Welcome back! If you’ve been following along, you know we’ve already covered the wild early days of cybersecurity—when dial-up tones were the internet’s soundtrack—and the major attacks that shaped the industry, like Stuxnet, WannaCry, and SolarWinds. But beyond the headlines and war stories, working in cybersecurity for 30 years has taught me a few things (besides the importance of caffeine and a reliable VPN).
Some lessons came the hard way—through breaches, late-night incident responses, and conversations that started with, “We don’t need security, right?” (Spoiler: Yes, yes, you do). Others came from watching how the industry evolved, how threats adapted, and how security professionals (somehow) kept up.
This article will focus on the key lessons learned over the decades. These challenges still haven’t gone away (looking at you, social engineering), and why cybersecurity is still a never-ending battle.
Lessons I Learned Over Three Decades
The Importance of Continuous Learning
Cybersecurity isn’t a field where you “figure it out” once and call it a day. Attackers are constantly innovating, and defenses must evolve just as quickly. Suppose I had relied on what I knew in the 1990s. In that case, I’d still be telling people to “just install antivirus and a firewall”—which, in today’s world, is about as effective as locking your front door but leaving all the windows open.
Every cybersecurity professional is responsible for their continuous learning—but companies also have a responsibility to support that learning. Security teams can’t be expected to defend against ever-evolving threats if they don’t have access to updated training, certifications, and professional development. Organizations that invest in their security teams’ education aren’t just strengthening individual skills—they’re protecting themselves from becoming the next breach headline.
People Are (Still) the First Line of Defense
Firewalls and AI-powered security tools are great, but nothing beats an educated user who doesn’t click on a suspicious link. From ILoveYou to modern-day phishing attacks, one thing has remained constant: attackers love exploiting human nature more than technology.
While AI is changing cybersecurity, it still can’t replace humans—no matter how many vendors claim their tool can “eliminate” threats with machine learning. AI can spot anomalies, analyze vast amounts of data, and automate responses. Still, it lacks a well-trained human analyst’s critical thinking, intuition, and adaptability. The best security teams use AI as a force multiplier, not a replacement.
Balancing Security and Business Needs
One of the most challenging lessons I learned was that perfect security doesn’t exist—especially in a business environment where time, budget, and user experience all matter. Early in my career, I thought security should come first, no matter what. But over time, I realized that security professionals aren’t just defenders—we’re enablers. Our job is to make security work within the business, not against it.
If security is too restrictive, users will find ways around it. If it slows down operations, executives won’t buy in. The best security teams understand the balance between protection and usability, implementing security measures that enhance productivity rather than hinder it.
Collaboration Is Everything
One of the most underrated aspects of cybersecurity is teamwork—whether within an organization or across the industry. I’ve seen firsthand how information-sharing, collaboration, and community efforts have stopped threats in their tracks.
In the early days, companies hesitated to share details about security incidents, fearing reputational damage. However, as threats became more sophisticated, the industry realized that a lack of information-sharing only benefited attackers. Today, threat intelligence platforms, public-private partnerships, and security communities are working together to share real-time knowledge. Cybersecurity professionals don’t win battles alone. The best defenders share knowledge, collaborate across industries, and continuously learn from each other.
Challenges That Persist
The Human Factor
Despite all the advancements in technology, people remain the weakest link. Social engineering is still one of the most effective attack vectors, and no amount of automation or AI can entirely prevent someone from clicking a bad link or reusing “password123”.
Attackers exploit human psychology because they know it works. Phishing, pretexting, baiting, and impersonation attacks remain top methods for initial compromise. Even the most sophisticated nation-state attacks often start with a simple phishing email.
Some of the most notable modern initial vectors include:
- Business Email Compromise (BEC): Attackers impersonate executives or vendors to trick employees into wiring funds or sharing sensitive data.
- Deepfake and AI-Based Attacks: Attackers now use AI-generated voices and videos to impersonate company leaders.
- Credential Reuse Attacks: Employees using the same passwords across multiple sites create a goldmine for attackers.
So how do we fix this?
- Better Security Awareness Training: But not the dull, checkbox-style training—real, engaging education that teaches employees how to spot and report threats.
- Phishing Simulations: Test and train employees regularly to recognize social engineering attacks.
- Stronger Authentication: Enforcing multi-factor authentication (MFA) and password managers to reduce credential theft risks.
The Complexity of Compliance
Security and compliance should work together, but sometimes, compliance is seen as a substitute for security rather than a component. Regulations like GDPR, HIPAA, and PCI-DSS were created to improve security. Still, they frequently result in organizations focusing more on passing audits than securing their systems.
Some of the biggest compliance challenges include:
- Regulatory Overload: Companies operating globally must comply with multiple frameworks, which often have overlapping or even conflicting requirements.
- False Sense of Security: Many organizations assume that because they are “compliant,” they are secure—but meeting compliance checkboxes doesn’t mean they’re protected against modern threats.
- High Compliance Costs: Smaller organizations often struggle to meet regulatory requirements due to financial and resource constraints.
The best organizations use compliance as a baseline but go beyond it to build real security resilience. Compliance should be seen as a minimum standard, not the goal.
The Cybersecurity Skills Gap
Cybersecurity is growing faster than we can effectively train new professionals. Companies struggle to fill security roles with competent professionals, and many teams are understaffed, overworked, and burned out. Meanwhile, attackers don’t have a talent shortage—they’re always hiring.
This problem isn’t new, but it’s getting worse:
- According to Cybersecurity Ventures, there are about 3.5 million unfilled cybersecurity jobs globally, including an estimated 750,000 in the United States.
- Companies struggle to find experienced talent or do not expand their staff, leading to burnout among existing security teams.
- Many cybersecurity roles require certifications and degrees, creating barriers for entry-level talent.
Some possible solutions include:
- Expanding Cybersecurity Education: Encouraging universities and training programs to offer practical, hands-on cybersecurity courses.
- Apprenticeships and internships: More companies need to invest in training junior talent rather than expecting fully trained professionals to appear suddenly.
- Automation & AI Integration: While AI won’t replace humans, it can help reduce the workload by automating repetitive tasks like log analysis and threat detection.
If we don’t address the skills gap, attackers will continue to have the advantage. The industry must find ways to train, mentor, and retain cybersecurity talent before the gap grows even more expansive.
—
Cybersecurity has come a long way, but some challenges are as persistent as phishing emails on a Monday morning. While we’ve adapted, improved, and built stronger defenses, attackers evolve just as quickly. The key is to keep learning, collaborating, and refining our approach.
In the final posts of this series, I’ll look ahead at What’s Next for Cybersecurity, exploring AI-driven defenses, the rise of quantum threats, and how the industry must continue to adapt. Then, I’ll wrap things up with Personal Plans Moving Forward, sharing my thoughts on the future of cybersecurity, my role in it, and what’s next for me after 30 years in the field.
What lessons have you learned in your cybersecurity journey? Share your thoughts in the comments, and stay tuned for the final article in this series!
#Cybersecurity, #LessonsLearned, #Infosec, #SecurityChallenges, #SmallBusiness
