I Lived Like Jack Dorsey for a Week. It Wasn’t Easy

Cold showers and fasting are hellish — but there are some advantages to the Twitter chief’s daily routine

Being Jack Dorsey isn’t easy. And I don’t mean it isn’t easy to run Twitter and Square, two Silicon Valley giants with a combined market cap of about $57 billion. I mean living like Dorsey isn’t easy.

For the last week, I’ve done my best to copy Dorsey’s daily routine, which he broke down on Ben Greenfield’s Fitness podcast. There were several adjustments I needed to make. Cold showers? Check. Fasting? You got it. Seven-minute workouts? Sure, why not.

I figured at minimum, this experiment would add a bit more structure to my life — and maybe, optimally, liberate the inner tech genius inside me. Maybe I’d finally invent a cool app and get rich, after thinking for about a day in 2014 that the world desperately needed an app that helps people find pickup basketball games. (A similar app already existed, of course, and I didn’t have the technical skills to get it off the ground at any rate.)

I’m not a tech genius — yet — but I am going to continue adopting some of Dorsey’s practices into my own daily routine moving forward. (Keyword: some. There were also a few things that I’m stopping today and never going back to.)

Not to be dramatic, but copying Dorsey’s routine was an undertaking that touched every moment of my day, from the minute I woke up to the minute I went to sleep. Let me take you through it:

The Wake Up: Frigid Cold 

Nothing wakes you up quicker than jumping into freezing water, I found out. Dorsey starts each morning with an ice-cold bath, saying it “unlocks this thing in my mind and I feel like if I can will myself to do that thing that seems so small but hurts so much, I can do nearly anything.” Invigorating.

Since the bathtub situation in my apartment is best described as “cramped,” I bypassed the morning soak and opted instead for a cold shower. I think I still got the gist of what Dorsey was saying, though. Despite being extremely unpleasant — I thought only people like Christian Bale in “American Psycho” took cold showers — I did feel much more alert afterwards. It was impossible not to. One negative externality: I’m blaming the cold showers for a blemish on my chin that looks straight out of my high school acne prime.

Before jumping in the shower, I’d meditate for at least 10 minutes. Dorsey said he tries to find up to an hour in the morning and an hour in the evening for meditating, but 10 minutes per session is his baseline. Meditation has had the “biggest impact” on his mental health, he stressed. This was something I’ve actually experimented with off-and-on for about five years now, and I welcomed bringing it back into my life.

I was rusty. My mind routinely wandered away from my breathing pattern and towards stupid stuff, like fretting about whether I’m slowly going bald, but it still helped “center” me for the rest of the day.

The Transportation: Slow

Dorsey walks the five miles from his home to Twitter HQ three times a week. (He works from home Tuesdays and Thursdays.) Moving at a “brisk pace,” Dorsey said he makes the trek in about 75 minutes.

My morning commute isn’t as daunting, since my office is only two miles away, but this still sounded like a pain in the ass. Like Dorsey, I tried to move quickly and listen to podcasts while walking, but it seemed to defeat half the reason for walking to work in the first place. Wasn’t this supposed to help me clear my mind?

I scrapped the podcasts and music after the first day and tried to just absorb as much of the neighborhood as possible. This was a good move. It was refreshing to take 30 minutes and just think about work, life, and why my beloved Lakers have turned into a circus act, without outside interference. I realized like most people my age, I’m probably pelting my brain with too much stimulation throughout the day — constant podcasts, or listening to music while working, or streaming Netflix or HBO at night. My morning stroll quickly turned from something I loathed into something of a mental refuge.

The Work: Slightly More Pleasant

Dorsey uses a standing desk, so I did too. It’s worth it — you end up leaving the office with more energy, feeling less lethargic. I’m not going to expand on it, just get a standing desk if you can, and don’t worry how silly it can look.

The Diet: Sparse

This was the hardest adjustment I made all week. Dorsey eats one meal each day — dinner — and that’s it. This was a problem for me. I usually like to eat breakfast, followed by some light munching throughout the day, then dinner, before culminating with dessert while watching TV, Tony Soprano-style. Instead, I was waiting until 6:30 at night before putting anything except water and tea into my system.

My body struck an odd balance: on the one hand, I seemed to have more energy, especially after leaving work, than normal. I liked that. On the other hand, my head was typically throbbing by that point of the day, insisting I eat.

“Your body really does need to eat several times throughout the day. That’s what keeps your metabolism going, that’s what keeps your digestive system working properly,” Annie Uttaro, a Los Angeles-based personal trainer and nutrition coach, explained. “As you experienced, if you don’t eat all day, you’re going to be so famished that you’ll probably shovel anything into your mouth. Your body thinks it’s starving, essentially.”

On several nights, I did shovel almost anything into my mouth. One dinner was especially embarrassing: I brought home a couple Del Taco spicy chicken burritos, two tacos, a shake, mixed in a salad and some fruit, a bowl of cereal, then topped it off with some chips. I don’t even like chips. When my girlfriend asked what I had for dinner, I was too ashamed to tell her. “Chicken,” I replied meekly.

The Exercise: Short and Sweet

For the amount of time I typically spend at the gym, I should have a body 75% as yoked as Dwayne “The Rock” Johnson. But I’m usually wasting a lot of time, texting, trying to find the right song, or generally just walking around, wasting time. That wasn’t an issue this week.

Like Dorsey, I started doing one to three “high intensity” seven-minute workouts, spread throughout the day. I leaned on the app Seven, which guides user through quick exercises that don’t require any weights, after my billionaire muse recommended it on Greenfield’s podcast.

The rapid-fire pushups and wall-sits I did were great, and left me no option but to actually focus on working out for a few minutes. But right as I would start getting into flow, the seven minutes would be up. I felt good in the moment, but by the end of the week, just felt weak.

And as it turns out, working out between 7 and 21 minutes each day isn’t optimal.

“If you have 7 minutes, [and] that’s all you have in your day for a workout, then 7 minutes is better than nothing,” LA-based fitness instructor Albina Katsman at The Studio MDR told me. “However, I feel to see results, and see change in your body or to just try and stay toned, you need to devote a minimum of 30 minutes [per day].”

 The Verdict: This Wasn’t A Waste of Time 

I might be hungry and scrawny while typing this, but this past week hasn’t been a waste. I get why Dorsey does it — he doesn’t have much free time. Running Twitter isn’t a cakewalk — I’ve criticized him in the past for failing to answer some of the key questions facing the company — and then you add Square on top of it. Most of these habits are about maximizing efficiency while, at the same time, taking mental wellbeing into consideration.

Some of this wasn’t for me. I’m not going to keep working out in seven-minute increments. But the meditation and morning walk to work are going to be staples from now on, as well as journaling before falling asleep — another Dorsey custom I picked up this week. You don’t have to be some tech hotshot to benefit from it — these are habits that can help us all take a step back from the rat race and collect our thoughts. It worked for me, at least.

Having said that, I look forward to stuffing a fat stack of pancakes into my mouth tomorrow morning and following it with a warm shower.

Beatrice Verhoeven contributed to this report.