The Office Menace We Can’t Ignore: The Story of Human Error
In the ever-shifting digital battlefield, where malicious code evolves faster than corporate policies and phishing attempts feel almost indistinguishable from daily communications, one pajama-wearing character emerged as an unlikely champion of cybersecurity awareness. This character, known only as Human Error, is the brainchild of Drew Freed, a self-described cybersecurity celebrity and seasoned comedian. Through an uncanny fusion of humor and stark reality, Human Error has become emblematic of the everyday blunders that compromise organizational security.
Drew Freed’s journey into the world of cybersecurity wasn’t paved with certifications or corporate suits—it started in the lively underbelly of New York City’s comedy scene. While performing at the Upright Citizens Brigade and pouring drinks behind a bar counter, Drew’s distinct persona caught the eye of a Mimecast producer hunting for the ultimate embodiment of collective workplace fallibility. The role required someone who could translate complex security principles into digestible, relatable content—a task tailor-made for someone with comedic timing and a grasp of human behavior.
The initial pitch was peculiar: portray a walking, talking metaphor for every single poor cybersecurity decision ever made. Despite—or perhaps because of—its absurdity, Drew leaned in. The character Human Error was born not in a polished studio but among the clinking glasses and neon-lit chaos of the nightlife. With a single audition, the synergy between actor and concept was clear. Drew’s improvisational prowess, honed on stage and behind the bar, made Human Error less of a character and more of an exaggerated mirror for corporate life.
The first shoot of the Human Error series was as low-budget as one might expect from a fledgling experiment. It adopted a now-iconic BYOP (Bring Your Own Pajamas) mantra. Many of the scenes were improvised, lending a spontaneous, raw humor that became the hallmark of the series. Production values were minimal, yet the authenticity and creativity infused into each moment transcended the constraints of a tight budget.
Despite its humble origins, the Human Error campaign exploded within the cybersecurity community. It wasn’t long before the character became a mainstay at events such as BlackHat and was recognized globally—from the U.S. to Australia. What began as a small project had evolved into a cultural touchstone within cybersecurity circles. The pajama-clad persona even received its own cartoon adaptation and collectible bobblehead—testaments to its resonance.
What set Human Error apart from traditional training content was its antithetical approach. Rather than lecturing users with dense jargon or fear-laced hypotheticals, it employed subversive humor to illustrate the absurdity of avoidable mistakes. Picture a digital Jiminy Cricket, not whispering words of wisdom, but shouting every wrong move just before it’s made. In one scenario, Human Error rollerblades through a park dispensing unsolicited password advice; in another, he gulps down spoiled milk while explaining why security tokens are just another thing to lose.
These bizarre antics, far from being irrelevant distractions, serve a pedagogical purpose. They make cybersecurity memorable. They anchor lessons in laughter, a neurological strategy far more effective than monotony. Drew’s approach draws from an intrinsic understanding of behavioral economics: people don’t respond well to lectures, but they remember what made them laugh.
The physical toll of embodying Human Error also underscores the commitment behind the comedy. Drew recounted being tackled by NFL linebacker Kyle Van Noy and members of the Melbourne Rugby team for various stunts. While he emerged unscathed, he jokingly admitted the hits provided impromptu chiropractic adjustments. These moments illustrate the lengths the production team went to deliver messages with visceral, comedic impact.
Yet, beneath the humor lies a sobering truth: these dramatizations reflect real-world lapses that companies deal with daily. Clicking malicious links, using weak passwords, ignoring software updates—these aren’t theoretical issues. They are, disturbingly, routine. Drew’s portrayal of Human Error underscores how omnipresent these vulnerabilities are. He doesn’t just satirize mistakes; he embodies the systemic oversight that lets them persist.
What makes the Human Error campaign especially poignant is its cultural timing. We live in an era saturated with anxiety—from data breaches and identity theft to ransomware attacks that shut down hospitals and city infrastructure. Fear is no longer abstract; it’s the ambient noise of our connected lives. Drew taps into this collective unease not to exploit it, but to diffuse its paralyzing effect with a disarming blend of satire and education.
The crux of Human Error’s impact lies in its relatability. Nearly everyone who’s ever worked in an office can recognize the archetype: the overly confident coworker who forwards suspicious emails, writes passwords on sticky notes, or assumes that IT will always have their back. Human Error’s charm—and sting—comes from how uncomfortably close to reality he resides.
The genius of this character lies in how it reframes the narrative around cybersecurity. Rather than isolating employees as weak links or liabilities, it encourages them to see themselves as integral to the organization’s digital health. The humor doesn’t belittle; it enlightens. It shows that mistakes aren’t just possible—they’re expected. And that’s exactly why vigilance is necessary.
When Human Error made his debut at major cybersecurity events, it wasn’t just a gimmick. It was a declaration. It signaled that awareness training didn’t need to be a dry, checkbox exercise. It could be dynamic, entertaining, even beloved. By turning what was traditionally a mandatory corporate drudgery into something both enjoyable and educational, Drew and the Mimecast team redefined the potential of employee training.
What began as an impromptu video project with zero wardrobe budget has become a cultural artifact, one that reflects and reframes our understanding of security awareness. Human Error has transcended his fictional role to become a totem of what makes cybersecurity simultaneously frustrating and fascinating: the human element.
While AI systems can be fortified, firewalls strengthened, and encryption keys rotated endlessly, the unpredictable nature of human behavior remains the wild card. And that’s precisely where Human Error strikes his chord. In showing us our flaws, he also shows us the path to improvement.
As organizations wrestle with increasingly sophisticated cyber threats, it is no longer enough to rely on digital fortresses. Education, particularly of the engaging and unforgettable variety, is the new frontline. Drew Freed, with his talent for making audiences laugh and think in the same breath, has carved out an unusual yet indispensable niche in this critical endeavor.
The rise of Human Error as an educational mascot is more than a novelty; it’s a paradigm shift. By holding up a humorous mirror to our worst digital habits, the character not only amuses but activates. He reminds us that behind every firewall failure or breach report is not just a line of code or a missing patch, but a real person making a real decision—often in haste or ignorance.
Human Error invites us to embrace our imperfections, not to accept them passively, but to become more mindful of them. In doing so, he makes cybersecurity not just a responsibility, but a shared cultural conversation. And perhaps, in that conversation, lies our best chance at a more secure future.
The Making of a Cybersecurity Icon: Behind the Scenes of Human Error
The phenomenon of Human Error didn’t just explode into relevance overnight. The journey from a scrappy pilot shoot to full-fledged cybersecurity icon was forged in creativity, resourcefulness, and a fearless willingness to embrace the absurd. In this second installment, we’ll crack open the behind-the-scenes evolution of Human Error—how the character developed, how the production scaled, and how real-world chaos was transformed into educational gold.
Back in the early days, when the Mimecast security awareness initiative was still a developing concept, there was no big studio backing or marketing machine to hype the series. Instead, Drew Freed and a small, driven team relied on guerrilla-style filming tactics and a heavy dose of improvisational energy to create something that didn’t look or feel like conventional training content. That was the point. Traditional cybersecurity awareness material often falls flat: it’s preachy, jargon-heavy, and completely forgettable. Human Error, in contrast, was designed to be a subversive response to that dull status quo.
The filming approach followed a minimalist philosophy—simple setups, natural lighting, and whatever props could be scavenged from nearby thrift stores or borrowed from friends. But this minimalism was never a limitation; it was an enabler. It allowed the team to focus on authenticity, to lean into the unpredictability of public filming and the spontaneity of unscripted moments. Drew’s background in improv and physical comedy gave every take an edge, often producing scenes that were unplanned but hilariously on point.
From day one, the creative team agreed that the Human Error character needed to be fundamentally human—not a hacker, not a villain, and definitely not some all-knowing security guru. He had to be flawed in a way that made people nod and cringe at the same time. That’s what made the pajama motif so oddly effective. It stripped away any air of authority or professionalism and instead suggested vulnerability, comfort, and naivety—traits we all share in moments of digital carelessness.
Each episode centered on real-life cybersecurity missteps but wrapped them in layers of situational comedy. From using the same password for everything to ignoring software updates to oversharing on social media, the scripts (or loose scene outlines) pulled from a universal lexicon of user mistakes. This relatability made the character feel like a colleague, not a caricature. Someone whose missteps mirrored our own, only exaggerated for comedic—and educational—effect.
As word of the videos spread, Mimecast gradually increased investment in the series. Production quality scaled accordingly. Sets became more controlled, cameras upgraded, and stunts got bolder. Still, the quirky DNA of the series never changed. One minute Human Error might be rollerblading through a city plaza with unsecured devices bouncing from his backpack; the next, he’s trying to log into a secure network using a coffee shop’s public Wi-Fi. Every misadventure was rooted in actual user behaviors that IT teams know all too well.
One of the most defining traits of the series was its ability to push boundaries—physically and metaphorically. Drew subjected himself to outrageous stunts to drive home key points. These weren’t just sight gags; they were physical metaphors for how serious the consequences of user error could be. When Drew got tackled by NFL linebacker Kyle Van Noy, it was funny—but it also made a lasting impression about the weight of responsibility employees carry when interacting with digital systems.
Even more jaw-dropping was the rugby scene filmed in Australia, where a team of burly players blindsided Human Error mid-sentence. It wasn’t choreographed or softened; it was a raw collision designed to show how unexpected and brutal cyberattacks can be. The physical comedy worked on two levels: it entertained while viscerally imprinting the lesson. If you thought the messages would be forgettable, you hadn’t seen Drew bounce off the turf like a ragdoll.
As the series matured, so did its reach. Invitations to speak at global cybersecurity conferences started pouring in. Drew brought the Human Error persona to live audiences, where he roamed expo halls in pajamas and interacted with tech pros in real time. These appearances often became the highlight of the events, drawing crowds who came for the laughs but stayed for the message.
Surprisingly, it wasn’t just IT professionals who connected with Human Error. HR departments, compliance officers, and even C-level executives began using the videos in their onboarding and training programs. Why? Because the content bypassed resistance. No one felt shamed or alienated watching a bumbling, well-meaning goofball make the same mistakes they had made. The tone was never accusatory; it was empathetic and inclusive.
This approach inadvertently created a bridge between technical and non-technical audiences—a gap that traditional training materials often fail to cross. The jokes weren’t rooted in obscure tech references; they were grounded in day-to-day digital behaviors. Forgetting to lock your screen when you leave your desk? Texting passwords to your own phone? Using “Password123” as your login? These habits transcend job titles and departments.
The ripple effect of this accessibility was enormous. Organizations began seeing shifts in behavior. IT departments reported higher rates of phishing simulation success. Employees started double-checking URLs and asking better questions about suspicious links. And most importantly, there was a newfound curiosity around cybersecurity topics. What was once a dreaded training module became a watercooler conversation.
But behind every laugh and visual gag was a serious undertone. Drew and the production team were acutely aware of the line between humor and trivialization. Every episode was vetted to ensure that the absurdity didn’t overshadow the urgency. The comedy served as a trojan horse—disarming viewers just enough to sneak in some hard truths.
What really elevated the campaign, however, was Drew’s ability to evolve the character without losing its essence. As digital threats grew more sophisticated, so did Human Error’s blunders. He began grappling with issues like deepfake scams, MFA fatigue, and shadow IT. The content kept pace with the times, maintaining relevance while retaining its absurdist charm.
Interestingly, the most impactful feedback came not from executives, but from everyday users. Employees across industries began sending in messages, not just of praise, but of confession. “That was me last week.” “I totally forwarded a sketchy attachment yesterday.” The videos sparked moments of self-awareness that most training sessions never achieve.
The rise of Human Error also sparked debate within the cybersecurity community. Some professionals questioned whether the humorous angle diluted the severity of the message. But defenders argued that desensitization was already a problem in the corporate world—constant security warnings had become background noise. By contrast, Human Error cuts through the clutter.
This approach also tapped into a deeper behavioral psychology principle: people learn better when their defenses are down. Humor lowers those defenses. It makes the medicine go down. And when done right, it transforms viewers from passive recipients into active participants in their own security literacy.
The success of Human Error underscores a crucial truth: cybersecurity isn’t just about software and systems. It’s about people. It’s about the hundreds of micro-decisions made every day by employees across departments. In that sense, Human Error is less a character and more a composite of every person in the modern workforce.
What began as a gamble—an improvised video in pajamas—has become a cornerstone of modern awareness training. Not because it’s perfect, but because it embraces imperfection. Drew Freed didn’t just create a character; he sparked a movement. A reminder that cybersecurity doesn’t live in the server room—it lives in every inbox, every password, every shared link.
Human Error isn’t a cautionary tale meant to scare people into compliance. He’s a comedic avatar of our shared vulnerabilities, a symbol of the tension between convenience and caution. And in the process, he’s made the concept of security awareness not only digestible but genuinely engaging.
As we examine the anatomy of the campaign’s growth, one thing becomes clear: the intersection of comedy and cybersecurity is no longer a gimmick. It’s a proven, potent strategy for cultural change. Through a clever blend of satire, relatability, and fearless execution, Human Error has cemented himself not just as a mascot—but as a mirror.
A mirror that reflects not just what we do wrong, but what we must do better.
The Anatomy of a Mistake: The Reality Behind Human Error
Human Error is more than just a character; he’s a living case study in how daily missteps expose even the most sophisticated organizations to digital ruin. The third chapter of this journey peels back the comic layer to expose the sobering truth behind the satire—that behind every phish, breach, and exploit is a very human moment of lapse, distraction, or misplaced trust. And Drew Freed, through his offbeat alter ego, has cracked open the curtain to show how that plays out in the real world.
Cybersecurity professionals have long wrestled with one simple but maddening reality: the biggest vulnerability in any system isn’t a zero-day exploit or rogue actor—it’s the user. That one team member who reuses passwords across platforms. The employee who clicks a convincing phishing link disguised as a shipping confirmation. The well-meaning intern who forwards a sensitive document over unsecured email. These aren’t malicious actions, but they are reckless in ways that technology alone can’t mitigate.
The videos that feature Human Error might exaggerate these behaviors, but their basis in truth is unshakable. The moment Drew walks into an office with a USB labeled “Salary Data – Confidential” and plugs it into his laptop, the audience laughs. But that’s because it hits close to home. We’ve all witnessed (or committed) that level of carelessness, thinking, “What’s the worst that could happen?”
According to industry research, nearly 95% of all security incidents are the result of some form of human error. That’s not a glitch; it’s a systemic issue. And it’s not because people are dumb or incompetent. It’s because the average employee wasn’t hired to be a cyber sentinel. They were hired to do marketing, accounting, HR, or sales. Security isn’t their first language—so when it becomes their responsibility, there’s bound to be friction.
Drew’s Human Error character works because he isn’t a villain. He’s your coworker. He’s you on a bad day. He represents that moment when you skip the VPN because the login portal is annoying. Or when you send an email to “Danielle from Ops” only to realize too late that it was “Danielle from Outside Vendor.” Those are the kinds of tiny, seemingly insignificant lapses that can lead to data leaks, compliance violations, and massive reputational damage.
And that’s what keeps Human Error up at night. The world is more digitally dependent than ever. Every tool we use, from Slack to Zoom to Dropbox to CRMs and password managers, is a new vector for exposure. We live in a time where a single misplaced click can trigger a cascading catastrophe that spills across departments, clients, and entire industries.
Through the comedic lens, Drew helps us see this for what it is—not an abstract risk, but an everyday reality. One of the most powerful episodes features Human Error navigating a seemingly harmless situation: connecting to free airport Wi-Fi. Within minutes, he’s unknowingly given up his login credentials to a spoofed network and compromised sensitive data. It’s slapstick in execution but chilling in implication. Because it happens. Constantly.
This fusion of levity and legitimacy is what makes the series so potent. It doesn’t talk at employees, it talks to them. It disarms them with laughter, then sucker-punches them with reality. And in doing so, it accomplishes what most PowerPoint-driven compliance sessions never could: actual engagement.
When Mimecast initially tested the videos internally, they didn’t expect the flood of feedback from employees admitting, with a mix of embarrassment and gratitude, that they had made those very mistakes. This wasn’t just entertaining content. It was a mirror. A conversation starter. A wake-up call.
And that wake-up call is sorely needed. The speed and scale at which cyberattacks now unfold leave little room for ignorance. Phishing emails aren’t clumsy scams anymore—they’re hyper-targeted, linguistically sharp, and increasingly powered by AI. Social engineering schemes are so well-executed that even seasoned professionals fall for them. And the margin for error? Razor-thin.
But here’s where Human Error truly flips the script. Rather than using shame as a motivator, it uses relatability. There’s no pointing fingers. No lectures. Just an invitation to laugh at our shared fallibility and, from that laughter, learn something vital. It’s vulnerability as pedagogy. And it works.
Organizations that have implemented these training episodes as part of their broader security awareness efforts have reported measurable improvements. Click-through rates on phishing simulations drop. Employees start reporting suspicious emails instead of ignoring them. Conversations around password hygiene become normalized, not niche. And slowly, the organizational culture begins to shift from reactive to proactive.
That shift is not accidental. It’s engineered through behavioral science, and Drew’s Human Error leverages that science in surprisingly nuanced ways. For example, the character’s attire—pajamas—is not just a gag. It signifies comfort, complacency, and the mental zone people are in when they assume they’re “safe.” That zone is precisely where cyberattacks strike. The relaxed employee who assumes the firewall has them covered is the ideal target.
Another recurring visual in the series is Human Error’s cluttered desk: sticky notes with passwords, an unlocked screen, coffee dangerously close to a laptop. These aren’t props. They’re symbols of our casual relationship with security. They’re how breaches begin.
What makes the messaging so effective is that it never breaks character. There’s no moment where Drew turns and says, “Okay, here’s what you should do instead.” The show trusts the audience to fill in the blanks. It’s built on the premise that people aren’t stupid—they’re distracted, overworked, and not always equipped with the tools they need to prioritize security. Show them the risk in a way they can feel, and they’ll start caring. That’s the secret sauce.
And in this always-connected, digitally entangled society, caring is half the battle. When employees care, they question. They double-check. They pause before clicking. That pause can be the difference between safe and sorry.
Yet not everything in the Human Error series is humorous. Some episodes take a darker, more introspective turn. One particularly haunting sketch involves the aftermath of a ransomware attack, shown through the eyes of Human Error wandering a silent, decommissioned office floor, unable to understand what went wrong. The atmosphere is eerie, the lesson clear: this isn’t just about data. It’s about livelihoods.
These tonal shifts are deliberate. They reinforce the idea that security awareness isn’t just a checklist item. It’s a mindset. A continuous process of vigilance. And yes, sometimes that process involves being called out by a guy in PJs rollerblading through your office with a rogue USB stick.
What Drew Freed and Mimecast have created is more than a video series. It’s a language. A framework for how we talk about mistakes without shame. A way to move past outdated models of training and into something that resonates with the digital workforce.
Human Error has become a vehicle for empathy in cybersecurity. He reminds us that mistakes aren’t anomalies—they’re inevitable. The solution isn’t to expect perfection. It’s to build systems, cultures, and habits that are resilient when those mistakes happen.
So next time someone giggles at the latest Human Error sketch, ask yourself: are they just entertained, or are they learning? The answer, more often than not, is both. And in a landscape where cyberattacks grow more ingenious by the hour, that might be the most ingenious countermeasure of all.
From Training Tool to Cultural Icon: The Legacy of Human Error
By the time Human Error became a regular feature at cybersecurity conferences, awareness trainings, and corporate town halls, it was clear this wasn’t just a clever gimmick. It was a cultural shift. The fourth and final chapter of this series dives into the legacy of the campaign—how a slapstick character in pajamas not only disrupted stale training models but redefined how organizations talk about risk, behavior, and digital resilience.
Cybersecurity awareness has traditionally been a bureaucratic afterthought. Mandatory e-learning modules, dry lectures, and outdated slide decks have long plagued the space. Compliance? Check. Engagement? Not so much. That’s the context into which Human Error swaggered in—or more accurately, stumbled in, tripping over his own shoelaces and accidentally leaking sensitive data in the process.
What makes this campaign extraordinary isn’t just its comedic edge. It’s the fact that it worked. It genuinely shifted how companies approach training, transforming it from a passive obligation into an interactive conversation. And perhaps more significantly, it democratized cybersecurity culture. It made it okay to talk about mistakes.
Before Human Error, admitting to a security misstep often felt like confessing to a crime. It was embarrassing. Sometimes even career-limiting. But when Drew Freed’s bumbling alter ego made those same errors on-screen, it gave everyone else permission to acknowledge their own lapses without shame. That transparency created room for dialogue, and in that dialogue, the seeds of cultural change were planted.
The ripple effects were subtle at first: IT departments noting a slight uptick in incident reports, a few more raised hands during post-training Q&As. But over time, it became a groundswell. Teams started using scenes from the series as shorthand for common blunders. “Don’t go full Human Error” became an in-joke with serious subtext. Slack channels lit up with memes, parodies, and gifs featuring Drew’s most notorious moments—not as distractions, but as reinforcements of core lessons.
Even the corporate C-suite, notoriously slow to embrace training culture, began to shift. Executives who would normally skim security briefings started attending sessions where Human Error content was featured. Why? Because the barrier of entry had been lowered. The humor created an access point. And once inside, even the most tech-averse decision-makers began to grasp the human stakes of cybersecurity.
One company implemented an internal challenge based on the series, encouraging departments to identify and eliminate risky behaviors modeled in each episode. The competition became unexpectedly fierce. Marketing took on Finance. Legal went toe-to-toe with Sales. But the real victory? Everyone was suddenly talking about security in concrete, behavior-based terms. The theory had become tangible.
The influence even began to trickle outside corporate walls. Universities began incorporating Human Error videos into their computer science and digital ethics curricula. Some government agencies quietly adopted the content for internal staff development. And perhaps most surprisingly, small businesses—often left out of the big-budget training game—found the series an accessible, affordable way to level up their defenses.
Drew Freed, once a creative risk-taker with a GoPro and an absurd premise, became something of an underground legend in the cybersecurity world. His onstage appearances in footie pajamas drew standing-room-only crowds. But it wasn’t just spectacle. It was resonance. He represented the absurd but painfully real dimension of modern digital life—the truth that your company’s biggest vulnerability might be someone texting their password to themselves while stuck in traffic.
What truly elevated Human Error to icon status, though, was its staying power. Most training campaigns fade quickly. They run out of ideas. Or they become stale from overuse. But this series endured because it evolved. As cyber threats mutated and digital behaviors shifted, Human Error kept pace. He wasn’t stuck in 2018. He was clicking on deepfake HR videos in 2024, falling for AI-generated scams, or trying to outsmart facial recognition software with a printed photo.
This agility made the character a living litmus test for emerging risks. Rather than constantly updating policy documents that no one reads, companies could drop a two-minute sketch and spark instant recognition. That kind of relevance is nearly impossible to buy, yet Human Error pulled it off with apparent ease.
The campaign also proved that the line between entertainment and education isn’t a line at all—it’s a spectrum. When done well, the two aren’t mutually exclusive; they’re mutually reinforcing. The laughter didn’t dilute the message. It amplified it. People remembered what made them laugh. And that memory became behavior.
What Mimecast tapped into with Human Error is the holy grail of training: internalization. The point where awareness becomes instinct. Where the thought process shifts from “I should probably report this email” to “Why does this look suspicious? Let me check the sender domain.” The moment someone thinks twice before plugging in that random USB. That’s the win.
But perhaps the most profound legacy of Human Error is how it humanized cybersecurity itself. Too often, the domain is portrayed as a battleground for tech wizards and cybercriminal masterminds. What this series proved is that the frontlines are much closer to home. They’re in your inbox. On your commute. In your kitchen while you work from home.
Cybersecurity became less of an enigma and more of a human concern. A behavioral science issue. A cultural dynamic. And Human Error—goofy, klutzy, painfully relatable Human Error—was the perfect emissary for that message.
This wasn’t just about protecting data. It was about protecting people. About making sure that users weren’t just the weakest link, but the first line of defense. And doing that with empathy, not fear. With connection, not command.
In the end, the true brilliance of Human Error lies in its paradox. A character built on mistakes managed to get everything right. A series designed to make us laugh ended up making us smarter. And a campaign built around failure sparked a cultural success.
So as the digital landscape continues to evolve—with smarter attacks, deeper risks, and more cunning threats—the legacy of Human Error will live on. Not just as a series of funny videos, but as a benchmark. A north star for how to make complex issues understandable, memorable, and actually meaningful.
It turns out, the most secure system isn’t just built with firewalls and encryption. It’s built with awareness, self-reflection, and a healthy dose of humility. And maybe, just maybe, a guy in pajamas who reminds us that even the dumbest mistakes can teach the smartest lessons.
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