Jack Wylder's Questionnaire

I live in South-Side Chicago, born and raised. It’s a city with grit and soul, equal parts poetry and practicality. The skyline cuts into the sky with quiet confidence, and the neighborhoods each carry their own rhythm. Chicago has range. It’s not trying to impress you, it’s too busy being something real. I stay because it has history, texture, and people who know how to show up when it matters. The winters are harsh, sure, but that first spring day when the lakefront reawakens, It makes it all worth it. I live in a brick three-flat in Canaryville, on the top floor. The apartment is rugged with original hardwood floors, high ceilings, and wide windows that catch the Chicago skyline right.

I work as a Private Contract Paramedic working at concerts, sporting events, public events and clinics. My favorite jobs to work are sporting events like baseball, hockey, and football games. I usually spend my money on myself like buying new gear for work. I also like going out on the town even though I was born and raised here, there's always something to do around town. My hobbies are firearms, fishing, and working out. I try to work out 3-5 days a week, I usually go shooting at least twice a month, and I try to fish every Sunday morning. I try to keep busy even though I love the silence in life but lately the demons in my head have been talking too loud. 

My Ambition: To Save Lives And Make a change in the world. I didn’t sign up to be a hero. I signed up to make a difference in moments that matter most. My ambition is simple but not small:To be the reason someone gets another shot. To be calm in chaos. To hold the line between life and death sometimes literally. It’s not just about skill. It’s about presence. I want to be the one who shows up when everyone else panics. The one who knows what to do when the blood’s real, when time is against you, when people are screaming or silent or already slipping away. I’m striving to be excellent—not just good enough to get by, but so sharp, so steady, so prepared, that I can give people a chance even when the odds are stacked hard against them.

I’ll skip sleep. Miss birthdays. I watch people die and still get up the next day and do it again. I’ll run toward danger when everyone else is backing away, because that’s the job. I’ll push my body, push my mind, burn through adrenaline until my hands shake and my bones ache and still kneel beside someone on the pavement and say, “You're gonna be okay. I’ve got you.”

Would I Kill for it that a load and tough question 

Would I die for it? Yeah. Not because I want to, but because sometimes that’s the risk. If running into a collapsing building or stepping between someone and a bullet is what it takes to keep someone alive someone who still has a future, a family, a fighting chance then yeah, I’d go that far.

The Bottom Line is that I don’t want glory. I want people to live, and if I have to stand at the edge of hell to make that happen even if no one ever knows my name I’ll do it because for me, "You're still breathing" is the greatest victory there is. Especially since I love my only love. 

The Call That Changed Everything: It was a wreck on I-55. Rain-slicked highway, three cars, one folded around a guardrail like tinfoil. I was only six months out of training, still green heart pounding every time the radio cracked to life. But that night? That call changed me forever and it happened in minutes. There was a kid in the backseat, maybe seven. His mom had been driving. She was already gone by the time we got there, her neck snapped on impact. But the kid? He was still conscious but barely. He looked right at me as I cut his seatbelt and said, "Is my mom okay?" And I  had lied. I said, "She’s fine. We’re getting you both out of here." I held his hand all the way to the hospital. He coded twice. We got him back both times. He lived. 

How It Changed Me: Up until then, I thought I could stay detached. That I could be good at this without letting it inside me. But that night showed me two things: 1. You can’t always save everyone. 2. But you damn well can try, Even when it breaks you. It taught me that this job is about showing up fully when it matters most. That telling a comforting lie might be the most human thing you can do. And that if you want to last in this line of work, you have to let pain shape you but not define you. That night is why I stopped treating this like a job and started treating it like a calling.

Now that I lost my love and there's no way to get her back I must find a way to heal these wounds. It’s also why I hesitated before signing The Contract because I knew it would ask me to become someone else entirely. And the version of me that held that kid’s hand? I wasn’t sure I’d be able to take him with me.

Kamila was my love that I lost She wasn’t perfect, but she fit into my life like a piece I didn’t realize had been missing. The kind of love that doesn’t crash in with fire but builds, slow and deep, like water wearing down stone. She made things quieter in my head. That’s how I knew it was real. We laughed a lot over dumb things, like grocery store mishaps or late-night takeout orders gone wrong. We had routines that turned into rituals: coffee on the fire escape, playlists for rainy drives, long talks that bled into silence and didn’t feel awkward. She didn’t fix me. She didn’t try to but she saw me and that was enough to feel like home. I still wish that I could get her back but she's gone and I couldn't save her.

Josh and Ben are my best friends, they aren't always the loudest in the room, They know exactly when to speak and when to just sit beside you, when to call you out and when to let you be soft. They remember the little things your favorite song from high school, that one things your mom said that still messes with you, how you take your coffee without even asking. We’ve been through things that could’ve broken us—distance, mistakes, time—but we always find our way back to each other like gravity. There’s a kind of trust between us that doesn’t need explaining. They’re not perfect. Neither am I. But somehow, we fit together in all the right places. That was all before I pushed everyone away. 

My Childhood was Complicated but it was real. I grew up on the southwest side of Chicago—brick buildings, corner stores, sirens at night. It wasn’t glamorous, but it was home. My world was small but full bike rides to nowhere, cracked sidewalks, scraped knees, secondhand everything. There were good moments, but nothing came easy. 

My dad was an ex army mechanic who worked in the warehouse district. He was quiet and kept everything close to the heart. He didn’t say much but when he did it usually meant something. Discipline came in the form of physical work like body calisthenics, around the house labor, and very blunt words being used. My mom worked her behind off as a cosmetologist to help provide for the family. There was a total of 6 of us, 2 parent and 4 kids. She was strong in that way women are when they’ve had to hold too many things together at once. She ran the house like it was a battlefield cooking, cleaning, chasing bills, keeping us alive with sheer force of will. She was warm but sharp. She loved us, no doubt. But survival came first.

School: Yeah, I went. Got decent grades when I actually tried, I worked my behind off to be an average student. I didn’t really fit in not because I was weird, but because I was busy surviving. While other kids worried about prom or Instagram, I was working part-time, helping out at home, learning how to fix things that were broken sometimes people, sometimes myself. I wasn’t popular, but I wasn’t invisible either. I just floated between groups. I had a couple close friends, the kind you don't need to explain yourself to. And that was enough.

I grew up fast. I learned to listen more than I talked. Learned that people don’t always need fixing sometimes they just need someone who won’t leave. That’s probably why I do what I do now. Why I show up on someone’s worst day and stay. Because not everyone had that growing up. And I remember what that felt like.

Yeah… I was in love once.
Her name was Kamila. She wasn’t one of those people who needed the spotlight she was the kind who made you feel like you mattered just by how she listened. Smart, curious, steady as hell. She was in school, studying to go into radiology. Always had her nose in a textbook, highlighter in hand, coffee close by. Said she wanted to help people, but without the adrenaline “You run into chaos,” she told me once, “I just want to understand it”. She liked solving puzzles. Loved anatomy. Could name every bone in the human body in under a minute used to quiz me just to mess with me. She had this quiet confidence that I leaned on more than I probably should’ve. We met through work she was shadowing a tech during a hospital rotation when I brought in a patient. Our second conversation was in the break room, over a bag of vending machine pretzels. I said something about how machines were smarter than half the people in administration, and she laughed. First time I saw that crooked smile of hers. After that, I was done for. We didn’t have forever...Not even close... It happened out of nowhere an aneurysm. One of those sudden, silent things that doesn’t give you time to prepare or say goodbye. One minute she was texting me about which frozen pizza to grab on my way over, the next…
she was on the floor. By the time I got to the ER, they’d already started compressions. I took one look at the monitor and knew. But I still begged. Still tried. Still stayed. Losing her… it cut deeper than anything I’ve ever seen on a scene. And that includes bodies in pieces, blood in the street, kids without pulses. Because this one wasn’t just someone. She was my someone. People talk about grief like it fades. But it doesn’t. It just settles in, changes shape. Some days I carry it like a scar. Other days it’s more like a second heartbeat. And the worst part? She had her whole life ahead of her. I was supposed to be the one with the dangerous job. The risks. Not her.