What event in your career made you decide to go a different direction?
Posted by JetreL@reddit | sysadmin | View on Reddit | 24 comments
Looking back on my career, there was one moment that really changed my path as a sysadmin. Years ago, I was stuck in front of a bare metal Windows server, patching it in the days when KVM switches were the norm and modern update tools hadn’t yet made things easier. It was a painfully slow process. I remember micro-sleeping at my desk, caught in that frustrating loop of waiting—no updates, no notifications, just watching a screen with no feedback and wondering when it would end. After what felt like an eternity (I think it was over two hours), it finally finished. But by then, I’d had a realization: there had to be a better way to spend my time than watching progress bars.
That experience led me down a different path. I decided to dive into networking and the Unix/Linux world. Sure, it had its own learning curve with compiling, configuring, and managing dependencies before package managers streamlined everything. I’d spend hours wrestling with ./configure; make; make install routines and tracking down missing dependencies, but at least there was feedback—a real sense of control over what was happening. I found that to be more rewarding and a better fit.
I’m curious if anyone else has had a similar “Aha!” moment that pushed them in a new direction. What was the experience, and what did it inspire you to do differently in your career? Would love to hear about those game-changing moments that steered your path!
FewerFans@reddit
I'm in the middle of transitioning out. Opening a business and if it hits even remotely close to my forecasts, and the forecasts the banks underwriters say, I'll pull in about $500k a year after taxes.
CheeseProtector@reddit
When I worked in retail a customer drooled onto loose change to hand to me, I switched to IT
Epileptric@reddit
Now you clean drool from keyboards
Sengfeng@reddit
and earwax from headsets because management is too cheap to buy new ones (despite the fact they cost $15 each - Can't have noise cancelling or anything else nice!)
Sengfeng@reddit
I'm at the cusp of doing this now - Clueless, ineffective, incompetent management will be what I would have to state.
bitslammer@reddit
I was doing Novell at the height of Novell, around the 4.11 days. To me this felt like a career pinnacle because things were really simple back then.
I was asked to fill in for 2 1/2 weeks for the site network manager as she was taking a long vacation. At that time the LAN was just Ungermann Bass hubs on some goofy thick coax cable. I was not happy. I though it was going to be an awful boring 2 weeks or I'd be dealing with these dumb boxes with tons of wires coming out of them in dusty closets.
Before she left the network manager showed me a few things including this new thing called a 'Sniffer" that she hadn't had a chance to work with yet. I figured I'd give it a try and BAM! It was like a blind person being given instant 20/20 vision. DHCP? Yep, I grabbed a trace of that and could see ever step happen packet by packet. Same for DNS, a Novell login, CCMail login, web page being fetched, ping, traceroute....you name it.
I learned more in those 2 1/2 week than any other time in my career or maybe life. Things just all made sense now and I was able to do what seemed like magic when it came to troubleshooting because I could see everything. I setup a sort of library of packet captures of things when they were working right so you could compare them to when things went wrong and the network manager was so happy to have that she asked if I might want to move over to help her as there was a huge project to migrate the old gear to this kind of new company called Cisco. I jumped at that chance it it kind of put my career on turbo. So thankful to her for giving me that chance and so happy I didn't blow it with a bad attitude.
ErikTheEngineer@reddit
Seeing that go from a physical luggable proprietary laptop, to super-expensive proprietary software, to WireShark, has been quite a ride.
pdp10@reddit
Our Network General was a rackmount. Probably the generation after the original luggable? With that one, and the Sun pizza box running
snoop
that replaced it, we brought the traffic to the sniffer instead of bringing the sniffer to the traffic. It worked well on campus, and there was never any reason to haul it out to a WAN site.Before someone bought a Network General, we used a few other tools, including a forgotten one called Gobbler than ran on DOS. Very little of production ran on PCs, but we always had old spare PC hardware around to turn into something useful.
bitslammer@reddit
And 'luggable' really hit the mark in terms of early briefcase like units. My favorite was that tiny Toshiba Techra laptop. Pop in that PCMCIA card that could do promiscuous mode and off you go.
BrainWaveCC@reddit
Brilliant! That would have been helpful to me back in the day, when setting up a packet capture was far more laborious than today. Today, I can just run one on a good system for comparison...
JetreL@reddit (OP)
That's pretty awesome! I manage engineers and developers now and I do my best to find ways to repay all the hand-ups everyone gave me when I was still pretty fresh. I even celebrate with others when I lose them to other companies that will pay them insane amounts of nickels.
Unable-Entrance3110@reddit
I suppose that I started with a mind toward programming. I was totally into writing BASIC programs on the Apple II when I was in middle school into high school.
Then we got a 286PC when I was a junior in HS and found that I enjoyed tinkering with the hardware and OS stuff more than I liked programming.
I was an early user of Linux (Slackware) when it distributed on floppy disks and was running my own e-mail server and web hosting on 256Kb DSL in the late '90s.
It wasn't until much later that I got back into programming in the form of Perl scripting and then later PowerShell.
So, I guess to answer your question, it was the move from Apple to PC that solidified my career path.
Had I stuck with Apple, I am not sure that my tinkering itch would have ever been scratched...
Thecardinal74@reddit
I've always been "good at computers" but was a crap student in school.
I ended up doing factory work after high school. Was so much more money than my friends had that I THOUGHT I was happy.
Then I saw old Bill P. He's long dead now but still want to respect his privacy, but I'll always remember him.
He was 80 years old, not strong enough to do the heavy lifting anymore, but drank his money away in a long life of bad choices. He swept the floor for a living.
It struck me one day.. and I looked around and a lot of the people I worked it, I was by far the youngest and everyone else looked like lifers. All had vices, some divorced and bitter, none seemed happy with where they were in life.
And I realized I didn't want to be 80 years old sweeping a floor so I could afford to stay alive.
So I traded shifts from afternoons to overnights, and did my shift, left at 6am, went home and showered, got a bite to eat, then went to class at a tech school.
Did that every day for 8 months, got a basic "foot-in-the-door" certification as an IT generalist, got lucky with a VERY low paying junior network admin position, and worked my way up from there.
Now I'm 50, my financial advisor says I should start thinking about how I want to spend my retirement and if I don't have crazy plans I'm in a position where I might be able to retire early.
All because of old man P.
He's long gone but I think of him often
DrDan21@reddit
I really despised databases but after enough years in desktop I was more than ready to move along. The company decided to open a DBA role our first ever and I applied and actually got it with near no actual experience
Started getting pretty good at the job and once I broke into six figures it was too late to go back
When I was younger I thought I’d end up being a windows sysadmin or a network admin specializing in Cisco devices
Special_Luck7537@reddit
I guess that would be when I was told that there was no next step up for me because I was irreplaceable, despite getting a masters in Mgt of Tech. So, they had to replace me.
WaldoOU812@reddit
It wasn't really anything in my career, but rather a PC video game, of all things. Computers weren't really all that common when I was growing up in the 70s and 80s, but I've always enjoyed games of various sorts, and while I had been exposed to them before and had even owned an Apple IIe, I was mostly a console gamer.
I always enjoyed looking at the PC games in my local Virgin Megastore, though, and one day I saw Darklands. I was enthralled, immediately purchased it, and convinced my mom to drive me to Best Buy the next day. Given that I only had about $50 to my name at the time, I applied for a credit card, was approved for $3,400 in credit, and took the voucher to the computer department, where I asked the guy what his "best" PC was. I couldn't afford the Acer he pointed at, since I also wanted a printer, so I bought a Packard Bell.
Spent three days manually sorting out IRQs, DMAs, and all that other nonsense, just so I could get the keyboard, mouse, video, and sound all working together, and from that point on decided I wanted to do that for a living.
https://en.wikipedia.org/wiki/Darklands_(video_game)
Fake_Cakeday@reddit
🫡
All those hoops to jump, just to play a video game and then you've spent hours getting it to work just before bedtime.
But then realizing you still had a fun day doing it.
WaldoOU812@reddit
I did. I had a blast. Of course, this was back when I was a lot younger and had a lot more patience for puzzles.
Fake_Cakeday@reddit
Patience and time for me as well.
Now I just want it to work before I'm too tired to bother with it.
BrainWaveCC@reddit
I know you're largely taking linguistic liberties, but all that nonsense we had to understand before, has helped us better understand what goes on behind the scenes even today. I'm grateful that I got to touch PCs just a they were making their mark in the enterprise...
orion3311@reddit
The same thing as you led me to focus more on cloud than on physical servers; if I never have to install another update again, I'm good.
robgarcia1@reddit
This is exactly why im putting everything on clouds right now
Sufficient_Theme5503@reddit
Replaced all our Cisco ASAs with Fortigates after spending way too much time messing around with Java to get ASDM working.
Feeling_Inspector_13@reddit
I noticed that everything above basic t1 helpdesk is way above my abilities, so now iam a Microsoft 365 engineer.