Behind The Scenes: My Coaching Clients, Part 2

In the previous issue, I wrote about 2 types of my coaching clients- Start-up founders and young managers. This week I will finish the piece with the other 2 types of clients- Business owners and corporate executives.

Before we dive into the serious stuff, here are a few things worth sharing:

1. One of the changes in 2022 for me was to read a bit of comic every day. I just finished Alison Bechdel's "The Secret To Superhuman Strength." I was surprised to find equanimity in her life experience, even though she and I could not be more different- a 60 year old white American lesbian artist versus a 40 year old yellow Hong Kong straight corporate dude.
2. Speaking of equanimity and inner peace, futureme.org lets you write an email to your future self. I strongly suggest you to try it. It will be a unique experience. (+ it is free)
3. Are you in the crypto-verse yet? If you are seriously thinking about it, I would urge you to listen to this podcast before you do anything. It gives you a very good primer on crypto wallets and how you should set them up in order to best protect yourself. The metaverse is crooked and unwieldy.  

On Leading:

In the last issue, I decided to share the generalizations of my coaching clients. I have found the insights of my clients helpful to my own career- Their superhuman strengths were inspiring. Their spectacular failures were cautioning. Their evolutions were enlivening.

Alright, here we go, business owners and corporate executives.

Business Owners:

• Most of my business owner clients were running stable businesses
• They did not have the pressure to hire a coach. They wanted to continuously improve and some of them were interested in my experience working for Nike and Apple
• They were battle tested. They all built something real and have gained significant experience
• Their skills were hardened by having "real skin in the game"
• They were effective leaders in their own ways, even though many of them didn't have "proper/traditional" training in leadership/management. This made them sometimes appear "rough around the edges," at least in the eyes of a corporate journey person like me
• They had fantastic stories to tell
• Amongst my clients, successful business owners were the most well-rounded and capable professionals. They were both naive and nuanced, both enthusiastic and even-keeled. They embodied an exquisitely tuned "beginner's mindset."

Pitfalls I Can Learn From Them:

• Many of them were reluctant to leap into the deep end of changing and transforming
• Many of them did not see the need to change. They had no urgent reasons to subject themselves to the grind of transformation
• They were more risk adverse. Many of them have experienced existential risks and were burnt badly. They were cautious with changing.
• Some of them have gotten rusty in learning. They have been engulfed in building and running their businesses their entire lives. They did not have time to learn learning.
• In summary, some of them were trapped in the comfort zone between success and stagnation-  "Everything worked, everything is still working, I am good where I am. I don't need to rock the boat."

Applying This Learning:
As I am building my own business, I want to succeed without stagnating and I want to develop a beginner's mind. I am going to force myself to carve out time to build something around the edges of my business, projects that are related to coaching and entrepreneurship.

For example, I have a weekly 30 minutes event on my calendar to work on a fringe project. The project is to build a DAO (a type of organization that exists on blockchains)  for coaches. This a reliable way to make me feel "insufficient," to stay close to the feeling of FOMO. This nudges me to learn something daunting, to learn to ask for help, and to not sway too far away from my core business.

Corporate Executives

• These clients were career corporate folks- directors and VPs with years of experience working for MNCs around the world
• Some of them were assigned to me by their supervisors. Some of them hired me on their own accord
• They were all well-versed and well-trained in leadership and management
• They were professional. They were measured and composed in their demeanour and words
• Similar to business owners, they had fantastic stories to tell

Pitfalls I Can Learn From Them:

• Surprisingly, authenticity was a real challenge for many of them. They weren't fake or disingenuous, but they were so engrossed in the language, context, and culture of the corporate metaverse they no longer could talk to themselves and talk about themselves accurately
• Except for the few C-level executives, most corporate executives were just cogs in a machine, no matter what they would like to believe. In reality, most of the decisions they needed to wrestle with, most of the problems they had to solve, were inconsequential
• Stealing from a saying from Nassim Taleb, tenured corporate folks grew weak because “bureaucracy is a construction by which a person is conveniently separated from the consequences of his or her actions.”
• What's worse was they've being honing skills from making inconsequential decisions. Imagine a senior handyperson, who's job was to paint over scratches on toilet seat covers inside the Titanic. No matter how good she has mastered her craft, all she would be able to do was to paint toilet seat covers. The skills they have honed were less applicable outside of the corporate environment

Reflecting on These Observations:

Many of my corporate executive clients exuded this undercurrent of dissatisfaction, helplessness, and despair. I have not researched into this and I suspected there were 3 causes:

1. The higher you climb the corporate ladder, the harder it is to leave the corporate world. The opportunity cost of unplugging from the corporate matrix is substantial
2. Some of them did take the bold step and left the corporate world to go after their dreams. But they struggled mightily in the "wild." They found it very difficult to operate outside of the structures, rules, and comfort of the corporate world. They felt grossly unskilled at the most basic tasks. Most of them ended up returning to the corporate world.
3. I also sensed that many of them were enduring a low level of chronic self deception. Many of them struggled to explain where they were and what they were doing in their career. They were constantly rationalizing, justifying, and compartmentalizing the dissonance in their heads.

I can't help but wonder, how much self deception can a person actually withstand? How taxing is chronic cognitive dissonance to one's mental health? Do years of corporate experience strengthen or weaken one's abilities and sense of agency? Does being a corporate person actually make you more fragile?

I wonder.

You can support me:

Reply to this and chat with me! Tell me what you think of this. Or whatever is on your mind. I will always reply, I guarantee it.

And if I fail to keep my promise? Email me and let me know at siu.david@hey.com 🙃

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Thank you for reading this. I think about leadership & psychology in the showers. I know it's odd, but these topics are important and fun. I hope you find them useful too.

Work diligently. You are bound to be successful.

David