I'm a planner. The kind that color-codes spreadsheets and builds contingency trees so detailed NASA would be jealous. It's how I keep my brain from spinning out. Planning gives me structure. Safety. A place to stand when everything else moves.
But here's what I've learned: there's a difference between planning and paralysis.
I was on the team that mapped how Apple Stores would handle the first iPhone launch. We planned everything down to the minute—staffing flows, training protocols, crowd management, system loads. We had scripts, backups, and backups for the backups. We had a “war-room”
Then the doors opened.
Lines wrapped around city blocks. Systems crashed under demand we'd never seen. Customers literally cried holding the device. Employees threw out the script and started improvising. The plan? It gave us a foundation. But the real work started when we had to adapt in real time.
And that never stopped. Every launch after that taught us the same lesson: no amount of planning eliminates the unexpected. It just gives you better footing when it hits.
Corporate culture hates this truth. It treats surprises as planning failures. Doesn't matter how much went right—miss one edge case and suddenly you're "unprepared." So we overcompensate. Fifty-slide communication plans. FAQs longer than novels. Stakeholder loops that water down bold ideas into beige consensus.
Not because it works. Because we're terrified of being wrong.
Fear does ugly things to smart people. When your amygdala hijacks the wheel, your prefrontal cortex—the part that solves problems and sees possibilities—goes offline. You stop building. You start surviving. You tighten up. You freeze. You second-guess bold work into safe mediocrity.
You see it everywhere. Project delays dressed up as "thoughtful iteration." Over-documentation that kills agility. Brilliant people hedging themselves into irrelevance because they're more afraid of criticism than committed to impact.
It looks strategic. It's actually trauma response.
Real readiness isn't thinking of everything. It's handling anything.
Fighters don't just train to throw punches—they train to take them. To stay loose, absorb impact, recover fast. New Yorkers don't avoid slipping on icy sidewalks. They learn how to fall safer.
That's not incompetence. That's capability.
You will miss things. You will mess up. The moment something goes sideways doesn't prove you're a bad planner. It proves you're human.
The question isn't whether you were ready for everything. It's whether you collapsed the second things went off script. Did you flinch and freeze? Or did you breathe, adjust, and keep moving?
Plan well. But don't hide inside the plan. Get loose. Stay loose. Trust your ability to land on your feet.
Because the unexpected isn't the enemy of good planning. It's the point of it.
So, what’s a hula-hoop got to do with any of this? Maybe nothing more than a fun way to spend time instead of over-planning.