Here’s a question for you: When was the last time you were truly bored?
Not frustrated. Not waiting in line scrolling through your phone. Not filling every micro-moment with a podcast or email check. But genuinely, profoundly bored—staring at nothing, thinking about everything, with no agenda whatsoever.
If you’re like most leaders, the answer is probably “I can’t remember.” And that’s precisely the problem.
At Team Simon, we love studying what makes great leaders great. We’ve explored the power of purpose, the infinite mindset, and why leaders eat last. But one of the most counterintuitive insights we’ve encountered is this: boredom itself is essential to visionary leadership.
The Boredom Walks That Changed Everything
Simon discovered this recently through a conversation with Elle Cordova, a polymath who transformed lockdown isolation into viral poetry and music. Elle shared her secret weapon with him: “boredom walks.”
“She calls them ‘boredom walks,'” Simon says, “leaving the phone behind to let ideas bubble up.” No destination. No podcast. No productivity goals. Just walking and being present with whatever thoughts emerge.
In our hyper-connected, hyper-productive world, this sounds almost rebellious. But here’s what Elle understood: creativity doesn’t happen in the frenzy. It happens in the gaps.
The Wisdom of Sitting Still
Simon shares another formative experience: “I once got advice to go to Central Park, grab a coffee, sit on a bench, and just watch people for an hour. No agenda, no notes. It sounded absurd at the time, but he was right.”
Think about what that advice required: giving up an hour of “productive” time to do absolutely nothing measurable. For most leaders, that sounds impossible. Our calendars are packed. Our teams need us. There’s always another fire to put out.
But that’s exactly why boredom is so powerful. It creates space for rumination—the kind where your brain connects dots it couldn’t under pressure.
Why We’re Addicted to Busyness
Remembering his conversation with Elle, Simon says, “we laughed about America’s ‘vomit reaction’ to boredom. We’re addicted to stimulation, convinced idle time is wasted.”
This addiction isn’t accidental. Our brains crave the dopamine hit of busyness—the ping of a notification, the satisfaction of checking off a task, the feeling of being needed. We’ve built entire cultures around glorifying “the hustle” and wearing exhaustion as a badge of honor.
But here’s what we’re missing: in a world of AI and endless productivity tools, human innovation comes from what machines can’t replicate—curious, unstructured thought.
Elle learned card counting for blackjack not from apps, but from daydreaming about probabilities. When Simon struggled writing Leaders Eat Last, it wasn’t another meeting or research session that unlocked his breakthrough. “A walk in New York and a friend’s call pulled me through,” he recalls. Boredom forced the clarity.
What Boredom Does for Leadership
A bored leader is a reflective leader. And reflection is where transformation happens.
When you create space for boredom, you:
- Reconnect with your WHY: The daily grind can obscure your deeper purpose. Boredom strips away the noise so you can hear what truly matters again.
- See patterns others miss: Your brain needs idle time to process information and connect seemingly unrelated ideas. Innovation lives in those connections.
- Shift from reactive to visionary: You’re not just responding to the urgent—you’re envisioning what’s possible.
- Model trust and confidence: Teams follow leaders who have the courage to pause and think deeply, not just react constantly.
Without boredom, we default to finite games—chasing short-term wins and metrics over meaning. But when you embrace the infinite mindset, boredom becomes your ally for trust-building and innovation.
