“Now listen up,” Reuven said, clearly annoyed. “You’re heading for nothing but trouble. You’d better stop before it’s too late. I wish you’d listen to my advice, Ari! I’m getting tired of always trying to tell you, but talking to you is like talking to the dang wall!”

Ari (the name has been deliberately changed here) had probably heard similar words a hundred times before. He was a young man of sixteen in my alternative high school program, Beth Rafael, in Miami. My program was nicknamed “Laz’s Last Stand.” They either made it in my program or ended up in rehab . . . or behind bars. Most, thank G‑d, graduated from my non-graded program, got their high school diploma, and have moved on to lead positive, productive lives.

He was close to the record, having been kicked out of more than ten schools in the past six yearsAri was a great athlete, full of life and personality, but he had some rough experiences in regular school. He was close to the record, having been kicked out of more than ten schools in the past six years. Unsuccessful in his close-knit community, he viewed himself as an outcast, and had turned to the streets for acceptance. Reuven, a fellow classmate, was trying to offer some words of advice. Ari, it seems, had once again been out all night long doing who-knows-what. He showed up mid-morning and laid his weary head upon the table.

“You don’t know how good you got it here,” Reuven continued. “But even this opportunity you’re gonna blow just like all the others! You’re gonna get locked up, bro . . . if you live long enough.”

With that, Reuven slammed his fist on the table, but Ari was either fast asleep or simply chose to ignore the commotion.

I put my hand out and motioned for Reuven to lay off.

“Look,” I whispered to Reuven, “talk to him when he wakes up. But I think maybe we should try a different approach.”

He shot me a glance of disbelief and remarked, “He’s gonna kill himself the way he’s going! Someone’s gotta do something!”

“Agreed,” I responded. “Wholeheartedly. But has this approach ever worked for him? That’s what he’s been hearing, probably from everyone who knows him, for the past two, three years straight.”

“So, what then? We should sit back, do nothing . . . and watch him slowly kill himself?”

“No. I’m just saying maybe there’s a better way to reach him.”

I promised Reuven that we’d discuss things together and try to come up with some strategies that might work. But there was this uncomfortable feeling, something that always bugged me but that I never quite verbalized. And yet, every so often, it would come bubbling up to the surface, like it was waiting to be validated, to be dealt with.

Then I had an epiphany and realized that all those thoughts of “doubt” were there for a solid reason. I had it all wrong—and, to a certain extent, we’ve all missed the boat here. Yes, I know that sounds like a mighty bold statement, but allow me to explain what’s been bothering me all these years.

I refer to that tricky and very sensitive notion of setting the other guy straight, a.k.a. “reading someone the good ol’ riot act.” You know the one, this murky gray area of us knowing what’s really proper (or thinking that we do), and putting our friends, family members, and even the “Joe Shmoes” we don’t know so well, in line. It’s the one that some folks have made it their special mission—rebuking your fellow human being.

This is a mighty sensitive area that, at best, requires “kid glove” treatment and some real thoughtful, deliberate actions—not rash, emotional responses. I speak from some experience, having raised seven children (now all adults on their own). I’ve also been working with alienated teens and individuals with special needs for more than thirty years. Not that I have any definitive answers per se, except that I know that when it comes to the art of rebuking, I usually keep a very low profile. Others, it seems, have given this equal footing and rank it right up there with the “Ten Big Ones.” Chabad philosophy stresses the angle that we have to help each other out on all levels. But it also teaches us that when it comes to spiritual growth, the real work, the hard work, starts with the “man in the mirror”—with ourselves first.

When it comes to the art of rebuking, I usually keep a very low profileWhat’s bugged me all these years is that the Torah uses a double-whammy expression to convey this message of rebuking others. It says rather bluntly, “hoche’ach tochiach”—which is usually translated as “you should surely rebuke”: not just one word indicating “rebuke,” but two Hebrew words to really get out there and give ’em the ol’ what-for! Knowing what we do about human nature, I ask you a question. Do we really need a double expression from the One Above telling us to rebuke someone? Was G‑d Almighty worried that we might not get in there and tell somebody, “Hey, you’re messing up, and I know better—I know what’s best for you!” Wouldn’t it have been enough for it to say in the Torah just the one Hebrew word tochiach?

There are those who seem to thrive on putting others in line, of telling them what to do and what not do, and getting some sort of holier-than-thou satisfaction of putting them in their place. They’ve become the “rebukers,” the crusaders to save us all . . . from ourselves!

It did help to study Tanya and listen to the deep words of the Alter Rebbe, the first Chabad Rebbe, on this double expression of rebuke. The Alter Rebbe stresses the latter part of that verse where it says you should surely rebuke et amitecha—the “one that is with you.” In other words, only those with whom you are very close, the Alter Rebbe explains in the 32nd chapter of Tanya, should you rebuke. Interesting that the number thirty-two in Hebrew corresponds to the word lev, which means “heart.” Furthermore, he writes, it has to be done with love and compassion. Let’s face it here, folks. No one enjoys being put in his or her place. Nobody relishes the experience of being on the receiving end of a personal “dis.” We usually accept this sort of stuff only from a loved one. A stranger telling us off doesn’t sit too well and, in fact, often leads to the opposite desired effect. We tell the guy to take a long walk off a short pier.

Change doesn’t come easy, and changing harmful or negative behaviors is tricky business—and often a long, uphill battle. The Alter Rebbe tells us that here it just might work if, in fact, someone who’s close to the guy messing up does it. The rebukee, if you will, knows that the rebuker is a close friend or family member and has his or her best interest at heart.

Upon further research, I discovered that this word “hoche’ach” is used twice in the Torah portion of Chayei Sarah. Both are in the episode of Eliezer, Abraham’s servant, being sent on a mission to find a wife for Isaac, Abraham’s son.

It’s quite a mission, and Eliezer, with Abraham’s personal instructions and blessing, succeeds big-time. Standing near a watering hole at the edge of town, Eliezer puts this wheel into play and calls out to the “G‑d of Abraham,” asking for some tell-tale signs to know who is the right pick for Isaac. He’s basically looking for someone who is a mentch, who shows kindness—even to a stranger.

Change doesn’t come easy, and changing harmful or negative behaviors is tricky businessIf she offers me water to drink, Eliezer stipulates, and also offers to give water to my camels, then this is the one that “hochachta” for Isaac. Seems like a mighty strange word to use here. It’s the very same root as the word for “rebuke.” The foremost biblical commentator Rashi picks up on this unusual expression here and says that it actually means “berarta”—“You chose.”

My cerebral cortex went in high gear. B’reirah in Hebrew means “to choose”, “to select” and “to clarify.” Maybe that double expression of “rebuke, rebuke” is mistranslated? Perhaps it also means more to clarify than to simply rebuke? The act of choosing and selecting is part and parcel of the act of clarifying. It’s a matter of shedding some light on the options and selecting the best possible choice. And, sure enough, when the same word is used twenty-nine verses later, Rashi explains that it means “to clarify, to inform—and so too for every expression of the word hochachah in the Torah”. Whereas all these outdated translations put in print for the double expression, “You shall surely rebuke!” Rashi is telling us that it really should read, “You shall surely clarify.”

It’s no small difference here. It’s a difference of night and day. Both may try to get the person to “see the light,” but one does it with a hammer, which has little chance of success, while the other does it with love, compassion and some common sense.

Furthermore, it’s not a matter of coming across as holier-than-thou. It’s not even coming from a “religious” perspective of “saving” this lowlife and getting another notch on the belt. It’s simply a matter of shedding some light on the subject and helping the person in need get things straight—to see with more clarity. Then, and only then, is he or she in the proper position to decide, to choose which direction to go. Our job, then, Rashi points out, is not to rebuke but to illuminate! Not to give ’em a piece of our minds, but to offer them peace of mind.

Let’s go back to the situation with Ari, and more specifically, how Reuven and I decided to handle things. It was a plan taken right out of Rashi’s sage interpretation and advice. First, I gave Reuven the “green light” to speak with Ari. Sometimes, more often than not, teenagers listen to a friend more than a teacher. I told Reuven that words of rebuke, the ol’ fire & brimstone routine, always fell on deaf ears, and thus, a new strategy was warranted. “Ari doesn’t respond to that. Why not try a total unemotional vibe. Put out the consequences of his behaviors. Spell it out. Maybe, just maybe, he’ll make some better choices. But in any case, I’d wait till he wakes up and has a good meal under his belt first.”

It wasn’t until a few days later that Reuven caught up with Ari. I couldn’t help eavesdrop from the opposite corner of the room as the conversation took a different turn.

“Ari,” he started. “Let’s analyze the situation here. Things are good now ’cuz business is rolling. But eventually you’re gonna get busted. It’s just a matter of time. If you stop now, you’ll make less money—at least for now, until things pick up in a proper and legal way—but you’ll have a clean slate. If you carry on this way, you’re probably looking at ten years minimum jail time, maybe more.”

He simply put the cards on the tableAri tuned in because Reuven wasn’t laying any guilt trip or holier-than-thou number on him. He simply put the cards on the table.

“One path might be tougher at first,” Reuven continued, “but you won’t have to worry about jail time or messing up your life. The other is great for now, you’re riding high, but sooner or later the bubble is gonna burst. Think how it’ll be then. For your friends and family. For you!”

I was amazed when Reuven suggested that they write down the choices, the pros and cons with all the consequences, on paper. Maybe, just maybe, I thought to myself, with the situation all spelled out and clarified, along with the concern and the friendship of a loving friend, Ari will make better choices.

Rashi is telling us that words of rebuke do very little to change the situation. Clarification, on the other hand, places the onus of choice on the person involved, without the guilt, and free of any rebuker’s ego.

Torah is often compared to light. In this regard, the deeper we look into the Torah, the clearer and sweeter things become. Thanks, Rashi. I owe you one. And maybe we all do.