The Midlife IT Career Crisis

Orin Thomas recently told me that the average IT Pro, in the Microsoft world, is 43 years old. Makes some sense; younger kids tend to be attracted to younger companies, and younger companies are largely deploying Linux for their big dot-com-startup projects (which is why Microsoft ?? Linux all of a sudden). So there are fewer young people getting into Microsoft-centric IT Ops.
And so we’re having a midlife career crisis.

We, as IT operations professionals, are seriously starting to exhibit some of the classic signs of age. Oh, not all of you, to be sure – but plenty of us. In fact, the ones who aren’t are really starting to stand out from the larger pack.
We don’t like change. Any change. We’ve figured out how to run our environments, we’ve got them basically running smoothly and reliably, and we’re completely uninterested in disrupting that. Are some of our job tasks boring and menial? Sure, but we get paid the same either way. We’ll just keep clicking “next” until it’s time to retire. It’s fine.
We really don’t like paradigm changes. Hybrid cloud? Yeah, whatever, I can come up with fifty reasons why my company “can’t” do cloud without even breaking a sweat.
We don’t agitate. We’re honestly not all that passionate about our jobs anymore – it’s something we do to get paid, it’s pretty comfortable, and we’ve basically figured it out. So we’re not pressing our company leadership too hard to do new, cutting-edge things. We know they’ll just say “no,” anyway, and it’s easier just to go with the flow.
We don’t punish bad employers by quitting. In your mid forties, we feel, is not a good time to be striking out for a new job. So we put up with badly run environments, misguided CIOs, and out of date technologies, because it’s easier and safer than finding somewhere better to work. And since we’re not punishing them by denying them quality IT people, these badly run companies keep doing it. 
I’m not suggesting that there’s a solution, here. I’m not entirely suggesting there’s even a problem. I’m saying it’s a situation, and if you’re in it, you at least need to acknowledge it to yourself. If you acknowledge it and decide, “yeah, fine, I’ll just go get a shiny red two-seater Xbox and keep doing what I’m doing,” fine. If that’s your thing, you go, girl. But a few of you may decide that Life Inertia can be overcome through a sufficient application of force – and decide to shake off your midlife career crisis and change. Change your tech. Change your job. Hell, change your career, if that’s what’s right for you.
All I’m saying is, choose to remain settled into a groove, if that’s where you are, or choose to lever yourself out of it. Don’t just let life occur. Get in the driver’s seat.

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Very insightful post. I think that field of Windows IT Pro's is indeed clustered in the mid-40's as you stated. I also think the field sort of hollowed out when the recession hit right after 9-11. When the first dot-com explosion occurred, many people rushed into the IT field that had no business being there.
Then the recession hit and those people couldn't find a job and left the IT field. Exacerbating this was the whole outsourcing trend in IT where companies were hiring low-level Windows engineers overseas. This made it harder for newbies to enter the field.
So now you have the mid-40's group who cut their teeth on Novell/NT in the 90's and then you sort of jump to the younger 20-somethings that embrace Linux and open-source. Experienced Windows engineers in their mid-30's seem to be hard to find.


Wow! That is exactly how I have been feeling here lately. I definitely fall in the age range at 46 years old. I feel like I have slept in my current job for the last 7 years and I am starting to do everything that I can to "wake up!"
I used to be very into tech and would try out every operating system out there that came up. I am still a gadget guy at heart but I feel like I have not kept up with all the latest trends.
I recently started reading and playing with PowerShell and it has really woken something back up inside me. It harkens to my Linux days and working with Bash and Perl. I am a command line junkie at heart so this is really right up my alley.
So here I am. I am not settling. I am actively working to increase my PowerShell knowledge and learning new technologies to automate local and cloud-based systems.
I see the same things that you are seeing. I see people who are content to work how they have always worked and then I see people who are actively trying to change. I want to be one fo the ones that change.


Hey Don even though i am still 27 this Post stirred me up.
I have few questions and would definitely love light from a person like you who has seen IT from cmd to PowerShell.
1.I am falling in love with PowerShell (Learnt from "PowerShell in Depth book" and forums(from 2years). I have given a serious thought and noticed writing scripts makes me forget time.
My technology is Citrix Admin.I want to know what should be my career path and focus of energy. Citrix is vast in itself and PowerShell too.
Right now I use PowerShell just to Automate Citrix related job.
2.People keep talking about so many things and say this is better and that is better.Pearl,Ruby,Chef,Puppet,Azure,Amazon,AWS,Full Stack Developement.. list goes on.
3.I am not even sure if I should leave a company just to get a better salary Package (assuming people I have taught are earning much more than me and I feel shy to ask my manager for a Hike.)makes me nervous sometimes.
Thanks so much for all your valuable posts.


Well.. IT hiring is broken. You don't know about a new shiny and better technology X which you can use to manage your hundreds servers more efficiently as your current company has no plans to switch to X and breaks whatever is working right now. Then you can't get a new job which is based on X since you don't know it really well. On top of that, they prefer to hire someone for minimum wages possible. Since you already have financial commitments, you can't agree to that. You can try to take the driver's seat but how do you make sure that existing driver is letting go of his seat for you.


Jon, I am in one such environment but things are changing like crazy and i know all the older folks feel exactly how you have described it here.
That being said, I would also like to share some other observations that might add more context to this situation:
a) IT professionals in their 43s have families, kids, and with the economy being tougher than before, they are focused on making their payments and mortgages. To be in IT and have a good family life balance is like achieving nirvana. This hold even more true if you want to spend time learning. So there is a huge shortage of time. During the day most spend their time fire fighting and maintaining SLAs, atleast in support
b) Companies have shitty training programs or none at all. I am in a huge one and there is almost zero cross training and furthermore there is no "training" beyond getting us to cram for and write some certs without any real hands on time. People want their hand helds like college or school , or atleast have some mandated time set aside for training
c) Big companies have massive silos and no one wants anyone to touch their stuff. So even if you do happen to learn some networking, if youre a server guy, you cant touch the network because of silos
d) Lack of development/test environments
e) Most windows IT pros are GUI addicts and rightfully so. And convincing someone at age 45 to use Powershell, much less bash, takes considerable effort -- i'm sure you can attest to that
f) Recent technology is advancing so fast, companies or even IT technicians cannot realistically keep up with it. And thats why they have thrown their hands up and now want to be shown the way, by the way of adopting techniques used at startups (such as the heavy use of open source technology). The spectrum of buzzwords used these days kind of sum up all the craziness: Scrum, Agile, DevOps, Cloud, Machine Learning, AI, Bitcoin, Apps, Containers, Big Data , BYOD & Mobile. You cant blame techs from being a little intimidated
And continuing off of what you said , to make the transition from a windows based GUI client OS to command line linux containers + devOps is not a simple task by any means. This is a challenge most windows IT pros are facing , powershell does a great job of easing them in, but these companies need to give their employees significant time, resources + hands on training.
But because of the "agile" rate of change and barrier to entry going through the roof (aka specialization and expectations from organizations) that is unlikely to happen. Instead, they would rather outsource and turn to contractors. Which is another trend in corporations in general, which is a topic for another day.


Excellent observations Ahmad.
a) At mid-life families take up so much time that we no longer have the luxury of burning the midnight oil immersing ourselves in technology. In my younger days I built my own mini-network and domain at home and built up a whole raft of skills. These days I'm restricted to reading tech manuals in my lunch hour - which leads onto point b) - zero training! Been in my current sys admin role for almost two years and had no training whatsoever but still expected to support all the new technology that comes along.
c) Yes, there are silos, but the main problem is that you can't move sideways because your boss doesn't want to find, hire and train someone else to do your job. It's also very difficult to move jobs due to family commitments and age discrimination - yes this does exist despite legislation that is supposed to prevent it.
d) See b)
e) This is the only one I disagree with - I've become a big fan and user of PowerShell and that's my preference these days, but then I did grow up with DOS command lines and batch files so that environment is more my comfort zone.
f) Problem here is with young career driven IT managers who want to 'modernize' in unrealistic timescales then rant and rave when the existing, reliable systems start to fall apart!


I try to push but at the same time, they know I am not leaving. One problem is I have to sell my house and relocate, pull my son out of a great school program, etc.
What I can't figure out how to transition to is a remote carrer. This would allow me to change my carreer without, uprooting my family.
I live in a rural area, there are 3 companies trading the same IT people back and forth.


Hey John, I can help; I routinely talk to IT guys looking to strike out on their own. Shoot me an email at and I'll send you some info.