SysAdmin Weekly - 056 - How People Actually Get Into SysAdmin Work

[asyrewicze]

Hey everyone!

Eric and I did something a little different this week. Instead of picking a technology, we picked ourselves apart: how each of us actually got into IT, what the first paid job looked like, and what we would tell somebody trying to do the same thing in 2026.

Here is what we covered:

• The stuff we broke before anyone paid us. Andy's 486 and the Windows 98 Matrix boot screen that got him told to change it back. Eric's VIC-20 loading off audio cassette, a hand-me-down Xerox 286, and overclocking a 486 with a box fan.
• The first IT jobs. A K-12 summer gig decommissioning Windows 95 boxes and running cable that came up a foot short of the patch panel, versus a freight dock job that turned into "we could use somebody who can work the computers."
• The first real failure. Andy deleted an application share holding student grades and district financials, and recovered it off tape. Eric deleted his dad's files off a 20MB C drive at roughly 12 years old. Both of us walked away with the same lesson about data.
• Advice that held up. The key to IT is laziness, so automate anything you do twice. Say "the end" at some point every day or the MSP queue will eat you. Being a decent human who can say "I don't know" beats being the smartest person in the room.
• Advice that did not. Anything containing always or never. Anything called a best practice with no traceable source. And "nobody ever got fired for buying IBM."
• Does this on-ramp still exist? Eric's answer is no, and that it does not matter. Surplus sites, thrift stores, and a hypervisor on a laptop cover most of what a rack full of gear used to.

Plus the usual: Meta's return to open source with Muse Glimmer, states starting to push back on data centers and battery storage farms steamrolling local zoning boards, a Black Hat demo on local LLMs writing M365 spear phishing, and Eric versus his home's vacuum conduit.

Relevant Links Below!

Podcast Episode - YouTube
Podcast Episode - Spotify

Alright, your turn. What was your first "oh no, I broke something" moment, and what habit did you walk away with because of it? Andy is collecting these with an eye toward doing a whole episode on them, so do not hold back.