Power Players

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

VIDEO4:3804:38
What it's like to walk 5 miles to work like CEO Jack Dorsey

Billionaire Jack Dorsey can afford to hire a car, or even charter a plane, to drop him off at work every day. Instead, the Twitter and Square CEO chooses to walk.

His Bay Area commute is about five miles and takes him a little more than an hour.

Taking the time to walk to work every day 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 audio books or simply to think and draw inspiration from the streets of San Francisco.

Dorsey posted his walking stats on Twitter in July 2018, noting that he's been commuting on foot "for 2 years now. Usually get it done in 1h 15m, but was feeling tired this morning."

I decided to spend a week replicating Dorsey's morning routine, which, in addition to the 5.3 mile walk commute, includes waking up at 5 a.m. to meditate and work out. Usually, I start my days at 6:15 a.m., which allows me two hours to exercise, shower and get ready for work before heading out the door for my 30-minute commute. So this is a bit of a shift but no big deal, right?

Here's what happens:

Monday

The first day of the week is by far the easiest to pop out of bed: I'm fresh and excited to see what Dorsey's routine is all about.

I make coffee right away. It's my reward for getting up. Plus, I find that doing something active with my hands — boiling water, measuring coffee grinds, brewing the French press — wakes me up a bit. I also make my bed, another task that isn't exactly strenuous but requires enough movement to help fire up my brain cells.

While my coffee steeps, I download the Headspace meditation app, which offers 10 free, basic courses. I've never meditated before this week and try to get through the first 10-minute course without falling back asleep. After, I prep my lunch, check email, and download podcasts for my upcoming walk.

Dorsey meditates in the morning, so I did too

My apartment is 4.7 miles from my office, which is pretty comparable to Dorsey's distance, but I tack on an extra 10 blocks (about 0.5 miles) to make my commute as similar as possible to his.

Having no idea how much time to budget for my commute — Dorsey does 5.3 miles in one hour and 15 minutes, which seems like an absurdly quick pace — I aim to leave at 7 a.m. and get out the door by 7:10 a.m. It's still dark out.

I fire up a podcast, "The Daily" with Michael Barbaro, and have several more on deck. Twenty minutes into the episode, though, my phone dies from the below-freezing temperature, leaving me a full hour to spend with no company but my thoughts.

Most of that time is spent kicking myself for not fully charging my phone and complaining about the cold. I even contemplate abandoning the walk commute and finding a train, but I march on in silence.

No phone means no concept of time. I'm pleasantly surprised when the clock outside my office reads 8:37 a.m., meaning I did the walk in about 90 minutes. Not as fast as Dorsey, but still, pretty good time.

Day One really takes it out of me and I'm in bed by 6:15 p.m. and fast asleep before 8 p.m.

Tuesday

I get nine hours of sleep and wake up before my alarm sounds. I'm feeling peppy enough to go for a jog this morning and even run into a friend who's a devoted member of the 5 a.m. club.

After my jog, I take a quick shower, throw on a warm, walking-friendly outfit and am out the door by 7:20. My phone is fully charged and I put it on airplane mode to try to conserve battery. It does the trick. I get through three podcast episodes this morning, more than I sometimes listen to over the course of one week.

By the time I arrive at the office, I feel sharp and ready to hunker down. I'm also ravenous and end up heating up my lunch at 11:15 a.m.

The author, commuting
Wednesday

I hit snooze for the first time of the week today. The 5 a.m. wake up call is becoming less appealing.

I also skip the workout and, instead, focus on lingering to-do list items: I do laundry, catch up on emails, revisit some work and personal goals and try to sit still through another 10 minutes of meditation. There is definitely something to be said for increased productivity during the hours when everyone else is sleeping.

I'm only running on about five hours of sleep, but just getting things done gives me energy and I carry that positive momentum throughout the morning.

After spending Monday and Tuesday's commute inside my own head or listening to podcasts, I decide to switch things up today and call my parents. Both of them answer and I get some updates on the family. By the time I hang up, I'm almost at work. Easy peasy.

Thursday
The face of defeat

My energy levels are at an all-time low today. I struggle to get out of bed and, while I do get myself downstairs to the gym, I can barely lift a dumbbell or hold a plank. I cut the workout short, make a second cup of coffee and fold all the laundry I washed yesterday.

A polar vortex happens to be going on in New York City and today's temperature is an alarming 3 degrees, and -11 with windchill! I put on three layers of socks, two pairs of mittens and the warmest coat I own, but no number of layers will make this journey bearable.

I decide to modify my walk and instead of taking the long route (5.3 miles) along the Hudson River, I take a more direct route (4 miles) through the city.

I can't feel my feet or hands, but the change of scenery is a nice distraction. I end up listening to music and observing the city around me for most of the walk.

Friday

By the end of the week, I'm tired, sore and cold. But I'm also so close to the finish line that I don't really notice.

I run on the treadmill, shower, pack my small commuting bag and cruise to work. I pass hordes of runners and can't help but think that by the time they finish running, showering and commuting, I'll probably still be walking uptown.

Here's an example of my morning commute, which I recorded on Strava. This was a particularly speedy day:

After a week of rising and commuting like Dorsey, here's what I liked and didn't like about the routine.

The pros

I was much more productive in the morning. There's a reason so many successful people get up before the sun: As I experienced this week, it can be an incredibly productive time of the day because it allows you to tackle tasks before distractions arise.

"When you have peace and quiet and you're not concerned with people trying to get your attention, you're dramatically more effective and can get important work done," psychologist and author of "Two Awesome Hours" Josh Davis tells The Wall Street Journal, adding, "No one is expecting you to email or answer the phone at 4 a.m. No one will be posting on Facebook. You've removed the internal temptation and the external temptation."

Sure enough, I didn't have any friends to text or Instagram posts to check, which meant I had more time to get things done: I meditated, exercised, caught up on emails, revisited some work and personal goals and even did laundry one morning. And I found that finishing small tasks early on made me feel more in control over my day.

The walk, while chilly, was also refreshing

The walk was refreshing and invigorating. 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.

Rather than sitting shoulder-to-shoulder with strangers on the subway and catching about 50 percent of my podcasts over the rumble of the train, I had both physical and mental space on my 90-minute walk. It was a time I had to actually listen and think, which felt like a luxury.

The thinking time was also invigorating: I found my mind wandering from one idea to the next, or planning my day and week and getting excited about bigger goals and projects for the year. When you live in a big and bustling city, it's easy to flit from one activity to the next and forget to carve out time for yourself, slow down and reflect. The walk commute opened up that time.

I got a lot of exercise. Over five days, I walked approximately the equivalent of a marathon: 26.5 miles.

I saved money. There are few things I love more in life than saving money. I typically pay $2.75 every morning to take the subway, meaning I saved about 15 bucks this week. Small, but satisfying.

The cons

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 and was hard to justify considering I had much more efficient alternatives.

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. Less than halfway through the challenge, by Tuesday night, 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. (See: Monday.)

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, which 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. That meant wearing a slight variation of the same outfit every day: black pants and a sweater. I didn't mind it for a week — it was one less thing to think about in the morning, after all — 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.

Would I rise and commute like Jack Dorsey again?

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 — and that's why I won't be commuting like Dorsey again anytime soon.

That said, there were aspects of his routine that boosted my productivity and quality of life: the early mornings and the extra thinking time. While I won't be waking up at 5 a.m. every day, I'll do it occasionally, when I'm feeling behind in work or life. And 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 walk at a more leisurely pace.

That way, I'll still save a couple extra bucks a week, too.

Don't miss: A day in the life of an Uber, Lyft and Juno driver who makes about $6,000 a month in NYC

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