The Unraveling Of Self Confidence

Recently, I returned to the workplace.

I took this offer because I was in a rut. My coaching practice wasn’t growing, and I was anxious about not having a steady income. The pressure of my family’s needs, though irrational, began to bother me more than I liked. I also fell into depression and melancholy often due to a constant sense of lack of meaning. I wasn’t handling it well, and it was bad for me.

The job was with an interesting company, one of the very few successful start-ups from Hong Kong. The role was exactly what I thought would energize me. It was an opportunity to lead a regional team again, which I enjoyed when I was the General Manager of Nike South. The job didn’t pay that well, but I didn’t care. I wanted the chance to lead a team again.

There were other reasons why I wanted this job—working with an exceptional founder and thinking this could be the last meaningful job I would get at my age and career stage.

When I joined, there were red flags—warnings that I knew would be problematic based on my studies on company culture and leadership and my coaching work with founders and business owners. The founder was difficult to work with, there were borderline unethical practices, and the company was built on toxic relationships. People operated out of fear.

For five months, I struggled daily to justify why I should succumb to the chaos and sacrifice my time for more important things, such as time with my wife, kids, and aging mother. My mood was unstable, and there were nights when I struggled to find peace.

Then things started to change for the better. I figured out ways to work with the founder and was building meaningful relationships. Most critically, I was able to be myself and do things in ways I believed were “right.” I was surprised by how little I cared about how I was perceived. I had fewer moments of regret and second-guessing. I was surprised by my inner confidence, something I never associated with myself.

This confidence was reinforced by successes, particularly in building trust with the founder and making some small but important decisions. Although I have not had any measurable successes yet—the business is still declining, teams are not functioning, and key hires are still to be made—I am not as worried or anxious.

I feel I am on the right path. Although I don’t think I am learning anything new about how teams work and how to navigate relationships and politics, I am applying what I have learned more than learning anything new. In other words, I am productive.

I am also growing, learning new things like digital marketing and trends. I am learning more about myself, particularly how I apply what I learned during the past four years of semi-retirement. I’ve learned that I am more self-aware, more equanimous, more patient, and gentle with people. I have been more intentional in my communication. I know I have grown and am still growing.

I still doubt myself. I wonder if I am losing my edge by being less pushy and driven. I doubt myself more in communication, sometimes feeling I am too nice and self conscious. Sometimes I feel my self-awareness is getting in the way of my intuition and instincts. But I am not too worried about this. I think this self-doubt is fantastic because it shows self-awareness is doing its job, and fundamentally, that’s a good thing. I have been applying what I learned and practiced in the last four years, from meditation to writing to the teachings of Buddhism, Stoicism, and Mungerism, making me more at ease and at peace.

I know I will face new challenges as I continue this professional journey. I will have to deal with dilemmas at work and at home and face struggles. Yet, I seem to be more open to all these because what I have witnessed in myself over the past five months is that a faint, emerging sense of peace has been revealed through every challenge, struggle, and moment of volatility and uncertainty. I think this growing sense of equanimity has become the source of my self-confidence, and I believe that, in addition to everything being okay, I, too, will be okay.






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