The Success Trap: Why High Achievers Struggle to Transform and How to Break Through

Let me start with a question that might make you uncomfortable: Who do you want to become? 

Not what you want to achieve. Not what revenue target you’re chasing. Not what title you’re gunning for. 

Who do you want to become? 

If you hesitated, you’re not alone. Most executives I speak with can rattle off their quarterly goals, their growth targets, and their strategic priorities without missing a beat. But ask them who they want to become as a leader, as a business owner, as a human being—and they go silent. 

Here’s the uncomfortable truth: success can be the biggest obstacle to transformation. 

You’ve hit 120% of your targets. You’ve climbed the ladder. You’ve built the business. And somewhere along the way, you stopped asking whether the way you’re achieving success is sustainable, scalable, or even aligned with who you want to be. 

I want to share three transformative takeaways from a conversation with an executive leadership coach Hilda Fainsod, who has spent over two decades helping senior leaders break through the invisible barriers that success creates. Her approach is rooted in a simple but profound belief: transformation is possible, but only when you’re willing to get out of your own way. 

These aren’t feel-good platitudes. They’re battle-tested strategies that have helped hyper-achievers shift from results-at-all-costs to sustainable, people-powered leadership. And they apply directly to you, whether you’re a founder, a C-suite executive, or a business owner navigating the next stage of growth. 

Takeaway 1: Success Can Be Your Biggest Blocker—Recognize When You’re Getting in Your Own Way

Here’s a scenario that plays out more often than you’d think. 

A senior executive gets pulled into a meeting with HR or their boss. They’re told: “You’re incredibly successful. You hit every target. But if you want to grow—if you want that next promotion, that bigger role, that seat at the table—you need to change. You need to be more of a people person. You’re too results-driven.” 

The executive is stunned. What do you mean I need to change? I’m delivering 120% every quarter. I’m the one carrying this team. 

And that’s exactly the problem. 

The Hyper-Achiever’s Blind Spot

When you’re a hyper-achiever—someone who consistently delivers beyond expectations—you develop a playbook that works. You push hard. You drive results. You don’t wait for permission. You make things happen. 

And that playbook got you here. 

But here’s the trap: the behaviors that got you to this level of success are often the same behaviors that will prevent you from reaching the next level. 

You’re so focused on results that you leave a trail of bruised egos, burned-out team members, and broken relationships in your wake. You don’t realize it because you’re winning. The scoreboard says you’re successful. 

But the feedback says something different: You’re not scalable. You’re not sustainable. You’re not the leader we need for the next stage. 

The Resistance to Change

When high achievers are told they need to change, the first reaction is resistance. 

I’m successful. Why should I change? 

This is who I am. Take it or leave it. 

I don’t have time for soft skills. I have targets to hit. 

This resistance is understandable. You’ve built your identity around being the person who delivers. Changing feels like admitting you were wrong. It feels like weakness. 

But here’s the reframe: Transformation isn’t about admitting you were wrong. It’s about recognizing that what got you here won’t get you there. 

The executive who delivers 120% by sheer force of will can’t scale. They become the bottleneck. They burn out. They lose their best people. 

The executive who learns to lead through others, to build systems, to empower teams—that’s the one who scales. That’s the one who builds something sustainable. 

The First Step: Awareness

The breakthrough starts with a simple question: What gets in your way? 

And the most self-aware answer is: I do. 

Not the market. Not the competition. Not your team. You. 

You’re the one who insists on doing everything yourself because “it’s faster if I just do it.” You’re the one who avoids difficult conversations because conflict is uncomfortable. You’re the one who resists feedback because you’ve been successful doing it your way. 

Once you own that—once you recognize that you are the blocker—transformation becomes possible. 

How to Break Through

Here’s a practical framework for recognizing when success is getting in your way: 

1. Audit your wins and losses. Look at your biggest successes in the past year. Now ask: What was the cost? Did you burn out? Did you lose team members? Did you sacrifice relationships? 
2. Seek honest feedback. Ask your team, your peers, your boss: “What’s one thing I could do differently to be more effective?” Listen without defending. 
3. Identify your default playbook. What do you do when the pressure is on? Do you micromanage? Do you take over? Do you shut down? Recognize the pattern. 
4. Ask the transformation question: Who do I want to become? Not what do I want to achieve—who do I want to be as a leader? 
5. Give yourself permission to grow. Success doesn’t mean you’ve arrived. It means you’ve earned the right to tackle the next challenge. And that requires becoming someone new. 

Executive Action Plan: 

• Schedule a 360-degree feedback session with your team, peers, and leadership. Ask specifically about behaviors that might be limiting your effectiveness. 
• Identify one behavior that has driven your success but is now holding you back (e.g., doing everything yourself, avoiding conflict, over-relying on speed). 
• Commit to experimenting with a new approach for 30 days. Measure the impact on your team’s performance and your own energy levels. 

Takeaway 2: Meaning Drives Behavior—Reframe Your Blockers to Unlock Transformation

Here’s a story that illustrates the power of meaning. 

A senior executive—a hyper-achiever, a great leader—came to coaching with a clear problem: “I struggle to approach conflict. I don’t like it. And here’s the secret: it’s the same in my personal life and my business.” 

The coach asked a simple question: “What do you think conflict is?” 

The executive rattled off a list: “It’s a fight. It’s a problem. It’s aggressive. It’s uncomfortable.” 

The coach pulled up a dictionary definition: “Conflict is a difference of interests.” 

The executive paused. “Wow. I can deal with that.” 

In that moment, everything changed. 

The Power of Reframing

Most of our blockers aren’t rooted in reality. They’re rooted in the meaning we assign to situations, behaviors, and challenges. 

If you believe conflict is a fight, you’ll avoid it. You’ll let issues fester. You’ll sacrifice clarity for comfort. 

But if you believe conflict is simply a difference of interests—something to be explored, understood, and resolved—you’ll approach it differently. You’ll lean in. You’ll have the hard conversations. 

The behavior changes because the meaning changes. 

Common Reframes for Executives

Here are some of the most powerful reframes I’ve seen in my work with leaders: 

Blocker: “I don’t have time to delegate. It’s faster if I just do it myself.” 

Reframe: “Every hour I spend doing work someone else could do is an hour I’m not spending on strategic priorities. Delegation is an investment, not a cost.” 

Blocker: “I avoid conflict because I don’t want to damage relationships.” 

Reframe: “Avoiding conflict damages relationships more than addressing it. Clarity is kindness.” 

Blocker: “I need to be the smartest person in the room to be respected.” 

Reframe: “The best leaders surround themselves with people smarter than them. My job is to create the conditions for others to shine.” 

Blocker: “Asking for help is a sign of weakness.” 

Reframe: “Asking for help is a sign of self-awareness and strategic thinking. No one builds anything great alone.” 

The Awareness-Meaning-Behavior Loop

Transformation follows a predictable pattern: 

1. Awareness: You recognize a blocker (e.g., “I avoid conflict”). 
2. Meaning: You explore the meaning you’ve assigned to it (e.g., “Conflict is a fight”). 
3. Reframe: You adopt a new meaning (e.g., “Conflict is a difference of interests”). 
4. Behavior: Your actions change because your mindset has shifted. 

This isn’t a slow, gradual process. Sometimes transformation happens in a moment—the moment you reframe the meaning. 

How to Reframe Your Blockers

Here’s a step-by-step process: 

1. Identify your blocker. What’s one behavior or situation you consistently avoid or struggle with? 
2. Explore the meaning. Ask yourself: What do I believe about this? What does it mean to me? Write down every association that comes to mind. 
3. Challenge the meaning. Is this belief true? Is it serving me? What’s an alternative way to think about this? 
4. Adopt a new meaning. Choose a reframe that feels true and empowering. Test it in a low-stakes situation. 
5. Measure the impact. Did the new meaning change your behavior? Did it create a better outcome? 

Executive Action Plan: 

• Identify one recurring blocker in your leadership (e.g., avoiding conflict, micromanaging, resisting feedback). 
• Write down the meaning you’ve assigned to it. Be brutally honest. 
• Brainstorm three alternative meanings. Choose the one that feels most empowering. 
• Commit to testing the new meaning in your next relevant situation. Reflect on the outcome. 

Takeaway 3: Transformation Is a Journey, Not a Destination—Design for the Long Run

Here’s the hard truth about transformation: it’s not a quick fix. 

You can’t attend a weekend workshop, read a book, or hire a coach for three months and expect to be permanently transformed. Transformation is a continuous effort. It’s a practice, not an event. 

And that’s where most executives fail. 

They get motivated. They commit to change. They see early results. And then something blocks them—a crisis, a busy quarter, a moment of stress—and they revert to their old playbook. 

The effort vanishes. The transformation stalls. 

Why Transformation Fails

There are three common reasons transformation efforts fail: 

1. Lack of clarity on who you want to become. You’re chasing outcomes (revenue, promotions, recognition) instead of identity (the kind of leader you want to be). 
2. No sustainable practices. You rely on willpower and motivation instead of building systems and habits that support the change. 
3. Impatience. You expect transformation to happen quickly. When it doesn’t, you give up. 

The Transformation Framework

Sustainable transformation requires three elements: 

1. Clarity: Who Do You Want to Become? 

This is the foundational question. And it’s not a one-time question. It’s a question you revisit at every stage of life and business. 

Who do you want to become in your 30s is different from who you want to become in your 50s. Who you want to become as a solopreneur is different from who you want to become as a leader of a 50-person team. 

The question evolves. And so do you. 

2. Relevance: What Matters to You? 

Transformation only sticks when it’s connected to something you deeply care about. 

If you’re trying to change because someone told you to, it won’t last. But if you’re changing because it aligns with your values, your vision, your legacy—that’s when commitment, passion, and responsibility kick in. 

Ask yourself: Why does this transformation matter? What will it enable me to do, be, or create? 

3. Practice: What Are You Doing Daily? 

Transformation is built on small, consistent actions. Not grand gestures. Not one-time efforts. Daily practices. 

If you want to become a better listener, practice listening in every conversation. If you want to become more strategic, block time every week for strategic thinking. If you want to become a people-powered leader, practice delegating one task every day. 

The practices compound. And over time, they transform you. 

The Role of Discomfort

Here’s something no one tells you about transformation: it’s uncomfortable. 

You’re learning new skills. You’re trying new behaviors. You’re slow at first. You’re frustrated. You feel incompetent. 

And if you’re someone who loves speed—someone who’s used to being the best in the room—that discomfort is excruciating. 

But discomfort is the price of growth. And the faster you accept that, the faster you’ll transform. 

How to Design for the Long Run

Here’s a 90-day transformation roadmap: 

Weeks 1-2: Clarity 

• Answer the question: Who do I want to become in this season of life and business? 
• Identify 3-5 values that will guide this transformation. 
• Define what success looks like in 12 months. 

Weeks 3-4: Relevance 

• Ask: Why does this transformation matter to me? What will it enable? 
• Identify the cost of not transforming. What will I lose if I stay the same? 
• Share your transformation goal with a trusted advisor or coach for accountability. 

Weeks 5-12: Practice 

• Identify 1-3 daily practices that align with who you want to become. 
• Build those practices into your calendar. Treat them as non-negotiable. 
• Reflect weekly: What’s working? What’s not? What needs to adjust? 

Ongoing: Iteration 

• Revisit the question “Who do I want to become?” every quarter. 
• Adjust your practices as you grow. 
• Celebrate progress, not perfection. 

Executive Action Plan: 

• Block 2 hours this week to answer the question: Who do I want to become in the next 12 months? 
• Identify one daily practice that will move you toward that identity. Start tomorrow. 
• Schedule a quarterly review to assess progress and adjust your transformation roadmap. 

Bringing It All Together: The Transformation Mindset

Let’s connect the dots. 

1. Success can be your biggest blocker. Recognize when the behaviors that got you here are preventing you from getting there. Own that you’re the one in your own way. 
2. Meaning drives behavior. Reframe your blockers by changing the meaning you assign to them. Transformation can happen in a moment when you shift your mindset. 
3. Transformation is a journey, not a destination. Design for the long run by clarifying who you want to become, connecting to what matters, and building daily practices that compound over time. 

This isn’t about becoming someone else. It’s about becoming the best version of yourself—the leader your team needs, the business owner your company deserves, the human being you’re capable of being. 

The Cost of Staying the Same

Here’s the question I’ll leave you with: What’s the cost of not transforming? 

If you keep doing what you’re doing, where will you be in 12 months? In 5 years? 

Will you still be the bottleneck in your business? Will you still be burning out your team? Will you still be avoiding the hard conversations? 

Or will you look back and realize that this was the moment—the moment you decided to get out of your own way and become who you were meant to be? 

The choice is yours. But don’t wait for permission. Don’t wait for the perfect moment. Don’t wait until the pain is unbearable. 

Start now. Ask the question: Who do I want to become? 

And then take the first step. 

Final Thoughts: Possibilities Are All Around You

One of my favorite words is possibilities. 

Because when you’re stuck in your old playbook, you can’t see them. You’re too busy executing, delivering, achieving. 

But when you pause—when you ask who you want to become, when you reframe your blockers, when you commit to the journey—possibilities open up. 

You see new ways to lead. New ways to grow. New ways to create impact. 

And that’s when transformation becomes inevitable. 

So here’s my challenge to you: Give yourself permission to grow. 

Allow yourself to explore a different path. Own your transformation. Look for the possibilities. 

Because the leader you’re capable of becoming is waiting on the other side of your willingness to change. 

Listen to the full episode on C-Suite Radio: Disrupt & Innovate | C-Suite Network 

Watch the episode: DI 116 Transformational Leadership and Self-Awareness with Hilda Fainsod

This article was drafted with the assistance of an AI writing assistant (Abacus.AI’s ChatLLM Teams) and edited by Lisa L. Levy for accuracy, tone, and final content.