Yesterday was my last day with Playboy Enterprises. I was with the company for just shy of 12 years.

Back in 2000 I was working at a small educational software startup as their Network Manager or somesuch title -- basically I was "the computer guy" for the whole company. I made some great friends there, but the company was not, in my opinion, being run very well. The company was trying to swerve it's fundamental mission to jump into the Internet IPO bubble, and were doing so right around the time the bubble started to pop, and there were personal issues between the founders, and really looking back I probably wouldn't take the job again. But there was I was, trying to do my best as a one-man IT department and getting very frustrated.

I got really mad about some decision of the CEO one day and thought about just quitting as a Dramatic Gesture. But then I wondered if I really did just quit without anything else lined up, how hard might it be to find another job. So I pulled up HotJobs.com and typed in "Chicago, Macintosh". About 60 jobs came up, which made me feel better. Out of sixty listings, surely I could get a job. And then I noticed that one of the listings was for Playboy. "Well," I thought, "that's a brand name. I've never worked for a brand name."

I had my resume with me as a text file (back then on a Zip disk or something?) and so I dashed off an online application. My cover letter was something along the lines of "I'm really mad at my boss today, so I'm very interested in this job. Please see my attached resume to see that I'm a hard worker." And sent it off.

Just sending the application was a relief, somehow like venting. I felt better just having done something about my situation. And of course I'd never actually get hired with a cover letter like that. I went back to my work with a lighter heart.

A few weeks later I got a postcard with the familiar Playboy rabbit head logo on it. "Thank you for your application. We are in the process of reviewing all applications and if yours meets our needs we may contact you. Blah blah blah." Oh well, I'm sure they send one of these to everyone who applies. I stuck it on the fridge as a fun conversation piece at parties.

And then a few weeks after that they actually called me and I went in for an interview and they hired me. Boring, I know, but my thanks to a great HR person for taking a chance on that cover letter.

I started as a Graphics Technology Specialist, which basically meant "Mac tech", working mostly with the magazine. I do have one credit in the magazine from that time, I did an infographic (basically just a map) for the February 2002 issue.

There's a pretty small set of questions that most people would ask when they found out I worked for Playboy. Let's get them out of the way.

Q: Do you all work in bathrobes?
A: No.

Q: Do you get a free subscription?
A: It's not a subscription exactly, but there was copy in my office inbox every month.

Q: Are there naked ladies walking around the office?
A: There was a photo studio in the Chicago office where they did a lot more product shots than anything else. But they did do model shoots sometimes. They'd put up signs that said "Hot Set, Do Not Enter". But they'd forget to take them down, so they'd be up for weeks, which tended to devalue them (the sign that cried wolf, as it were). So there was this one time when I had been trying to track down one of the photo assistants for some software install and I went barrelling into the photo studio and was half-way across the room calling out the photo assistant's name when the head photographer quietly said, "Fuzzy, it's kind of a bad time." I glanced up and there was a model half-draped in a curtain standing in front of a fake window. I said Sorry about 600 times as I made my way out of the room even faster than I'd come in.

Q: Have you ever met Hef?
A: Not really. I did go to the Mansion out in LA in 2001, to do some work on the Macs in Hef's home office, and walked by an office and noticed that he was there with back turned to me. He seemed to be busy, though, and I hate to interrupt people. I did get to meet some spider monkeys, though.

Hef rarely came to the Chicago office, but he did in 2005 with the Girls Next Door Girlfriends(tm). They stopped by the office and it was kind of a zoo, but as swept by I did get introduced to the Girls(tm) who thought my name was cute and then I shook his hand and then he was swept off to the next part of the office.

There are ways it was a crazy job. I mean, yes, there was a party put on by the Special Editions group once a year that featured models in lingerie standing around in our employee break room.

But it was, of course, also a job. For the vast majority of the time I was there, Playboy was a publicly-traded corporation. After Enron, that meant we had to comply with the Sarbanes-Oxley rules. The number of User Account Change Permissions Request helpdesk tickets I have completed…

And really it's about the people. We had people come and go, but I was lucky enough that a core group of the IT department was the same for most of the years: all my bosses I'd now call friends. I have friends who came to work there, and coworkers who became good friends. (I had some links to people's site in that paragraph, but I took them out--there are too many people and I'm going to forget someone.)

By the end there, I was Director of IT and oversaw the IT part of the team who closed down the Chicago office. The giant bronze bunny came down and the offices are now occupied by admin staff of Children's Memorial Hospital, who recently moved to a new building in the neighborhood. Yes, that is a twist, isn't it?

I worked from home for a bit after the office close, and now I'm done. It's all a little bittersweet, but hey, at least now my sweet mother doesn't have to be embarassed about where I work.

And now I'm going to take a little time off. I vacillate between a list of 600 awesome projects I'm sure I'm going to conquer, or just playing some video games. We'll see my friends.

(I'll be getting off the couch at least a little, because Impress These Apes starts its seventh season on Monday and I'm the new host. Won't you join us at ComedySportz on Belmont for a show?)