This is an excerpt from Zero to IPO: Over $1 Trillion of Actionable Advice from the World’s Most Successful Entrepreneurs by Frederic Kerrest, pp. 164-171, (McGraw Hill, April 2022). Kerrest co-founded Okta – an enterprise identity management company – in 2009 and currently serves as its executive vice chairperson and chief operating officer.
I’ve heard a lot of people talk about work-life balance, and I think the sentiment is well intentioned, but it overlooks a key opportunity. Running a company is hard as hell. Even in good times, it can be a grind. It’s definitely critical to carve out personal time, but you should also think about ways to bring more of your life into your work. I like to think of it as work-life integration.
Let me give you an example. I love ice hockey and play late every Tuesday evening and early most Sunday mornings as part of a Bay Area league. It’s something I’ve done the whole time I’ve been building Okta. Getting on the ice is my way of clearing my head and blowing off steam. For a couple of hours, I get to leave my stress and responsibilities behind.
But I also try to fold hockey into my workday where it makes sense. For example, when I travel for sales meetings, I regularly invite prospects, customers, and investors to come to a game with me. I’ve gone so far as to plan trips around the NHL calendar. It has a lot of upsides. I get to spend time with customers in a fun way. It distinguishes Okta from competitors. And it often leads to more business.
I also carefully guard my family time. I am home for dinner with my wife and children every night (unless I’m out of town). I put my phone on our foyer table when I arrive home, and it stays there until the kids go to sleep. I don’t take work calls on weekends unless it’s an absolute emergency. And I attend every parent-teacher conference (even if I have to do so by phone when I’m in another city).
It’s easy to take family for granted and allow yourself to get pulled into never-ending work demands. It takes discipline to switch gears and focus on your partner and children. But the work demands will never ever stop. And your family time is both precious and fleeting. My children will never again be the ages they are now. I love spending time with them, and I want to be involved in helping them grow. So I invest time in the upstream work – hiring really great people, establishing clear goals, and giving the team the autonomy to execute as they see fit. That way, when I come home, I don’t have to worry that the company will collapse if I step away for a few hours.
People in business and tech talk endlessly about fundraising, product-market fit, design thinking, the latest tech, management techniques, consumer trends – everything except the need to keep yourself in fighting shape. That’s crazy. Building and running a startup is exhausting. All founders need to create strategies to stay fit – mentally, emotionally, and physically. You don’t want your company to implode simply because you never carved out time to exercise or sleep.
The rigors of startup life are certainly difficult in the beginning. Unfortunately, they’re also difficult in the middle, and even after you’ve gone public. My company brings in more than $1 billion dollars a year in revenue, and yet I still wake up in the middle of the night obsessing over work. In this chapter, I share advice on how to take care of yourself. What’s most important is simply to be aware that you need to. Here are practices that have worked for me:
- Find founder peers at the same stage as you, or slightly ahead. Develop relationships with other entrepreneurs who’ll understand what you’re going through and the problems you need help with. Your friends and family can offer general moral support, but none of them will really get it the way a fellow founder will.
- Follow the “oxygen mask” rule. You know the old flight-safety advisory: “Place your mask over your own mouth and nose before assisting others.” You can’t help your company if you’re not able to perform at your best. Create routines to stay physically, emotionally, and mentally fit.
- Take vacations. You’re going to feel like you can’t. But [just like you might need to pause in order to upgrade a system or process], sometimes you will need to upgrade yourself, even if it means stepping away from the company (which won’t slow down because you’ve built a well-oiled machine that runs well without you, right?) so you can recharge your batteries and get energized for the next leg.
Don’t keep up with the Joneses: Every business is different.
In the early days at Okta, [co-founder] Todd [McKinnon] and I kept a spreadsheet where we’d track other startups’ performance. The sheet included: year started, money raised, number of employees, revenue, and next-year forecast. At lunches with friends or industry gatherings, people would often mention other companies’ numbers for various of these variables. As soon as I’d get back to the office, I’d dump the new intel into our sheet. We wanted to assess how Okta was doing as compared with other companies.
It was a silly thing to do.
Startup founders tend to be competitive. Of course they want to know how they stack up. But there’s no single roadmap to success. Every company is different. Consumer companies are different from enterprise ones. Startups selling to small businesses will grow differently than those selling into the Fortune 100. It’s useless to compile the information we were tracking. It might give you the illusion you’re assembling some kind of useful insight. But you’re not. It’s a waste of time – time that you don’t have to waste.
In competitive auto racing, they teach drivers to “focus on the road, not the wall.” Look at the wall and you’ll crash. To win, you need to keep your eye where you want the car to go. I share the same principle with new founders: Don’t worry about what anyone else is doing or how they’re performing. Just focus on your own road, your own race.
Depression among founders: It’s more common than you think.
Founders have been shown to have higher rates of depression than the average person. That doesn’t mean that a founder will definitely become depressed. But when it does happen, a founder should know it’s not particularly unusual. According to a study conducted by the University of California, San Francisco’s Dr. Michael Freeman, approximately a third of entrepreneurs reported that they suffered from depression, about twice the rate as the study’s comparison group. Other studies have also looked at this question. Their findings vary on whether entrepreneurs have meaningfully more depression than the general public – but, Dr. Freeman says, none has found that they have less.
There’s no single reason for this phenomenon, says Dr. Freeman. While many people, no matter their occupation, may have a genetic disposition for depression, it never becomes an issue because they never find themselves in the kinds of situations that might flip the depression switch. It’s similar to how some people may have a genetic propensity toward diabetes, but as long as they eat well and maintain a healthy weight, the diabetes may never appear. So if you put someone with a preexisting vulnerability to depression in the pressure cooker that is startup life, it could be triggered. “A lot of people get overextended,” Dr. Freeman says. “They don’t get enough sleep. They eat junk food. They get socially isolated because they’re spending so much time at work. They might have conflicts with their cofounders. They might get slapped with a lawsuit or get pushed out by their board. At a certain point, you cross over the tipping point.”
Some of this is simply the expected result of the unique blows you suffer in the entrepreneurial life. “When you’re trying to disrupt the status quo, there are a lot of forces that don’t want to be disrupted. So you run into pushback, and the frustrations involved can be demoralizing,” Dr. Freeman explains. There’s also the constant rejection, especially in the beginning. “Many entrepreneurs make the mistake of believing that their identity and their value as a person are the same as the success of their business,” he adds.
When they pitch venture capitalists and get rejected over and over, it’s devastating. “If you can’t see that the investors are rejecting the concept or the technology, and you personalize it, that can lead to demoralization, low self-esteem, and, ultimately, depression.”
I’m not bringing this up to alarm you. Just the opposite. This might never affect you, except possibly in discrete episodes in response to specific blows. If so, you’ll probably recover with no lasting effects. But if this does sound like you, know that you’re not alone. Take a look at the successful founders you see at conferences, on TV, or in magazine profiles. You can bet that a chunk of them deal with mental health challenges. It still isn’t widely discussed in the industry, unfortunately, but it is par for the course. As such, it’s not an impediment. Just something to manage.
Miss a deadline every now and then: The case for (sometimes) letting things slide.
You’ll constantly feel like you need to run all out. You’re going to set deadlines and milestones that you’ll convince yourself you must hit. Because your money has a fuse on it . . . because nothing happens until someone sells something . . . because you have to keep the main thing the main thing, and the main thing is growing this business – fast.
But sometimes, it’s OK to slow down. Let’s say a release is scheduled to go out tomorrow. But it can’t really get done without everyone working crazy hours (after weeks of already working crazy hours). Will it really matter if you postpone it to next week? If it means you (and your team) get a mini break, and you can take your head (and body) out of the game briefly to recharge elsewhere, then why not? If the release date was arbitrary, and it’s not going to make a huge difference to change it, go ahead and push it back.
Building a startup really is a marathon. A trade-off now in favor of everyone’s physical and mental health will pay dividends down the road. Don’t do this on the big stuff: the numbers you have to hit for the year, the money you have to raise in the next round, the international office you have to open in three months. But the smaller stuff ? Every now and then, give yourself permission to let things slide.
Technology, innovation, and the future, as told by those building it.