I Never Expected To Learn These Things (And Still Have Much To Learn)
I’ve spent the last 10 years coaching, advising, interviewing, and occasionally just sitting quietly near high-performing CEOs, hoping their brilliance would rub off through osmosis.
Turns out, it doesn’t.
But what did rub off? A few hard-won lessons. Some inspiring. Some uncomfortable. All worth stealing.
Here are 7 things I’ve learned from the top 1%—with just enough sarcasm to keep it real.
1. They Don’t Trade Time for Money
Average leaders sell hours. Great ones buy freedom. High-performing CEOs think in terms of value, leverage, and results—not time. You’ll never hear one say, “Well, I put in 12 hours today, so I must be crushing it.”
Instead, they ask, “How do I get this outcome without becoming a hostage to it?”
Lesson: Stop measuring your worth in 15-minute blocks like a hungry corporate lawyer.
2. They Make Complex Things Simple
They walk into chaos and come out with a whiteboard diagram and two clear priorities. It’s kind of annoying. They’re allergic to jargon. They don’t flex their intelligence by complicating things—they flex it by explaining it so their kids could understand it.
Lesson: If it sounds smart but no one can act on it, it’s not smart.
3. They Insist on Clarity (Even if It’s Awkward)
High-level leaders don’t leave room for assumption. Ever.
They’d rather endure five seconds of awkward truth than six months of polite dysfunction. They ask, “What are you really asking for?” and “Are we clear on what success looks like?”
Lesson: Clarity beats comfort. Every time.
4. They Avoid Time Traps Like a Ninja with a Calendar
They don’t “grab coffee just to catch up.” They don’t “hop on a quick call that turns into a TED Talk.” They don’t attend meetings just because they got an invite.
Lesson: If you want CEO results, you can’t live on a middle manager’s calendar.
5. They Take Their Health Seriously (Finally)
Eventually, every high-performing CEO figures it out: your business can’t outrun your biology. They hire trainers, get blood panels, and eat like someone’s watching (because someone is watching). Not out of vanity, but because their health is a business asset.
Lesson: If you don’t schedule your wellness, your body will schedule your breakdown.
6. They Play at Their Work and Work at Their Play
They bring an element of joy, curiosity, and risk into their work like it’s a game. They know that “balance” is a myth so they seek integration in their lives. Then they bring elements of discipline, goals, and focus into their free time just as they would in the board room.
Lesson: Balance is not the goal—integrating the best parts of life into work and play is the goal. Your life isn’t split in two. It’s one whole, curious and glorious experiment.
7. They Don’t Need to Be the Hero
This one surprised me the most. The best CEOs don’t want to be saviors. They want to build systems where they aren’t needed at all. They don’t build around themselves—they build around the mission. And they make everyone else the main character.
Lesson: The higher up you go, the less it’s about you.
The Punchline?
High-performing CEOs are not superhuman.
They just stopped tolerating the stuff that makes everyone else feel stuck.
They stopped chasing shiny things.
They started designing their lives like they design their companies.
And they stopped pretending they didn’t know what to do next.
Now you know too.
So maybe it’s time to quit managing like it’s 2005.
Your calendar, your clarity, your energy—those are your empire.
Lead like it.
