Five troubleshooting habits that actually get you paid. The cert was just the cover charge.

GM IT pros,

Happy Sunday. New format I'm trying — call it Sunday Sharpening. The Friday roundup tells you what happened. Sunday Sharpening is the one thing worth getting better at this week.

This week's thing: troubleshooting. Specifically, the version of troubleshooting that separates someone who passed the A+ from someone who actually fixes the printer.

A cert can get your resume past the filter. It will not save you when Outlook is broken, DNS is lying, the printer is possessed, and the user swears they "didn't change anything." That part — the part where you stop guessing and start figuring out what's actually wrong — is the entire job. Nobody tests you on it. Everybody pays you for it.

So: five habits. Build them and your career compounds whether you ever take another exam or not.

-Stetson

Five habits. Boring on paper. The reason senior people get called instead of you.

The single biggest gap between a junior and a senior is this: juniors start fixing. Seniors start reproducing. If you can't make the bug happen on demand, you don't understand it yet — and any "fix" you ship is just a coincidence wearing a tie. Get the user to walk you through it. Watch it break. Then form a theory. Skipping this step is how you end up "fixing" three things, breaking a fourth, and writing the postmortem on Sunday night.

DNS. Auth. Network. Storage. Permissions. Time sync. Disk space. The ticket says "Outlook is slow" — it is almost never Outlook. Burn this into your brain in this exact order so you stop reaching for the exotic explanation when the answer is a full C: drive or a cert that expired at 2 AM. The boring stuff causes 80% of outages and gets fixed in 80 seconds. Save the deep magic for the 20% that actually deserves it.

If you change five settings and the issue resolves, congratulations — you have not fixed anything, you have just stopped seeing the symptom. You don't know which change did it, you can't document it, you can't repeat it on the next box, and when it comes back in three weeks you start from zero. Change one thing. Test. Revert if it didn't help. This is slower for ten minutes and faster for the rest of your career.

Open a scratch file at the start of every weird ticket. Two columns: what I tried, what happened. That's it. Keep it for the duration of the incident, then paste the highlights into the ticket when you close it. This is the single highest-leverage habit in the whole list. It turns one ticket into reusable knowledge, makes you look organized when management reads the ticket later, and means the next time the same problem hits, you find your own answer in fifteen seconds via a quick search of your notes folder.

The GUI is going to lie to you. The service status will say "Running" while every connection times out. The disk usage chart will show 60% while a hidden log file is eating the partition. The web console will hide the actual error in a tooltip you have to hover for. Knowing enough shell — even just tail, grep, df, ss, journalctl — flips you from "I have to escalate, the GUI says it's fine" to "I can see what's actually happening." Five commands. The career delta is enormous.

Tape this above your monitor. Five questions, in this order, every time something breaks:

1. What changed? (Last patch, last config push, last user action, last reboot.)
2. Who is affected? (One user, one team, one site, everyone?)
3. Where in the stack? (User / device / network / app / global?)
4. Can I reproduce it? (If no, get the user on a screen-share before guessing.)
5. What does the log actually say? (Not what you think it says. Open the file.)

Most tickets get solved at question 1 or 2. The hard ones get solved because you didn't skip 4 and 5.

Habit #5 is the one most people skip because the terminal feels intimidating. That's the entire reason I built Shell Samurai — hands-on Linux, real commands, browser-based sandbox, no signup wall to read the first lesson. Spend twenty minutes tonight, walk into Monday and stop flinching when someone says "SSH in and check." app.shellsamurai.com if you want to skip the pitch. Built by yours truly. Shameless plug, zero regrets.

If you've been doing all five of these for years and you're ready to get paid for them somewhere new, the ITSG job board has fresh listings every week — community-sourced, IT-only, no recruiter spam. Yesterday's roundup pulled out a few in the $90k–$200k range if you missed it.

One more thing before you log off: I vet every sponsor before they ship. The one below made the cut — give it ten seconds of your scroll, and if it's for you, click it. If it's not, at least you know I didn't waste your inbox.

That's it. Pick one habit. Just one. Practice it on the next three tickets that hit your queue and notice how much less of your week you spend re-fixing things you already "fixed."

Back to the regular snark-filled roundup next Friday.

Stay paranoid. Stay patched. See you next Friday 🤠

-Stetson