Walk 5 Miles to One Meal a Day: The Dorsey Way
Golden light cascades down San Francisco's hills as a self-driving car navigates the morning gridlock. A woman in Lululemon inside a vehicle frantically texts her workout challenge group: "Just crushed a 45-minute HIIT on the Peloton. Late to my meeting. Uber surge pricing is at 3.6x!"
The camera pans across the intersection clogged with rideshares, each a mobile island of tech workers chugging Soylent while their phones erupt with Slack notifications. "We need that deck by 10 AM!" shouts one into his AirPods. "Tell them we're not some bootstrapped startup — we're a pre-unicorn with legitimate Series A potential!"
On the corner, a disheveled man sits cross-legged on cardboard, ignored by the vehicles streaming past. His sign reads, "Need cash to pay off my second Tesla – Venmo accepted".
The traffic momentarily parts, and there — striding down the empty sidewalk in solitary contrast to the vehicular chaos — is a figure dressed in black. His beard is trimmed with precision, his gaze fixed forward with quiet certainty. Wait. Is that...?
Jack Dorsey's habits read like a Silicon Valley post-IPO founder's wishlist: meditating, eating once a day, taking ice baths. Yet, the ritual that truly stands apart — the one that defies productivity-as-identity cliché — is the long walk he once took to Twitter's offices every day.
Eighty minutes, rain or shine, step by thoughtful step. While others multi-tasked their way through inbox triage or nursed their third single-origin pour-over, Dorsey walked. Not chasing quantified-self metrics, not hacking longevity. Just to create space.
I admit my bias: choosing Jack as a model here isn't neutral. It's not just that I've walked those same streets. Fifteen years ago, I met Dorsey briefly. And he struck me as a rare breed: the old-school hacker who didn't chase money and fame but quietly attracted it, almost as if by accident. But there was no accident.
I've seen a quality in him that felt out of sync with the performance culture he helped enable — and yet refused to embody. There's discipline beneath his eccentricity. Stillness beneath the spectacle. In a city wired for optimisation, Jack seemed to walk a different route — literally and metaphorically. Maybe I want to believe that is still possible.
Walking five miles a day in a culture obsessed with efficiency feels almost rebellious. We've been trained to see time as currency, yet here was someone willingly spending nearly an hour and a half to cover a five-mile commute. Yet, this isn't waste — it's at the heart of deep work and inner work. A long walk becomes meditation — a slow unfurling of thoughts, a space where tangled worries loosen, and half-formed ideas rise to meet you with startling clarity.
What others dismiss as wasted time is often where meaningful transformations quietly occur. Breakthrough ideas, too — those strange, golden insights that never come when you're hammering away at a screen, but drift in during mile three, unhurried and fully formed, as if they've been waiting for you to slow down enough to notice. These walks silence the constant internal chatter and reconnect you to your personal wisdom, buried under the noise of distractions and ambition.
Jack isn't in this series because he's rich and peculiar. He's here because I've seen something quietly instructive in the way he operates. He models someone who found a way to move through the world without letting it move him. Not by wearing beanie and beard. But by virtue of the discipline. The restraint. The refusal to identify with efficiency just because the culture demands it.
You don't have to adopt his specific routines: meditating, fasting, walking. But it's worth asking yourself:
- Is urgency my own — or something I've picked up from others?
- How can I reclaim any routine — as an intentional practice?
- What's one thing I do on autopilot that deserves my full attention?
- If I walked more slowly through my own life, what might I finally catch up to?
The unreasonable life isn't about escaping the world. It's about choosing meaning over momentum, and presence over performance.