It’s been five years since my last post. The last time I wrote here, I had just landed my first IT job as a help desk analyst at a managed service provider. I said I’d follow up with the details. I didn’t. I was busy doing the job.
So here’s the follow-up, five years late.
Where I started
In 2020 I was a repair engineer for a medical device manufacturer, leading a repair team. Before that came the Marine Corps, then years of electrical work and fabrication. I was working full time, going to school full time, and had a family at home. I started this site to keep myself accountable.
By mid-2021 I had an associate’s degree plus CompTIA A+, Network+, Security+, and Apple ACSP. That got me hired on an MSP help desk.
The route since then
- 2021: Level 1 help desk at an MSP
- 2022: Level 3, about nine months to a year after I started
- Next: Help desk manager
- Then: Central services administrator
- Now: Senior systems administrator at a different MSP
Along the way I added CySA+ and AZ-900, and I’m studying for AZ-104 now. Between the two MSPs I’ve supported more than 80 client organizations. I’m still finishing my BS in Cybersecurity.
What got me off the help desk fast
I took the hard tickets. On an MSP help desk, the tickets nobody wants are the ones that teach you the most: escalations, strange network problems, the client nobody else wants to call back. I grabbed those. You learn faster, and the senior techs notice who’s willing.
The certs kept coming. I didn’t stop after Security+. Studying while working meant the next cert was always tied to something I was seeing in tickets that week, and that made both stick.
My trade habits transferred. Electrical work teaches you to troubleshoot in order: verify power, isolate the circuit, test one thing at a time, don’t guess. That’s exactly how you work a network outage or a broken sync. Working the problem in order instead of guessing stood out.
What I’d do differently
Skip the coding detour. My second post on this site was about The Odin Project and Ruby on Rails. I put real time into it, and it didn’t lead anywhere for the work I ended up doing. If you’re aiming for infrastructure, spend that time on the cert path and a lab instead.
Apply sooner. I waited until I felt ready. Nobody feels ready. If you have A+ and you’re studying for Network+, start applying for help desk jobs now.
Build a lab earlier. Reading gets you through the exam. A lab gets you through the interview and the first month on the job.
Go Microsoft sooner. At an MSP, almost every client runs Microsoft 365, Entra ID, and Intune. I’d start the Microsoft admin certs right after Security+. That’s why they’re Phase 2 on the roadmap.
The parts that weren’t smooth
Full-time work, full-time school, and a family at home don’t leave much room. Some weeks studying didn’t happen at all. Progress was slower than I wanted, and it still added up.
Not long ago I had a job offer pulled after I negotiated. It stung. The lesson I took from it: keep your other options moving until you’ve signed.
What’s next
I’m working toward AZ-104 and finishing my degree. This site is coming back with the things I wish I’d had in 2020: career guides for people coming from the military and the trades, cert roadmaps, and home lab builds.
If you’re where I was back then, start with the free IT career roadmap. If you have a question, ask it here. The best ones become posts.