Holiday or Not: 5 Thanksgiving Thoughts Every CEO Should Realistically Have
Thanksgiving is meant to be a moment of pause—good food, family, a little downtime, maybe a nap you swear you won’t take but always do. But if you’re a CEO, your mind rarely takes the full day off. And honestly, that’s not a bad thing. Reflection can be a powerful part of leadership.
Here are a few healthy, realistic, and practical thoughts that should be running through a CEO’s mind this Thanksgiving—especially from a business-risk, continuity, cyber, and insurance perspective.
1. “What went right this year—and where did we get lucky?”
Resilience isn’t just about planning. It’s also about acknowledging the moments you dodged a bullet.
A cyber incident that almost happened
A key employee who almost left
A vendor failure that almost disrupted operations
Luck is not a strategy—but recognizing where it played a role helps you build better ones.
2. “If we were hit with a cyberattack tomorrow, would we survive the holiday weekend?”
It’s a sobering question, but an essential one.
Do we have offline backups?
Do we know who we’d call within the first hour?
Does everyone know their role?
Is our cyber insurance aligned to today’s risks—not last year’s?
Cyber incidents don’t take holidays… but companies sometimes unintentionally do.
If you think threat actors take Thanksgiving off… they don’t. In fact, they prefer holidays.
Cyberattacks spike 30–60% during holiday weekends, and the average time-to-detection increases by 3–4x.
A breach that would normally be identified in two hours can take eight to ten during a holiday—giving attackers time to expand access, encrypt additional systems, exfiltrate significantly more data, and increase their ransom leverage.
Ransom demands typically rise 20–30% during holiday attacks, and 60% of holiday ransomware incidents start with a compromised remote login. Travel, hotel Wi-Fi, and remote access create the perfect entry point.
3. “Do we truly know where our single points of failure are?”
Every company has at least one:
One key vendor
One irreplaceable employee
One fragile process
One outdated system everyone hopes survives through Q4
If that one thing went down, what would break? And do we have a plan?
4. “Have we built a culture where people would tell us if something looks wrong?”
Most breaches, compliance issues, and operational failures weren’t surprises—they were ignored warning signs.
Ask yourself:
Would my team speak up early?
Do they feel safe raising concerns?
Are we rewarding transparency over perfection?
Culture is a risk control—arguably the most important one.
5. “Is our insurance keeping pace with how our business has evolved?”
Your business changes every year. Your insurance should, too.
CEOs should reflect on whether they have:
The right cyber limits
Adequate business interruption coverage
Proper professional liability
Supply-chain or vendor-failure protections
Updated asset valuations
Insurance isn’t a formality—it’s strategy in action.
Closing Thought
Thanksgiving isn’t about worrying—but it’s a great moment to reflect on what’s going well, what needs attention, and where to build strength for the remainder and coming year.
If you're thinking about continuity, cyber readiness, and risk resilience—congratulations.
That’s not worry.
That’s leadership!
Happy Thanksgiving from the Armada Growth Partners (AGP) family — Wishing you a chaos-free holiday!