Most companies have decent reactive security. Vulnerability scanners. Patch management. Maybe a security team that responds to incidents.
But there's a gap that rarely gets addressed—the space between "this is broken" and "this is about to become a problem."
Two Different Problems
I think of security needs in two distinct categories:
| Reactive Security | Proactive Maintenance |
|---|---|
| "A vulnerability was just published for a package you use. Patch now." | "Your framework version goes end-of-life in 6 months. Start planning." |
| Urgent. Immediate action required. | No urgency yet. Easy to ignore. |
| Clear ownership. Security team handles it. | Unclear ownership. Falls through cracks. |
Most teams have the first covered. Few have the second.
Why Proactive Is Harder
The proactive stuff isn't glamorous. No urgent alerts. No CVE numbers. No "security incident" to rally around.
Just... tracking what versions you're running and knowing when they age out.
- When does your database version lose support?
- When does your framework stop getting security patches?
- When does your cloud provider deprecate that API you depend on?
These questions don't have dashboards. They don't trigger PagerDuty. They just... sit there, slowly becoming urgent.
Maintenance debt becomes security debt the moment a vendor stops releasing patches. By then, you're already behind.
What Proactive Security Looks Like
Real proactive security means knowing, right now:
- Technology inventory — Every framework, library, and service you depend on
- End-of-life dates — When each one stops getting security updates
- Upgrade complexity — How hard the migration will be (before it's urgent)
- Business impact — What breaks if you can't upgrade in time
This isn't a one-time audit. It's a living system that updates as your stack evolves and vendors update their roadmaps.
The CFO Question
Here's a question worth asking in your next leadership meeting:
"Are we tracking our tech stack's expiration dates?"
Not vulnerabilities. Not incidents. Expiration dates.
Because the most expensive security problems aren't the ones that trigger alerts. They're the ones that were foreseeable six months ago, when you still had time to plan.
The Bottom Line
Reactive security is table stakes. Every company needs it.
But the companies that avoid the big, expensive scrambles are the ones that know what's coming. They're not smarter—they just have better visibility into the future they're building toward.
The gap between reactive and proactive isn't a technology problem. It's a visibility problem. And visibility is solvable.
