Ask someone who’s the head honcho of Twitter nowadays and you’ll likely hear “Elon Musk”. But long before he was the first name to come to mind, Jack Dorsey had been the best fit for that role.
Dorsey is the co-founder of Twitter and the ex-CEO of it too, but now his main hat is the CEO of Block Inc (previously and more popularly known as Square), another company he co-founded.
Regardless, we’re not here to talk about his many accomplishments, but rather, his daily routine.
I’ve tried quite a few (three) morning routines by the uber-rich and entrepreneurially successful in the past, but Dorsey’s was, by far, the most daunting.
Keep reading and you’ll know why.
5AM: Up and at ‘em
Over the years, there have been many differing accounts of what time Jack Dorsey wakes up, but that’s because he himself has changed things up over time.
The latest source is from 2019, when Dorsey was on a podcast with Ben Green. Here, he shared that he had adjusted his morning routine to wake up at 6:15AM.
However, the most popular answer online—and the most eye-catching one, I suppose—was that the entrepreneur wakes up at 5AM.
To challenge myself, I decided to go for the 5AM wake-up call too.
I failed this on the first day, which was disappointing, but not entirely surprising. I’ve grown so used to snoozing my alarm that I don’t realise I’ve gotten out of bed to get my phone from the charging station until I officially wake up at 7:30AM.
To mitigate this, I changed my alarm ringtone to one of dogs barking to scare myself awake. Pro tip.
Waking up at 5AM at times feels like an out-of-body experience. Why am I doing this, I wondered. What is it all for?
Well. For this article, I suppose.
5:30AM: Zen time (but not really)
You might think that meditation is calming, but have you ever tried sitting criss-cross applesauce for an hour straight, with no lumbar support, trying to “clear your mind” and “focus on your breathing”?
You read that right. An HOUR of meditation.
Dorsey used to meditate for way shorter, at 30 minutes, but this hour of meditation just felt non-negotiable considering how into it the Twitter co-founder is. The man has gone on 10-day detoxes where he meditates nearly the whole day away.
Admittedly, I tend to either fall asleep or just zone out completely in daydreams while doing this morning meditation, especially when I opt to lie down instead of sit up.
Have I managed to find nirvana during this practice? Unfortunately, no, I don’t think I have. (I mean, has Jack Dorsey?)
6:30AM: Seven-minute workout, times three
After my meditation comes the seven-minute workout. A concept popularised by The New York Times, Dorsey uses an app called Seven which has a plethora of seven-minute workout routines.
Downloading the app, I am offered an annual subscription at RM79.90. Thankfully, I was given a seven-day free trial of the app, which I gladly accepted.
The app was actually one of my most favourite things about this routine. Most of the workouts were easy to follow, and the seven-minute format makes things feel a bit more digestible.
The app would pick out routines for me, such as Full Body, Calorie Burn, Low Impact, and Bikini Body. Instead of doing the same routine thrice, I picked out a few others to try such as Yogalates, Yoga Stretch, Quick Starter, Belly Burn, and more.
7AM: Icy-cold shower
Usually, Jack Dorsey first goes for a sauna session using something called SaunaSpace, which was interestingly devised in Columbia, Missouri, where I studied (Dorsey is also from Missouri himself).
Sadly, I do not have a sauna barrel like he does, so I just skip right to the exciting ice-cold shower he takes right after. His barrel also chills to around 3 degrees Celsius, but I can barely make enough ice for my usual iced coffee, so a cold, cold shower will have to do.
And trust me, it was already shocking enough being smacked by cold water that I suspect is around 10 to 15 degrees moments after a workout.
I’ve talked about hating showering in the morning before because of the humid feeling it leaves me with, so I think the extreme cold showers help with keeping the humidity low.
7:30AM: Let’s get caffeinated
After the cold shower, it’s time for coffee. To be fair, he doesn’t say whether this is an explicit part of his morning routine, but I don’t think I can make it out of a day that started at 5AM without having some coffee in my system.
To be fair, I did check for whether or not he’s even a coffee person, and judging by responses he’s given during an AMA session on Product Hunt, it’s safe to say he does (or did) drink coffee.
8AM: Leave for the office
Now, Dorsey usually does something crazy, like walk a whole hour (five miles) to work.
Not to make excuses for myself, but due to a combination of Malaysia’s sweltering heat, our underdeveloped pedestrian system, and the fact that it would take me three whole hours to get there, I chose to not do that.
However, my usual commute does involve around 20 minutes of walking (and 30 minutes of standing on the LRT), so that’s good enough for me.
9AM: Work begins
Work actually starts at 9:30 for me, so I opted to spend my first half an hour in the office doing random tasks such as caring for our office foster cat, Cocoa (who is up for adoption at the time of writing, by the way).
Dorsey’s work life, like his personal life, is very structured, and he has mentioned that his days are themed.
So, Tuesday is for product, engineering, and design. Wednesday is marketing, growth, and communications. Thursday is partnership and developers. Friday is company and culture.
Basically, his days are 24-hour blocked. Since my job scope is a “little” different, I wasn’t able to put this into practice.
12:30: Working through lunch
Dorsey practices the One Meal a Day (OMAD) lifestyle, which is basically a kind of intermittent fasting. I’ve tried these diets in the past, but as a foodie, this was one of the least fun parts of the routine.
For my mental well-being, I still took a small break around lunchtime as I watched my colleagues all leave. On some days I also opted to consume something small, whether it be a drink or a meal replacement from a homegrown brand I’ve reviewed in the past, Oatler.
Honestly, it wasn’t so much the food or hunger that got to me, but the fact that I wasn’t able to connect with my colleagues. Lunch isn’t just a time to nourish the stomach, but to nourish your social needs, too.
So, on one of my work days, I actually opted to eat lunch instead of dinner, and I actually much preferred that.
7:30PM: The one meal of the day
After clocking out at 6:30, I make my way back home.
Dorsey shares that dinner is usually “a really big meal” with a lot of protein and greens. He never explicitly said that he doesn’t eat carbs, but I’m assuming it’s not a major food group for him.
So, for the bulk of the work week, my dear sister would prepare some protein and vegetable-heavy dishes such as salads, which I actually really enjoyed. Thanks, sister!
9PM: Another cold shower and meditation session
Dorsey takes all his showers cold, so after another painfully icy time in the bathroom, I would settle down to do my second hour of meditation.
The night meditations were a lot less sleepy than the morning ones, but admittedly, I still couldn’t stay focused for the full hour as I would start to get restless. In my opinion, a short 10 to 15-minute meditation would have sufficed.
10PM: Digital journaling
Dorsey shared that he has been journaling since he was 14, a habit he tries to cultivate daily as he’s wrapping up the day.
He uses the Notes app on the iPhone, since it’s very searchable and accessible. I did the same, taking down random notes like things I have to accomplish the next day, or ideas that popped up in my head during the meditation (which seems counterintuitive, but oh well).
11PM: Lights out
By 11, any energy reserves I had been desperately holding on to would be completely gone. I usually fall asleep very easily anyways, but the sleepiness or fatigue usually isn’t as intense as it was during this week.
Dorsey is a man of discipline and structure, and his morning routine is a reflection of that. It’s not just a morning routine that he happens to have, but one he has tailored, trimmed, and perfected over time. It has been intentionally designed to support his lifestyle and wants.
Due to our differences in lifestyles then, there were elements of the experience I liked, such as the Seven app, and ones that I really despised, AKA the hour-long meditation.
Meditating for an hour is largely just not worthwhile for me, and a 10-minute guided meditation is much more reasonable.
While the OMAD diet wasn’t as bad as I imagined, I’m reminded about how much I love having lunch with my colleagues, so if I ever do want to try out intermittent fasting again, I would not choose lunch to skip.
I think perhaps for a leader like Dorsey, being somewhat of a lone wolf is doable, but for me, whose work life heavily involves my teammates, missing out on lunch with them somehow felt… sadder.
The biggest surprise was how energised I was even waking at 5. The endorphins from the workout and the icy bite of the shower were some of the highlights of my days, and they might just be habits I’ll try to cultivate.
- Read more articles in this morning routine series here.
- Read more articles we’ve written about entrepreneurs here.
Featured Image Credit: Jack Dorsey / Vulcan Post