The Bruises from Being a Corporate Man for 20 Years

I have been a corporate person my entire life. Recently I had interactions with the real world. Those experiences unearthed bruises all over me.

My ability to “don’t give a fuck” is artificially inflated.

I thought I was thick skin. I spoke my mind. I didn’t care too much about how people thought of me. I could be relentless, deliver results, and be courageously confrontational because I didn’t give a fuck. I was confident of my values. I was clear with my intentions. I was a master of self awareness. I was THE cocktail of vulnerability + authenticity cocktails. I was a Buddha Stoic lion. Fuck you, and just do it. (Roar!)

Then I realized, these were only true, in the confines of a corporate job. Once I was out in the wild, I was no longer a lion. I was not even a cat. I was one of those small domesticated loud dogs — timid, squeaky, ineffective.

I could say ”I don’t care how you think of me” at work, because I was very clear of which part of me projected the ideal me, while which part of me needed to be protected and hidden. I learned to understand the dynamics between what I needed to be perceived and career progression (and pay-check). Most important of all, I was very good at appearing someone who was unapologetically authentic, courageously vulnerable and oozed conviction(s).

For example, I would appear to be very strategic and be very bold about “stepping back” and “the bigger picture” when a discussion called for that. Or I could be very direct and provocative in a one on one coaching conversations. I knew exactly what the confines were, where the boundaries of my counterparts were, and what the magical balance was between appearing confident and not exposing myself. Even when I was interacting with external people, the clear awareness of my position and what I meant to them, helped me find the sweet spot to being a consistent brilliant asshole. I am an acquired taste, move along!

But in the real world, the boundaries were very foreign to me. The expectations were also very fluid. My counterparts were now unknowns. All of a sudden, I was suffocated by the “what ifs.” The ambiguity was so daunting that I was instantly enlightened by one of Bruce Lee’s famous lines, “Be like water” (my ass!)”

I was in a meeting with a serial entrepreneur. He had been very successful, and he was also a KOL with many followers. Early in the conversation, we were chatting about the business of co-working. I found myself constantly hedging my comments. I wasn’t able to speak my mind. I was very concerned with how he perceived me because I had no idea which direction any of the things I said would lead him to.

I also became acutely aware of the limits of my knowledge, therefore I was less sure of any of my viewpoints. Then I noticed, after 20+ years of conditioning in the confines of a corporate job, I was constantly concerned with “winning” or “making a point” or “he knows what he is talking about” or … “am I being impact(ful)” or … “am I leading and changing your fucking life”. I was constantly distracted. All the mindfulness sessions from the wellness activities at work instantly felt like the biggest scam since Vitamin Water. Welcome to the real world.

Towards the end of the chat, everything became more apparent to me: My so-called “I don’t give a fuck-ness”, was very peasant in the real world. I thought I didn’t care about how I was perceived, but all I had been doing, was to sculpt my image. What I actually achieved, was I simply got very good at convincing myself that I didn’t care, and then perfecting how to to project an image of “I don’t give a fuck” within the four walls of a corporate office.

I talk weird

Recently I got to do two presentations. One was a routine business update, and another one was a baby battle cry for a group of newer leaders. I was very comfortable with the content and the audience. Everything came comfortably. People didn’t all fall asleep. 2% participated. Everything was predictable. It felt nice. What immediately followed, though, was a painful reminder.

My title was part of the reason why they listened to me. The effectiveness of my presentations was partly due to my skills in fitting into the systems of these companies.

I had an experience that was a bit like the sudden realization a seasoned LinkedIn user might get the moment he/she tried to launch the snapchat app. “Oh my god, my thumbs just choked.”

The founder of a cool startup company invited me to speak with his young team. The topic was around teamwork and culture. During the meeting, I noticed they were not responding much, or when they did chime in, they would add completely unrelated points to the conversation. I paused in the middle of the chat, and asked them, “Are you guys actually following what I have been trying to say?”

What followed was quite a slap in the face.

“Yea we were following. It was just a bit boring. It’s okay. We expected you to be like that.”

“Oh, okay. I see. Please say more!”

“Well, that, right there, was one of those phrases.”

“ I am sorry, but could you expand that a bit?”


“To ensure that I am truly bringing value to you all, I need your help to unpack this.”


They were actually quite nice and did “unpack” their points. They shared that I asked too many useless and pretentious questions, “What does an effective team FEEL like?” “What are your communication strategies?” “How do you cultivate an environment of collaboration?” “How do you empower excellence?”

They also didn’t like how I seemed to answer a question with another question, “In order to build a team that truly focuses on innovation and creativity, you have to first think about what stops creativity.”

Lastly, they really didn’t like the cliches. I kind of knew that going in and intentionally tried to refrain from using words like wellness or empathy or servant leadership or trust or intention or inspiration or vision. Alas, to them, there were still way too much.

Next Steps/Plan B/Action Plan

I have been working for 20 years, yet the most overwhelming feeling I have now is the feeling of losing all my crutches. WIthout the matrix of the corporate world, I am naked. Literally, for the first time in my life, I could literally caress the essence of the ✌🏼 comfort zone ✌🏼.

I now believe the realization will be very similar, if I review my other “strengths” … my operations excellence, my business acumen, my leadership capabilities, my ability to scan my badge at the gates. I guess the most positive thing I got out from all these realizations, was the awareness of how pathetically ridiculous I actually am to most people in the real world.

I am in my mid-40s, I am going through mid-life crisis, and I have pinned the Porsche webpage on my world wide web browsing software. I am now witnessing what it was like when my parents and their friends transitioned into retirement. One of my uncles, after spending his entire life in the government, was very excited about retirement. He thought of all the things he could do, all the places he could visit, and also how he would be able to share his knowledge and significantly contribute to the all the poor souls in the world. He then started to really struggle with working with different groups of people. He actively participated in the apartment complex he was in, but it turned out to be a very unenjoyable experience. He wasn’t able to get things moving and was constantly getting into shouting matches during meetings. He struggled to live with his family, because 3 hours of family time after work versus 8 hours of idle time at home, were two very different things. He started complaining about how little value he felt he had. He missed the environment that made him feel useful. He fell into depression very quickly, and after about a year, he killed himself, leaving his wife and two kids behind.

I am painfully aware of that I am concerned with how you, the reader, might think of me. I also know, by sharing this, I am making this one small attempt to experience and hopefully then accept, “Sorry, nobody actually cares. You ain’t that important.”

I am okay, but this shit was real.






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