Cadillac ran a great ad on TV not long ago. Some white-toothed, studley guy zips around joyfully in a silvery, leather-rich Caddy, smug as can be. Things are obviously good. Very good.

Then comes the pay-off line: “Life,” the narrator intones, “is just high school with money.”

No kidding.

And because I’m headed to my 40th high school reunion next month, I think about this a lot.

Did I say ‘headed’? What I’m doing is jumping into Mr. Peabody’s Way-Back Machine, closing my eyes and dialing up 1972. I haven’t seen 97 percent of my high school class since the day I was handed my diploma. I haven’t been back to my home town in 35 years. This, as they say, is a Big Deal. I’m not sure I’m ready for it.

Am I thin enough? Do I have enough hair? Is my house big enough? Am I cool yet?

As everyone knows, we are permanently forged in the crucible that is high school, and spend the subsequent decades compensating for it. The bill is now due. A jury of my peers is about to present me with the ultimate report card.

Did I make the honor roll?

Smart, beautiful wife? Check. Three handsome boys? Check. Lovely home under construction in leafy Boston suburb? Check. I have been fortunate, and no one knows it better than me.

Then the metric gets a little more complicated. What did you do with your life? Have you put it to good and meaningful use?

I like to think it’s a bit early to decide. But on the journey I’ve tried to follow the advice of iconoclast Edward Abbey, who said that the only thing one truly and genuinely owns is one’s personal experience. So I would happily trade, a second time, economic security for adventure – the chance, once again, to eat cold, boiled seal meat with the Eskimos, to party in the Kremlin, to witness that mutiny on the Upper Nile.

I head into this little soiree with far less confidence than I might affect. As English novelist L.P. Hartley observed, “The past is a foreign country: they do things differently there.”

But it should allow me to answer some critical questions.

Like, who of that post-hippie/late-Vietnam generation is still with us, and who has passed on?

Have my classmates led rich and fruitful lives, and how have they chosen to define those terms? Do I have the maturity, confidence and restraint to judge them not, lest I be judged?

And, most importantly: Will my old girlfriends be there?

It should be amusing. I’ll let you know how it goes.

Written for Accion’s employee newsletter, September 2012

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