An Error Has Occurred.

I am in the school that says regret is to be avoided, that regret ages you. What qualifies as a regret? For me, it's something you think of, several times a year, for several years. It’s something that you will never really, truly feel OK about.

Overall, I’ve managed to avoid getting too worked up over things I have or haven’t done. I mean sure, if I had waited to secure another job before quitting the one that was making me absolutely miserable in the spring of 2002, I probably would have largely avoided the cycle of low-level debt that I only just emerged from this year. There are, in retrospect, many many life situations that I could have handled better. I’m alright with it all.

But a couple of things, despite my trying to move past them, have become bona fide regrets. One of them is never having learned a musical instrument until now. The other occurs to me even more frequently.

In the year 2000, I met with the assistant managing editor of Entertainment Weekly magazine. At the time, I was the “entertainment editor” of “FoxNews.com.”

I had been the one to push for and launch a new entertainment section at Fox two years before, and in retrospect, it’s hilarious what I got away with. Since we were so low on the media totem pole, and since my bosses were just happy to have an enthusiastic person going out and reporting stories for our new section, that meant a raft of interviews with Erykah Badu, Brian McKnight, Ben Folds, the guy who played Ben on Dr. Katz, Professional Therapist and a whole bunch of other stuff that I’m pretty sure our readership couldn’t have given two craps about.

A Fox contributor put me in touch with the EW person when I mentioned I was looking around for a place where maybe more than 500 people would read the stories I was doing.

To me, meeting this editor was a big deal. I had started reading Entertainment Weekly in my early 20s, and I knew the magazine like the back of my hand. When I decided at age 23 to move to New York, I wrote to their movie critic at the time, Ty Burr, told him that he was my favorite reviewer at the magazine and asked him if he would have an informational interview with me. I wasn’t just arse-kissing, either – I was that big of a geek. I thought Ty Burr was one of the cleverest, most intelligent entertainment magazine writers I’d read. And Ty turned out to be nice, too – not only did he answer my letter, he took me out to lunch and got me a meeting with the assistant managing editor.

So here I was, meeting with a new assistant managing editor some six years later, only this time I’d written stuff. I actually had some experience, and some confidence. I was psyched. After weeks of meetings and phone tag and a very rigorous writing test, the editor called me up one day. “Here is what I would do with you,” she said. “You gave us a very strong writing test, and I think you have potential. But you still need to develop your voice. If you were interested, I would offer you a very junior position here, probably assistant editor. And I would pay you about $45,000.”

The minute she hit that salary figure, my face fell. $45K? That was significantly less than I was making at Fox. I mean sure, I could live on that little, if I stopped drinking $10 martinis and going to my chi chi gym and generally living my modestly comfortable life. But why should I? Why not just stay at Fox, where I had tons of autonomy and a better salary, “develop my voice” there, and go back to EW when I had more bargaining power? With a pit in my stomach, I said no thanks. I was freelancing for this fabulous new magazine and Web site, Inside, and other places. If I stayed the course, a better opportunity was bound to emerge, right?

Wrong, oh, wrong, oh, wrong.

I got laid off from Fox the next year, and Inside collapsed the year after that. I interviewed again at EW, only this time at the Web site. My former contact there was gone. I made it through two rounds of cuts and then failed to get an offer.

It’s possible that if I’d said yes to that woman back in 2000, I’d now be wrinkling my nose at the prospect of writing yet another fricking summer movie preview or power 100 listing or CD capsule review. It’s possible I’d be fantasizing about writing about “meaningful” stuff, or just plain getting out of New York.
Still, I can’t help but think that my answer to that phone call was a big, big mistake. It’s done, and I accept it. But I earnestly, painfully regret it.