before, particularly in skill areas outside my sysadmin comfort zone.

What I need help on today is how to identify a niche beyond sysadmin I can be credible and profitable in, and how to proceed from there.

If you were in my situation, I'd like to hear from you about how you found yourself there and what you did to pivot to success.

My additional personal complications are 1) a far better doer than salesperson 2) onset of some physical disability, 3) no car 4) tied to my local area which is 5) South Bay/Silicon Valley. I broke out #5 because being there rather than in, say, the Midwest, is probably the big reason why my FTE search was such a struggle.
posted by Quesaak to Work & Money (12 answers total) 8 users marked this as a favorite
IT generalist is a pretty broad field, and it can be a bit hard to find something specific that you can latch on to. As an "ISP generalist," as I was once called by a fellow ISP generalist, we learned everything from wiring up T1's to arcane C coding, and everything in between, to deliver the first generation of Internet service providers (nothing like what people know today). IT generalists, and I know a bunch, typically suffer from some of the same problems, which are that it's a huge skill set, but you might not be a paper expert in any one particular thing. Typically problem solvers who are able to find answers to most problems, but probably not have them immediately on-hand, IT generalists are well positioned to consulting roles because of their abilities to see a larger picture than many of the highly stratified specialists today. The problem is, you probably do need to look at your skill set to see if you have some specific strengths, and then see if you can use that to open doors and move forward. If you've done work with virtualization, connect with local communities like VMware User Groups. If you've done SQL, check for local SQL user groups. Attending some of these and just chatting with people is a great way to create new connections within the community. Getting involved on professional technical forums is also a reasonable idea. I'm not looking for leads, but I do a lot of work on the TrueNAS Community forums and probably see potential opportunities every month or two.
posted by jgreco at 5:23 PM on July 27

Best answer: Learn AWS - very high demand skill and also popular in government, where you likely would have a better shot of landing something more permanent. It's a big bucket, but your sysadmin skills should slot in nicely as a starting point.
posted by COD at 5:25 PM on July 27 [6 favorites]

You and I are pretty much in the same boat. I had to leave IT for about 10 years doing something unrelated and that job eventually went away, leaving me competing in a delivery job with kids half my age. I actually spent the money and went to webdev bootcamp, but nobody wants to hire a junior web dev in SF Bay Area. :-( I can probably figure out K9 and devops if I have an environment to play with for a few days and a stack of books (which I have, keep buying them off Humble Bundle) and as soon I mentioned I'm an IT generalist, they ask where's your A+, N+ and S+? I'm like "never needed them before", they're like well, you need it now. See ya. :-\

I can probably go learn AWS, as a lot of the training is free from Amazon itself. Cert cost $$$ though.
posted by kschang at 5:26 PM on July 27 [3 favorites]

Mefi mail me a link to your resume
posted by evilmonk at 8:31 PM on July 27 [1 favorite]

FWIW, I moved from that to writing infrastructure automation tools - in my case, catering to enterprise customers. This did involve learning docker and friends, but if you've got both a sysadmin and developer background it shouldn't be a huge leap, and you'd be shocked how rare this combination actually is in the corporate world (the young devops crowd doesn't want to deal with our shit ;)).

I did this at 40. though, which is probably younger than you're thinking.
posted by jaymzjulian at 9:05 PM on July 27 [1 favorite]

Large labs and departments at universities often need a sysadmin and don’t need kubernetes and all that new crap. The pay is often lower than industry, but the work environment is often better and comes with fun university amenities.
posted by congen at 9:37 PM on July 27 [1 favorite]

I'm 51 on a longer than expected sabbatical from university infrastructure for 50+k people with fingers into everything. Writing a resume is impossible, you just sorta have to already know what sort of things just happen and are handled over the 16 years. Many stories, hard to resume/cv/cover-letter. Still a bit of a pigeon hole. Advice from my younger years would be to just lie, or flat out tell them you're smarter than they are but need the job like an actor waiting tables. Both sorta work.
posted by zengargoyle at 10:13 PM on July 27 [2 favorites]

Learn AWS
Or if you have any AD experience looking into Azure training/certs. Seems like every org is moving to Microsoft 365.
posted by LoveHam at 4:32 AM on July 28 [2 favorites]

>I want to put together an IT contracting practice in a more current niche than sysadmin
Today is setting up cloud infrastructure and transitioning to rented servers in someone else's datacentre, tomorrow will be diagnosing performance and security issues on those platforms. There's a lot of online training for cloud adoption, I'd focus on working with teams to do upfront work making it easy to diagnose and recover stuff is a very useful direction to head in.
posted by k3ninho at 4:49 AM on July 28 [1 favorite]

I'm about 20 years older than you. In the late 1990s, I was writing client/server apps as a freelancer. I had just a taste of the new thing, which was writing writing for the web with HTML, javascript, and C#. I made the decision to stick with client/server and let the young guys worry about the internet. I figured that legacy systems would generate enough work to keep me employed.

It worked out well for me once I survived the dotcom crash. I got a job with a small company with approx 50 employees that didnt have any significant internet presence. The IT dept was a guy to keep the network running plus me. So I always suggest being open to smaller companies; they need generalists.

Also, consider the importance of business/industry knowledge. Insurance is different from banking is different from retail is different from manufacturing.

OTOH, big companies are collections of small departments. Some have systems stuck in the past, and there is opportunity there though I think the work with COBOL has finally dried up. :)
posted by SemiSalt at 5:19 AM on July 28 [3 favorites]

I don't really have good advice other than to say that ageism is real and it's the likely reason you can't get hired for an FTE role. Even paying for your own training and certification might not be enough now. I got laid off from my last tech job in 2017 and I'm pretty sure my IT career is over at this point, but I have no idea what I'm supposed to be doing next.
posted by fedward at 8:57 AM on July 28

Response by poster: Thanks for the responses. Marking the most favorited as best because answers simply confirmed what I already knew.
posted by Quesaak at 9:28 PM on August 8

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