How I “Keep Up” with IT and My Career

I’m often asked how I manage to “keep up” with everything that’s happening in technology. Along those same lines, I’m almost constantly pressuring my peers and colleagues to do the same. I recently had a conversation with a fellow IT Ops guy, and the conversation got onto virtualization, when I mentioned containers. He said, “huh?” I groaned. You just gotta keep up, in this industry.
So how do I do it?

I should point out, before we begin, that everyone has their own methods. What works for me won’t necessarily work for you. But I think it’s really more about mind-shift than anything else, so perhaps illustrating my shift will help you find your own.


I think the first thing you have to know is that “keeping up” doesn’t mean you need to be a world class expert in every topic. That’s insane. But I have to point this out, because many IT professionals I run across truly don’t feel they can have an intelligent conversation about something unless they’re an expert. 
Take containers. I’m not an expert. I’ve never used them in a production environment. But, I know what they do, I know who the major players are, and I know the business and technology needs that they address. I know some of their current weaknesses (they’re essentially a Linux-only thing as I write this, although we know Windows containers are coming). I know where I can go to learn more about them. I know how they differ from “competing” technologies like hypervisors. That knowledge – which frankly, I’ve picked up simply by doing some cursory research and reading – is enough to give me context. I can speak to other people about the topic, at that high-level perspective. I have enough context, and know enough jargon, to learn more about the subject as it evolves. I subscribe to a couple of RSS feeds that tend to focus on the topic, because I feel it’s important, so I can keep my thumb on the story as it evolves.
That’s it. Yes, I do this across a couple dozen topics, but each one doesn’t involve more than an hour of my time a month – most require less time.


Like many of you, my employer doesn’t specifically pay me to sit around and play with new technologies. Implementing technology isn’t even part of my job, nor is maintaining it. I’m basically a manager. But I spend a few hours a month playing with whatever new technology interests me. I have a Gigabyte BRIX (you can get them on Amazon; I have an older i7 model that’s still doing well) with 8GB of RAM and I think 256GB of SSD. It’s enough to run four or five virtual machines (people tend to over-provision their VMs; stop it and you’ll get better density) in a very compact home lab. Mine runs Hyper-V Server, and I’ve got PowerShell Web Access running on it. So I can browser into PWA from my Mac, manage VMs, and then RDP into those VMs as needed. I usually run one client VM that I RDP into, and then jump off to servers via Remoting from there. I think the whole rig cost me – me, not my boss – $700 or $800. And yes, that’s money my family couldn’t spend on something else, and yes, it was absolutely worth it to make sure the primary breadwinner could continue winning bread. If you’re not willing to spend money on your career, nobody else should do so, either. 
Point is, I just play. I indulge my curiosity. If you’re the type of person who needs structured hands-on lab exercises in order to play, then you’re not playing. If you can’t exhibit some childlike fascination and desire to just poke at things, then you’re probably going to have a tough time playing keep-up in IT.
Right now, I’ve got three VMs running so I can play with WMF5. I snapshot them, so every time I break something, it’s easy to roll back to a starting point and begin again. I’ll often turn some of my discoveries into a blog post. Or, going the other way, I’ll come up with some task I want to accomplish, and write an article about how I did or did not get it to work. That stream-of-conciousness writing doesn’t always get published, but it helps me cement what I’ve learned.


I find that one reason people slow themselves down, when keeping up, is by asking “why.” And doing so in a specific, “why is this being done to me?” sense. “Why did Microsoft do it this way? It seems so much harder!” and then they’ll spend time going down the rabbit hole, rather than continuing to learn. Me, I don’t care so much about the why. At least, not at the detail l even. Sure, I care about why a business might use whatever I’m learning, but I just kind of accept that “this is the way it is,” and try to learn more about it. In other words, I don’t fight the learning, I just let it happen.
This is a huge barrier, and it’s difficult to describe the barrier in specifics, which makes it hard for people to realize they’re doing it.
I’ve written before on how we constantly say that kids learn easily, when in fact they don’t. Kids don’t “learn” at all; they absorb. They just take in new knowledge without running it through filters, questioning it, or anything. That’s why “learning” is easy for them. New facts don’t get run though a process and contextualized; kids don’t memorize. New information changes who they are, immediately and effortlessly. As adults, we start to compare new information to what we already know. We question the value of new information, and in doing so, we slow ourselves down. Adults dislike having core principles called into question, and so in some cases we avoid new or contradictory information because of the tensions it creates.
I’ve taught myself not to do those things. In many cases, I’ll just absorb what information I can, and not even worry about where or why it might be useful. Your brain actually does contextualizing in the background, while you sleep. So I’ll spend my hour or so of productive learning time each day (your brain can only absorb about an hour’s worth of learning in a day, hence my Month of Lunches series design), and then go about my other business. The next day, I’ll have more specific questions and curiosity, which I’ll research for an hour or so… lather, rinse, repeat.
Adult brains are actually wonderful at learning. We just don’t trust them at it. We feel that memorization – remembering every fact – is key, when that’s not so. People take notes, instead of just letting information flow into them. See what your brain captures. They next day, you’ll want to refresh certain things that don’t seem quite clear – but you’ll end up doing so in more detail, because your hindbrain has identified gaps, and you’re seeking to fill them. Learning should be fairly effortless.
College teaches us otherwise, because most academics are horrible teachers. They make learning difficult, they rely on rote memorization rather than contextual presentation, and they cram too much information into a given amount of time. That’s why many adults dislike learning and don’t think they can do it well – college teaches us to dislike learning.


This will sound cheap, but this is pretty much my approach. Learn a little, every day. Let my brain digest, and repeat. Periodically play around with stuff, purely to satisfy curiosity, without any structure or goal. Read a lot (if you’re not good at reading, you’re going to have a hard time keeping up). Watch videos a lot (people are moving more and more knowledge into video form). Make learning as much a part of your day as eating (I often learn while eating – it’s a good time to read or watch videos).
Always learn, and you’ll be keeping up.

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I don't know why others want to become experts but I know I want to become an expert because I'm responsible for too many disparate systems. And not only that but it's getting worse.
I've been the IT manager of a small company for 15 years.
After reading this, I don't think I truly want to be an expert on one or even two things, but I would definitely like to be much more well versed in seven things rather than 20+. (I just made up those numbers but they feel reasonable.)


Totally agree on these points Don. Especially "play time". I did similar to you but spent substantially more and it has paid me back many times over.
I could get exposure to technologies and have a better understanding.
BTW your CBT webinars on Powershell is fantastic. I have constantly reviewed the seminar.


Well said Don, I'm definitely in the "I'm not an expert so I can't talk about it" crowd. Despite all the feedback that my boss constantly gives me. The issue with IT definitely is that damn rabbit hole. Once you start looking into one thing, 4 hours later you're still progressing and diverting and onto something completely different! Being the only SysAdmin at my work, I do get distracted with other tasks easily but that's one of the things that I love about it. Won't stop me from yearning for those younger days where I had all the time in the world!
By the way, are you using DSC for the automated re-build of your virtual environment?


I do. And I should point out that "play time" for me is outside work hours, for the most part.


I need to definitely get on this PowerShell bandwagon aside from using it here and there for random stuff.
Ehh my "play time" outside work hours involves toy trains, wooden blocks, and diapers... 😛 Maybe in a few years it'll be different...I hope!


What would you recommend as far as getting copies of Server 2012 for a lab/test environment? Do you reinstall trial versions after they expire?


That's a big expense. I do tend to just re-build every so often, although of course I have that automated ;).


I was at the dupsug yesterday, where I saw many PowerShell professionals. And they are all good; but not in every aspect of PowerShell. And that's OK, because you learn slot from eachother. And that is also a way to learn, sharing your knowledge and absorb knowledge with / from other people. I agree on the way you do it Don, you need to play with it. I also do it, except the writing part. I like to use mindmaps for that purpose. As Jeffrey Snover also said yesterday, IT professionals owe it to themselves to keep up. And how better than to spend lab time on your passion? It's my passion anyway 🙂


There is some good advice here. I appreciate the "AN INCH DEEP. WELL, MAYBE TWO." portion. Learning to know a little about a lot is a skill and its one that more people should cultivate. Not only for your own awareness of a technology but who is in fact a valuable expert when you do need to go deeper. As you said too many people in IT feel the need to be "experts" to undertake some project or deeper discussion. I don't know too many people who were experts before they started something. They became experts because they've done a thing. I've also not met too many experts who weren't more than happy to tell you all about the thing they know. Having at least an understanding of the vocabulary about the technology is key to asking the right questions of the right experts when the time comes.
When it comes to "experts" I'm always reminded of Scott Hanselman's "I'm a Phony, Are you?" blog.
The idea of "experts" is always kind of a nebulous idea for me. To me the traditional idea of "experts" seems to align with geologic time, where there is one tallest mountain in the world. It’s factual and it exists likely for thousands if not millions of lifetimes. However we live on internet time and the mountains and valleys are built and destroyed overnight sometimes. It’s not about knowing how to get up a particular mountain and planting a flag but where everything is and how to navigate it. Not just in the context of the business you presently work for but for your own practical independent career. Your career needs to withstand internet time even if your business does not.


The problem I have with Video learning is it makes poor reference material to go back to in 6 months when you want to do hands on with what you absorbed.