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The Best Advice I’ve Ever Gotten: “Don’t Be Sorry, Be Smart”

“Don’t be sorry, be smart.” That pithy piece of advice was given to me — and a couple thousand high school students over the years— by my English teacher, who I’ll call Mr. Blake for the purposes of this essay. It may sound glib or even obnoxious at first listen, but this clever tidbit has stuck with me for over three decades.

It was originally doled out as a rebuke to those sorry souls attempting to apologize for their forgotten homework, their tardiness to softball practice, or their lack of comprehension of Faulkner’s indecipherable prose. But really, it applied to just about every issue large and small in our adolescent lives, from safe sex to sobriety to basic human kindness — none of which were paramount to the reckless, thoughtless teenagers we were at the time.

Kids can sniff out pretty quickly who’s preaching and who’s teaching and it was clear Blake was no pastor. Perhaps his words meant more than they might have had he remained the righteous Pilgrim his Yankee ancestors probably were. But he was far from perfect. When his first marriage crumbled, he seemed as lost and angry as anyone would be in that situationBut ultimately, his choices turned out to be dead on, right down to the beautiful blended family he eventually created.

Blake remained a source of frank advice for me long after the 11th grade. He counseled me about where to head to college, a complicated decision due to my complicated home life. A couple of decades later, I picked his brain again when the time came for my sons to apply to school.

“Don’t be sorry, be smart” is a terse reminder to think before you speak, to take a beat before you act. That’s not always easy. As an adult, I try to pause before hitting send — figuratively and literally — as often as I can remember to do so. I ask myself, are you sure? If not, can this decision wait? Might my words or actions come back to hurt me or someone else? Would inaction be more effective than action this time around?

My kids — now grown — have heard me say these five consecutive words so many times now, the phrase has become a family punch line. But my sons know it’s more than a joke. It’s part of a larger life lesson about circumspection and self-reflection. Will it stop them from making mistakes? Not always, but it just might on those occasions when they think about which of these outcomes would feel better: doing something right or apologizing for doing it wrong.

That doesn’t mean that this advice is only about avoiding mistakes. Turned on its head, it’s a positive push to take chances when opportunities knock, to move outside of your comfort zone, to go for “it” — whatever your personal “it” might be. How many times have you kicked yourself for what you didn’t say or do when you had the chance, whether it was telling a friend you love her, or trying out for that play or that team or that job. “Don’t be sorry, be smart” is far more than an acerbic rejoinder to sentences that start with the words “I wish I hadn’t…” It’s an antidote to sentences that start with the words, “If only I had…”

With that in mind, the next item on my to-do list is to find Mr. Blake and tell him how valuable this little piece of advice has been. I’d be sorry if I didn’t.

Filed under: Work + $$


Amy Barr

Amy Barr is a veteran magazine editor. She started her career as an editorial assistant at Working Mother magazine and rose through the ranks to become Executive Editor before joining Time Inc. to launch the online edition of Parenting, where she served as managing editor. Amy was also part of the online launch teams for, What to Expect When You're Expecting, The South Beach Diet and Everyday Health. You can find Amy on Twitter at @amylbarr.


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