Bleary-eyed and running on fumes, a Silicon Valley executive rushed into the conference room, late for a critical client meeting.
As heads turned, the silence was broken by his client asking, “What are you doing here? Didn’t your wife give birth just last night?”
He froze. The question hung in the air, impossible to deflect.
Surely leaving his newborn and wife meant his business was up in flames. That this was a make-or-break moment in his company’s trajectory.
But the truth was troubling: there was no emergency. No crisis demanding his specific expertise. Nothing that couldn’t have been handled by someone else.
So why was he standing in this conference room instead of by his wife’s hospital bed?
How “Yes” Becomes Your Default
Let’s rewind a few months. This executive had just sold his company. The acquisition was everything he’d worked for. This moment, the pinnacle of his success, should have been liberating.
But the opposite happened. Instead of having more freedom, his calendar became more congested than ever. The acquisition brought a deluge of integration meetings and strategic opportunities. Each day arrived with an avalanche of emails marked “urgent.”
With every “yes,” control over his time slipped further away. What began as occasional compromises quietly evolved into an autopilot routine that pulled him further from his plan to exit and focus on his growing family.
By the time his child was born, the pattern was set. Going to work the next day was his default response.
Greg McKeown tells this story in Essentialism: The Disciplined Pursuit of Less, this month’s Lifeworks Book Club selection. McKeown uses it to illustrate something most of us don’t notice happening in our own lives: the gradual erosion of our power to choose.
A Word That Lost Its Meaning
Here’s something that stopped me in my tracks. When “priority” entered the English language in the 1400s, it was singular. For 500 years, people understood that by definition, you can only have one priority. One thing that comes first.
It wasn’t until the 1900s that we pluralized it.
We now talk about our “priorities” without a second thought, as though having five first things is perfectly logical. McKeown argues this linguistic drift mirrors a deeper problem. We’ve convinced ourselves we can do everything, and the cost of that belief is that we do nothing with our full attention.
He draws a sharp line between two mindsets. The non-essentialist operates on autopilot, saying “yes” by default, believing everything is obligatory. The essentialist stays engaged, exercises control, and accepts that choosing one thing means deliberately not choosing others.
The executive in that conference room had crossed from one to the other without noticing.
The Scan He Should Have Caught
McKeown tells a second story that raises the stakes considerably.
A respected physician stares at a scan on his computer screen. The mass is unmistakable. Frantically, he pulls up the original scan he had reviewed and cleared six weeks earlier. There, a smaller shadow. A shadow he should have flagged.
The cancer had advanced. Treatment options that would have been available weeks ago were off the table. Precious time had been lost.
How had he missed it? Colleagues sought his expertise on difficult cases. Medical students competed to train under him. His attention to detail was something he prided himself on.
But then he replayed the day he’d reviewed that initial scan. A Thursday. Morning rounds. Full clinic. A committee meeting crammed into lunch. A backlog of paperwork that stretched into late afternoon. When the scan came in, he gave it what he believed was his usual thorough review.
It wasn’t. His attention that day had been divided across too many responsibilities. His scatterbrained state may have cost his patient their life.
Years later, this physician described the moment as a turning point. He stepped away from non-essential elements of his practice to ensure he had proper bandwidth for what mattered most: providing excellent care.
The Glass and the Rubber
When I first read Essentialism, I was in the early days of building Lifeworks. I was overcommitted from saying “yes” more often than “no,” buckling from the weight of everything feeling so important.
McKeown uses a metaphor I think about often. When you’re juggling a dozen responsibilities, not every ball is made of the same material. Some are glass. Drop them, and they shatter. But most of them are rubber. They’ll bounce right back.
The problem is that we treat every ball like glass. We stress equally over the rubber ones, and the constant vigilance leaves us exhausted and unable to protect what’s fragile.
The executive missed his child’s first day alive for a rubber ball. The physician missed a shadow on a scan because he’d been juggling too many rubber balls to focus on the glass one in front of him.
The Freedom of Fewer Things
What strikes me about both stories is that neither the executive nor the physician was lazy or careless. They were accomplished, driven people who cared deeply about their work. They failed at selection. They hadn’t decided what deserved their full attention, so everything got a fraction of it.
I’ve seen a version of this in my own life and in conversations with people I admire. The overcommitted professional who hasn’t had dinner with their family in weeks. The entrepreneur who works every weekend but can’t name their top priority. Even retirees fall into it, filling every hour because sitting still feels like wasting time.
McKeown’s prescription is uncomfortable but clear: if you don’t choose what matters, someone else will choose for you. And their agenda won’t match yours.
Since reading this book, I’ve been asking myself one question I want to pass along to you: What should I remove from my life?
The responsibilities that flatter my desire to feel important but contribute nothing to the people who matter most. The rubber balls I’ve been juggling as though they were glass.
What about you? What’s one commitment in your life right now that doesn’t align with your deepest values? This week, I’d challenge you to reclaim that time. Not from a place of defiance, but from a position of clarity about what deserves your attention.
Your future self will notice.
If you’d like to explore how any of this connects to your own financial picture, we’d be glad to talk.
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