As a mid-20s Windows sysadmin focussed on automation for web hosting, getting laid off in '01 really kicked my ass. Want someone who knows how to reliably and

As a mid-20s Windows sysadmin focussed on automation for web hosting, getting laid off in '01 really kicked my ass. Want someone who knows how to reliably and "securely" (by 2001 standards) host hundreds of ASP sites on Windows 2000? Only a few people know how to do that and I was part of the team who figured it out first. Want to turn a hundred freshly racked servers into Windows hosts in a couple hours? I'd just finished building a system to do that. Nobody was hiring for those skills. For years. Web hosters were struggling to stay alive and automation wasn't on their radar. Enterprises were building servers as pets, not cattle. Virtualization hadn't really arrived yet. I'd get interviews because my resume was interesting but in a buyer's market smart and gets shit done is less valuable than particular experience. It was two years before a local hoster was hiring for technical roles, and took another two to claw my way back to the type of work I enjoyed. As the broader IT market started catching up to my specialty, I took a couple year detour into our IT department so I wouldn't risk being caught out again without more broadly-applicable experience. Better to be easily employable than maximize my earnings... --- Something I don't see mentioned in the comments here is that the 2000-2001 apocalypse launched the bootstrapped startup economy (and YC). Talented people couldn't land full-time W2 jobs, so many of them launched startups on a shoestring financed with their savings or by consulting. They'd gain some traction and become a "lifestyle business", or more, or be acquired by one of the big DotCom survivors.