Myth: Over-Achievers are Great Leaders

The conventional definition of leadership is far from sustainable, driven by a foundational story that is fundamentally flawed

Holly McCann
Grail Leadership
6 min readMay 1, 2024

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Photo by Jordan Whitfield on Unsplash

I worked hard and became a “successful leader” ~ but I never felt worthy of it, never felt I was doing enough to earn all that I was receiving.

From a very young age, I took on the number one lesson of the Success Playbook: “Hard work is the key to success.”

That belief led to another one: Leaders are those who worked the hardest, took on the most responsibility, and therefore got the most success. So, it was clear what I needed to do….

The trap of the over-achiever

For as long as I could remember, I was the classic overachiever ~ perfectionist, highly self-critical, solely focused on the future, and never satisfied. Criticism of any sort was devastating, because that implied failure ~ and failure was never an option.

I became a workaholic, continually sacrificing my health, quality time with my family, and any sense of my own needs, desires or passions.

I had no idea how to rest or how to play, which could only ever come after the work was done. And the stern taskmaster in my head constantly reminded me that the work wasn’t yet done ~ that I hadn’t accomplished enough and certainly hadn’t earned a break to relax, play, or enjoy all that I was working so hard for.

It seemed like a reasonable trade-off at first. Work really hard, get it all right and be a leader so I could earn what I most wanted ~ financial security, more authority, more power and control over my life.

The problem with this bargain was that I never felt like I had done enough to have earned it.

I was in a perpetual catch-22: the more I achieved, the more responsibility and money I was given; yet the more I received, the more I needed to work even harder to prove I was worthy of the added responsibility and income.

Life just kept upping the ante, raising the stakes higher and higher … until I folded.

Leaders are burning out

My story is not unique. In fact, the conventional business model is set up to reward overachievers ~ and to breed more of them ~ by making them leaders.

By and large, those who are promoted to higher and higher leadership positions are the over-achievers. And why not? When productivity is paramount, the hustle and grind are glorified.

The belief that over-achievers make great employees, and that this somehow makes them great leaders, is extractive and short-sighted.

In this environment, decisions are made from a place of significant stress, fear and anxiety. There’s no time or space for tuning in to what really wants to emerge, for solutions that will truly benefit the organization and those it is meant to serve. And many organizations are in a churn-and-burn cycle with employees: lure them in with amazing benefits, extract all that you can from them until they leave, rinse and repeat.

Over-achievers put themselves under tremendous pressure. As the heat inevitably gets turned up, the pressure in the cooker is intensified. At some point, it will blow up.

And we’re seeing the cracks in the system. Burnout and depression are at all-time highs. Employee disengagement and “quiet quitting” have become our new normal. And it’s no wonder.

For the first time this year, Gen Z make up a larger portion of the workforce than Baby Boomers. The Millennials, Gen X and Gen Z have all seen what happens when you work hard ~ you get promoted, which means you need to work even harder and take on even more responsibility. They don’t want to follow that playbook, but don’t know what else to do, leaving them in a limbo land of doubt, uncertainty and hopelessness.

Photo by Andrew Neel on Unsplash

What’s really going on?

We’ve come to simply accept without question that hard work is a way of life. But hang on a minute…

How did we as a civilization first come to believe we had to work so hard? When did we start needing to pay for our survival, to earn our keep, to be deemed worthy of our very existence?

The society we have been existing in for millennia is based on a foundational belief that our world is one of scarcity ~ that we need to live in fear, fighting for our survival, to take what we need before someone else does ~ perpetually playing a win-lose game.

In a scarcity-based world, getting more of what I need or want means that someone else gets less. Because we are fundamentally sensitive caring beings, we are unconsciously carrying around a great deal of guilt and shame over this. So our psyche searches for ways to ease that guilt ~ by trying to prove to ourselves and the world that we are deserving, that we are somehow worthy of having more than those who will inevitably end up with less because of us.

This shows up everywhere in our culture ~ the criticism and judgment of others, the virtue signaling {see, I’m a really good person}, the obligation to give to those who are “less fortunate”, and the pressure to achieve.

How do we shift this?

We get to the deepest core of the issue.

The story of scarcity, rooted in fear and separation is the foundation that upholds the beliefs that life is hard, that resources are limited, that we need to fight for what we need, prove our worth, and earn our keep.

That story is absolutely not true!

We live in a magnificent world that is fundamentally abundant and interconnected. Human beings are innately loving, generous and kind. {Ever notice what happens in an emergency or a natural disaster?}

We’ve just been living through millennia of immense conditioning and suffering repeatedly passed on as unresolved ancestral and collective trauma. We’ve been believing in a false story of Separation & Scarcity for so long and so deeply that we’ve formed the very systems and structures of our society around it.

Now is the time we get to live a new story

Now is the time in our evolution where we’re coming full circle, finding our way back to the origin story from which humans and the entire planet were birthed ~ a story of infinite unconditional love, relentlessly regenerative life, and profound abundance and beauty.

And you, dear pioneer, are one of a relatively small group of courageous souls who couldn’t wait to be here now at this incredible time. You agreed to go in deep, experiencing first-hand the pain caused by the flawed belief system, while carrying the knowing deep in your cells that it doesn’t need to be this way ~ and ultimately being among the first to break through the illusion and embody the true essence of this magnificent world.

In this new and ancient story, leadership is not about working the hardest to survive and extracting the most from others. Instead, it is all about stewardship, contributing to the highest potential for all life to thrive {including your own}.

The true pioneers of our time are those who have chosen to be on the leading edge of evolution ~ transmuting their greatest wounds into their greatest gifts, thereby supporting others in doing the same ~ and modeling what’s possible by living into the story of our original design and infinite potential.

Where do you see this notion that “hard work is the key to success” showing up in your world? How are you living into a more regenerative story?

Please leave a comment below to share your experience and insights. And, if it resonates, please like or share this post!

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Holly McCann
Grail Leadership

Founder & Vision Keeper of Grail Leadership, helping pioneering leaders and their businesses fulfill their mission and thrive in alignment with Nature.