We all deal with stress in our lives. Kids, mortgages, relationships, the job. Unless we have a magic wand, stressful circumstances will always show up. That’s no different whether you’re a CEO, a teacher, or a busboy. So let’s find out why Jack Dorsey started meditating.
Being the CEO of a publicly traded, world-famous company can be incredibly stressful. But make that the CEO of two major companies and you’re just asking for trouble.
As CEO of both Twitter and Square Payments, he had the weight of the world on his shoulders. From investors to government regulators, from employees and also to his customers, they all depend on him. That’s a lot for anyone. Additionally for Jack, worrying about the impact Twitter has on the world makes a perfect recipe for a mental health disaster.
Many of us have heard the stories of how Jack Dorsey meditates for two hours a day. Here we’ll explore why Jack Dorsey started meditating and also how it helps him. We’ll dive into how he fits it into his busy schedule, as well as how we can all benefit from meditation.
Why Would the Man Who Has It All Meditate?
Stress isn’t something that only the rest of us have to deal with. Like the great poet-philosopher once said, “Mo money, mo problems.” The only difference between the super-wealthy and everyone else is that money is not one of their problems. But they still deal with stress just like everyone else.
There’s a lot of pressure when every little decision you make could cost thousands of your employees their jobs. Or when your choices could cost your investors billions. Not to mention the pressure when your actions could upend democracy as we know it.
No matter how rich you get, relationships can get messy. Illness and death happen to everyone. And even tiny inconveniences can set you off.
In fact, the richer and more cushy our lives become, the less able we are to handle unpleasant experiences. You’d be hard-pressed to find an unhoused person complaining about the temperature of their soy mocha latte—or that there were two stevias instead of three.
The Double-Edged Sword of Wealth Caused Jack Dorsey to Start Meditating
The more efficient and pampered our lives become, the more any minor stressor becomes blown out of proportion.
As nations become wealthier and technology becomes better, we see this effect in everyone around us. A website takes an extra 3 seconds to load and we get upset. A 4-minute line at the bank and we lose it.
The screens in our pockets that will show us anything we want to see or hear instantaneously have made us all easily stressed—and also quick to anger. Just watch videos of fights on planes if you don’t believe me: the one time we have to put our phones away.
Why Meditation Can Help With This
Luckily, there is a solution to this. Meditation is the antidote to stress for many reasons. But one of those reasons is that we can’t immediately act on our impulses.
- Want to pull out your phone? Too bad, you have to wait until your meditation is over.
- Want to impulsively snack? Can’t do it.
- Want to light up a cigarette or do any unhealthy things when bored? Nope.
In meditation, we retrain our mind to be patient, calm, and rise above our base impulsive instincts. We become the boss of our mind. We no longer let its childish, undisciplined desires rule our lives.
Instead, we simply observe our impulses and desires arise and fall away. We become highly aware that they don’t control us and that they are only temporary. We recognize them for what they are—background chatter. It does not define who we are, and through observing them, our higher intelligence can take back the reins.
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How Jack Dorsey Got Started Meditating and Why He Still Does It
When Jack returned as CEO of Twitter in 2015 while still running Square, he knew he had to get serious about his health.
To manage the stress of running two major companies simultaneously, he took silent meditation retreats and began meditating for two hours a day. He learned Vipassana meditation, which is also commonly referred to as mindfulness or insight meditation.
How to Meditate Like Jack Dorsey
Vipassana consists mainly of two types of practice: breath awareness and body scanning. Vipassana recommends starting with breath awareness meditation for a few days or weeks before moving on to full body scanning.
Sit on the floor with your legs crossed if that is available to you. Close your eyes, breathe naturally, and put your entire focus on your breath. Begin by either focusing on your expanding and contracting belly, or by focusing on the area from the bridge of your nose to the two corners of your lips, forming a triangle.
Feel every little subtle sensation of your breath. When your mind wanders off, gently bring your attention back to your breath. Just feel it. Make your breath your entire area of awareness.
After a couple of days, your senses will heighten. Then, narrow your focus to just the “Charlie Chaplin mustache” area of your face—the middle part directly above your upper lip.
Tune into the very subtle feeling of cool air brushing by as you inhale, and warmer air coming out on the exhale. Do this for however long is right for you as you work your way up to 20 minutes or so.
Now that you have laser-like focus, start this meditation the same as before. Sit on the ground (or a chair if you need to) and close your eyes.
Put all of your focus at the tippy top of your head. Imagine a grid of vertical lines covering your body from this point to your toes, spaced an inch or two apart. In whatever order you prefer (make sure to keep the same order every time), move your focus down each line, sensing every spot of your body.
Feel your body from the inside and on the surface. Make sure you are really sensing whatever each spot is feeling—whether it’s clothes, heat, tingling, coolness, or the contact with the floor. Whatever sensation is there, just feel it.
If you can’t feel anything in a particular spot, stay with that spot until you feel some sensation. Our nerve endings are always picking up signals and sending them to our brains. The more you do this, the more connected you will be with your body.
Move your attention down each line from head to toes (roughly 10 to 15 minutes). Once you’ve scanned your whole body, move your focus from your toes back to your head in reverse order. This completes one full cycle. Do as many or as few as you like.
For those who find silent focus challenging, pairing your technique with breath and mantra meditation offers a powerful alternative to settle mental chatter.
Why Jack Dorsey Started Meditating in the Morning
Let’s face it, we’re all busier than ever these days. We’ve also got great excuses not to do things: too tired, too busy, don’t wanna… But few people are busier than Jack Dorsey. That’s why Jack Dorsey started meditating first thing in the morning.
In the morning, our willpower and discipline are at their highest. Also, the unexpected emergencies that come up during the day haven’t started yet. Furthermore, morning is the best time to make new habits stick.
Core Reflection
Usually, “too busy” is the most common excuse for not meditating even 10 minutes a day. But if a two-time CEO can fit in two hours, really no one else has an excuse not to dedicate a few minutes every single day.
In the morning—preferably before we check our phones—our minds aren’t racing yet. It’s the optimal window to have a deeply relaxing and powerful session. Distractions haven’t crept in, making it the ultimate way to set your entire day up for success.
ALONENESS TO ONENESS
To help visualize how our thoughts and ego shape our perception, take a moment to watch this short film before moving into the next exercise.
