Keith Berenson

With my 40th birthday approaching, I’ve found myself taking stock a lot recently, reflecting on where I’m at in my life. When I do, I can’t help but wonder how much differently things might have turned out if, in my high school years, I’d somehow been wiser in the ways of the world. Yeah, I know—hindsight is 20/20. But man, it’s so tempting to consider. What if I’d known then all the stuff I’m still completely clueless about now?

I can only imagine what that would have been like!

It’s fun to think about, though: me at age 17, armed with all the knowledge, sophistication, and life experiences that most people besides me appear to accumulate by the time they turn 40. I’d face all the same adolescent woes, to be sure, but this time I’d be able to keep those challenges in perspective, benefiting from a level of maturity I lacked as a teenager and continue to lack today.

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It’s a tantalizing prospect. There’s no telling what my financial situation might be like today if I had understood the value of a dollar in high school, or of a hard day’s work—things that, to this day, remain a total mystery to me. In a similar vein, what kind of career might I have now if, back then, I’d just been able to buckle down and study with the kind of dedication and attention span that, two decades later, I still don’t have?

Honestly, I’d give anything to go back in time, meet my younger self, and impart to him valuable life lessons about maybe friendship or perhaps cherishing your youth or something—I’m not really sure, as I’ve still yet to experience any of these realizations. But how great would that be?

And don’t get me started on high school girls! Man oh man, if I’d had the ability at 17 to just ask a girl out on a date without experiencing the crippling anxiety I still suffer as an adult? And with the increased confidence other people apparently develop in their 20s and 30s? You can be sure I’d have been roaming the halls with the cocksure swagger of a true ladies’ man, able to walk right up to any girl and talk to her about her interests or whatever it is people who have gained some level of self-assurance talk to them about? Wow! Mothers, hide your daughters!

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Of course, it’s not just about the prom dates my younger self could have had. If he were equipped with the basic knowledge most of my normal, well-adjusted thirtysomething peers seem to possess, my high school self would be able to get good grades, ace the ACTs, and get into a great college—later landing a good job and having a rich, rewarding life. Talk about a leg up, which I could in no way give him!

The truth is, I think constantly about what it would be like to start over again as a teenager who understands the importance of believing in himself, a good night’s sleep, generosity, perseverance, alcohol moderation, well-rounded interests, personal hygiene, and moral courage. Because I still have absolutely no idea about any of those things, and that stuff seems like it would be useful to know at any stage of life, high school or otherwise.

Maybe it’s indulgent and pointless to sit around fantasizing about the youth I could have had. I don’t know. But if it is, there will no doubt come a day 20 years or so down the line when I’ll look back on the man I am at this moment and wish I had known now what I still won’t know then.

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