Career on Pragmatic Tech

The Mistakes I Made (And Why They Led Me to Build My Own Password Manager)

Pragmatic Sysadmin — Thu, 26 Mar 2026 12:00:00 +0000

The Mistakes I Made (And Why They Led Me to Build My Own Password Manager)

Every IT professional has a graveyard of mistakes behind them. Most of us just don’t talk about them until we’re several drinks in at a conference, or until we’re writing a blog post that we hope will save someone else the same pain.

I Was the Only IT Person for 3 Years: The Documentation I Wish I'd Written

Pragmatic Sysadmin — Wed, 04 Mar 2026 07:10:00 +0000

The Call I Didn’t Want to Get

Three weeks after leaving my job as the only IT person at a mid-sized company, my phone rang. It was Mike, the guy they hired to replace me.

“Hey, uh, do you remember that backup script you set up? The one that runs on Sundays? It’s throwing an error and I can’t find where it’s configured.”