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I feel like I do not understand computers and feel stupid working in IT

July 14, 2026 · Andrew Minga

Every senior IT pro I respect has a version of this story.

A thread on r/sysadmin this week went viral for one reason: honesty. Someone admitted they feel like they do not understand computers and feel stupid working in IT. Hundreds of replies. All from experienced practitioners who feel the same way.

Here is what the vendor industry will never tell you: the complexity is not a skills gap, it is a product strategy. Microsoft alone ships hundreds of feature updates per year across Entra, Intune, Defender, Purview, and Azure. No one person fully understands it all. The feeling of falling behind is not incompetence. It is the correct response to an environment designed to outpace you.

The dangerous version of this is when that feeling leads to silence. Teams stop asking questions. They accept defaults. They skip the review because admitting confusion feels worse than the risk. That is exactly where misconfigurations get buried and stay buried.

This is the kind of thing the team at C Spire Business talks about openly with IT leaders in the Southeast. The goal is not to know everything. The goal is to have the right conversations before something breaks.

If you have stayed quiet in a vendor meeting because you did not want to look uninformed, what would it take to change that?

#MicrosoftIT #ITLeadership #CyberSecurity #MSP #EnterpriseIT

According to the 2023 Verizon Data Breach Investigations Report, misconfiguration and errors accounted for 21% of breaches, making human mistakes the second most common root cause, surpassing many forms of external attack. The report notes that these errors often stem from complexity and time pressure, not carelessness.

Originally posted on LinkedIn on July 14, 2026.