Jill Mastroianni (00:00) What if I told you that the most dangerous place your child can be isn’t a dark alley or an empty parking lot, but their own bedroom?

What if the threats aren’t outside your house, but inside the device you gave them?

And what if the tools we grew up believing kept our children safe, locked doors and closed windows, don’t even begin to protect them anymore?

Today’s episode is not about estate planning. It’s not about wills, trusts, probate, or powers of attorney.

It’s about why death readiness is really life readiness, and how learning what’s happening inside the digital world, the algorithms, and the predators who hide within it has become part of protecting the people you love most.

This is an episode for every parent. And if you’re traveling over the holidays, especially with teenagers or pre-teens, it’s one I hope you’ll listen to together.

(00:56) Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.

When my daughter April was little, she and my husband had a bedtime dialogue that went on forever, the sort of drawn-out, endearing routine only a child and her dad could create.

It always started with the same question:

“What are you grateful for?”

Then, “What do you have to put away?”

They were simple questions, but they taught April to check in with herself, to notice what was filling her up, and what was weighing her down.

(01:55) But when kids grow up, their world expands. Their fears get more complicated, and their mistakes get bigger. What they’re carrying becomes harder to name. And suddenly the “What do you have to put away?” is about things they don’t know how to talk about: shame, pressure, cyberbullying, predators, algorithms that pulled them in too deep.

And that’s the terrifying part of parenting teenagers:

You don’t know what they’re carrying because they don’t want you to know.

Back when April was little, life was simpler, and so were the things she carried.

And every night, after those two questions, came the script.

It always started with “Goodnight. Sleep tight. Don’t let the bed bugs bite.”

Then came April’s two safety questions:

“Can you make sure the doors are locked?”

“Yes.”

“Can you make sure the windows are locked?”

“Yes.”

(02:50) And it always ended with the same request about her four-legged friend: 

“Tell Oliver he’s the best dog in the universe.”

“Okay.”

After all of that, I’d walk in and say simply, 

“Goodnight, my girl,” and that was the end of the ritual.

What I didn’t realize at the time is that everything she feared could be kept out with a deadbolt.

But little girls turn into pre-teens, and pre-teens turn into teenagers, almost imperceptibly.

And somewhere in the middle of all that growing, the monsters relocate.

They stop lurking outside in the dark. They now live inside apps and algorithms and anonymous accounts.

Locked doors don’t protect our kids anymore because the danger isn’t outside the house. It’s in their hands.

When I was in Nashville last week, I had dinner with a woman whose daughter, Ava Smithing, hosts a podcast called Left to Their Own Devices. I’ll link to it in the show notes.

(03:49) I started Episode 1 as I pulled onto the highway leaving Nashville, and I binged all ten episodes before I made it home to Michigan. Ava’s podcast is unsettling in the way truth often is, not sensational, just a clear look at what’s already happening right under our noses.

And as I listened, I realized this information belongs inside the conversation about death readiness, too.Because protecting our families isn’t just about wills, trusts and powers of attorney. It’s also about protecting our children from the wolves at the digital door.

Today, I’m going to take you through my 4 main takeaway’s from Ava’s podcast.

#1. Our kids are growing up in a world very different from the one we grew up in.

When I was twelve, the scariest things lived outside, in the dark, or in a rumor, or in a moment that passed. Danger didn’t follow us into our bedrooms, and it definitely didn’t live in the palm of our hands.

(04:50) Teenagers today are navigating much more than hormones and homework. They’re navigating a digital landscape intentionally designed to addict them, track them, shape them, and trap them.

Even adults struggle to escape these same traps. But adults have fully developed brains. Teenagers don’t.

And when I think about my teenage experience, I think about running. I was a very competitive long distance runner in high school. Then I got mono the spring of my junior year. It wiped me out for months. When I came back for cross-country my senior fall, I was heavier than I’d ever been. And I was slower, too. I wasn’t back to my usual self.

If there had been an online forum, or photos posted, or competitors mocking me in real time, I don’t think I would have coped well. Plenty of other elite high school distance runners struggled with eating disorders. We were thin, driven, and constantly comparing ourselves, and that was without social media.

(05:54) Back then, the worst judgment came from a local newspaper headline or a few sentences in an article. It was common for the local papers to write about student athletes.

After a bad race, I’d walk down the stairs from my bedroom, find my parents reading the newspaper in the living room, and ask, “How bad is it?” And even that felt fragile.

But what if I had been alone in my room instead, not waiting for a newspaper and confronting the contents with my parents there to support me, but reeling from comments online, from bullying I couldn’t escape, from strangers weighing in on my body or my worth? I don’t know if I would have survived it.

That’s the part adults forget. Kids today aren’t just dealing with pressure. They’re dealing with an entire digital world that accelerates it, amplifies it, monetizes it, and follows them everywhere.

(06:53) When, at 40 years old, I found myself scrolling Instagram at night, and feeling increasingly worse about myself, I deleted the app. I knew it was harming me. I had the life experience and perspective to leave.

Teenagers don’t have that. And they don’t have the fully developed risk-assessment abilities, regardless of how smart they are. Their brains just aren’t ready for it yet.

Not only are the stakes higher for them, but the predators are more sophisticated than anything we ever had to face.

#2. Sextortion is real. And sometimes kids think death is the only way out.

Sextortion is when someone tricks, pressures, or manipulates a person into sharing a sexual image, and then uses that image to threaten, shame, or demand money from them. It’s extortion with a sexual image at the center, and it’s a predatory scam increasingly targeting kids and teenagers.

(08:01) One of the most unsettling things I learned from Ava’s podcast was just how organized, scalable, and sophisticated sextortion has become. I’m not talking about a handful of creeps on the internet, but an entire industry.

There’s an organized network of West African cybercriminals, known as the Yahoo Boys, who have turned the extortion of teenage boys into a full-blown business model. And it’s working.According to Left to Their Own Devices, sextortion cases involving teens have increased 18,000 percent in just two years. That number sounds impossible until you realize how the scam works.

The pattern is brutally simple: A predator poses as a girl online, chats with a boy, sends a nude photo and asks for one back. The boy sends one nude photo and within seconds, he’s trapped. The threats start immediately. Pay me or I’ll send this to everyone you know. Your parents, your school, your team, your coach.

And these kids believe every word. Not because they’re naïve, but because the predators are convincing, the threats are specific, and the shame is instant and overwhelming.

A loving, close-knit family in Pilot Mound, Manitoba knows this pain intimately. Their son, Danny Lints, died by suicide after falling victim to one of these scams. His parents talked to him about online safety. Danny even told them he’d learned about Amanda Todd, the 15-year-old who also died after a sextortion attack. And yet Danny was still pulled in.

(09:50) He accepted a message request from someone on Snapchat who seemed like an attractive girl his age. She gave him attention. She asked for a photo. And once he sent it, the threats began.

Danny was a good kid. And he was caught in something far bigger, far darker, and far more sophisticated than he could possibly understand.

Snapchat alone receives 10,000 reports of sextortion every month. And yet the scams continue.

School bullying can be brutal. But this online sextortion is different. Here, the predators aren’t classmates. They’re coordinated, financially motivated adults who know exactly how to weaponize shame.

The predators’ goal is singular: Make a child believe there is no way out. 

They want the shame to feel too big. The fear too immediate. The imagined fallout too suffocating.

So what do we do?

(10:52) We talk. Even when it feels awkward, and even when our kids roll their eyes.

I suggest listening to Episode 6 of Left to Their Own Devices with your kids. Tell them that they can come to you with anything. That there is no mistake too big, no situation too shameful. And that nothing, absolutely nothing, is worth their life.

Then say it again. And again. 

#3. Social media engineered algorithms are not neutral.

Ava Smithing, the host of Left to Their Own Devices, developed an eating disorder when she was a young teenager. And she talks openly about one of the major contributing factors—the Instagram algorithm.

(11:43) She lingered a second too long on a bikini image. Instagram decided that must be what she wanted. Her feed transformed almost overnight into perfect bodies, “what I eat in a day” videos, weight-loss hacks, and workouts promising to shrink you, tone you, starve you. 

Ava wasn’t looking for anything dangerous, but the algorithm found her vulnerability. It studied her hesitation, scrolling speed, replays, and zooms, and mapped out her insecurities before she even knew she had them. And then it regurgitated those insecurities back to her until they became the only thing she saw.

Algorithms exist solely to maximize profit. They don’t care about mental health, safety, or the fragile identity of a developing child. Their job is singular: keep your kid hooked.

(12:39) And when that carefully curated system meets a teenager whose prefrontal cortex is still under construction, it’s not a fair fight. The algorithm moves more quickly than their impulse control, faster than their emotional regulation, and far beyond their ability to assess risk. It’s engineered to outrun a teenage brain and that’s exactly what it does.

#4. Death readiness means confronting the realities that terrify us, the realities we don’t want to talk about.

As a parent, the thing I fear most is something bad happening to my child. And after listening to Ava Smithing’s podcast, I realized something I didn’t want to admit: the danger isn’t hypothetical anymore. It isn’t some distant, dramatic, far-fetched scenario. It might already be happening, quietly, on a device we paid for, inside an app we don’t understand, and in messages we’ll never see.

(13:44) When Ava’s mental health was pulled under by the Instagram algorithm, she didn’t even have a smartphone. My 14-year-old daughter, April, doesn’t either. She can’t participate in group chats. She can’t send or receive images.

But you know what Ava did have? An iPad mini. My stomach dropped when I heard that. 

Because April got an iPad from my dad last Christmas. And, while, we keep her iPad and her phone in our bedroom at night, after listening to Ava’s story, I realize that’s not enough.

We can’t simply keep social media away from April forever. We’ll need to help her develop the skills to navigate and moderate her use of the internet as much as we do.

And, I need to have more conversations with April. Real ones. Repetitive ones. Annoying ones. The kind she will roll her eyes at. The kind she’ll insist she doesn’t need. Because if your teenager is anything like mine, she already knows everything.

(14:53) Left to Their Own Devices is beautifully produced, but it’s not just entertainment. It is a warning. And, for me, more importantly, it’s a conversation starter.

If you’re traveling for the holidays, I encourage you to listen to it in the car with your kids. I’m going to do exactly that with April when we drive to my dad’s home in the Adirondacks next month.

The conversation may feel awkward. It may feel unnecessary. It may feel like you’re overreacting.But the alternative, silence, is far more dangerous.

I think back to that bedtime ritual with April—the gratitude list, the putting-away, the checking of the doors and windows, the “tell Oliver he’s the best dog in the universe.”

Back then, everything she feared could be kept out with a lock.

(15:52) Today she’s older, and the fears are different. The locks don’t work the same way. But the ritual still matters.Not the words, but the message: “I see you. You’re safe with me. You can tell me anything.”

That’s what death readiness is about. Not paperwork, binders or checklists, but showing up before the crisis hits. Talking about the hard things. Preparing the people you love for the world they’re actually living in.

If this episode pushed you out of your comfort zone, good. It pushed me out of mine, too. And if you’re listening to this while driving, fold these next five minutes into a real conversation with the kid sitting next to you. Trust me, they need it more than they’ll ever admit.

Thanks for listening today.

(16:50) This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.

Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast.  While my mom is an attorney, she’s not your attorney.  The Death Readiness Podcast is for educational and entertainment purposes only.   It does not provide legal advice.  For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.  To learn more about the services my mom offers, visit DeathReadiness.com.