Failure: The fast road to self-authorship

Have you experienced failure in your life? How did it shape you? Do you embrace failure, or avoid it at all costs?

In the book I’m writing about leadership and Asian American culture, I argue that many Asian Americans struggle to become self-authoring, a developmental shift essential for effective and sustainable leadership. The term self-authoring comes from Robert Kegan’s Adult Development Theory. It describes a stage of growth where we move beyond living to meet others’ expectations and begin living from our own values, principles, and purpose.

This idea isn’t new. Throughout history, many philosophers and writers have emphasized the importance of becoming oneself by breaking away from tradition and social pressure. The Transcendentalists (Emerson, Thoreau, and Hawthorne) urged individuals to trust their inner voice over societal conformity. European thinkers like Kierkegaard, Nietzsche, Sartre, and de Beauvoir similarly wrote about self-definition, personal freedom, and rejecting inherited belief systems, including religion.

So how do we become self-authoring? One of the fastest and most powerful catalysts, I believe, is failure.

Failure comes in many forms. Sometimes, it’s as simple as receiving critical feedback. If we can move beyond the sting, it opens a door to learning. Other times, it’s a deeper personal or professional breakdown that shakes our sense of identity. While painful, these moments can become the very force that pushes us to examine who we are, what we believe, and how we want to live. That was my experience in my early 30s. 

After working to develop new markets in Asia, I was assigned by a U.S. energy company to open and lead a new office in Korea. I moved to Korea, my mother country, for this role. It was my first major leadership position, and I felt validated, as if all my past work had prepared me for this moment. I worked hard to build a business around an innovative way to support the electric grid in Korea. I felt proud to bring this new innovative service to my home country. I was especially excited to lead in a new way. With experience in both the U.S. and Korea, I envisioned a company culture that blended Korean drive with American egalitarianism, a team motivated by shared purpose, not hierarchy.

My core team included two expats from HQ and strong professionals we hired locally. Many of them were eager to grow beyond the limits of their traditional career paths in Korea. Together, we navigated many challenges, language barriers between HQ and local staff, building new business processes, educating customers and partners, winning clients, and preparing for high stakes operations. Through dedicated work and a compelling vision, we outperformed expectations. Within a short time, we became #2 in the market and hit major performance milestones.

Then, one day, my president asked me to fly to Boston. He told me that while our financial and operational results were strong, he was concerned about employee engagement and specific comments about my leadership. I later learned that he and the HQ HR team who conducted the survey had withheld the results from me. He had decided to replace me with someone local partly to address the team’s concerns, and partly so I could return to Boston sooner.

I was shocked. I felt blindsided and betrayed. Embarrassed. Ashamed.

Paul Klee, Senecio

And yet, deep down, I knew I had been struggling  with leadership, emotional regulation, and stress management. I thought if I just worked harder and pushed my emotions aside, things would improve.

At the heart of it, my biggest challenge was an inner tension: I had lost confidence in two key team members but didn’t know how to either fully bring them in or let them go. The unresolved friction drained me emotionally, and I’m sure others could feel it. On top of that, I was living alone in Korea and feeling isolated. Alongside the betrayal and embarrassment, I also felt a strange sense of relief. Still, I wished my president had asked me how I saw the situation. We could have had an open conversation. Maybe we could even arrive at a mutual decision.

It took months of reflection to see this failure with fresh eyes. While I maintained the appearance of non-hierarchical leadership, through sitting in the same cubicle, chatting with everyone, I struggled with emotional regulation and patience. Especially with team members I viewed as underperforming or misaligned, I avoided giving calm, direct feedback. Instead, I reacted  with excessive questioning, raised voices, or sarcasm. Then I beat myself up for it afterward. The pattern repeated. 

Ironically, what I intended as egalitarian leadership likely came across as emotionally erratic and, in a different way, just as authoritarian as the hierarchical culture I had tried to escape.

In hindsight, I also see:

• I didn’t engage with all key team members with equal respect, care and curiosity.

• I failed to see two critical members from their perspectives.

• I became overly anxious about speed and results, and couldn’t model calmness, assertiveness, and grace.

• I didn’t recognize my own frustration patterns or how they played out in others’ perceptions of me.

And yet, over time, I began to view this failure as a blessing. I first turned to books by Carl Rogers, Karen Horney, Harriet Lerner to understand what had happened. The Dance of Anger helped me name the emotional loop I was stuck in. Then, I started opening up to friends. One of them recommended an executive coaching program. Through coaching education, I began to understand myself more deeply not just what I had done, but who I was in those moments. I also began to see similar dynamics in others: how many people are unaware of their emotional habits and impact — even when they’re trying to do better.

Most importantly, I learned that growth is possible when we reflect, seek help, and take ownership. Without this experience, I would not have made the shift.

So back to you: Have you experienced failure in your life? How did it shape you? Do you embrace failure — or avoid it at all costs? And do we really need a big failure to become self-authoring?

So how can we apply this to our lives? Do we need to fail big to become better leaders?

Here are three thoughts:

1. Don’t be afraid to run fast — and fail fast.

Yes, it will hurt. But you will learn a lot about yourself.

When I work with Asian American young leaders, I often see two types: those who drive themselves hard and are convinced of their way, and those who are more reflective and learn from smaller setbacks. I respect both. In a way, I see a bright future in the first group. They will likely face bigger failures, but I have no doubt they’ll correct course quickly and grow from it.

2. Learn to fail small and well.

Don’t wait for a major collapse to start learning. Pay attention to your small failures in daily operations: feeling puzzled, unsettled, or frustrated. I now try to notice these moments as early warning signs. When I do, I pause, journal, talk with my coach, and give myself a few days to let a new perspective emerge.

Even now, I sometimes feel defeated when I fall back into old patterns. But I’ve learned to appreciate gradual progress. Growth isn’t linear. it’s made of small recoveries, not perfection. When we treat discomfort as data, we start learning in real time — not just in hindsight.

3. Work with a coach.

Many of us are afraid to look deeply at our failures, especially big ones. In cultures where saving face, perfectionism, or family honor are emphasized, this fear can run even deeper.

That’s why coaching can be so powerful. With deep trust and psychological safety, a coach helps you stay curious about your failure and see it from new angles. It’s not about fixing you. It’s about helping you see yourself more clearly, including your blind spots and default patterns.

Coaching doesn’t have to be a formal or paid arrangement. Start by seeking someone who can listen without judgement and challenge you. 

I wish I could go back and tell my past self to find a coach or at least a trusted confidant without a conflict of interest. I wish I could say: “Dream big. But don’t underestimate how others might perceive your leadership especially through the lens of culture.”