The Hidden Emotional Cost of Entrepreneurship

How to avoid the trap of success and inner emptiness

Though idealized in modern media, the demands placed upon founders to build profitable businesses for their investors is rarely discussed in detail.

Most articles focus on generating hype.

They are motivational pieces that glorify achievement, worship workaholics, and promise quick solutions to immediately increase productivity. And while these short reads may temporarily boost morale, they do nothing to address the underlying emotional consequences of high-stakes entrepreneurship.

At best, these articles inspire diverse individuals to think outside the box — to follow their passion even if it does not yet exist and gives them the extra motivation needed to overcome exhausting days in hope of building a better future.

But at worst, the exclusive portrayal of techniques and admiration spin the dangerous and shortsighted narrative that there are no limits. That you can be consumed by work and the pursuit of profit without any emotional consequences.

And there are consequences.

On the surface, many people buy the notion that seeking materialistic success is the “right” thing to do.

They’re excited by the chance to make Stanford CES jealous, create a product that no one can live without, and collect enough wealth that they can tell any and everyone to bugger off. They don’t consider that this pursuit, for some individuals, has far-reaching implications that alter the way they relate to themselves, others, and the world.

As a cofounder psychologist who has spent the last five years working with entrepreneurs, I have a different story to share.

It’s not as glamorous — it may not leave you inspired to take the big risk of betting on yourself and seeking funding, but it’s far more honest. And it’s connected to the lived experience of a real person who spent his life chasing something that never brought him what he truly wanted.

His story is similar to many clients I’ve worked with. You may think that you’re the exception — that his story has nothing whatsoever to do with yours.

I hope you’re right.

Note: Names and details have been changed to protect the client’s identity.

Mark is a c-suite executive and co-founder.

He spent the last seven years building and scaling a luxury-based construction company. He makes a generous income, dates a beautiful woman with an insatiable sexual appetite, and drives whatever sports car he wants.

On the surface, he is the definition of success.

He’s earned multiple degrees, started several companies, and is looking to take a handsome exit from this current venture. He feels admired by acquaintances who want to learn from him and desired by his girlfriend of five years who gives him freedom to follow his passion as long as he saves some for her a few nights each week.

He’s achieved every goal he set for himself, except one.

Mark is deeply unhappy.

He’s spent his entire life doing what other people wanted him to do. When he went to graduate school, he was praised for his intellect. When he started creating companies, he was admired for his relentless work ethic. And when he started making gobs of money, everyone wanted a piece of him — they fought to be in his presence, hoping that they could absorb an ounce of what made him the textbook definition of success.

All of this external validation provided ample motivation to justify his inner dissatisfaction.

To be honest, Mark hated his co-founder. They had a contentious relationship. Mark felt undervalued for his significant role in scaling the company and he was angry at his partner’s cutting remarks in moments of disagreement.

He also disliked his uninspiring employees — a bunch of yippity yes-men who functioned more like skittish fan-boys than the scrappy agile team he wanted.

Like an arthritic knee, these dynamics ached more each year and bugged him each time he walked into the office.

Mark lost his passion for the work years ago.

Not only was he sick of his team and frustrated with his partner, he no longer felt challenged in his role. Lacking investment in tasks, Mark discovered that he could outperform his incompetent peers using about half of his normal effort. He forced himself to gulp espresso and tried to show his face around the office, but noticed himself cutting corners — leaving earlier and earlier, seeing how much he could get away with.

His lifestyle was lifeless and uninspired.

Mark was living an inauthentic life. In psychological terms, he was living a life based on the values of friends, family members, and society at large rather than following his inner truth.

A famous psychoanalyst named D.W. Winnicott would say that Mark was living as a “false self.”

“In the cases on which my work is based there has been what I call a true self hidden, protected by a false self.

This false self is no doubt an aspect of the true self. It hides and protects it, and it reacts to the adaptation failures and develops a pattern corresponding to the pattern of environmental failure.

In this way the true self is not involved in the reacting, and so preserves a continuity of being. However, this hidden true self suffers an impoverishment that derives from lack of experience.”

— D.W. Winnicott, 1955–56

Winnicott believes that Mark’s false self was developed to protect his more vulnerable self, his true self.

He theorizes that a false self is created when parents fail to provide a healthy and supportive emotional environment for their children. Winnicott conveys that this false self serves an important function — protecting the true self from further damage. But the cost is that the true self remains hidden and under-developed.

In short, Mark is disconnected from his innermost thoughts, feelings, experiences, and desires.

Carl Jung calls this protective mechanism a “persona,” the skin-like mask that we all wear to engage with the world.

“The persona is a complicated system of relations between individual consciousness and society, fittingly enough a kind of mask, designed on the one hand to make a definite impression upon others, and, on the other, to conceal the true nature of the individual.”

— C.G. Jung, 1928

Jung emphasizes that when the persona is too rigid and disconnected from our ego, it restricts our psychological development.

In the quote above, he notes that the persona is designed to elicit a certain response from the environment. In Mark’s case, his mask was created to elicit the admiration and validation that he was not receiving in childhood and to protect his inner world.

In other words, Mark wore this mask — the mask of achievement, success, and entrepreneurship — because society values and worships those factors. Thus, if he presented himself as possessing these traits, he would become valued and admired.

Mark’s psychological development clearly impacted his relationship with himself. But it also changed how he engaged with others.

In his need for achievement, Mark perceived other people as objects. He viewed them as things that either enhanced his self-image or detracted from it.

His model girlfriend added to it. His partner, though irritating, added to it. His less-than-inspiring team detracted from it. All people were viewed through this cost-benefit analysis: Do they add value or do they get in my way? Are they useful for me or not?

Perceived through this lens, the world is a game about exploitation and domination: Will I be the winner or the loser? The abused or the abuser? And after hearing more about Mark’s childhood, the deeper root of these patterns began to make sense.

As we went deeper in our coaching, it became clear that Mark had many understandable reasons for living an incongruent lifestyle.

His parents were poor. His father, an alcoholic. His mother was cold, resentful, and the victim of domestic violence from her husband’s whiskey-fueled rage.

What’s the one thing a child growing up in an environment like that doesn’t receive? Validation. Support. Encouragement. They aren’t allowed to feel the joy of playing in the spotlight — it’s abruptly shifted in traumatic moments onto the abuser and then the abused. There’s no light, no loving attention left for him.

Mark needed to protect his mother, to save her from his father. And he needed to save himself too.

The only way to do that was to build armor.

To defend against his sense of inferiority — the inevitable outcome of feeling unimportant to emotionally unavailable parents — by seeking achievement.

On an unconscious level, Mark thought, “If I can become rich and successful, women will love me. They won’t be cold and dismissive anymore. And men will want to be me. I’ll never have to feel powerless again.”

Over time, this mindset led him to reduce people to objects. He made people feel powerless in the same ways he experienced as a child. His mother’s cold indifference and his father’s unrestricted rage were constellated in others who felt used and discarded, of no use for Mark’s glorious conquests.

This inner compulsion to compensate for his deep emotional pain led Mark down a path of material wealth and inner poverty.

Despite having all of the things — a mansion, a model partner, and a sports car — he was alone.

Mark’s true passion was music. It was the one thing that he could do to express his inner pain. It was the one moment in the world where he was free to play, create, and never have to share the spotlight.

He spent decades honing his craft.

After long days in the office, he focused on singing. He taught himself how to produce, edit, and mix music. He learned five instruments, each to an astonishing degree of mastery. He wrote songs about his life and occasionally allowed friends listen to his well-crafted lyrics.

Mark’s friends were impressed.

They told him that he had real talent — something that they wish he’d share with others. And he agreed. Mark knew that he was talented and hard-working. He was aware that he had the ability to be successful in the music industry, given his entrepreneurial acumen and network.

But he was afraid.

He didn’t want to risk failure. He was scared to bet on his true self and lose. And shifting away from this title would change the way he was perceived: He’d go from founder to failure — someone who couldn’t cut it.

Mark worried that he’d be dismissed and rejected in the same manner he was as a child.

He felt stuck.

But he was faced with a choice: Continue living a safe, inauthentic life to appease others and feed the illusion of his all-powerful persona, or leave the life he spent decades sculpting — the one he thought he always wanted — and purse a less lofty career more aligned with his spirit.

After sitting in this state of inner tension, Mark came to see me. We met regularly for a year. That was all he needed.

Mark made significant changes to his life.

He quit his job. He broke things off with his girlfriend, whom he realized was everything his ego wanted, but not what he needed. And started pursuing music, his true passion, so that he could connect with himself each day in a more authentic manner.

The road to getting to that point was not twelve months. It took Mark, an insightful and self-motivated individual, most of his life to work up the courage to listen to his psyche and tolerate the discomfort of addressing his childhood wounds.

For him, the move to music symbolized the return to his true self.

While not everyone can or should make a career change, the most important factor was Mark’s choice to prioritize connecting with himself. I call this “fighting the good fight” because your true self is always worth fighting for, especially when feeling lost in the mask of success.

All he needed was support — genuine encouragement, empathy, and validation for following his true heart’s desire.

He also needed to be challenged: To have interpretations about the ways in which his past patterns were limiting his present circumstances. And for those past experiences to be acknowledged, mourned, and understood.

“Until you make the unconscious conscious, it will direct your life and you will call it fate.”

― C.G. Jung

I’m thankful for the opportunity to witness Mark’s transformation.

I’m humbled by the courage that was required to bet on his true self knowing that it would result in the loss of status and validation that he previously needed to survive. But I’m immensely proud that he took that leap of faith. It exemplifies the strength of his hard-earned self-esteem.

Mark’s lived experience shows that there is a significant price to be paid for chasing success. When sought with the wrong intention, it can result in a significant disconnection with yourself, others, and the world.

Though well intended, Mark’s pursuit of materialistic success and achievement led to severe emotional consequences. It gave him what he wanted: The ability to overcome his circumstances, earn admiration, and feel the illusion of power. But it didn’t give him what he needed: An authentic life based on his values and inner truth.

While his life appeared great on the surface, the underlying wounds that prompted his compensatory pursuit took most of his life to address. That’s a profound cost.

Many aspiring entrepreneurs are also in it for the wrong reasons.

They are seeking approval and recognition from the masses because they were unable to receive it from the people that mattered most.

They are in love with the accolades — the money, the mansions, the cars — not the process. And the process has a price.

Are you willing to pay it?

And if you are, do you have faith that you’ll be able to listen to your soul’s call when it’s time to step away?

What’s your motivation for starting a company?

Until your unconscious motives are understood, you may be setting yourself up for a life of achievement, success, and emptiness.