See Mom, watching movies all day DID lead to a career!
“9 to 5…what a way to make a living” - Dolly Parton… -Wilderness Jack
I was on location in the Blue Ridge Mountains, filming Hook Security’s latest annual training featuring the great Wilderness Jack. Jack is a character I created with my brother during the pandemic. My brother’s not an actor by trade, but he does an excellent job playing the character Jack in our training. Jack’s an outdoorsman/cyber genius, and He’s been our premier character for the last 5 years.
So I’m watching Jack standing in a hot tub pretending to be on a call with HR (just me, it makes sense). HR tells him, “Jack, in this office we work Monday through Friday, 9 to 5.” Jack’s original line was “That’s a full week!” But suddenly, I could only hear two things in my mind.
First, the iconic Dolly Parton belting out the song “Workin’ 9 to 5, what a way to make a living” song. And second, the classic scene in Dumb & Dumber: “I can't believe we drove around all day and there's not a single job in this town. Nothin-nada-zip! Yeah unless you wanna work 40 hours a week.”
I thought Dolly’s words were more fitting for our character, so we changed the script and went with it.
It’s a subtle change, a small line, and most people won’t even catch it in the moment. But for those who do, something happens in their brain. It’s like a small lamp gets turned on in a dark room. For creatives and engineers alike, this recall moment is built into our brains. Movies, songs, jokes, and stories imprint on us. They stay with us and constantly find their way into our everyday lives. As Jonah Hill once said, “Sick reference, bro, your references are out of control, everyone knows that.”
Growing up, my friends used to call me “Pop-Up-Video.” A reference to the classic VH1 show that would give interesting facts, stories or behind-the-scenes knowledge to the viewer of the music video they were watching. To this day, I don’t know if it was a compliment or a cut down. I grew up loving movies. To this day, even with the rise of numerous streaming TV shows, I prefer movies 10 to 1 over a TV show. I don’t want to invest 10 hours in a show for only one thing to happen. Give me a beginning, middle, and end, and do it in two hours. I got too much ADD for all that. My mom used to say to me “I am not sure you can make a career out of knowing movie trivia.”
Well, Mom, guess what, that’s kind of what I do now! (Actually, my Mom is one of Hook’s biggest fans so she loves what I do).
I’m the Director of Content at Hook Security. I’ve been with the company since its start 6 years ago, and I still love every minute of it. One of the things I love the most is the problem we were working to solve. Training is often boring, and people tend to forget things they find dull. So, from the start, I was given the freedom to create content that ordinary people would enjoy and remember.
Before Hook, I worked at a high school, and if you’ve ever tried to keep the attention of a room full of teenagers on a Friday afternoon, you know exactly where my storytelling skills were forged. I learned fast that facts alone rarely stick, but a story does. So do jokes, oh, and a movie clip. LOTS of movie clips! The second I could make the students laugh, they’d lean in. The moment I could connect a concept to a scene from a movie or a relatable story, they remembered it.
What I didn’t know then, but know now, is that this isn’t just a “me thing.” I certainly didn’t invent this! Haha!
It’s neuroscience! Humor and storytelling trigger dopamine in the brain, which helps with focus, motivation, and memory retention. A 2015 Edutopia article explained that laughter literally “activates the brain’s reward system,” making it easier for learners to absorb and recall information. In other words, when something makes us smile, our brain labels it as important! Amazing. You see, we remember the feeling, and the information attached to it comes along for the ride. That’s why our recall for movies, TV shows, and music is so acute!
That same principle is exactly what we use at Hook.
The truth is, adults don’t learn all that differently from kids. They just hide their boredom (or their phones) better. If something feels stale or overly serious, it tends to go in one ear and out the other. That’s why, when we built Hook’s training philosophy, we built it around something we call Psychological Security, or PsySec. It’s the belief that we can’t build secure organizations without first understanding how people learn and behave. PsySec combines humor, storytelling, and repetition to train not just the logical brain, but the emotional one, the part that actually decides what to click, share, or report.
So instead of giving you a slide deck showing the dangers of phishing emails, we tell a story…
Sometimes that story comes from our favorite rugged outdoorsman, Wilderness Jack, trying to survive the wild world of office life. Sometimes it’s a two-minute “Instant Training” video that plays right after someone falls for a phishing test, turning a mistake into a teachable (and funny) moment. And sometimes it’s one of our short micro-courses that use a single character, joke, or pop-culture reference to make an otherwise technical topic feel human.
We don’t do this because we think people need to be entertained. We do it because it works. When people laugh, they relax. When they relax, they learn. And when they learn in a positive emotional state, they remember what they learned far longer. It’s the same reason people can quote entire episodes from The Office but can’t remember last year’s compliance slide deck.
Storytelling also builds something deeper than memory; it builds connection. It gives training a heartbeat. When someone sees Wilderness Jack stumble through a “phishy” situation, they don’t just absorb the lesson; they see themselves in it. It’s not a lecture; it’s a mirror. When we see ourselves in characters, we know their failures are the end of the story; just the beginning. So when Jack learns, we learn.
And that’s the difference between checking a box and changing behavior.
Over the past six years, we’ve developed a comprehensive library of content that demonstrates security training can be effective without being dull or fear-based. And we believe we are the best at it.
Humor, empathy, and relevance can take you further than any scary statistic ever could. A recent Harvard Business Review piece summed it up perfectly: “Humor, used thoughtfully, can increase engagement, reduce anxiety, and build trust.” Or as Mary Poppins taught us, ‘In every job that must be done, there is an element of fun.”
That’s what we see every day at Hook. Fun doesn’t hurt our work; it empowers it. Companies who once dreaded training now share clips from it. Employees talk about “that one Wilderness Jack episode” months later. One of the highest compliments I’ve ever gotten about our training was when someone sent us an employee dressed as Wilderness Jack for their office Halloween Party! Name another training company that does that!?!?!?!
At Hook, we’re not just teaching cybersecurity; we’re teaching humans, and that means something to me. When I’m writing scripts or filming, I try to think of the people watching the training. Are they bored? Is this too much information? Would I enjoy this? Does this make me feel anything? Feelings matter because humans matter, and humans remember the things that evoke emotions in them.
So yeah, Mom, all those hours spent watching movies, quoting comedies, and memorizing useless trivia weren’t so useless after all. They became the foundation of how I teach people to stay safe online, through humor, story, and connection. As it turns out, there was a career in watching movies all day.
And for the record, Dolly was right. “Workin’ 9 to 5” is a funny way to make a living. But helping people learn, laugh, and stay secure? That’s the best job I could ever ask for.
