Esquire Artcile
https://esquiresg.com/the-success-trap-why-fear-holds-leaders-back/
Episode Transcript
The transcript is computer generated. There may be errors.
Hi everyone! Welcome to "How to Live," a podcast that explores ways to live a good life. I'm your host, Sharad Lal. This is Episode 90.
I've worked with thousands of high performers hitting their 40s and beyond for the past 10 years. And I've noticed something fascinating.
All of these successful people follow one of two paths.
Some go on to do remarkable things. Others plateau.
The difference between them is simple.
The ability to evolve.
But what prevents people from evolving when they've already achieved so much?
I call it The Success Trap.
"Why should I change when everything is working? The world sees me, applauds me, and rewards me for being this way."
At first glance, this might look like overconfidence, inertia, or complacency—but the truth runs deeper.
At the core, it's FEAR.
All our success creates an identity—an identity the world sees and rewards.
Maybe you became the smartest problem-solver in the room.
Maybe you became the charismatic leader who could inspire and motivate any team.
Over time, this identity brings success, respect, and incredible opportunities. It feels great.
But we don't realize that we're clinging to it. We hold onto this identity so tightly—because we are terrified of losing it.
And that's where the problem begins.
My Story: Hitting Rock Bottom
I learned this lesson the hard way.
Over a decade ago, I was at my peak—multiple successful businesses, a fulfilling personal life, and the respect of everyone around me.
Then, I suffered a huge personal loss. I lost loved ones. My world shattered.
For years, I struggled to recover. But I'll never forget one moment during that time—when I had lost everything, I felt something unexpected.
Relief.
It shocked me. How could I feel relief when I had lost everything?
The Root of Fear: The Identity We Cling To
As I searched for answers, I turned to spirituality, psychology, and leadership research.
In Buddhism, I found the concept of clinging—when we have everything, we grasp onto it tightly out of fear of losing it. The fear of loss becomes so overwhelming that we stop enjoying what we have and instead focus on protecting it.
That's why when we lose it, we lose the fear—and suddenly, we are free to make bold changes.
In psychology, fear-based behaviors are rooted in protective mechanisms that prioritize safety over exploration.
In Carol Dweck's research, I saw how the fixed mindset makes us cling to what made us successful, treating failure as a threat rather than an opportunity to grow.
This fear shaped my identity.
Since childhood, whenever I did something smart, people clapped. So I kept being smart.
When I became successful, I subconsciously held onto that success, because I was terrified of losing it.
The fear of loss became greater than the joy of success.
And while that fear once helped me grow, at a certain point, it started holding me back.
Then, when I lost everything, something shifted.
For the first time, I questioned who I really was beyond the labels and achievements.
I started making bold decisions, taking risks I wouldn't have before, and most importantly, I evolved.
From entrepreneur to keynote speaker.
From relying on frameworks to storytelling and influence.
From being the Solver—the one with all the answers—to becoming the Enabler, empowering others to solve for themselves.
But those core strengths didn't disappear—they evolved into something bigger.
The same intelligence, discipline, and drive that once fueled my success were still there—but instead of limiting me, they expanded. I let them adapt, grow, and serve me in new ways.
The Realization: A Case Study on The Success Trap
Recently, I worked with a senior leader at a top company who had fallen into this exact trap. He was the go-to problem solver—brilliant, decisive, and analytical. His success had always come from being the smartest person in the room.
At first, this identity helped him thrive.
He was trusted with high-stakes decisions.
He grew businesses in challenging markets.
He was fast-tracked for promotions.
But then, he hit a wall.
His team stopped speaking up because they feared his criticism.
His collaboration suffered—colleagues found him difficult to work with.
His growth stalled—he wasn't developing new skills, just reinforcing his old identity.
When we dug deeper, he realized the root cause—fear.
Fear of being sidelined.
Fear of being seen as dispensable.
Deep down, the biggest fear? "If I'm not the smartest person in the room, then who am I?"
The fear didn't just sit there quietly—it created overcompensatory patterns.
He would argue unnecessarily in meetings, just to prove his intellectual superiority.
He became overly critical of other people's ideas, picking them apart to showcase his own insight.
He'd jump in to solve problems before his team had a chance to figure things out themselves.
These behaviors had serious consequences.
His team developed a transactional relationship with him—they'd approach him only for answers, not mentorship.
He lacked deep connections, making long-term team loyalty harder to build.
He frustrated colleagues and bosses with unnecessary conflict.
This fear-driven identity wasn't just limiting him—it was costing him opportunities, relationships, and future growth.
That's when I asked myself:
"How can high-performing, successful leaders experience this kind of transformation—without first having to lose everything?"
That's when I realized:
Most leadership workshops fail because they focus on surface-level issues.
They try to fix beliefs and behaviors, but they don't address the core identity that leaders are clinging to.
To truly evolve, we need to first understand these identities and the fear that fuels them.
The Six Identities of Successful Leaders
As I worked with thousands of senior leaders—through coaching, podcast conversations, and workshops at companies like Google, Unilever, and HSBC—I kept seeing the same patterns.
Successful leaders fall into six core identities—identities that once propelled them forward but eventually hold them back.
The Solver – This is the smartest person in the room who always has the answers. They thrive on fixing problems but fear being seen as dispensable. This leads to micromanagement and over-involvement.
The Perfectionist – This leader sets impeccably high standards but fears not being good enough. They create delays and resist delegation because perfection isn't just a goal—it's protection against criticism. Every imperfection feels like a personal failure.
The Workhorse – They work tirelessly, putting in longer hours than anyone else. But underneath, they fear they don't truly belong. They overcompensate with relentless effort, risking burnout. Their drive comes from a place of insecurity, not inspiration.
The Charmer – They inspire others and build connections effortlessly. But they fear rejection, so they prioritize likability over making difficult decisions. They avoid conflict at all costs, even when honesty is what's needed most.
The Taskmaster – They execute efficiently but fear uncertainty and ambiguity. They resist change and stifle creativity because unexpected variables threaten their sense of control. Their rigidity comes from deep insecurity about navigating the unknown.
The Visionary – They see the future with remarkable clarity but fear irrelevance. They generate endless ideas without following through because completion means potential failure. By staying in ideation mode, they never have to test whether their visions actually work.
Most of us are a blend of these identities. I certainly was.
But here's what's important to understand: these identities aren't inherently bad. They're what got us here. They brought us success, recognition, and achievement.
The problem isn't the identity itself—it's how tightly we cling to it.
It's how fear turns what once was a strength into a limitation.
Think about it.
How many opportunities have you missed because you were too busy protecting your image as the smartest person in the room?
How many innovations were stifled because you couldn't let go of control?
How many talented team members haven't reached their potential because you couldn't stop solving problems for them?
Our success trap isn't just hurting us—it's limiting everyone around us.
Understanding Your Own Success Trap
So what's the first step toward breaking free?
Understanding. Understanding how your identity formed, how it's been reinforced over the years, how it serves you, and most importantly—what fear drives it.
Take a moment now to reflect.
Which of these identities resonates with you most?
What patterns do you see in how you respond to challenges?
What are you afraid of losing if you were to change?
The first step isn't changing—it's seeing. Seeing yourself clearly, perhaps for the first time.
In our next episode, I'll share concrete strategies for evolving beyond these fear-based identities. But for now, I invite you to sit with this awareness.
Because you can't transform what you don't understand.
Notice when your identity kicks in throughout your day. Notice when fear drives your decisions. Just observe, without judgment.
This awareness alone is powerful. It's the beginning of freedom.
This is Sharad, and you've been listening to How to Live. Here's to understanding the success trap—the first step toward breaking free from it.
Hi everyone! Welcome to "How to Live," a podcast that explores ways to live a good life. I'm your host, Sharad Lal. This is Episode 90.
I've worked with thousands of high performers hitting their 40s and beyond for the past 10 years. And I've noticed something fascinating.
All of these successful people follow one of two paths.
Some go on to do remarkable things. Others plateau.
The difference between them is simple.
The ability to evolve.
But what prevents people from evolving when they've already achieved so much?
I call it The Success Trap.
"Why should I change when everything is working? The world sees me, applauds me, and rewards me for being this way."
At first glance, this might look like overconfidence, inertia, or complacency—but the truth runs deeper.
At the core, it's FEAR.
All our success creates an identity—an identity the world sees and rewards.
Maybe you became the smartest problem-solver in the room.
Maybe you became the charismatic leader who could inspire and motivate any team.
Over time, this identity brings success, respect, and incredible opportunities. It feels great.
But we don't realize that we're clinging to it. We hold onto this identity so tightly—because we are terrified of losing it.
And that's where the problem begins.
My Story: Hitting Rock Bottom
I learned this lesson the hard way.
Over a decade ago, I was at my peak—multiple successful businesses, a fulfilling personal life, and the respect of everyone around me.
Then, I suffered a huge personal loss. I lost loved ones. My world shattered.
For years, I struggled to recover. But I'll never forget one moment during that time—when I had lost everything, I felt something unexpected.
Relief.
It shocked me. How could I feel relief when I had lost everything?
The Root of Fear: The Identity We Cling To
As I searched for answers, I turned to spirituality, psychology, and leadership research.
In Buddhism, I found the concept of clinging—when we have everything, we grasp onto it tightly out of fear of losing it. The fear of loss becomes so overwhelming that we stop enjoying what we have and instead focus on protecting it.
That's why when we lose it, we lose the fear—and suddenly, we are free to make bold changes.
In psychology, fear-based behaviors are rooted in protective mechanisms that prioritize safety over exploration.
In Carol Dweck's research, I saw how the fixed mindset makes us cling to what made us successful, treating failure as a threat rather than an opportunity to grow.
This fear shaped my identity.
Since childhood, whenever I did something smart, people clapped. So I kept being smart.
When I became successful, I subconsciously held onto that success, because I was terrified of losing it.
The fear of loss became greater than the joy of success.
And while that fear once helped me grow, at a certain point, it started holding me back.
Then, when I lost everything, something shifted.
For the first time, I questioned who I really was beyond the labels and achievements.
I started making bold decisions, taking risks I wouldn't have before, and most importantly, I evolved.
From entrepreneur to keynote speaker.
From relying on frameworks to storytelling and influence.
From being the Solver—the one with all the answers—to becoming the Enabler, empowering others to solve for themselves.
But those core strengths didn't disappear—they evolved into something bigger.
The same intelligence, discipline, and drive that once fueled my success were still there—but instead of limiting me, they expanded. I let them adapt, grow, and serve me in new ways.
The Realization: A Case Study on The Success Trap
Recently, I worked with a senior leader at a top company who had fallen into this exact trap. He was the go-to problem solver—brilliant, decisive, and analytical. His success had always come from being the smartest person in the room.
At first, this identity helped him thrive.
- He was trusted with high-stakes decisions.
- He grew businesses in challenging markets.
- He was fast-tracked for promotions.
But then, he hit a wall.
- His team stopped speaking up because they feared his criticism.
- His collaboration suffered—colleagues found him difficult to work with.
- His growth stalled—he wasn't developing new skills, just reinforcing his old identity.
When we dug deeper, he realized the root cause—fear.
- Fear of being sidelined.
- Fear of being seen as dispensable.
- Deep down, the biggest fear? "If I'm not the smartest person in the room, then who am I?"
The fear didn't just sit there quietly—it created overcompensatory patterns.
- He would argue unnecessarily in meetings, just to prove his intellectual superiority.
- He became overly critical of other people's ideas, picking them apart to showcase his own insight.
- He'd jump in to solve problems before his team had a chance to figure things out themselves.
These behaviors had serious consequences.
- His team developed a transactional relationship with him—they'd approach him only for answers, not mentorship.
- He lacked deep connections, making long-term team loyalty harder to build.
- He frustrated colleagues and bosses with unnecessary conflict.
This fear-driven identity wasn't just limiting him—it was costing him opportunities, relationships, and future growth.
That's when I asked myself:
"How can high-performing, successful leaders experience this kind of transformation—without first having to lose everything?"
That's when I realized:
Most leadership workshops fail because they focus on surface-level issues.
They try to fix beliefs and behaviors, but they don't address the core identity that leaders are clinging to.
To truly evolve, we need to first understand these identities and the fear that fuels them.
The Six Identities of Successful Leaders
As I worked with thousands of senior leaders—through coaching, podcast conversations, and workshops at companies like Google, Unilever, and HSBC—I kept seeing the same patterns.
Successful leaders fall into six core identities—identities that once propelled them forward but eventually hold them back.
The Solver – This is the smartest person in the room who always has the answers. They thrive on fixing problems but fear being seen as dispensable. This leads to micromanagement and over-involvement.
The Perfectionist – This leader sets impeccably high standards but fears not being good enough. They create delays and resist delegation because perfection isn't just a goal—it's protection against criticism. Every imperfection feels like a personal failure.
The Workhorse – They work tirelessly, putting in longer hours than anyone else. But underneath, they fear they don't truly belong. They overcompensate with relentless effort, risking burnout. Their drive comes from a place of insecurity, not inspiration.
The Charmer – They inspire others and build connections effortlessly. But they fear rejection, so they prioritize likability over making difficult decisions. They avoid conflict at all costs, even when honesty is what's needed most.
The Taskmaster – They execute efficiently but fear uncertainty and ambiguity. They resist change and stifle creativity because unexpected variables threaten their sense of control. Their rigidity comes from deep insecurity about navigating the unknown.
The Visionary – They see the future with remarkable clarity but fear irrelevance. They generate endless ideas without following through because completion means potential failure. By staying in ideation mode, they never have to test whether their visions actually work.
Most of us are a blend of these identities. I certainly was.
But here's what's important to understand: these identities aren't inherently bad. They're what got us here. They brought us success, recognition, and achievement.
The problem isn't the identity itself—it's how tightly we cling to it.
It's how fear turns what once was a strength into a limitation.
Think about it.
How many opportunities have you missed because you were too busy protecting your image as the smartest person in the room?
How many innovations were stifled because you couldn't let go of control?
How many talented team members haven't reached their potential because you couldn't stop solving problems for them?
Our success trap isn't just hurting us—it's limiting everyone around us.
Understanding Your Own Success Trap
So what's the first step toward breaking free?
Understanding. Understanding how your identity formed, how it's been reinforced over the years, how it serves you, and most importantly—what fear drives it.
Take a moment now to reflect.
Which of these identities resonates with you most?
What patterns do you see in how you respond to challenges?
What are you afraid of losing if you were to change?
The first step isn't changing—it's seeing. Seeing yourself clearly, perhaps for the first time.
In our next episode, I'll share concrete strategies for evolving beyond these fear-based identities. But for now, I invite you to sit with this awareness.
Because you can't transform what you don't understand.
Notice when your identity kicks in throughout your day. Notice when fear drives your decisions. Just observe, without judgment.
This awareness alone is powerful. It's the beginning of freedom.
This is Sharad, and you've been listening to How to Live. Here's to understanding the success trap—the first step toward breaking free from it.