>The CEOs who don't feel successful

>The CEOs who don't feel successful

You're readingThe CEOs who don't feel successfulGeneration ProjectSuccessShare on FacebookShare on TwitterShare on LinkedinShare using EmailShare on WhatsappClose navigationSimilar Articles>The CEOs who don't feel successfulCan 'pods' save us from open offices?>The CEOs who don't feel successfulThe office where phones are banned>The CEOs who don't feel successfulKorea’s ‘condescending’ old peopleFeel like success is a moving target? You’re in good company. Why it can seem like you can never quite do enough at work, no matter your triumphs.>The CEOs who don't feel successfulBy Sam Blum 12th August 2019


By many measures of success, Laura Moore had surpassed expectations and done everything right. After co-founding healthcare start-up Mobile Heartbeat at the age of 19, she’d built the company into a force, selling it for an undisclosed sum to the Hospital Corporation of America (HCA) before her 30th birthday.

The deal marked a crowning achievement for her young career and fashioned her as a budding star in the start-up world. But the acquisition occurred behind closed doors. Since it wasn’t followed by a splashy PR announcement and media blitz, she walked away somewhat unfulfilled.

“That was like 10 years [of work], and there’s a lot of value in that. But I feel like I have to justify it because there’s no number I can attach to it legally,” says Moore, who declined to comment on the specifics of the sale. She was successful, yes, but the private nature of the deal didn’t provide her a way to trumpet her credentials to prospective venture capital firms or media outlets.

To be sure, selling a company for a nice paycheck, regardless of the sum, would be a win for most. But to Moore, her success wasn’t quite enough.

Moore is among many start-up founders – and millennial leaders in general – who have been left wanting more in the face of their own triumphs. The phenomenon of feeling perpetually dissatisfied on the job is pervasive across industry fields, socioeconomic divides and international borders. But for the young founder – a highly diligent, media-savvy and ambitious class of entrepreneur – professional success often breeds personal disillusionment.

>The CEOs who don't feel successful

Big checks, big recognition and big success – the image of a young leader is highly curated, but harder behind the scenes (Credit: Getty Images)

‘A very lonely job’

Part of the feeling of chasing that elusive, dangling carrot of success is fostered by the highly competitive nature of Silicon Valley and the tech industry. In the environment that birthed Steve Jobs and Elon Musk, founders are constantly striving not only to raise money and change the world, but to become era-defining stars in some cases.

In order to stay above the competitive fray, one needs to project an image of success, no matter how taxing the day-to-day grind becomes.

“It can be a very lonely job to be a start-up founder,” says Alisa Cohn, an executive coach based in New York, who works with executives and founders across several industries. “Everybody around you feels like they’re killing it, so it’s like you’re the only one who’s got problems” when things don’t work out.

Start-up founders often labour in the dark for years, Cohn says, and usually won’t see any praise until their company goes public, gets acquired, or makes tons of money. The public only sees and celebrates the winners. Without buzz and fanfare, a lucrative sale or IPO might only register with the faintest of thuds in a founder’s mind. Cohn recalls one client who sold a business for an eight-figure sum, but left the deal feeling more distraught than jubilant.

“We don’t see the toiling in the wilderness for five or 10 or 15 years, and that’s what it takes to build a start-up,” says Cohn. “The net of all that is that you’re striving and striving, and it always feels that someone is ahead of you.”

Everybody around you feels like they’re killing it, so it’s like you’re the only one who’s got problems – Alisa Cohn

And, although many people often feel that success is a moving target, millennial leaders are particularly susceptible to feeling disillusioned.

Jamie Gruman, author of Boost: The Science of Recharging Yourself in an Age of Unrelenting Demands, and a professor of organisational behaviour at Canada’s University of Guelph, says millennials feel less in control of their own fates than other generations. The fact that millennials “grew up in an era when the world was in flux, the economy wasn’t good, there were terrorist attacks” makes feelings of helplessness more palpable, he says.

Then there’s social media and press. Feelings of inadequacy can become exacerbated through their constantly churning natures, which emphasise success nearly constantly – and publicise failure, too.

“There are even more celebrity CEOs, and the media with the notion of treating people like royalty plays into all of that,” says Cohn. “And it feels like ‘that’s what I have to aspire to’.”

Behind closed doors, however, it’s often a different story. Matt Wheeler, 35, who helped co-found the college athletics recruitment website Sports Recruits, notes that many CEOs get together not to boast about their accolades, but to vent about their anxiety.

“What you read on Twitter is very different than what you hear when you get into a room with a bunch of start-up CEOs,” Wheeler says. “Everybody is ‘crushing it’ on Twitter and worrying about running out of money behind closed doors. I am involved with a CEO group and our time together feels like therapy. The discussions happening there are not happening on Twitter.”

>The CEOs who don't feel successful

Facebook founder Mark Zuckerberg is among the most visible 'celebrity CEOs', whose success and failure is often headline making in global media (Credit: Alamy)

The boss’s boss

“There’s a misconception that when you’re an entrepreneur or start your own company that you don’t have a boss,” says founder Moore, now 31. After her exit with Mobile Heartbeat, she now runs the healthcare start-up Nell Health, which specialises in genetic and blood testing.

As the company’s CEO, Moore is still greatly drawn to the calling of her job. But she knows that the life of a founder can give way to a periodic “trap” or two.

She says there’s an “outside portrayal of founder life as this amazing journey that you have to make look so exciting and so high growth all the time. I think there’s just an inevitable crash for a lot of people when they feel they’re not living their real life.”

Like many executives in tech, Moore is beholden to her VC financiers. She often feels an unrelenting pressure to perform publicly, either through speaking events, media appearances or different avenues. If she doesn’t perform the dual function of corporate executive and public figure, however, potential backers might turn off the financial spigot in favour of someone else.

There’s just an inevitable crash for a lot of people when they feel they’re not living their real life – Laura Moore

“There’s an endless amount of things you could be doing to make yourself look amazing, and there’s big pressure to do that,” she says. “You have founders trying to achieve success on multiple fronts, whether it’s media attention, revenue growth, etc., and that’s where the trap sets in.”

Moore says the pressure only begins with traditional business demands. It becomes a deluge when combined with other expectations, presenting the feeling of a pile-on. “You have to have a profile and look really wealthy and look awesome on panels when you’ve slept two hours the night before.”

Matthew Bischoff, 28, the co-founder of the software development company Lickability, agrees. Bischoff says there’s constant demand not only to succeed on the job, but to impress one’s counterparts with a side hustle or two.

“Even though you’re running a company full-time, you’re expected to be contributing to open source and have side projects,” says Bischoff. “I think that doesn’t leave a lot of space for family and friends and hobbies outside of tech.”

>The CEOs who don't feel successful

"You have to have a profile and look really wealthy and look awesome on panels when you’ve slept two hours the night before" – Laura Moore, millennial founder (Credit: Alamy)

Capturing success

The perception of running a disruptive company – and the romance of affecting change and improving people’s lives – is often a far cry from reality.

Gruman says that people often enter the start-up world because they enjoy laying the foundation for a company and leaving a personal impact on an organisation. But values can get muddled and even lost when an organisation expands, giving way to new conflicts.

When people aren’t “getting their hands dirty anymore, they’re not able to do what they love and they forget what they love about the job”, he says. “For some people the work can end up not being very meaningful.”

So how should overworked founders and executives actually take heed of their successes and feel good about their accomplishments?

Cohn advocates an easy and practical approach: “Do a look back every few months with the specific intention of noticing progress made and milestones hit”.

Gruman also advises a soul-searching founder to examine the personal side of their work: “What would objective outsiders think about your success?” he asks. “Would they be impressed?”

The answer, in almost all instances, is a resounding yes.

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