ABOUT THIS EPISODE
We throw an alert when a disk hits 85 percent. Nobody has ever built the monitoring system for the person who gets the alert.
Andy Syrewicze is joined by Paul Croker, a UK IT pro who founded 404 Stress Not Found, a nonprofit built because tech and cyber people had nowhere safe to talk about burnout. Paul walks through the perfect storm that put him on a Berlin stage telling his own story, and Andy gets into the MSP years that surfaced a generalized anxiety disorder. They get specific about hero culture, the all-nighter nobody asks questions about, and why a wellness app and a pizza do not touch the structural problem underneath.
Chapters:
00:00:00 - Cold Open: An Industry That Is Good at Breaking People
00:01:11 - Welcome and Episode Intro
00:02:12 - Meet Paul Croker and 404 Stress Not Found
00:03:15 - News React: AI Agents Climbing Out of the Sandbox
00:06:31 - The Agent That Hacked a Gym to Get Into Pilates
00:08:13 - News React: September Patch Tuesday
00:08:56 - A Record 974 CVEs and What Is Driving the Curve
00:11:53 - Where Do These Vulnerabilities Actually Live?
00:14:58 - Nerd Hour Begins
00:15:44 - Dan Scott's BES Server Post and the Flashbacks
00:16:27 - Andy's Novell, AS/400, and BES Nightmare
00:18:15 - Paul's First BlackBerry Deployment
00:20:21 - BlackBerry Messaging as a BCDR Channel
00:22:33 - Sonic on a Phone While Everyone Else Played Snake
00:23:23 - Nerd Hour: Andy's Static Site and Caddy
00:25:10 - A Two Line Config, and Why Simple Wins
00:26:19 - Main Topic: Burnout, Anxiety, and Mental Health in Tech
00:27:07 - Paul's Path From IT Generalist to MSP Owner
00:29:31 - The Pax8 Berlin Talk and the Perfect Storm
00:32:57 - Building the Meetups, and Richard Tubb in Newcastle
00:35:08 - Andy on Generalized Anxiety and the Job That Got Away
00:37:48 - Pressure Arrives in Layers
00:39:56 - The Nasty Gram That Was Not About Work
00:41:36 - We Alert on 85 Percent Disk and Nothing on People
00:42:39 - Heartbeats: The Monitoring Metaphor That Actually Fits
00:45:43 - The People Who Show Up to Learn the Warning Signs
00:47:37 - Why IT Is So Good at Breaking People
00:48:32 - Every Interaction Is a Problem, and It Wears You Down
00:51:08 - Attackers Need One Win, Defenders Need All of Them
00:52:04 - Hero Culture and the All Nighter
00:53:31 - Missing Documentation Is Why the All Nighter Happened
00:55:05 - What Does Not Work: Wellness Apps and Pizza
00:57:13 - Go Kick Some Leaves
00:58:28 - Communities Are the Fix Nobody Reaches For Soon Enough
01:00:10 - The Free 404 Portal and Resources
01:01:19 - The Mentor Who Taught Andy to Say "The End"
01:02:26 - You Are Not Your Job Title
01:03:12 - How to Reach Paul
01:04:07 - Wrap Up and Outro
Resources / Show Notes:
- 404 Stress Not Found - Paul Croker's nonprofit for IT and cyber mental health: https://404stressnotfound.org
- Paul Croker - LinkedIn: https://www.linkedin.com/in/paulcrokeruk/
- Richard Tubb - Tech Mental Health Spaces: https://richardtubb.co.uk/404-stress-not-found/
- The Cyber Express - Patch Tuesday hits a record 974 CVEs: https://thecyberexpress.com/patch-tuesday-september-2026/
- Anthropic - Claude Mythos Preview, AI finding and exploiting zero-days: https://www.anthropic.com/research/mythos-preview
- ABC News Australia - AI agent hacks a gym website to book a Pilates class: https://www.abc.net.au/news/2026-08-10/ai-assistant-hacks-gym-website-aus-cyber-attack/107007986
- Caddy - single binary web server with automatic HTTPS: https://caddyserver.com
- SysAdmin Weekly: https://www.sysadminweekly.com
- SysAdmin Weekly Newsletter: https://newsletter.sysadminweekly.com
- AndyOnTech: https://www.andyontech.com
- Project Runspace: https://www.projectrunspace.org
- GitHub Discussions: https://github.com/ProjectRunspace/sysadmin-weekly/discussions
