The Crippling Anxiety of Being a Startup CEO

November 13, 2014

9:00 am

“The hard part is waking up at 3 am in the morning just drenched in sweat, where your bed is soaked, because the anxiety is just gnawing at you even when you’re not awake.”

Matt MacInnis had spent over 7 years at Apple, including time running their global market development for education, but he still found himself struggling as a startup CEO.

In early 2014, MacInnis’s startup Inkling was working on consumer and enterprise offerings, and they had to decide whether to shut down the consumer side and go all-in on their B2B offering.

It was around January when MacInnis realized he would have to make a decision, but he dragged his feet. There was no deadline to decide, and maybe they could save both? He spent time watching the metrics and waiting for both businesses to take off, trying to shave off little expenses to save money, and having unsatisfying conversations with his board of directors. Meanwhile, the consumer and enterprise teams had to run separate staff meetings, and each was starting to get envious of the other.

“At the end of the day, the decision is yours and everyone is staring at you wondering if you’re going to do something,” says MacInnis. “The hard part is the inability to focus on the things you enjoy because there’s always this voice in the back of your head screaming that you’re failing.”

It wasn’t until May when MacInnis walked into work with his decision, ready to lay off many people from the consumer team.

“It was the hardest day of my life to walk in and conduct a layoff and wonder whether we had just destroyed the company,” he says.

And, of course, he then had to stand up in front of everyone and explain why he was confident in his decision.

The uncertainty of the startup CEO job

This crippling uncertainty is something all startup CEOs experience, says MacInnis, whether you’re a first-timer or a seasoned pro. The reason is simple: the buck stops with you. You don’t have a boss to make decisions for you, and the people below you usually don’t have all the information to base a decision on.

One of the most profound differences between any job in the world and being CEO is you have neither bosses nor peers,” says MacInnis. “The more difficult and horrible the problem, the more likely it is to land on your desk.”

What MacInnis learned from four months of hesitation is that the hard decisions need to be made sooner. They only get harder as time goes on, and you probably have an intuition about what to do.

“The natural emotional reaction to a tough decision is to avoid it,” he says. “The great CEOs are the ones who face it head on and sooner rather than later, and that’s a constant struggle for every CEO.”

And acting confident in your decision is part of the job, he says – even if you’re filled with doubt. Why? Because if your team senses your uncertainty, they won’t go forward full throttle, and then you’re bound to fail. MacInnis never lies to his team, but he does tell them: this path is our most likely route to success.

Six months later, Inkling’s focus on their enterprise business seems to be the right course. MacInnis says they’ve made more money in the last two quarters than the whole two years before. More uncertainties are up ahead, for sure, but now he has some idea how to deal with them:

“Trusting your intuition and just acting is such an important skill to learn, and it’s not an easy one to master.”

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Kira M. Newman is a Tech Cocktail writer interested in the harsh reality of entrepreneurship, work-life balance, and psychology. She is the founder of The Year of Happy and has been traveling around the world interviewing entrepreneurs in Asia, Europe, and North America since 2011. Follow her @kiramnewman or contact

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