180 days to Bar Mitzvah: cautionary tale

I once had a very long and in-depth conversation with someone about the value of setting a good example for your child. It was back when I was masquerading as a real estate agent -- and failing miserably, badly enough that all I thought about each day was how I could extricate myself from this latest mid-life career change and go back to the old one. Except on Tuesdays, when I'd drive around and look at houses. Looking at houses can cheer anyone up.

Looking down at the rubble I'd made of my professional life, I figured that its value to my child was as a cautionary tale. "Don't be like me," I could say. "See what happens?"

"I disagree," said my conversant. "You need to stick it out so he can see you overcome something. You want him to think of you as a successful person."

The point was well-taken, but I ditched real estate a month later, a full two weeks after being called into my broker's office and threatened with termination unless I started selling some houses. So I got to quit and be fired, sort of, which makes the guy staring back at me from the mirror seem like a real stud.

Over the past two-and-a-half years, the Jawa has been an active party to my latest career ups and downs. These ones are unique, as the job I have started out great, only to slide downhill in a series of small-yet-constant managerial changes. It could have -- and was, for a year -- the best job I've ever had. Instead, I come home sullen and angry, like Kevin Arnold's dad.

Unfortunately, here's what my son has learned: my dad's boss is out to get him.

Which is of course wrong. It's much more complex than that. Nobody's "out to get me," and it'd be a folly to assume that I was important enough for anyone to spend a minute devising ways to "get" me. But he's twelve years old and all he sees is that his dad goes somewhere every day and comes back in a lousy mood. Obviously, it can't be that his dad made a series of really bad career decisions and non-decisions, ending up with exactly what he deserved, could it? If he knew that, how could he help but conclude that his father was unsuccessful?

Problem is, now that he's twelve he's going to make his own mind up about everything he sees. The time where I had the option of demonstrating grace under pressure is over. I should have listened, maybe not to the point of flogging an obviously dead real estate horse but instead by taking charge of yet another career change. I could have hunkered down in the style of my friend Martin McNally, who once spent eight hours a day for almost an entire year trying to find a job. I could have shown my Jawa that kind of focused effort. "I may not end up with a great job," I could have said, "but one thing I know is that whatever I get will be something of my choosing, and that I will go into it prepared to give 100%."

So what is he seeing now? A cautionary tale along the lines of what I just told Ray, the 28-year-old market analysis guy who sits across the row from me, the "writer." "Ray," I began expansively after setting off the latest in a long series of conflicts with the sales people who own my soul, "pay attention to what you do in your 20s and 30s. Because if you don't, you'll end up like me."

Now, says the "woe is me, yeah, right" crowd. How bad is it to be you? I'm not saying it's awful to be me. I've got this great wife, this only occasionally privacy-demanding Jawa, a stupid dog that everyone loves. It's not like I'm pandhandling for change on Market Street. But I know who I am. I know that these are the consequences for not taking it seriously when everyone else was out there chasing careeres in their 20s. I'm not shiftless; I'm aimless, but it still stung a little bit when I learned that the $1.3 million house I was writing about a few months ago had just been purchased by a kid I'd coached back at Saratoga High School in 1987.

I don't say it so Ray will think, "Wow, that guy's got it bad." I'm saying because I know I screwed up in my 20s and 30s and I'd be a deluded fool to tell myself anything else. Instead of chasing a career, I prolonged my adolescence for as long as possible, diving enthusiastically into new careers, then torpedoing them after a year or so, or accepting jobs even though so many sirens had been going off in my head during the interview process that I could barely hear what the guy across the table was saying.

Maybe the biggest risk of presenting yourself as a cautionary tale is that it makes it seem like you're looking for pity. Not me. I'm being realistic. I'm also letting him know the reason why it's unlikely he'll be getting the same latitude I got during my formative years.

The hard part is that you want, with all your heart, to find a way for your child to avoid your own pratfalls. Or maybe he should, so he can learn for himself. Twelve years in and I have no idea which is preferable, but all of this is done with an eye toward helping him become a happy, successful adult. And I'm here to tell you that if the career part of your life isn't what it should be, and it's your fault it ended up that way, well, it gets pretty gloomy on some days.

But there's no way to sugarcoat it and the game's not over yet. Why screw things up if not to learn from it? I think there's value in him seeing how bad decisions can trip you up, leaving you in situations equal parts confounding and frustrating.

He's at least lucky that, while he's got me as an example of poor management, he's got his mother to show him the benefits of focus and drive. The kid wants to discuss the meaning of life, have fun figuring out difficult math problems, deconstruct words or explore the hidden meanings of popular culture, I'm right there. He wants to learn how to succeed, that's Sandra Bullock's arena. Between us, we've got it covered.

Back to that conversation from a few years ago. I'll admit that I was only partly right, and there is some big value in the comeback story. Who doesn't love tales of redemption? Should I manage to get it together before he hits adulthood (or even after), you'd better believe I'm going to go all evangelical on him, preaching from whatever pulpit the values of never giving up, staying focused and working toward a reachable goal. And most of all, the hardest one, of not losing faith in yourself even when everyone else has long since gotten tired of your sad little story.