I was working at a dotcom, a geocities knockoff, that had recently gone public and had climbed up to around $30/share. I had options that I had already exercised as I was being clever thinking I'd sell them after holding them for a year. But I was still locked out as an employee, and we all watched as the the price dropped over a period of weeks. After a while it was under my exercise price so I lost money. All told it wasn't a lot of options and not a lot of money I lost either. A couple of decades later I sold the position to take the loss and offset other stock gains.
The layoffs happened in two rounds - the first round the severance packages were rumored to be generous. The second round, my round, we got two weeks pay.
This was spring of 2001. People had trouble finding a job, but they were still out there. I got another one for summer of 2001 but they laid me off after three months, and then 9/11 happened ten days later.
After that it was brutal. Up here in Portland, no one was hiring at all. One time a job opening came up and all the applicants were taken to a large conference room where we all took a silent written exam together, with applicant names anonymized to protect against discrimination. I got that offer and rejected it, which completely freaked out the agency recruiter that was representing me. Nike and Intel would occasionally advertise programming contracts for $12/hour - php, perl - and they would be swarmed with applicants. I'd talk to agency recruiters but they kept getting laid off, so it'd be a different one every couple of weeks.
I was taking unemployment, I toyed with a business idea, and I eventually thought I'd try out contracting - I cold-called a prospective client that had a small company, and he brought me on for $25/hour, usually working at his condo with him and ordering pizza together. A few months later - Feb. of 2002 I believe, I got my first more official-ish contract for $55/hour, and I've been in business as a backend architectural contractor/consultant ever since.
Over that period of tim, I found that consulting is kind of a leading indicator of the economy. When times are bad, maybe you can get good gigs at employers that need help but are reluctant to commit to an employee. But if times are just starting to go bad, non-employees can be let go quicker.
Anyways, remember that the dotcom crash got mixed up with the post-9/11 chaos, so the next crash probably won't have the same impact. Also, remember that recessions are cyclical. It gets better by definition. I still believe that 2001 and 2007 were Weird in a way that recessions usually aren't. And a recession might even be good for the younger generation since they tend to clear away people that have jobs but shouldn't, leaving more future openings for the folks that are still hustling and learning.