Feeling Lost in Life?

Let me help you get more clarity in 20min.

When I first met Derek, I was surprised by his calm, almost repressed, demeanor. He spoke so softly that I had to crank up the sound of my MacBook to the max to hear him clearly. 

Since high achievers like Derek are great at talking about their work, I often lead with an unexpected question to break their narrative and see who they really are. As I learned more about his interests and passions, I saw a man who struggled to feel safe in his own skin. 

Below is a vignette from our conversation: 

Me: You are clearly very passionate and bright. What made you hold onto the story that you are not good enough to achieve what you want?

Derek: I keep comparing myself to other people. I haven't looked deeply into myself. I haven't truly viscerally realized and seen what I have that's valuable. 

Me: How has this behavior served you?

Derek: It hasn't. Nothing good has ever come out of it. It is preventing me from doing great things of which I know I'm capable. It's hampering personal and professional relationships. It's preventing me from fully expressing myself. 

Me: Sit with the sensation. When was the first time it appeared in your life?

Derek: Pain from abuse in boarding school. My mother told me afterward that it happened because I was different. So I avoid expressing myself because I don't want to feel the pain of rejection.

Me: What is scary about the pain?

Derek: I am afraid of finding out that I have nothing left for myself. I will die. Physically, emotionally, spiritually, psychologically, mentally. The only way to survive or thrive is to do the opposite of whatever feels safe.

In twenty minutes, we drilled deeper and arrived at the core of how he felt. Once we uncovered his underlying fear rooted in early trauma, we got to heal the fear that held him back and limited his ability to take effective action. In the end, I provided Derek an action plan to feel less shame and become more of himself. 

Long before I coached other people to accomplish their dreams… 

I noticed that most people didn’t know which problems they wanted to solve. Therefore, the very first thing I did was to understand their problems and reframe those problems in a way that highlighted the various paths that might lead to a solution.

I’ve had the good fortune to work with many talented leaders in the creative and tech industries. All showed a willingness to explore something new in life. I rarely gave advice. Instead, I trusted my client’s wisdom and posed questions that would create deep reflection. During each session, I put on my detective hat to look for subtle cues, getting my clients to search underneath the thought layers, and often a new, deeper, larger problem emerges. Hidden under symptomatic concerns is the real problem they have been avoiding for decades.

I love seeing my clients fire up. 

Once I have a client’s full attention, I want to know how much they are willing to invest in solving the problems right now. The fact is, not everyone is willing to speak their truth. Not everyone is willing to see an old part of them dying. And not everyone is willing to take full responsibility to make their dreams happen.

To understand where they are coming from, I start by asking the following questions: 

  1. How much time would it take to solve this problem? 

  2. What is your hourly rate? How much do you value your time? 

By doing simple math of multiplying the hourly rate and time, I get my clients to see the invisible opportunity cost they are paying for not solving the problem. 

Another comment I often get is that they don’t have time right now. While this is true in some cases, more often than not,  the underlying message is  “I am not ready to solve my big, burning problem yet.” This means that they are either prioritizing solving other people’s problems or solving less important problems. In both cases, it helps to delve into the whys. 

By helping my clients define their problems and visualize what is at stake, the question now becomes how to get started. 

I try to offer both value and trust upfront.

Because I love to optimize and build systems, I created a value coaching exercise to help clients connect with their intuition, identify fundamental values, and make better decisions—all in twenty minutes. While the total conversation only takes twenty minutes, the attention and presence are so intense that I’d have to lie down and restore my energy for one hour after each call. 

However, the system by itself is not enough. Creating an intimate space to share vulnerabilities and allowing people to reach into their truths matters just as much. 

Growing up with my mom and grandma, I learned to listen deeply without any agenda or biases because I wanted to see the world from their eyes. In addition, I have been an engineer, entrepreneur, consultant, investor, and product manager, so I am able to relate my background to that of many other people, speak in their language, and cultivate a space of psychological safety. Establishing trust allows me the chance to ask vulnerable questions that prompt my clients to let out the intimate and scary thoughts in their minds. 

Those vulnerable moments beget deep transformation. Once a client takes the courageous and vulnerable leap, we begin to see incredible results in two weeks.

I want to bring my coaching to more people.

My love for coaching inspired me to create our six-week group coaching, the LivingOS Fellowship. It was made for people who are ambitious, curious, and eager to grow as a leader and a human, so no decision feels too big, no problem feels impossible.

The feedback was so good that we were able to launch three cohorts in three months. Once people started to share their transformative experiences in the community, a lot more people reached out.

Over the past year, we’ve helped 150 high achievers level up their life in an immersive, high-touch coaching program. Our latest version of the Fellowship is designed for people who desire to address key problems that kept showing up in life. 

The next cohort kicks off in late July. Applications are open until midnight July 10th

If you have any questions, feel free to hit reply. I look forward to hearing from you.

PS - Folks who got in the fellowship will get a complimentary value coaching session with me.