64 days to Bar Mitzvah: career menopause

My final day as an official employee of the San Francisco Examiner (actually, just “The Examiner,” but if I throw that “San Francisco” in there it makes it seem like I’m working for the paper that Wm. Randolph Hearst used to own, not some weird little freebie whose web presence is powered by citizen journalists) was full of confusion. Appropriately, since the last two years of my tenure has been notable mostly for weird gaps in management and job status changes that suddenly appear without prior warning. I posted something about this being my last day on Facebook and drew mostly concerned inquiries and comments saying, simply, “Whaa?”

So for everyone out there wondering what happened, it’s a good thing. It’s been in the works for months. And the end result, unless someone calls me Monday morning and says, “Game off. We were just trying to get rid of you without having to pay unemployment,” is that, like Jay Leno and NBC, I’ll be signing off only to reappear the following week in a different format. That is to say that starting Monday, I’ll have the same job – populating the paper’s two Sunday regional real estate sections each week – but will be doing so as a freelancer, not as an employee. Yes, it is what I wanted.

Even though it’s what I wanted, I understand that it could go a number of ways. This isn’t the first time I’ve stepped back, tore my keycard off its lanyard and declared myself a “freelancer.” I could be back in six months, stuck in some other cubicle somewhere else, a little bit more dead than I was this time. We’re hoping that’s not what happens.

Because this could also mean that today is the last time I’ll ever have to sit in an office. What if it works, and Monday is the beginning of this great run that ends only when I keel over one day, sitting at my desk in some retirement resort, while the retired Sandra Bullock is out riding a bike or cross-country skiing or whatever you do when you only age chronologically? What if in five years I’m signing books at Barnes and Noble and we both look back and say, “Wow, why did I wait so long to do that?” How great would that be?

Because my last week coincided with Sandra Bullock’s trip to Zurich, it has been lacking most of the “we’re going to miss having you around here” events that normally accompany a job change. The most I could manage was including my boy Ray in my usual Friday falafel outing. Weirdly, it marked the first time I’d ever gone out to lunch with a co-worker at The Examiner. Normally, I go the loner route, shoved into the corner at Noah’s Bagels, reading the “other” newspaper. Or worse yet, slamming down a sandwich at my desk, my back to the room, looking at si.com.

Some people are cut out for the workaday world. My wife, for example, is always hooking up with “work friends,” going on work-sponsored outings, meeting for happy hours. She even keeps in contact with her former co-workers, getting together a few times a year for dinner. If there’s one thing we all should know by now, it’s that it is unwise to try to compare Sandra Bullock’s work experience with mine. You just don’t want to go down that road, unless you’re trying to make me feel bad. And anyone who didn’t spend their childhood tying tin cans to puppies’ tails or pulling the wings off of butterflies would not begrudge her success. My hat is off to her, revealing a growing bald spot.

I’ve got to hand it to me. Here I am, 23 years out of college, and I’m still walking around trying to be a writer. I didn’t fall into some vague – yet insanely lucrative – consulting career. I didn’t become a lawyer, as good of a son as that would have made me. You’ve heard the joke about the Jewish mother whose son is flailing about in the ocean? “Help, help! My son the lawyer is drowning!”

Nope. In the face of what has often been crippling feelings of failure, the disheartening realization that what everyone tells me is a “gift” is only worth about 10% of what I’d make if my “gift” were an ability to analyze the stock market, and the sickening feeling that comes from using my “gift” to do things like help sell Fords, I’ve persevered. It helps that Sandra Bullock functions as not only my wife and partner but also as the modern-day equivalent of a Renaissance art patron.

At age 45, quitting my job now is like getting a tattoo of a spider web across my face. It puts me one step further from employable. All of the pieces are in place: my biggest fear, the couple of times I’ve tried to freelance in the past – and make no mistake, I absolutely loathe the word “freelance” – I’ve panicked a couple of months in because of money. “I need income!” I’d shout, just before signing on to a contract job at AOL, even though I’d had lunch with the guy who would be my boss and couldn’t hear most of what he was saying because there were flashing red lights and sirens going off in my head, saying, “DO NOT TRUST ANYONE WHO DESCRIBES THEMSELVES AS A ‘STRAIGHT-SHOOTER.’ NOTHING GOOD WILL COME FROM THIS. YOU WILL BE TRAUMATIZED BY THIS MAN.”

Six months later I was gone, my legacy a blistering email to my boss, which, I later heard, sent him into an existential tailspin that lasted the length of time it took him to drive to Napa with his wife the following Saturday.

As Elvis would say, and has said, “It’s now or never.” That’s the scary part of next Monday. If the powers that be at The Examiner have been telling the truth, I’ll have the same income six months from now as as I had six months ago. That takes care of the money panic. Three years of writing a weekly newspaper column should give me some kind of leg up on the me of ten years ago, shouldn’t it? Someone must have read the thing. My name’s got to ring a bell somewhere.

And then there’s this blog thing. Several months ago, I sat at Barney’s, a hamburger restaurant in Noe Valley, with Teduardo and his clan. “You should write a book about the year leading up to a Bar Mitzvah,” he told me over garden burgers.

“I’ve got folders on my desktop full of 25-, 35-, even 50-page semi-novels,” I thought. “I’ve got unfinished screenplays, short stories, three-page plays. They sit around collecting virtual dust. I grow older and the number of people who think I’m talented shrinks each day.”

“The only way I’m going to finish something is if I know people are expecting to read something from me every day,” I said, and left it at that.

If I’m any good, you’ve been reading the results of that conversation for the past six months. Now, with every obstacle, real and invented, out of the way, it’s up to me to turn it into something someone might want to buy someday.

Wish me luck.