Home Billionaires 8 Ways Successful CEOs Handle The Stress of Running a Huge Business

8 Ways Successful CEOs Handle The Stress of Running a Huge Business

Wesley September 3, 2017

Our reality is essentially constituted by order and chaos, and our lives are essentially a process of navigating the line between the two.

You encounter chaos when you don’t understand what’s going on, you can’t easily predict what’s going to happen next, or you don’t experience the results you expect to when you take a certain action.

You experience order when you understand what’s happening, you can pretty easily predict what’s going to happen next, and you get the results that you expect to have when you take a certain action.

When you experience too much chaos it can cause a lot of stress. Uncertainty means you don’t know what you’re facing, so you feel like you’re facing everything, and that takes an immense toll after very long.

When you experience too much order, it can also cause a lot of stress. Too much order is tyrannical, it’s soul crushing, it’s mind numbing, and it’s tedious, and it’s boring.

What you want to have in your life is the exact right mix of order and chaos. You want to have one foot in order and the other in chaos. So you have a “home base” so to speak, and a new territory to explore.

You don’t want so much chaos that you’re terrified, and you don’t want so much order that you’re dead inside.

Instead the ideal balance gives you a sense that time is passing correctly. When you strike the ideal balance between chaos and order, you’re interested in what you’re doing and you forget about yourself. You get lost in the moment. You’re engaged. You’re exploring, learning, and likely creating something.

If you feel overwhelmed by stress in your life, and that stress is sapping your energy instead of charging you up, it may be that the balance of chaos and order in your life is off somehow.

Sometimes this is unavoidable, especially if you are in the pursuit of greatness and relevance and usefulness to your society. As you take on responsibility for more (and that is what becoming successful ultimately means, it means you are given greater and greater responsibility as you prove yourself worthy of it to your society), there are more encounters with both chaos and tyrannical order.

Reckoning with this, transforming total chaos into balanced order by leaning into it and bringing your attention and energy to bear upon it, to understand it, make sense of it, and map it out to gain mastery over it- is the work of the successful among us.

Also: transforming too much order into chaos, by introducing disruptive (and better) thinking into an overly ordered system is the work of the most successful among us.

Here’s how the CEOs of some of the world biggest companies, the people who do this best and have to do it the most, successfully handle the stress of running a huge business.

NEW YORK, NY – SEPTEMBER 24: Bill Gates, chairman and founder of Microsoft Corp., listens during the Clinton Global Initiative (CGI) meeting on September 24, 2013 in New York City. Timed to coincide with the United Nations General Assembly, CGI brings together heads of state, CEOs, philanthropists and others to help find solutions to the world’s major problems. (Photo by Ramin Talaie/Getty Images)


1. Bill Gates

Bill Gates, the richest man in the world for many years running, and the founder of the world-bestriding, software titan, Microsoft Corporation, deals with the stress of running the world’s biggest software company (and the world’s biggest charity, The Bill and Melinda Gates Foundation) by reading before bed.

He likes to read before he goes to sleep every night, and is so committed to the habit that he always reads for at least an hour before going to sleep, no matter how late it is. The difference in the self-reported amount of reading done by the rich versus the poor according to studies is staggering.

The average member of the one percent (the top one percent of income earners in the United States) reads 60 books a year, which comes out to 5 each month. The average member of the bottom 25% of income earners in the United States reads 0 books a year. It turns out that reading every day both increases the amount of knowledge you have (and remember that knowledge is power), and is also a great antidote to stress.

Words are inherently the imposition of logical order on a disorderly and chaotic world by the thinking human mind. Reading every day puts you in the mindset of doing this, and of doing it well. Thinking clearly and critically is not easy, but it can be learned just like any other skill, and we all generally have a very high aptitude for developing this skill to its utmost.

The written word is the most effective form of clear thinking. Committing words to writing requires the mind to organize them clearly and think about them critically. Running your brain through this process is one of the most important things you can do on a daily basis both to combat stress and sharpen yourself. By participating in the act of organizing and reckoning with the chaotic world through written words, you train your brain to do this in your every waking moment.

Young Gates has taken a lot of advice from mentor Warren Buffett throughout the years, and Gates says that the key to Warren Buffett’s success is keeping things simple. Once in an interview with Fortune Magazine, Gates told the interviewer about Buffett:

“His ability to boil things down, to just work on the things that really count, to think through the basics — it’s so amazing that he can do that. It’s a special form of genius.”

Daily reading sharpens the mind’s ability to think clearly about a subject and reduce it to its most simple essentials.

“We don’t collect a lot of your data and understand every detail about your life. That’s just not the business that we are in,” Apple CEO Tim Cook said Thursda


2. Tim Cook

Tim Cook is the CEO of Apple and it is under his oversight that the world renowned maker of incredibly beautiful, elegant, and downright sexy computers, phones, and music players grew to the point of being the most valuable company in the world.

These Cupertino, California cats have just literally billions of dollars, cash on hand, sitting around in bank accounts. It’s insane the kind of money the world has eagerly poured into their coffers for their electronic devices.

Managing a business that powerful and that important is one of the most high stress positions to be in on the entire planet by far. Tim Cook has to deal with the ever changing marketplace and the breakneck speed of technological innovation, especially in software. On top of that, he has to fight off other multi-billion dollar corporations that are gunning for his profits, both through market competition, and through endless legal actions over intellectual property disputes that keep Apple fighting in the court system for hundreds of millions of dollars.

So if you think your job’s stressful, listen to what Tim Cook says to do about stress. The Apple CEO was recently given an honorary degree from the University of Glasgow, and in his address to the students of that college when he visited to accept his degree, Cook advised students to simply tune out the noise of cynics, and critics, and haters, and negative thoughts:

“In today’s environment, the world is full of cynics and you have to tune them out. Because if not, they become a cancer in your mind, in your thinking, and you begin thinking that you can’t or that life is negative.”

Stay true to a vision and ignore the voices that tell you all the reasons you can’t, all the reasons you should be hesitant, all the reasons you should be fearful, or anxious, or timid. You don’t need to hear that garbage. You really don’t.

NEW YORK, NY – NOVEMBER 02: Meg Whitman, CEO of Hewlett Packard, gives a television interivew on the floor of the New York Stock Exchange after ringing the opening bell on November 2, 2015 in New York City. Hewlett Packard officially split into two companies, Hewlett-Packard Enterprise, focused on businesses and HP, Inc, focused on consumers. (Photo by Andrew Burton/Getty Images)


3. Meg Whitman

Meg Whitman is one of America’s most successful and capable CEOs with an amazing career at several Fortune 100 companies such as Proctor & Gamble, eBay, and now Hewlett-Packard. One thing Meg Whitman does to reduce stress in her extremely high stress jobs, is she goes fly fishing with her son about six times a year.

Engaging in leisurely activities, especially with a physical component and aspect of communion with nature is about the most important way you can decompress and recharge your batteries to keep fighting the good fight and handle the stress of making your way to the very top of your field of work.

Nature is where our ancestors started not very long ago. Our understanding of nature is hardwired into us by instinct. Even if you had never seen a snake in your entire life, and had never been told what one was, the first time you saw one, you would jump so high your head would hit the ceiling. And you would keep your distance from it. And probably, you would be intensely fascinated with it and have trouble looking away from it.

The same is true of your experience of a sunset, waves crashing on an ocean beach, a bubbling stream of water passing over smooth river stone in a creek, or stepping into a forest. Even if you’d never seen a forest before and had no cultural context for understanding it, you would some how feel both at home and in a mysterious and magical place with regenerative properties for your mental health.

Going out into nature and spending a relaxing time doing a nice outdoor sport like fly fishing or whatever it is that you personally like, brings everything back into proper alignment. It smooths out the rough places in your mindset, war weary from the many battles of your struggle upward. It restores your sense of awe and wonder.

It gives you a living picture of the balance and harmony of nature and civilization, chaos and order, and you will bring that picture back with you into your work and pursue your goals with renewed vigor.

Warren Buffett, chairman and chief executive officer of Berkshire Hathaway Inc., smiles during an interview in New York, U.S., on Tuesday, Oct. 22, 2013. Warren Buffett and his late first wife, Susan, gave and pledged billions to each of their three children to fund charitable foundations. Howard, an Illinois farmer, picked global hunger as his target. Photographer: Scott Eells/Bloomberg via Getty Images


4. Warren Buffet

Warren Buffet is the most successful investor in the history of the world. He has made not only himself, but tens of thousands of people who have invested with him, billions upon billions of dollars in profits while fueling economic growth by pumping billions of dollars worth of investor money into undervalued and highly productive enterprises.

Frankly the best economic stimulus package the U.S. government could undertake would be to say, “Here, Warren. Please invest this $50 billion where ever you think it will get the greatest return. We’ll have the Federal Reserve write you the check for it tomorrow. You da real MVP!”

That’s how good this guy is. He’s going to be a legend for centuries. And the multi-billion dollar business he runs investing in hundreds of other businesses would seriously stress out most of us and burn the best of the rest of us mere mortals up in a month. The sheer force of all those billions of dollars weighing on this man’s shoulders, a burden he shoulders with confidence, serenity, grace, and even humility.

Watch the HBO documentary on Warren Buffet sometime. Just Google “warren buffett documentary” and the YouTube upload for it will turn up in the search results. He deals with stress by staying grounded in routines. He goes through the same fast food drive thru window every morning for breakfast, and get this- if markets are down, he has one order he gets, and when markets are up, he has another more expensive order.

Like when his business is up tens of millions of dollars that morning, he’ll spend two more dollars at the fast food drive thru and get a nicer breakfast, and tighten his belt for a leaner sausage biscuit when Berkshire Hathaway is down tens of millions in the last 24 hours. That’s how he keeps it real.

Sheryl Sandberg, chief operating officer of Facebook Inc., looks on during a news conference at Station F, a mega-campus for startups located inside a former freight railway depot, in Paris, France, on Tuesday, Jan. 17, 2017. Facebook Inc. will open a startup incubator at Paris’s soon-to-debut entrepreneur campus created by billionaire Xavier Niel, as Sandberg vows to keep investing in France. Photographer: Christophe Morin/Bloomberg


5. Sheryl Sandberg

Facebook COO Sheryl Sandberg has a lot to stress about. Being the Chief Operating Officer of the world’s biggest and most powerful social media giant is not a cake walk. Whatever you think you’ve got on your plate, try being responsible to the shareholders of Facebook, Inc. And don’t think being on top is any source of security for Facebook either.

It’s in a very chaotic market that can get disrupted easily. There used to not even be a Facebook, remember? There was Friendster and MySpace and other social media platforms. Facebook knocked them out of existence. And don’t think people aren’t gunning for Facebook. One of its biggest threats is other social media platforms like SnapChat snapping up all the youngsters and carving out Facebook’s market share. For the Generation Y kids, Facebook is something their parents is on. And the costs of failure are billions of dollars. The stakes are as high as it can get in the world of business.

Still Facebook is doing well at managing and maintaining its preeminence among social media services. When Sheryl isn’t running Facebook, she keeps stress at a minimum by staying off of social media when she should be relaxing. She takes that time and recharges her batteries. She makes it a rule for herself not to scroll through social media or open her email at night, and she enforces it by just turning her phone off.

She even told USA Today in an interview once that it’s painful to unplug at night, but she needs to do that to unwind and be able to get a better night’s sleep as well. This allows her to pounce on her morning refreshed and energized to tackle the stressful problems of the day and win. You could make this a rule for yourself and try it out for 30 days to see what kind of difference it might make in your life. Pick a reasonable time and turn your phone off at that time every night. Or set it in a drawer or something.

6. Jack Dorsey

Jack Dorsey is the co-founder and CEO of Twitter. You know, it’s only the social media platform on which Donald Trump threatens nuclear war with another country every other week. No stress to deal with there, right? Well the way Jack deals with all the pressures and stresses of the chaotic and ever moving landscape is by budgeting his time. He creates a schedule… and sticks to it.

Jack’s week is divided up into days, so he can compartmentalize important tasks into a certain day each week. Mondays are for having meetings. Makes sense. Start the week off with updates and directives to the chain of command. Plus it’s easy to remember. Meeting Mondays. Then on Tuesdays Jack spends the day on product development for Twitter. Wednesdays are his marketing day. He focuses on how to continue expanding and evangelizing the platform.

Thursdays are networking days: reaching out important contacts and maintaining relationships with key partners. Jack focuses Fridays on paying attention to and crafting the company culture at Twitter. Saturdays are Jack’s day off. Gotta take a day off once a week. Even if you’re a workaholic. Actually, especially if you’re a workaholic. Got to make yourself take one day off in seven. Sundays are Jack’s recruitment day.

In an interview with Forbes, Jack once said:

“I think generally stress comes from things that are unexpected. The more you can set a cadence around what you do and the more ritual and the more consistency you can build in your schedule, the less stress you’re going to have.”

PS: New York Magazine says Jack goes for a six mile run every morning. Exercise might be more important than anything at breaking up your body’s stress response and filling your blood and brain with all the really good, healthy, and necessary by-products of those work-out stimulated metabolic pathways.

7. Susan Wojcicki

Susan Wojcicki is the CEO of YouTube, the video platform subsidiary of Alphabet Inc., the parent company of Google. Life managing YouTube is about more than managing a social media platform for sharing video. It’s like managing high dollar talent at a big studio. Her biggest and best performing content creators make millions of dollars apiece for both themselves and the platform.

They keep users coming to YouTube to serve up all those gazing eyeballs to advertisers. Keeping content creators happy and treating them fairly is a lot of work. Then on top of that, keeping advertisers happy, you know the people who are pouring millions of dollars into the platform, is several full time jobs in itself. Susan’s got her unfair share of reasons to be stressed out.

Her stress management philosophy is mostly focused on taking enough time off for herself and her family. She says: “I think it’s really important to take time off. I’ve also found that sometimes you get really good insights by taking time off, too.” If you’re not where you want to be yet in life (notice how I said yet!), and not even close to the YouTube CEO level of society, you may be tempted to say you don’t need that advice yet. But you might be wrong.

If you are just flogging yourself to be productive and it’s not working, and it feels like a strain, and you’re just suffering and anxious as opportunities and tasks pile up, continuing to flog yourself to get through it almost never works. Really think about it. Does that ever work? You’re obviously in some kind of mental state that is not allowing you to push forward when you face that kind of strong mental resistance.

Sometimes the best thing to do if you find yourself stuck in this mental riptide, is unclench, step back, relax, give yourself permission to disengage from what you’re doing, and just take some time to go for a walk; have a slow breakfast watching a show, or YouTube channel you like, or listening to music; organize your room some or clean up around your house; do some non-work related thing that you’ve been meaning to; maybe catch up with an old friend or spend some quality time with a family member.

8. Elon Musk

You want to hear about some stress? Remember the year 2008? Yeah I do. I was graduating the next year into the worst job market in recent American history. The economy was in shambles. Imagine being a CEO at the time. Big companies can wobble and fall very easily. It can be a vicious cycle when your company shakes out and a bunch of your best people leave. Then you perform even worse the next two quarters and even more of your good people leave.

Back in 2008 with the global economy on fire and multiple major legacy car companies going bankrupt, it was a terrifying time to be a car company CEO. Not only was Elon Musk’s baby, Tesla Motor Company, struggling during this time, he was also going through a divorce. Talk about chaos with lots of zeros on it dragging you through a hurricane by the heart strings. Elon persevered through it by staying calm and making smart, unemotional decisions along the way.

At the Dublin Web Summit in 2013, he explained his relationship with fear and shared a secret of great success that most Silicon Valley entrepreneurs have: They just aren’t afraid of failing. “Fear is finite, hope is infinite. We are afraid of failing, but it doesn’t stop us from trying. People should certainly ignore fear if it’s irrational. Even if it’s rational and the stake is worth it, it’s still worth proceeding.”

It has never been easier to fail in the history of the world. What I mean by that is the price of failure is not what it has been in times past. You are probably safe and secure in a way that past generations could not have dreamed of. People like Elon Musk are disruptive. The had a word for disruptive people in the Middle Ages. They called them heretics. You could get burned at the stake for being disruptive in those days. That was the price of failure. Today even our bankruptcy laws are unbelievably lenient, written to favor the bold, the risk takers. Whatever your big idea is: just get one or two good partners and floor it!