Startup CEO: The Loneliest Job in the World?

January 22, 2015

2:30 pm

The presidency was dubbed the “loneliest job in the world” in 1961, when New York Times photographer George Tames snapped a black-and-white photo of President John F. Kennedy alone in the Oval Office.

The US president is arguably the most powerful person in the world, but also the source of endless blame. Their decisions affect thousands or millions of people, and inevitably some of them aren’t happy.

Startup CEOs may not be launching wars or negotiating treaties, so perhaps it’s unfair to compare them. But loneliness is a human emotion, plaguing startup CEOs and presidents alike.

In a startup, there's maybe no position lonelier than the CEO/founder,” says Adam Lyons, CEO of

As it turns out, being the ultimate decision-maker is a lonely job. Lyons and his team were trying to improve car insurance buying by offering price comparison, but car insurance companies weren’t happy. They started sending cease-and-desist letters, and some of Lyons’s team wanted to back down. Lyons was the one who had to disagree and push through to make contracts with these companies, but there were doubts along the way.

The nature of the job in a startup is that you're doing what hasn't been done before, so there aren't a lot of folks who will get it, or have more information to make a decision than you. You're the final say,” he says. “Mentality is so important – when you start to question everything, it can be a really negative situation.”

Another particularly delicate issue is hiring and firing. Startups are more than a team – they’re often friends, comrades. But sometimes one of those friends isn’t pulling their weight, and only the CEO knows it. What will everyone think if I fire them? But you can’t worry about that; you do what has to be done, and face the consequences.

When the work day is over, startup CEOs sometimes return home to a family and friends who don’t understand them. The long hours, little sleep, and sheer obsession of being an entrepreneur can be lost on people who have no desire for that lifestyle. It’s hard for outsiders to understand why you’re constantly missing your relatives’ weddings or nights out with friends.

What’s the solution to this? For Lyons, it’s about setting expectations – for entrepreneurs and for their loved ones. The loneliness isn’t as bad if you’re prepared for it, so Lyons urges would-be entrepreneurs to find out what they’re getting themselves into.

“Often times folks contemplating taking the leap into starting a company or wanting to try the entrepreneurial route don't realize the serious commitment that it is, and how challenging of a lifestyle it can be,” he says. So read about the harsh reality of starting up, talk to current entrepreneurs, and don’t assume your experience will be much better.

As for family and friends, sometimes it takes a lot of patience and empathy to explain why you’re doing what you’re doing. “Setting expectations with friends and family takes time, but after a while they start to understand where you are in your life and the sacrifices around the board you're making to improve the world and the lives of others,” Lyons says. It helps that he can now tell people: hey, my company raised $4.5 million, Mark Cuban is one of our investors, and we have 30 employees.

Another huge cause of loneliness that Lyons didn’t mention is self-induced: not talking with other people about your problems (also known as “founder’s disease”). The biggest barriers can be the ones we construct ourselves, but if you want to succeed and stay sane, you’ll have to learn to break them down.

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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