“This,” I said eagerly, “Is the very latest Apple Macintosh, the easiest way to learn graphic design on a computer. Even turning it on is simple!” I pressed a button and –bongggg!!!– the screen came to life. “See?”

She burst into tears, burying her face in her hands.

Sometimes fate, or maybe something deeper, drags you face to face with what could have been.

I think that happened to me last week.

There’s a fellow at work no one likes. To be fair, maybe I think that because I don’t much care for him either, except that I’ve heard the same story from almost everyone: “No matter what you do, TJ* will screw it up, then blame you.”

At first, I thought TJ was simply misunderstood, so–bastion of diplomacy that I am–I took him to lunch to work things out. His first words: “The web marketing team is incompetent and stupid. You people don’t know the first thing about marketing. Or web.”

Since I’m on the web marketing team, that wasn’t exactly a stellar start.

I stared, aghast, at the sobbing woman. Her companions, eleven older, carefully groomed men and women, glared at me. They refused to touch the training guides I’d spent hours carefully crafting. Each sat in front of a brand new Mac computer that I would have given my eye teeth to own.

They wouldn’t so much as touch those computers.

“I-I don’t understand,” I stammered, “Aren’t you here to learn Mac publishing?”

An old guy in the back stood, picked up the computer, dropped it on the floor, and walked out.

My lunch with TJ, off to a bad start, rapidly got worse. I smiled, I cajoled, I reasoned. He glared. The web team was arrogant, stupid, and never listened. Nobody, especially not some idiot information architect (i.e., me), was going to change TJ’s mind.

In four years, it’s only gotten worse. Any idea my team suggests to TJ will be rejected, any approach we take will be met with contempt, and TJ will be so wildly unpleasant that every project is an end-to-end ordeal.

Their unemployment cards were waiting at the corner of each student’s desk. At the end of every lesson I was supposed to sign each card, certifying that the student was eligible to receive an unemployment check.

At the rate we were going, I thought desperately, the entire two hours would pass without so much as a mouse click. Was I still supposed to sign those cards?

Last week’s meeting with TJ left me as close to tears–or possibly homicide–as I’ve ever come in a professional setting. A coworker also in the meeting must have noticed, because he hastened to apologize for TJ’s behavior.

“I think that chip on his shoulder is because he used to be some bigwig ad sales guy,” he explained, trying to soothe my ruffled feathers.

Whoa. ” TJ was in ad sales? In media?”

“Yeah. He worked for some national magazine or other, got laid off.”

If that’s true, then maybe, just maybe, I know why TJ hates us so much.

I got tough. “Maybe you don’t want to be here,” I said, sternly, “but if you don’t at least try I can’t sign your cards. Now, please! Turn on your Macs!”

I stared at my 11 remaining students and held my breath. At last, my tearful lady reached for the computer….bong. Soon I heard startup chords all over the room. My students weren’t happy, but they were trying.

“Open your workbooks to the first chapter: Making a Nametag,” I said.

My very first computer job, way back when, was teaching desktop publishing to out-of-work typesetters. Steve Jobs’ dream of a graphically rich computer, which positioned fonts and images wherever you wanted them on the page, had indeed revolutionized publishing. Now anyone with a Mac could publish professional-looking materials without a typesetter.

Typesetters had been the ubergeeks of the publishing world. They could glance at your text and translate it into the code needed to turn it into a page on a printing press. (Ironically, the languages they used became the forerunners of modern HTML and XML)

But now, thanks to the Mac, almost overnight these guys had become unnecessary and unemployed. And, often, bitter.

Very bitter.

The state of California decided to retrain them by hiring a “young people” (me) who knew Macs and desktop publishing as an instructor/evangelist. I fit the bill: I was barely 20, I loved Macs, and I was working three jobs to save up for one of my own. My third job was now teaching these guys “technology transitioning skills,” i.e., how to desktop publish with a Mac computer.

I was, as yet, too young to really get the irony of that: The state had hired a naive young gadget freak to teach embittered, unemployable gadget freaks to embrace the very machine that had made them embittered and unemployable in the first place.

That it actually worked–my students became pretty daggone good computer graphic artists over the next six weeks–had almost nothing to do with me. Instead, in a testament to bravery, experience and just plain old smarts, I watched a dozen (well, eleven–the old fart who broke my dozenth Mac never came back) devastated professionals rebuild themselves in that class.

I hope they all got jobs; I know at least eight were hired by the end of the class.

It took me years to put it in context, and even longer to understand just how privileged I’d been to have that experience. I have never, ever seen a more graceful recovery than those typesetters turning themselves into desktop publishers.

In the last decade, ironically enough, the publishing industry that abandoned those typesetters has itself tottered, thanks to the Internet. Publishing houses have never really figured out how to play nicely with the web, and the world that once gave me a great, fulfilling career is pretty much gone.

Of the several hundred people I knew in the industry, I can count on both hands those actually still employed in print magazine publishing.

Some of us flourish. Some of us recover. Some…don’t.

Those who sold print ads were the real moneymakers in media; the guys who worked like dogs and sometimes pulled in Ferrari-level salaries. They were especially hard-hit; web advertising all but sucked the print ad business dry. I’ve talked to some mighty bitter former ad sales guys.

So, TJ…is that what’s behind all your nastiness? What would it be like, spending your last few years to retirement working with a web marketing team? Having to listen to some idiot IA named Cynthia telling you to do the same things that tanked your former identity?

Am I right back where I started, all those years ago with the typesetters?

Heck, TJ. Maybe I’d act like a jerk, too.

*(short for “The Jerk” and not his real name)