Unraveling how my life reflected my deepest fears
In middle school, a few kids always teamed up at recess to make sure I never won any of the games we played. I dreaded foursquare, wall ball, and tetherball. Nobody ever wanted to be on my team during PE Class. The harder I tried, the more they laughed and teased me when I lost. Even the person who I thought was my “best friend” became one of the bullies. I felt more alone than ever.
I learned much later in life that we all adopt specific strategies, character traits, and behaviors to cope with the experiences we go through as children. These are the false stories and beliefs we created to survive our childhood when things don’t go our way.
The story that I told myself was that I wasn’t accepted because I wasn’t good enough at anything. I believed that I needed to be successful above all else; otherwise, no one would like me.
This story ruled my life for the next ten years. Winning became everything throughout my teens and early twenties.
For half a decade, I trained and competed in fencing for 300+ days each year. I was relentless. I poured my heart and soul into athletics because I thought that it could be my liberation from the pains of my childhood.
At some point, you could say that I started “winning” from the outside. I represented the United States in seven World Cups in France, Poland, Hungary, Germany, and Italy. I competed in regional and national tournaments every month and brought home over fifty medals, eight of which were from nationals.
But I wasn’t thriving; I was surviving. I strived to do well, but not because I genuinely loved playing the sport. I worked ridiculously hard because fencing was my central source of self-esteem. My results determined my entire sense of identity and self-worth, which made competitions some of the most stressful times of my life.
Losing during a tournament felt like the end of the world. Even after bringing home gold, the feelings of happiness would only last a few days before I began worrying about the next competition. There was a void in my life that no medal could ever seem to fill.
When I was in college, the approaching end of my fencing career gave me tremendous existential angst. Who would I be without this sport?
I looked for something else to pour my heart and soul into once again. But what? I knew I needed to get a job, but I had tasted what it was like to be among the best in the world at something. My ego pushed me towards the idea of running my own company. I didn’t want to get an entry-level job like my peers. I wanted to be the CEO.
So the startup bug bit me when I was 20 years old. The idea that I could invent something that millions would use enchanted me. It would be my life’s work, and everyone will know me for it. Winning medals no longer cut it. I wanted to win startup competitions, be on the cover of magazines, and make the Under 30 lists. I tried to change the world, all by myself.
Oh, yes, I started “winning” from the outside. Inc. Magazine hailed us as one of the top emerging companies in the US and then in the world, and my face was one of five on the front cover. We presented in front of global leaders at the World Trade Center and the New York Stock Exchange. We checked all the boxes — graduated from an accelerator program, received several grants, won an award, and raised funding twice. Above all, we had paying customers.
On the outside, it looked like I was living the young entrepreneur’s dream. But deep down, it was the same survival game as my fencing career. I strived to do well, but not because I genuinely wanted to make a difference in the lives of others, even though that’s what I kept telling myself. I worked 100+ hour weeks because my company was my central source of self-esteem. How good the company looked determined my entire sense of identity and self-worth. I did everything I could to ensure that we looked as if we were continually winning. Yes, even at the expense of everyone’s quality of life and ignoring the most critical questions of the business. My sole focus was on attaining more external success.
After two years, the house of cards fell. We built a product based on assumptions of the market need, with little material proof that organizations would pay the amount we projected.
With the help of my coach at the time, Tom Collopy, I was able to finally see that continuing to pour money into the company wasn’t a responsible thing to do. Tom guided me compassionately towards one of the hardest realizations of my life: the business I started wasn’t a sustainable one. I had to tell my entire team that I couldn’t continue paying them.
For the next year and a half, I felt more stuck than ever, in a dark hole of shame, feeling like a complete failure.
It was the wake-up call of my life.
I finally had the chance to confront the fears and stories that had driven my life. Here is what I learned about how my childhood had influenced the way I lived my life and how I ultimately ran the company I started.
A life of quiet desperation
We are all quietly coping with deep inner struggles. We work desperately to try and fill a complex, seemingly inexpressible void. We try to fill it with things such as money, possessions, and accolades. We value these because we’ve convinced ourselves that they will make us happy. When they don’t, we seek more of them instead of digging up the root cause of our unhappiness.
Henry David Thoreau calls this living a life of “quiet desperation”—something he says the majority of us live. I certainly did.
I convinced myself that more medals and more accolades would bring me the fulfillment I was craving. If I just work harder, then I will achieve all that I want to achieve, and my life will be complete. I deceived myself into thinking that I was making progress by finding bigger and bigger temporary fixes.
But the truth is, nothing on the outside will ever bring you lasting fulfillment. A sense of completeness can only be nurtured from within, with what you have today. When you feel incomplete, it is time to dive within to dig up the root of your unhappiness. When you feel stuck, it is time to uncover the fears, insecurities, and false stories that have been driving your life.
Embarking on this journey was the most important thing I ever did for myself.
The fear that was the root of my unhappiness
When I met Kwiri Yang, I had just reached the depths of my despair — I was lost and didn’t know what to do after my company didn’t work out. She was a successful serial entrepreneur, so I asked her for guidance. Instead of comforting me, she started to ask me the hard questions. She had a tremendous amount of wisdom and compassion for what I was going through because she had experienced the same pains. Kwiri eventually invited me to join her in starting her fifth company, where she would continue to coach me and impart her wisdom.
Over the next year and a half, she guided me out of the dark place I was in by giving me space to dive into and process my pains fully. She encouraged me to go through personal development programs designed to help me unravel my internal struggles.
The priceless gift she gave me through her leadership is best summarized by what Jerry Colonna calls radical self-inquiry: “a process by which self-deception becomes so skillfully and compassionately exposed that there’s no mask that can hide us anymore.”
Kwiri regularly shared the lessons that she’d learned from confronting her shadows. She made it the norm to discuss our fears, insecurities, and the masks we wore to protect ourselves. We held each other accountable for shedding those masks and letting go of the beliefs that no longer served us.
Kwiri’s radical tough love was a mirror through which I saw the lie I’d been telling myself since middle school:
If I achieve enough — win enough medals, start a successful enough company — then all the people I feared who would not like or accept me because I wasn’t good enough at anything would love me forever.
I thought that this belief served me. It was an incredible motivator. It was my driving force for so many years.
This belief, I discovered, was the root of my unhappiness. The accolades created a facade of security and belonging that temporarily filled the void in my heart. Chasing them led me down the same unfulfilling paths.
If I didn’t confront this head-on, I knew that I would spend the rest of my days running away from this fear of not being good enough.
Most importantly, I began to see how these shadows from my childhood had shaped me into a particular kind of founder who led from fear. I started noticing how this fear became the foundation of the company I built.
A company and culture built from fear
Nobody has ever been born wanting to be a lousy boss, colleague, partner, or friend. We only become that person when we try to put on a mask pretending that our most deeply-rooted fears don’t exist.
Life inherently creates baggage, and it shows up everywhere, whether you take responsibility for it or not. The art of growing up is learning what baggage we’re holding onto, and how to let it go gracefully.
If we don’t unpack the baggage that we carry — go on an inward journey to unravel the pain, resentment, and shame from our past — we will project it onto the people in our lives. We will unconsciously ask our families, partners, and colleagues to carry it for us.
As Parker Palmer says:
The darkness that we carry within ourselves [is] the ultimate source of the shadows that we project onto other people. If we do not understand that the enemy is within, we will find a thousand ways of making someone “out there” into the enemy, becoming leaders who oppress rather than liberate others.
When I started my first company, I hadn’t done any of the inner work. I was suddenly a CEO without any of the tools, experience, or self-awareness to grasp the impact I had on the people I hired. So even though I was able to lead a team to build a revenue-generating business, the environment I created was light-years away from one that I would be proud of.
I led from a place of fear that others would think that I wasn’t a good enough entrepreneur.
Here are some of my reflections from the impact it had:
On the business
My fear: People would think I wasn’t a good enough entrepreneur.
Impact: I focused more energy on making sure the business looked good through fast/impressive wins rather than testing our riskiest business assumptions. I avoided asking all the hard questions.
- More impressive (free) users vs. satisfied paying customers
- More new accounts vs. more active users
- More data points we could report vs. higher NPS scores
- Raising & spending more money vs. making more money
- More features launched vs. more customer engagement
- Hiring more people vs. more wins from our existing team
- Fancier technology vs. better proof of the viability of the business
On the culture
My fear: People would think I wasn’t a good enough entrepreneur.
Impact: I created a culture that was in service of maintaining an image of success rather than a working environment that people loved and grew in.
- I worked 14-hour days, nights, weekends, and holidays and expected that my team does the same, rather than prioritizing rest and recovery.
- I talked at everyone, telling them how I saw things, instead of listening to people’s thoughts and needs.
- I labeled unhappy employees as “not a good fit”, instead of asking myself how the work environment I created could have caused their unhappiness.
- I praised skill and results over character and integrity.
- I placed blame on others, situations, and circumstances instead of taking responsibility for them.
- I defended myself, my ideas, and my decisions instead of being open, curious, and committed to learning how I can be a better leader, teammate, and friend.
I started a company without confronting the baggage from my childhood, and it showed up everywhere—lessons for a lifetime.
“I am not what happened to me, I am what I choose to become.” – Carl Jung
Transforming pain into purpose
This pilgrimage was not an easy one for me. There were countless days where I struggled to get out of bed in the morning, dreading to do work because I didn’t know why I was doing work anymore. There were moments when I questioned whether I was doing the right thing; I had so much passion sprinting towards these external achievements. Why did I give all of that up? It was as if I had lost my most reliable source of motivation to run faster and faster each day.
Little did I know, I needed to stand still in my pain to discover a purpose more valuable and everlasting than any external measure of success: helping others find a sense of belonging at work.
My deepest pain from what middle school denied me, transformed into my highest purpose for the organizations that I start and serve in my lifetime. Creating spaces of love, safety, and belonging is the core of who I am as a founder, leader, and friend.
I hope that in sharing this that you too will embark on this journey and rediscover who you are. Nobody can say that they had a perfect childhood. I certainly can’t. What I can say is that beneath all the muck are the keys that will unshackle you from your past. You will emerge knowing what your greatest gifts are, what your purpose is, and who you wish to be for the people in your life. You will come out more capable than ever to serve the organizations that you start and run in your lifetime.
So talk to a coach, boss, therapist, colleague, friend, or family member about your childhood. Make it a routine to reflect on what fears you are running away from and what stories are still running your life. Commit to unlearning the habits that no longer serve you. Then share those lessons with everyone. It’s how you inspire the people around you to do the same.
This pilgrimage is the opportunity of a lifetime to know yourself better than ever and transform your deepest pain into your most profound purpose. Don’t wait. Work on it today. Work on it like your life depends on it… it does.