The Cannae Problem: How Success Becomes a Trap
Why the strategic pause, not dashboards, is the only safeguard against invisible failure.
IMG SRC [I’m sharing the map versus the art here for perspective, because it really is incredible to consider that this battle had over 80,000 lives reduced to a single maneuver. This example should be a great reminder of how easy it is to get lulled into old ways until the cost comes due.]
Hannibal didn’t just defeat Rome at Cannae. He exposed a fatal habit: success turned ritual. Rome’s legions didn’t fail because they were weak. They failed because they couldn’t stop winning the same way.
Joan Westenberg refers to the Cannae Problem in her recent blog (a master class in storytelling btw), and it’s not ancient history. It’s leadership, today. Take one recent thread where someone suggested, in all seriousness, that “AI might be recalled because it was bad.” Forget the weakness of the argument for a moment. What matters is this: leaders are either starting to think this way, or they’ll be forced to lead in a world where others do. Cannae isn’t just a story about Rome. It’s what happens when success (or inertia blinds us to drift, when we keep marching on the old map long after the terrain has changed.
The greatest risk to your leadership isn’t failure; it’s success left unexamined. Success has a half-life. What worked yesterday decays in silence. First, it’s muscle memory. Then it’s ritual. And then, one day, you’re marching in formation — straight into a kill box you built yourself.
Rome didn’t lose to Hannibal. It lost to its own certainty.
Reflection vs. Ritual
Reflection is the difference between reacting and re-seeing. Without it, we mistake rituals for strategy. Dashboards, KPIs, “best practices”—they all start looking like maps. But maps aren’t terrain.
Reflection is the pause that tears the paper in half and forces you to look up. Sometimes, a Strategic Pause is the only thing that keeps the ground visible.
Because without it, success doesn’t just calcify. It blinds us.
From Self to System
Cannae isn’t personal. It’s systemic.
Unexamined habits harden into unexamined governance. Autopilot becomes culture. And culture, left unchecked, becomes policy — until one day, the very systems built to protect you are the ones marching you over the cliff.
No dashboard will ever flash red when you’re winning your way into a trap.
If we want adaptive systems, we need reflective leaders. Leaders are willing to interrupt their own momentum long enough to see what’s shifted under their feet.
The Pause Rome Never Took
Leadership isn’t just about direction. It’s about interruption. It is the courage to stop marching long enough to see where you are.
Trusting the old model until it does you in is the quietest danger in leadership. Success carves grooves in the mind. Familiarity feels safe. Efficiency feels virtuous. And before you know it, your playbook is running you.
This is why I wrote Driving Your Self-Discovery. Not as a manual, but a map-breaker. A way to surface what’s been hiding in plain sight: the drift, the blind spots, the habits that once made us strong but now hold us back.
It’s how leaders and teams take the pause Rome never took—before success becomes ritual, certainty becomes strategy, and before you find yourself at your own Cannae.
This isn’t soft work. It’s survival. The question is whether you build that pause into your system, or wait until the system forces it on you.
Rome didn’t get a second chance. You do.
Recommend Lead With Alignment to your community
Leaders who don’t design for reflection inherit ritual. Agency breaks the pattern. Governance sustains progress.