Power Players

I woke up at 5 am and walked 5.3 miles to work like Jack Dorsey for a week—and I'll never do it again

What it's like to walk 5 miles to work like CEO Jack Dorsey

Twitter and Square CEO Jack Dorsey walks 75 minutes and 5.3 miles to work every morning.

Taking time out of his morning to commute by foot is the most worthwhile investment he's ever made, Dorsey told author Tim Ferriss for his book "Tools of Titans." During the five-mile trek, the self-made billionaire unplugs. He doesn't email or text. He uses the time to listen to music and audiobooks, or simply to think and draw inspiration from the streets of San Francisco.

I decided to spend a week replicating Dorsey's morning routine, which includes waking up at 5 a.m. to meditate and work out, in addition to the 5.3 mile walk.

I learned after the experiment that he prepares for the early alarm by getting nine hours of sleep. He tweeted, in response to my challenge: "Most important thing in these routines is to constantly experiment to see what's right for you. Oh, and sleep! I try to get 9 hours."

dorsey tweet

My apartment in Manhattan is 4.7 miles from my office, which is pretty comparable to Dorsey's distance, but I tacked on an extra 10 blocks (about 0.5 miles) to make my morning walk as similar as possible to his. The biggest difference between our commutes is our location: He's in the Bay Area, while I'm in New York City. If he has the advantage of a more mild climate, I have the advantage of terrain: There are no hills to climb in NYC.

Most mornings, I was up at 5 a.m. to exercise or meditate, out the door by 7:15 a.m. and in the office by 8:45 a.m.

Five days of rising and commuting like Dorsey was plenty for me. Here's why I won't be adopting his full morning routine anytime soon.

Most days, I hit a wall around 3 p.m.

Waking up at 5 a.m. on a daily basis and schlepping five miles to work is exhausting, and that really hit me most afternoons.

My solution was to front-load my mornings, so I made sure to finish the most mentally demanding tasks early in the day and save the more menial items for the late afternoon. By Tuesday afternoon, I was already counting down the days to the weekend, not because I desperate for time off from work but because I was desperate to sleep in.

A particularly hard morning

An active commute requires a lot of logistics

If you're going to walk, bike or run to work, you have to plan ahead, and I wasn't always prepared. On Monday morning, for example, my phone died 20 minutes into my commute, meaning I couldn't listen to podcasts or music. I had to spend a full hour with no company but my thoughts.

Besides making sure my phone was fully charged, I also had to download podcasts ahead of time to save data and pack a light backpack that would be easy to carry. That meant no room for heavy Tupperware, extra books or my laptop.

Perhaps most challenging, I had to wear clothes that were appropriate for the weather, for walking and for work. Because temperatures hit 3 degrees that week, I needed to stay warm and comfortable while still looking professional. I ended up wearing a slight variation of the same outfit every day: black jeans and a warm sweater. I didn't mind the redundancy for a week, but I didn't like feeling limited.

And even though I wasn't working up a sweat from the 90-minute trek in the dead of winter, I still felt a bit disheveled by the time I made it to the office.

The author, commuting

Walking was highly inefficient

My on-foot commute took triple the time the subway takes. And while I did my best to make the 90-minute journey a productive one, it still felt like a big time commitment. It was hard to justify, especially considering that I had much more efficient alternatives.

Overall, I felt like my entire morning centered around my commute: It gave me a strict early departure time and dictated things like what I wore and what I could and could not pack in my bag for the day. Again, this wasn't a big deal for one week, but it didn't seem sustainable.

That said, there were aspects of his routine that definitely boosted my productivity and quality of life: I got a lot done before 7 a.m. Besides meditating and exercising, I had time to catch up on email, revisit some work and personal goals and I even did laundry one morning.

And walking was refreshing. New York City, with its jackhammers, sirens and traffic, is a loud and sometimes obnoxious place to live. My early morning walk, which took me along the Hudson River, was a refreshing escape from the racket. It was a time I had to actually listen to podcasts or simply think, which felt like a luxury.

Plus, I got a ton of exercise and saved a few bucks on public transportation.

While I won't be walking 5.3 miles to work ever again, I would walk home from work, when I'm less pressed for time and can go at a more leisurely pace.

As for the 5 a.m. club, I was a big fan of the early mornings, but they took a toll on me. I'll revisit becoming a permanent member when I can consistently get nine hours of sleep like Dorsey does.

Don't miss: Jack Dorsey wakes up at 5 a.m. and walks 5 miles to work—here's what happened when I tried that routine for a week

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