The Cost of Over-Optimization
How Wandering Aimlessly Is Useful to Our Performance
Jack Dorsey once ran two billion-dollar companies, Twitter and Square, simultaneously.
His days were a choreography of discipline. He woke before sunrise, meditated, walked five miles to the office, then split his day between both companies. Each minute was mapped. Each habit is deliberate. He even scheduled time for ice baths and journaling.
To outsiders, he was a monk of productivity. Inside, he was juggling two full-time CEO roles, two boards, and thousands of decisions.
Over time, cracks appeared. Investors questioned his focus. Teams felt stretched. And despite his rituals of calm, Dorsey eventually admitted he couldn’t sustain it. In 2021, he stepped down from Twitter to lead just one company.
That wasn’t a sign of weakness; it was wisdom. Even for someone who seemed superhuman, total optimization had its limits.
My Own Version of Over-Optimization
I’ve never run two companies. But I’ve lived like I was managing five.
For years, I treated my life like a system that could be engineered for peak performance. My mornings were a checklist of optimizations:
- Wake up at 6 a.m.
- Meditate for ten minutes
- Journal
- Stretch
- Read ten pages
- Make a pour-over coffee
- Start work by 8 a.m.
Every task had a rule, a number, or a tracker.
The more I optimized, the more fragile everything became. If I skipped a workout, the day felt ruined. If I woke up thirty minutes late, I carried guilt for hours. My systems promised freedom but delivered pressure. I wasn’t tired from working too much. I was exhausted from maintaining the machinery of self-improvement.
At the time, I thought optimization was progress. It made me feel like I was moving forward. In reality, I was just in motion. Everything looked productive, but very little was creative.
I was measuring life by how efficient it felt—not how alive it was.
When the Brain Solves Problems by Doing Nothing
In a study from the University of California, Santa Barbara, researchers asked participants to think of as many unusual uses for common objects as possible. A brick, a shoe, a paperclip. It was a creativity test.
Then, halfway through, they interrupted the task. One group was told to rest quietly. Another continued working. A third group was asked to do a demanding task that required focus. And the last group did a simple activity—something like sorting numbers or identifying shapes on a screen.
After a short break, everyone went back to the creativity challenge. The results were striking.
The group that did the simple, undemanding task—the one that allowed their minds to wander—came back with more original ideas than everyone else. The rest and the hard-work groups didn’t improve.
In other words, creative breakthroughs came not from total rest or relentless effort, but from a state in between: light engagement that frees the mind to wander.
You’ve probably experienced this yourself:
- The shower ideas
- A solution that hits you while walking
- The sentence that writes itself during a drive
Those moments aren’t accidents. They’re the brain’s natural recovery cycle at work. When we stop forcing progress, the subconscious starts doing its best work.
The Restorative Power of Mind-Wandering
The same researchers then explored what happens inside the brain during these moments in another study. When your attention drifts, different regions start talking to each other. The prefrontal cortex—the part that plans and controls—loosens its grip. The “default mode network,” which links memory, imagination, and emotion, lights up.
In simple terms, the brain switches from execution mode to connection mode.
That’s why insights arrive during everyday moments. You’re not distracted. You’re allowing your mind to reorganize and connect ideas in the background.
But our obsession with constant input—scrolling, listening, optimizing—blocks this process. We fill every idle moment with noise, leaving no room for useful wandering.
How to Wander Usefully
Optimization isn’t the enemy. It’s just incomplete.
Like any system, it follows diminishing returns. The first few habits make you better. The next few make you efficient. But after a point, every new rule adds friction, not freedom.
What I’ve learned is that performance isn’t a straight line. It’s a rhythm. The best progress comes from alternating between sprint and stillness, focus and drift, control and surrender.
Here’s how to practice that rhythm in everyday life.
1. Work in waves
Treat your energy like the tide. Sprint when creativity peaks. Rest when it ebbs. It's called sprint–rest–sprint. Even elite athletes train this way—the work happens in cycles, not constants.
It's about managing your energy rather than your time. When you rest, rest fully. When you work, go deep. Momentum is born from rhythm, not relentlessness.
2. Leave space unoptimized
Not every hour needs a purpose. Keep pockets of unscheduled time. Mornings without meetings, evenings without screens. These “blank spaces” are where incubation happens.
The irony is that rest feels unproductive only because we don’t see the background progress it creates.
3. Redefine progress
I used to track everything: habits, steps, sleep, macros, even the time I spent thinking. It gave me a sense of control but also constant anxiety.
Now I measure progress differently: by energy and clarity. Did I feel present today? Did my work move something forward, even slightly? Numbers can measure efficiency. Only reflection can measure meaning.
4. Protect your boredom window
For years, I tried to outsource everything, believing it would buy me more “productive time.” What I didn’t realize was that these small, repetitive tasks are perfect for creative wandering.
Some of your best ideas will come when your hands are busy but your mind is free. That’s why walking, showering, or walking the dog can be surprisingly creative. They put you in a state of light engagement—just enough to quiet the mind but not enough to suppress it.
Don’t fill those moments with podcasts or calls. Let silence do its work.
Redefining High Performance
Eventually, Jack Dorsey stepped down from one company to focus on the other. He didn’t quit—he recalibrated.
That’s what I had to learn too. I stopped designing my days like an endless checklist to be perfected. I started designing them like a rhythm to be lived.
When I gave myself room to wander, my focus deepened. When I worked less, my output improved. When I stopped trying to optimize every minute, my ideas finally had space to breathe.
In Four Thousand Weeks, Oliver Burkeman writes that the more we try to control time, the more it controls us. The way out isn’t to manage time better—it’s to accept its limits and live fully within them.
Optimization promises control. It rewards discipline and looks impressive on paper. But it quietly erases the very conditions that make great work—and a meaningful life—possible: curiosity, spontaneity, and stillness.
Useful wandering restores those things. It’s the art of stepping away just enough for the mind to reconnect ideas, to notice what it’s been missing. It’s not laziness or distraction—it’s how deep thinking happens when the conscious mind gets out of the way.
