The $3,900 Question: Is Your Technical Debt as Sick as My Dog? (And What You Can Do About It)
Hey there, fellow cybersecurity leaders! G Mark Hardy here from CISO Tradecraft. I recently had a wake-up call that hit incredibly close to home – involving my beloved Pomeranian, Shelby – and it perfectly illustrates the hidden, compounding dangers of technical debt in our field. You might be tempted to skip this if you don't have a dog, but trust me, the lessons learned here could save your organization a lot of pain, a lot of money, and maybe even a major crisis.
I was just getting ready to report back from RSAC 2025, the newly renamed conference formerly known as RSA. I had my content creator badge and a plan to attend talks and bring you insights. But life, as it often does, threw a curveball. I had to rush home early. The other big reason I couldn't give much of a report from RSAC is that my little dog, Shelby, was seriously ill. As I navigated that personal crisis, the parallels to our professional world became starkly clear. It made technical debt very, very real for me.
What Exactly IS Technical Debt in Cybersecurity? It's Costing You.
Let's cut to the chase. In the cybersecurity world, technical debt is the accumulation of compromises, shortcuts, and outdated practices that we tolerate in our systems, processes, or infrastructure. It's born from that "we'll fix this later," "we'll get around to it" mentality. This can manifest as outdated software, skipping patches, or delaying the implementation of more robust security controls. It's not always intentional, of course. Sometimes it's due to budget constraints, sometimes it's driven by tight deadlines to get something out the door, and sometimes, honestly, we just don't know any better.
But here's the absolutely critical part, and where the analogy to interest on a loan comes in: technical debt doesn't just sit there; it compounds. It gets worse over time. It's like interest on a bad loan with an absurdly high rate, say 29.99%. It relentlessly increases your risk, complexity, and cost over time.
And because risk is measurable uncertainty, while you don't know if something bad is going to happen because of this debt, you absolutely know that when it does, the consequences could be a whole lot worse.
So, who ends up holding the bag for this mounting debt? It's a shared burden across the organization. Leadership might prioritize speed over necessary security implementations. Developers might cut corners to meet aggressive deadlines. Your IT teams might struggle heroically just to keep pace with the constant rate of change. But the consequences? They're pretty much universal and they hurt everyone:
Vulnerabilities that attackers are just waiting to exploit.
System failures that can dramatically disrupt your critical operations.
Severe compliance failures that bring fines and reputational damage.
Significant and often hidden long-term costs.
An erosion of vital trust from customers and partners.
Slowed down innovation because you're constantly putting out fires.
Completely drained resources that are forced to scramble and clean up messes that could have been prevented.
Consider this statistic I came across: organizations burdened with high technical debt reportedly end up spending about 50% more on IT remediation. It's truly like running up a credit card bill you can't afford with punitive interest rates – that debt builds up incredibly fast and becomes crippling.
Shelby's Story: When Technical Debt Gets Personal (And Expensive)
My five-year-old Pomeranian, Shelby, has been my best friend for five and a half years, a constant, healthy companion. She usually spends her time right here on my desk while I work. I never planned to breed her, and since she wasn't around other dogs, spaying seemed unnecessary. It felt like a low-risk choice at the time, perhaps like skipping a non-critical software update. I was told there might be a higher risk of something remote like breast cancer, but that felt like a distant vulnerability I didn't need to prioritize right then. This was my first mistake, a piece of technical debt I unknowingly allowed to accumulate in her care. Spaying would have cost maybe $99, not terribly expensive, and pretty routine.
Fast forward to March of this year. After her heat cycle, which seemed normal initially, something was off. She didn't bleed much at the end of her cycle. In hindsight, this was like a loss of telemetry. It was a signal, but I didn't have the tools or the knowledge to properly interpret it. In cybersecurity, that's like losing visibility into your network logs or dismissing an anomaly because it doesn't immediately fit your expected pattern. You might even think, "Okay, fine, maybe it's a little easier cleanup".
Over the next couple of weeks, her behavior changed. She became less playful, more withdrawn. I initially chalked this up to her cycle ending, much like you might attribute a system slowdown to normal traffic spikes. But then the symptoms worsened. She stopped wanting to eat. Her abdomen started to swell up a little bit, and she would moan when I tried to pick her up. These were clear red flags, but I misattributed them. Maybe she ate something bad outside, I thought. Maybe she was just tired. This is like misattributing a system slowdown or assuming everything is fine after just running a basic vulnerability scan that didn't scream "critical". I even did a Google search on her symptoms, but nothing urgent jumped out. My mistake? I didn't include a key element in my search: "unspayed female dog". It's like running that basic scan and assuming everything's fine because the report didn't scream critical, so you just keep going.
Then came the crisis moment. While I was at RSAC, three time zones away, I got a call from home: "Your dog's really seriously ill". The call didn't go through immediately because my phone was in sleep mode due to the time difference. This was a decision maker unavailable moment. I never thought about this in my tabletop exercises, where I always include the scenario of a key decision maker being on a plane and unreachable. At home, there wasn't a designated alternative decision maker. My initial suggestion, unfortunately, was to wait three days until I could get back. That was another mistake, more debt piling up at a critical moment.
Thankfully, my wife called the vet's receptionist who, bless her heart, mentioned a condition called pyometra. I had never heard of it. It's a life-threatening infection of the uterus that strikes unspayed dogs. It fills up, infects, and can eventually burst, killing the dog. I thought, this is like a non-expert diagnosis moment. It's the receptionist, like a junior analyst who flags a potential issue but might not have the authority to escalate it properly.
A quick Google search on pyometra was terrifying. The symptoms matched perfectly: lethargy, abdominal swelling, loss of appetite, rapid breathing. It's a ticking time bomb; it kills your dog in only a few days, and several days had already passed since her symptoms started. I immediately called back home and insisted she go to the vet today. My wife got an Uber, and thank goodness she did. The vet confirmed the diagnosis and performed emergency surgery right then and there. He told her point-blank, "if you waited 12 more hours, you wouldn't have a dog".
The surgery was drastic. They removed two and a half pounds of infection from my 11-pound dog. That's nearly a quarter of her body weight! Imagine having to shut down a quarter of your critical systems because you can no longer depend on them. Shelby is recovering now, but it was an incredibly close call that could have been avoided if I had addressed that initial piece of technical debt – not spaying her – years ago.
Key Lessons for Cybersecurity Leaders from a Pomeranian's Plight
Shelby's ordeal offers critical, painful insights into managing technical debt in our organizations:
Small Decisions Compound into Big Risks: Not spaying Shelby years ago seemed like a low-risk, minor choice at the time. Just like skipping a single software update, delaying a security audit, or using slightly weaker controls initially. But these seemingly small choices accumulate silently and build up into much bigger, often unseen, risks that you don't even recognize until it's almost too late.
Loss of Telemetry is a Dire Warning Sign: Her lack of bleeding was a missed signal. I didn't have the context or tools (the knowledge about pyometra) to interpret it correctly. In your environment, this is not having adequate real-time monitoring, neglecting log analysis, or dismissing anomalies simply because they don't fit your pre-conceived mental model of what's normal. You are flying blind without visibility.
Misattribution Delays Critical Action: We initially thought Shelby's symptoms were due to something minor or benign, like eating something bad. This is exactly like the common tendency to initially blame a data breach on simple user error instead of digging deeper to find the underlying vulnerability or systemic issue. Misattributing symptoms prevents you from addressing the true, often more serious, root cause. Root cause analysis is absolutely critical. Don't stop at the surface.
Accessibility and Informed Decision Makers Matter: My partner couldn't reach me immediately. Then, my initial suggestion to wait was based on not truly understanding the severity of the situation. If your key decision makers are unavailable, or if bureaucratic friction makes it incredibly difficult to get authorization quickly, it can turn a potentially manageable security event into a full-blown crisis. Decision makers also need to be willing to invest time to understand the severity and implications of security issues. Once I Googled pyometra, I immediately understood the urgency.
Non-Experts Can Be Your First Warning System: That vet receptionist saved Shelby's life by suggesting pyometra. She wasn't the vet, but she had encountered this before and knew the signs. In your organization, be willing to genuinely listen to your junior analysts, the help desk technicians fielding calls, or even just observant end users who say, "Something doesn't feel quite right". They might not have the full technical picture, but they could be the very first ones to spot trouble.
Shelby's emergency surgery was our equivalent of emergency remediation. It was a high-stakes fix for a problem that was entirely preventable. And it was costly. The surgeon's bill alone was $2,800, and with everything else thrown in, it totaled about $3,900. When you think about those kinds of expenses in cybersecurity, it's exactly like calling in an expensive incident response team whose bill starts the minute they engage – and believe me, they are not cheap. You're also covering their travel, lodging, meals, plus your own team's overtime. It adds up very, very quickly. It's like paying millions to patch systems and recover from a ransomware attack that exploited a known vulnerability you could have patched months ago but didn't because you were putting it off, it looked too difficult, or you didn't want to disrupt business functions.
Actionable Recommendations for CISOs: Don't Wait for Your Pyometra Moment!
Shelby's story underscores a crucial point: technical debt isn't just a technical issue; it is fundamentally a business risk. Managing it is the difference between proactive investment in security hygiene and stability versus reactive panic during a crisis.
So, as cybersecurity leaders, what concrete steps can you take to start tackling this beastly technical debt before it triggers its own expensive, potentially catastrophic "pyometra moment"?
Launch a Formal Technical Debt Assessment Initiative: Don't guess where your debt lies. Start by systematically assessing your technical debt across all your systems, applications, and infrastructure. This isn't just running a vulnerability scan; it's identifying outdated software versions, unsupported hardware, legacy systems that are fragile or costly to maintain securely, missing security controls, and processes that rely on manual, error-prone steps.
Prioritize Ruthlessly Based on Risk: You can't fix everything at once. Based on your assessment, prioritize your critical updates and remediation efforts. Focus first on the debt that introduces the most significant risk (highest likelihood and highest impact) to your organization. This might involve critical vulnerabilities on internet-facing systems, compliance requirements, or debt that affects core business functions. Use a risk framework to guide your prioritization discussions with business stakeholders.
Build Remediation into Project Lifecycles: Shift from seeing remediation as a separate, backlogged activity. Integrate technical debt reduction into ongoing projects and operational budgets. When upgrading a system, allocate resources to retire the legacy component it replaces properly. When developing new applications, enforce secure coding standards and modern architecture practices to prevent new debt from being created. Make "paying down debt" a standard part of your development and operations cycles.
Invest Heavily in Visibility and Monitoring: You need to see those "loss of telemetry" moments and those subtle symptoms. Invest in visibility tools like robust SIEM (Security Information and Event Management) systems, EDR (Endpoint Detection and Response), and continuous monitoring solutions. Ensure these tools are properly configured and that your team is trained to interpret the signals they provide, even the anomalies that don't fit typical patterns.
Empower and Train Your Team (and Listen!): Your team members are often the first line to spot technical debt and its consequences. Invest in training so your team can identify the signs of technical debt and understand its risks. Crucially, build a culture where security is everyone's responsibility, and where analysts at any level feel empowered to raise alarms about potential issues, even if they don't have the full picture or official escalation authority. Listen actively to their concerns.
Educate Leadership and Stakeholders on the Business Risk: Frame technical debt not just as a "tech problem" but as a clear, quantifiable business risk and cost. Use analogies like the compounding interest on a bad loan or, yes, even a preventable, expensive medical emergency. Help decision makers understand the severity and long-term implications so they are willing to invest the time and resources needed to address it proactively. Ensure there are clear authorities for taking action, even when primary decision makers are unavailable.
Act Now. Seriously, Now. This is the most critical piece. Don't delay. The longer you wait, the more expensive and risky it becomes. Start somewhere, even if it's small. Pick one area, assess the debt, prioritize the worst parts, and make a plan to fix them.
My hope is that Shelby's story sticks with you, not just as the tale of a beloved dog who got seriously ill and almost died, but as a powerful, personal wake-up call. You need to tackle your technical debt aggressively and proactively before it becomes a full-blown crisis that forces your hand, costs you dearly, and puts your organization at existential risk.
If you've got stories of your own about pets or cybersecurity crises that taught you about technical debt, drop us a note on LinkedIn or connect with me directly. I'd love to hear from you.
Stay safe out there, and go check on your technical debt!
G Mark Hardy Host, CISO Tradecraft