I

’d never been the type of parent to doubt or question myself, or overthink things. Until it came to Shimi and this rough patch he’d hit shortly after he turned 14… and never actually emerged from. Not yet, anyway.

It was hard to pinpoint where it began. A headache here, a stomachache there, going late, or skipping school entirely. Occasional became habitual and eventually a pattern no one could ignore; not his rebbi, not the school, not us.

At first, we went down the usual route: wakeup calls, firmer reminders, letting him face the consequences at school.

It didn’t work. It just made things worse. Shimi was shutting down, avoiding us, avoiding everyone.

“That’s because every time you push, he’s not learning responsibility — he’s learning shame,” the therapist we finally spoke to explained to us. It was a lightbulb moment.

We continued speaking to the therapist, Menashe, having several sessions even before Shimi agreed to go for help himself. Slowly, we began internalizing another approach: gentler, slower, lowering the shame, helping Shimi build internal motivation without jumping to rescue him or swinging to frustration or pushing too hard.

“For a kid like Shimi, who’s struggling with anxiety or depression or a combination, pressure is the worst thing,” Menashe emphasized. “It makes him freeze, not move. It tells him he’s failing before he’s even begun, and that pattern gets wired in if we’re not careful.”

And so, slowly, painfully, we changed our approach.

We still woke him in the mornings, encouraged him to leave on time.

But we let go of the outcomes, lowered the pressure, made sure he knew we accepted him regardless.

If he got up at 10 a.m. and went to school, we celebrated it quietly, like the small win it was.

If he slept in till 3 p.m. and came down moody and grumpy and ashamed, I offered him an omelette and kept my face neutral — not disappointed, not proud, just, it’s okay to have a rough day. This isn’t who you are.

And slowly, slowly, something shifted.

He began getting up on time here and there. He surprised us one Shabbos by sitting through the whole meal, beginning to end, just because he felt comfortable enough to. Or he woke up late, but still went to catch half of morning seder. That was also something.

Going to therapy helped Shimi a lot, and we continued speaking to Menashe regularly as well, to make sure we were setting ourselves up for success and supporting Shimi in the best way possible.

Sometimes, I felt a little despairing.

All this time, effort, money, working on myself and my reactions — for what? Shimi was still struggling.

But Menashe reminded us that this was a long game.

“Your job isn’t to get him perfect,” he told us. “Your job is to keep the door open, to make the climb safe enough that he can try again tomorrow. These tiny shifts you see? They add up. They’re the beginning of real change — the kind that lasts.”

I wanted so badly to believe him.

And now, several months later, we were holding on tight to the approach we’d committed to. No pressure, no intensive motivational attempts, just love, presence, encouragement, and gentle reminders.

It wasn’t easy to stay calm when I wanted to clench my fists and scream just get up already!!

But it was the only way. I knew firsthand that the other option had backfired badly.

So I continued doing what I had to do: knocking gently on his door with a good morning reminder, and giving him space if he rolled over and went back to sleep, or asked for a few more minutes, or ignored us completely. Let him get up when he felt ready.

When he did make it to school at a normal hour, the good feeling was incredible, because he did it on his own, not under threat or pressure or with exhausting both of us with an unwinnable power struggle.

And when he didn’t — it was okay. Because with months of excruciating work, I’d learned to let go of the outcome.

Thankfully, his rebbeim were amazing. We were in contact regularly, I kept them posted if Shimi was having a hard morning and would be coming late or not at all, and they made a big deal out of pumping him up with positivity when things were going well.

It was a struggle, a rough patch that was more than a patch — we’re talking almost a year already — but I could see glimmers of hope.

And then something strange happened.

F

rom one day to the next, Shimi was no longer struggling to get out of bed.

It was one Tuesday when I noticed. Shimi got up and left the house, on time, and it was the second day running.

Whoa.

When it happened again on Wednesday — Shimi racing out the door with barely a muttered ‘bye’, just in time — I was really confused.

What was going on? Was our hard work paying off? So why did it feel so… off?

Naftali was as clueless as I was, and I decided to broach the subject with Shimi directly. Over late-night shawarma sandwiches — his favorite supper, it couldn’t hurt — I found a moment when no one was around, and asked him casually, “I noticed you’ve been waking up earlier recently, which is amazing. Any special reason or just finding it easier these days?”

Shimi shrugged, mouth full of spiced chicken and barbecue sauce. He swallowed, and then said, “Yeah, Uncle Avi told me if I go to morning seder every day until Chanukah, he’ll take me to Florida. I’m up for the challenge.”

I froze a little. Wait — what?

“He… promised you a trip to Florida? With him?”

Shimi shrugged, playing it down, but clearly proud of the deal. “Yeah. He said he’s going for Chanukah; he’ll take me along. And he calls me every night to check if I went. Said he’ll check in with my rebbi also, randomly. But he doesn’t have to, I’m doing it.”

Pride at my son’s perseverance fought with anger, betrayal, fear. What was Avi playing at here? And how could he do it without even asking us first?

And the whole idea — a chart, an incentive system. Clearly he assumed that what worked for his six-year-old would be the game changer we’d never thought of for our teenage son. But he was wrong.

“This,” I hissed to Naftali later that night, when Shimi retreated to his room, “this is exactly what Menashe warned us against. The big flashy external motivations that end up pushing you backward, because when they’re over, everything regresses…. We’ve worked all year to try build his internal motivation, what was Avi thinking?”

“He’s trying to help,” Naftali said evenly, and okay, he was trying to help — but you don’t help by interfering and undermining the parents who have invested time, sweat, money, effort, and who knows how many tears to try and support their child healing in his own time and pace.

Avi’s help… I had a bad feeling about it.

I

was right.

Within a couple of weeks, the situation became very clear.

Shimi was going to morning seder every day, on time. And then he would show up back at home sometime in the early afternoon and crash. Or he’d make it till the end of the school day, but spend all evening holed up in his room with his earphones in, stay up half the night playing on the computer, or disappear to hang out with a friend and not go to sleep till way too late.

Yes, he was going to school every day — consistently, punctually. But everything else was floundering — his sleep, his internal motivation, even therapy appointments. “I’m fine, I don’t need help,” he told me at some point, asking me to cancel his next therapy session. “I’m going to school every day, see? Uncle Avi told me I won’t need therapy when I’m back to myself, and I am.”

But he wasn’t.

I could see the hollowness, the cracks forming, the way he collapsed into bed after morning seder and never even tried to get up for Shacharis — “Uncle Avi said morning seder is enough, we can add more later,” he told me one evening.

Since when was my little brother a psychologist? I swallowed the sharp retort on the tip of my tongue — this wasn’t Shimi’s fault, — and finally made the call I should’ve made right away.

“A

vi,” I said, when he picked up the phone. “What’s this about a Florida trip and Shimi?”

“Oh, he told you?” I hear my brother’s grin in his voice. “Knew it would help. He’s doing good, no?”

“Actually — not really.” My voice was uptight, I knew, but I couldn’t bring myself to tone it down. “He’s going to morning seder, yeah. But that’s all. Everything else is going downhill, all the stuff we’ve been working on. And — there’s a reason we’re not doing charts and prizes. We’re working with—” I caught myself. It wasn’t Avi’s business, the therapy stuff. “We’ve been working very hard on helping Shimi. This plan — it’s going against everything we’re working on.”

“But it works,” Avi said. His voice was genuinely confused. “Miri, it’s working, you see it’s working. And he’s happy, and committed, and doing it.”

I closed my eyes briefly. How to explain that short-term doing it might come back to haunt us in the long run?

How to explain that coming in with a whole new incentive scheme in the middle of a fraught, complex situation wasn’t helpful or healthy?

How to explain that actually, we didn’t want Shimi flying off to Florida with his uncle during Chanukah, which was a special family time, and something we wanted Shimi to be a part of, however he could show up?

Avi exhaled loudly, like I was the one overcomplicating things.

“Miri, this isn’t such a big deal. He needed a push, I gave him one. And it worked. That’s all.”

“It’s not ‘all,’ Avi.” My voice cracked despite myself. “You’re seeing one piece. We’re seeing the whole picture. And this push might have helped on the outside, but it’s tearing apart everything we’ve been doing to help him.”

If I could tell Avi one thing it would be: Your help is causing far more harm than good.

Avi

I’ve always had a thing for struggling teens. Maybe because I was always the energetic kid getting into trouble in yeshivah, too many ideas, couldn’t sit still, that type.

These days, the very same thing that made my rebbeim tear their hair out is the reason I have my own flourishing real estate business at the age of 29, and after having spent years building myself up after feeling like a failure for all my teen years, I feel like I know a thing or two about what kids in the trenches need.

And it’s not the tough love I grew up with, the shape-up-or-ship-out thing that was the reason I got kicked out of two yeshivahs and spent an entire painful year trying to find my footing somewhere good for me.

But also, the hands-off, give-them-time-and-space approach? I don’t see it working that well, either.

Take my nephew, Shimi. Great kid, sense of humor, we’ve always gotten along. I don’t know when it started, but he’s been clearly struggling a little recently — and I watch Naftali and Miri tiptoe around him like they’re scared to trigger a landmine.

I don’t want to judge — I’m not in their place, and my Ayelet is just 6, though you’d better believe she can bring on a teenage eye roll like the best of them when she’s in the mood. But I get frustrated watching sometimes — I get Shimi, I could help him, and what they’re doing… it’s sweet, it’s not bad or anything, but let’s face it, it’s not working.

Like that Shabbos meal when we were in their house.

Everyone sitting around the table, ready to start, Shimi’s not there.

“He’ll come when he’s ready,” Naftali said, and Miri shrugged, and I just thought — why?

All he needed, I was sure, was a little push, someone who had some expectations of him — not pressure, not anger, just a confident “let’s do this.”

“Let me try,” I told them.

I could tell Miri was a little nervous, but I’m not scared of grumpy teens. They don’t intimidate me; I’m too close to being there myself to get scared off by a kid who’s just lost and stuck.

I knocked on his door like it was a regular thing, not timidly like I was scared of poking the bear, not assertively like I was there to tell him what to do. Just like I expected him to want to be part of the world again.

“Shim?” I called out, keeping my voice light. “Come on, man, we’re holding up Kiddush. Not starting without you.”

A beat of silence. Which didn’t bother me at all.

“Listen,” I said through the door, lowering my voice and keeping it light. “If you come down now, I’ll make sure you get first pick of dessert. That caramel truffle thing Chaya brought? It’s yours.”

Another pause. Then a sound like a groan from inside. “Avi, leave me alone.”

“Nope,” I said, cheerfully.

A thud, like he’d just landed on the floor. “Fine. I’m coming.” “Good,” I said, and I waited outside till he appeared — sweatshirt and sweat pants and a scowl that didn’t fool me for a second.

I grinned, clapped him lightly on the shoulder. “Come on, bro. Let’s go make an entrance.”

Walking back down the stairs with him behind me felt good — like I’d unlocked something simple that didn’t need to be complicated.

We talked a lot during the meal, or rather, I talked a lot, and Shimi responded first with grunts, then a word or two, and finally, actual conversation. We talked about sports, and about my job, and about the vacation home we’d bought in Florida, we were planning to go for Chanukah. His eyes went wide at the description.

That was when I had my great idea.

I

ran it by Chaya first. She was okay with it, which was honestly really nice of her — it would be our first time going — but I thought taking Shimi could make a real difference to him.

I called him Sunday evening.

“Shimi, man, you have a minute? I want to run something by you.”

He sounded like he was rolling over and sitting up in his bed. “One sec. Yeah. What’s up?” His voice was pitched low and a bit hoarse, like he was trying to sound energized but was still waking up. It was 6 p.m. I felt a pang. This boy needed help, motivation, something to give him energy and drive, not this soft “whatever you want” message that was leaving him to drag himself out of bed late in the evening and hate himself for it.

“Remember I told you about the Florida trip we’re taking for Chanukah?” I said.

“Sure?”

“How would you like to come along                                                                         ?”

There was a sharp intake of breath, and a long silence. “You… mean it?” Shimi asked, finally. There was a new note in his voice, like something inside him had come back to life.

“Wouldn’t have offered if I didn’t.” I leaned back, let the moment settle.

“Wow,” Shimi said, finally. “I mean… that’s really nice of you. Are you sure?”

“I’m sure,” I said. “But there’s a condition. This is a deal, okay?”

This time, the silence was a little fraught. I waited a moment, then said, “This trip is a big thing. And I want it to feel earned, I want you to feel good coming, like you did something real to get here, right? So here’s what I’m thinking.”

I paused, but he didn’t respond. I took that as a sign that he was listening. “Morning seder. Every day. From now until Chanukah. From beginning till end, no lateness, no skipping, no excuses. You do that, you’re on that plane.”

There was an even longer silence.

“Every day?” Shimi’s voice sounded like it was teetering on the edge of disappointment. “I mean… I don’t know. I don’t know if I can….”

“Shim, listen to me,” I said, lowering my voice. “You don’t have to know you can do it. You just have to start. One day at a time. And I’m telling you, I know you. You’ve got way more in you than you think.”

“Yeah. Okay.” His voice warmed up a little. “I’ll try. I’ll do it. How many weeks till Chanukah?”

I laughed. “Just over three. You got this.”

A

nd he did. He really did.

I wondered from time to time what Miri and Naftali thought of their son’s transformation. I assumed he’d told them right away about the trip; either way, he was doing something he hadn’t been doing for weeks, maybe months: getting up every single morning and getting to school on time.

And I kept my end of the deal: I checked in every single night. “How’d it go? Man, you’re killing it! Keep it up, bro!”

I could’ve won a prize for motivational quotes by the end of the first week.

And Shimi was thriving. Some nights he didn’t say much, some nights he opened up a little more. I started to hear about his struggles, his fears, how this was really boosting his self-esteem.

“I actually understood what we we’re learning today, ’cuz I’ve been there for a few days running,” he confided one night. “I don’t remember the last time I understood what was going on in the classroom.”

Which broke my heart a little, but also? Made me realize just how important this progress was for him.

“It’s actually becoming weirdly normal to get out of bed before 9 a.m.,” Shimi told me one day, laughing, and I cheered like this was worthy of major applause. Honestly? For Shimi, it was.

I was a little surprised I didn’t hear anything from Miri. But I assumed she was busy, and I didn’t reach out either, not wanting to intrude. Maybe this whole thing was hard for her, seeing that Shimi had needed something different than what they were doing. But obviously, she was happy with his incredible turnaround. Who wouldn’t be?

W

hen my phone rang late Motzaei Shabbos and Miri’s name flashed on the screen, I answered with a smile, assuming it was — finally — an acknowledgment of Shimi’s amazing progress.

“Hey, big sis! What’s up?”

“Avi,” she said, her voice weirdly tight. “What’s this about a Florida trip and Shimi?”

“Oh, so he told you.” I shrugged. “Yeah, I figured it would help. He’s doing good, no?”

There was a pause.

“Actually… not really,” she said.

I blinked. “What do you mean ‘not really’? He’s up every morning. On time. Doing what he hasn’t done in months.”

“Avi,” she said again, and this time her voice had an obvious edge, like she was trying not to lose it. “He’s going to morning seder, yes. But that’s all. Everything else is going downhill. And there’s a reason we’re not doing charts and prizes. We’re working with—”

She stopped short.

“Working on what?” I asked bluntly. “I’m not trying to judge, Mir. But whatever was going on — it didn’t seem to be working. And this trip, it brought him back to life. You don’t see it?”

She exhaled. “We’ve been working very hard on helping Shimi. This plan — it’s going against everything we’re working on.”

That made me annoyed, because it sounded good in theory, but did it actually make sense in real life?

“But this is working,” I said. Why didn’t she see that? “Miri, it works. You see he’s doing it. And he’s happy. Motivated. Showing up. Don’t you see that? Isn’t that what you wanted?”

She sighed, wearily. “Of course we wanted progress. But not this way. This is — more harm than good.”

Okay, now this was really getting out of hand. Maybe she didn’t like my reward system, fine. But it wasn’t harming Shimi. It was giving him the first chance he had in months to feel good about himself, to see visible progress in something.

“Miri, this isn’t such a big deal. He needed a push, I gave him one. And it worked. That’s all.”

“It’s not all, Avi.” She stopped again. I could hear her swallowing. “You’re seeing one piece. We’re seeing the whole picture.”

I felt a stab of sympathy then — not because I agreed, but because she sounded so tired.

But I still didn’t get it.

“I’m just trying to help him,” I said. “He’s a great kid. He could go far, but he’s lost his drive. And people respond to goals. To incentives. He needed to believe he could do something again — and now he does.”

“I know,” Miri said. “But help isn’t help if it breaks something we’ve spent a year trying to rebuild.”

Breaking? Was she for real?

If she didn’t want to thank me for putting myself out there to help her son, fine. I could handle it.

But to criticize like that, to blow this all up and turn me into the villain? That I wasn’t going to stand for.

Besides, to me? It looked like Shimi wasn’t breaking at all.

It looked like he was finally coming to life.

If I could tell Miri one thing, it would be: I’m not trying to ruin anything, I’m just trying to give him one success to build on — and it’s working. 

(Originally featured in Mishpacha, Issue 1091)