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Chapter 2: On One Condition

I explained Donny’s ultimatum — access to one inappropriate site in return for blocking all the others

ASa general rule, being the filter guy doesn’t make me very popular with teenagers.

Especially not teenagers like the ones in a yeshivah I’ll call Derech Chochmah. The yeshivah is home to boys who are struggling in their Yiddishkeit, at home, and in school, and they often use technology as an outlet, albeit an unhealthy one.

Boys like the one the rosh yeshivah, whom I’ll call Rabbi Feldman, asked me to meet — a tenth-grader who was using his phone to access inappropriate material online.

“He’s waiting for you in here,” Rabbi Feldman said, pointing into the large conference room.

Then he lowered his voice to a whisper. “Donny has a great deal of potential, but it’s buried under a lot of resentment. I’m warning you, Yossie, he’s probably going to be your toughest client. Just do whatever you have to do to help him.”

Rabbi Feldman ushered me into the room and inclined his head toward the far end, where a boy in a black hoodie was sitting, glowering at me.

Like I said, I’m not popular with teens.

Seeing Rabbi Feldman, the boy rose a few inches in his seat and adopted a less confrontational expression.

“This is Donny,” Rabbi Feldman said, gesturing at his talmid.

“Hi, Donny, I’m Yossie Strickman.”

He didn’t respond.

Rabbi Feldman clapped me on my arm. “I’ll leave you to it.”

He walked out, and then it was just me and Donny.

I sat down next to Donny and placed my laptop on the table.

“Hi, nice to meet you.”

Donny made a dismissive noise and looked away.

I didn’t want to pressure him to speak, so I opened my laptop quietly and started setting up his account. Out of the corner of my eye, I could see Donny staring at me intently, but I acted oblivious.

After a few minutes, Donny finally broke his code of silence.

“So, how exactly are you going to ‘help’ me today?”

Donny spat out the word “help” like it was toxic.

The filter will have to wait, I decided. There were other issues we needed to address.

“I’m guessing you don’t think this filter is going to be very good for you,” I said mildly.

“No, I don’t.” Donny’s eyes were flashing. “Every time someone with a beard offers to help me, I end up worse than before.”

I knew that Donny couldn’t be open to having a filter put on his phone while he was holding such intense negative emotions inside, and I prodded him gently.


Donny laughed bitterly. “Yes, really.”

And with that, he launched into a tirade about rabbis, yeshivos, and Judaism in general, which is usually how my meetings start.

Over and over, he said, “They don’t really care about me,” as if everyone in his life — his parents, teachers, and rebbeim — had only ever acted out of obligation to him, rather than true concern. Since they didn’t really care, Donny rejected everyone’s support and ensured that their efforts did more harm than good.

But while he was doing a good job of disguising his feelings with self-righteous indignation, it was clear Donny felt terribly misunderstood.

It wasn’t that they didn’t care enough. It was that they didn’t listen enough. But over the course of my career, I’ve found that teens can rarely tell the two apart.

I knew that for Donny to allow me to filter his phone, he needed to know I cared about him enough to listen, so that’s what I did. I let Donny speak, responded empathetically, and tried to make him feel heard.

After about twenty minutes, Donny ran out of steam. When he finished, his shoulders dropped, his face softened just a bit, and he finally looked open to hearing what I had to say. I wanted to bring his attention back to the filter, but first I had to make him realize that I wasn’t there because his technology abuse was destroying his Yiddishkeit. I was there because his technology abuse was destroying his life.

Most teenagers in Donny’s situation believe that Judaism is the reason they can’t use the Internet freely to do what they want. In truth, the kind of material Donny was accessing would have been unhealthy for anyone, no matter what his religion.

But I have a beard, so it wasn’t going to be easy to convince him of that.

“Donny, I’m here to help you learn how to use technology correctly so you can live a normal, healthy life. The things you’re doing now are going to affect every aspect of your future. You won’t be happy if you feel dirty and isolated all the time. You’re not going to have functional relationships or a good marriage if you have all this schmutz in your head. This isn’t about Yiddishkeit. It’s about you.”

“Okay,” he said after a pause. “I’ll let you put a filter on my phone.”

“Donny, I’m impressed with—”

He held up his hand, stopping me. “On one condition.”

“What’s that?” I asked, already back on my computer managing his account.

“Leave this site open.”

Donny took out his phone to show me the name of the website he wanted me to leave unblocked. My fingers froze over the keyboard of my laptop.

There’s no way.

“That’s my condition.”

Donny leaned back in the office chair and folded his arms across his chest. He wasn’t going to budge.

I was at a loss. I usually use GenTech’s filtering program, configured to my standards and adapted to meet my clients’ needs, but I knew they would never allow access to a site full of explicit content. And even if they did, could I sanction such a thing?

I nodded slowly and pushed my chair back from the massive table.

“Let me call the filter company and see what I can do.”

“I’ll be here.”

I left Donny alone in the conference room and hurried outside, dialing my rebbi’s number.

“I’m working with a boy who will let me filter his phone, on one condition,” I said.

I explained Donny’s ultimatum — access to one inappropriate site in return for blocking all the others — and asked my rebbi if I should even entertain the thought of asking the filter company to override their system and allow it.

My rebbi was silent, so I elaborated.

“As of now, this kid is using his phone to access a lot of inappropriate content. My end goal is to block his access to all of it, but today that seems as impossible to him as swimming across the Atlantic Ocean. If I let him keep just one site on his phone, the whole transition will seem manageable.”

My thinking was that with the availability of this one website, Donny would feel like he could cope with the loss of hundreds of others. Loosening the filter just a bit would mean it wouldn’t suffocate him.

“If that’s the case,” my rebbi said slowly, “then you can allow it, on one condition. Check in on the boy in a week and discuss it again. Maybe he’ll be willing to change his mind.”

I agreed right away. Next, I dialed my GenTech contact, who wasn’t enthusiastic, but granted permission once I explained the situation. Relieved, I went back inside, updated Donny, and installed the filter.


A week later, I called Donny to check in on him.

“Hi, this is Yossie Strickman speaking, how are you?”

The line went dead.

I updated my rebbi, who said not to push.

“Call him again in another week.”

We didn’t last another week. Two days later, I got a call from GenTech.

“I’m sorry, Yossie, but we can’t keep this up,” the manager said apologetically. “What you’re trying to do for this kid is incredible, but we need to either block this site or remove the filter from his phone.”

I had known that the site wouldn’t be allowed indefinitely, but Donny wasn’t ready to take the next step yet.

“I understand. I’ll get back to you later today,” I assured him. Now what?

It didn’t take long for me to figure out a course of action, because my phone rang not twenty minutes later. It was Donny.

“I hate my filter,” he said before I even had a chance to say hello. “I want it off.”

Well, that was simple, I thought wryly.

Donny wasn’t the first client to ask me to remove his filter so shortly after having it installed. Pressure in such a case is counterproductive; it just reinforces opposition to the filter and suggests that the user never actually had a choice about it in the first place. When a teenager realizes he (or she) has the freedom to remove his filter, he understands he’s been in charge all along. And if the teen asks for his filter to be reinstalled, he feels empowered by the filter instead of controlled.

Because I know that fighting with teens only makes the situation worse, I accept this part of the process with equanimity. My only job, in such cases, is to show that I’m working for the teenager by doing what he wants me to do. I don’t — I can’t — push.

So, with no other choice, I logged into Donny’s account and removed the filter from his phone.


Three weeks went by.

Then, one night, Donny called. It was close to midnight, too late for client work, so I let his call go to voicemail and made a mental note to return it in the morning.

Within a minute, my phone dinged — a text from Donny.

Can we talk about my filter?

I was looking forward to speaking to him, but I make it a point never to answer clients’ texts that late. I would have to be in touch with him the next day.

But Donny wanted to speak right that minute. Within 30 seconds of sending the text, Donny called a second time. He’ll need to wait, I thought, letting the call go to voicemail again.

After two WhatsApp voice calls and a FaceTime, I realized that Donny wasn’t going to stop trying to reach me until I picked up. At least he’s persistent.

I turned off my phone so I wouldn’t be kept up by its incessant ringing and pinging and went to sleep.

The next morning, on my way home from Shacharis, I called Donny back.

I knew that if I sounded angry at Donny, I would lose whatever trust he had in me, so I didn’t mention that I had woken to 19 missed messages.

“I think I missed a call from you,” I said nonchalantly.

“Can you put the filter back on my phone? Without access to that site.”

Without hesitating, I pulled over to the side of the road to reinstall the filter before Donny could change his mind.

A few days later, I went back to Derech Chochmah. I spotted Donny in the hallway and made my way over to him.

“I’m really proud of you, Donny,” I said, putting my arm around him.

Donny beamed. He obviously wasn’t used to being a source of nachas.

“But tell me, what happened? Why did you want your filter back all of a sudden?”

“Two reasons,” Donny answered. “Number one, I wasn’t ready before. I couldn’t handle the filter. I’m ready now. And number two, you passed my test.”

“Test?” I asked incredulously. “What test?”

“When I needed you to leave me access to that site, you made it happen. When I asked you to take off the filter, you did it right away. You showed me that you’re going to work with me on my terms, you’ll let me grow at my own pace.”

He paused for a moment, and then he added, “You proved you’re on my team.”


Identifying details have been changed to protect the privacy of subjects, their families, and all other parties.


Yossie Strickman is the founder of Project TRUST, an initiative that offers comprehensive support to those navigating the dangers of technology, including exposure to improper content, unhealthy Internet habits, and cyberbullying. He is based in Passaic, New Jersey, and speaks about safe technology use across the United States.


(Originally featured in Mishpacha, Issue 1001)

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