From Sleepwalking the Golden Path Towards My Most Alive Life

My path to becoming a self-employed professional coach

My immediate reaction was panic. I had just quit my tech job, with no plans to get another. My role in tech was one many had coveted at the time - in product management - and not only was it paying me more than double my parents’ income, but it was also one I was really quite good at and overall, I intellectually enjoyed the work. I knew I could grow in the career, hop around companies to work on more Missions-I’m-Passionate-About™, earn progressively more, and make my immigrant parents proud. Yet I felt a deep sense that I needed to leave this path, ASAP.

My younger self was appalled at my quitting. My younger self followed the rules and knew how to push herself along the “Golden Path” that her parents (and society) told her led to “success.” And when she started to win awards and land top colleges and top jobs, she learned she was good at this Golden Path. And luckily for her, she even enjoyed it. She loved learning, thinking, and mastering new concepts, skills, projects.

So she pushed herself not just to stay on the Golden Path, but to want it in the first place. She pushed this wanting so hard that she unconsciously developed a belief that a good life should cost something. And again, it didn’t cost her that much: “I’m good at it, aren’t I? And I actually really could like this. I should feel lucky.”

But it did cost me. On this path, I felt like I was sleepwalking. I would awaken briefly when I achieved the next milestone or got a new level of external recognition or praise - and even that moment of awakeness was brief, and shallow, like opening my eyes but not really experiencing. My days would blur into each other. I didn’t realize there could be more to life than drudgery punctuated by moments of fun. There was no room on this path to listen to myself and most importantly, no room to dream up a different life. At some point (near when I decided to quit), this way of living became untenable. I realized there just NEEDED to be a better way. To stay on a path that was only OK, one where I’m sleepwalking, one where I don’t feel fully ALIVE - well, that’s costing me my life.

Not to be dramatic.

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So in mid-2021, I found myself making the decision to leave my nice job, panicking that I walked off the Golden Path into a dark Mystery Forest.

Immediately, I missed the Golden Path - so much so that I tried to recreate it in the Mystery Forest. I did socially accepted things on a “work break” — joined an intensive founders fellowship (somehow in tech, starting a company is the “best” reason to quit a job even though 99% of startups fail and 72% of founders say it’s affected their mental health), traveled the U.S. and documented it, and even created “OKRs FOR MY BREAK” Notion docs. Yikes.

And while that could be the right path for someone else, I knew it wasn’t right for me. I think I always knew - I just had trouble accessing that knowing sometimes (more on that in a future post).

So what happened?

Suddenly, I had the aforementioned room to listen to myself. Also more room to feel feelings, overthink, ruminate, spiral…but ultimately, room to get to know myself: my thought patterns, energy levels, values. Who is Cissy, not Cissy-on-the-Golden-Path? Some of the things I discovered:

• She is best as a leader when she feels free, autonomous, and supportive.

• She’s deeply curious. Especially about people and patterns, especially across disciplines. She loves an elegant story just as much as she loves an elegant metaphor or proof.

• She loves the type of conversation that generates new possibilities that weren’t there before and transforms people.

• …

As I unearthed more of myself, I started wondering - what does “success” actually mean to this Cissy? What does being alive look like for her?

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The whole point of life, almost tautologically, is to live it. So it follows that Successful Life = Most-Alive-Life. I think we all intuitively know this, but we forget it sometimes (sometimes, for decades), when we are sleepwalking the paths laid out for us. We forget for so long that we forget to dream, to even desire a better way.

Fast forward two years after this realization, and here I am, closer to my Most-Alive-Life:

• I’m a full-time, self-employed professional coach, who gets to work with high-achieving leaders and entrepreneurs who want to become the best leaders they can be, but also want to find their aliveness - for themselves and for their teams & businesses.

  • P.S. Your aliveness will look different than mine (don’t worry, I won’t make you quit your job…) - but that’s the point! It could mean major life changes, or subtle shifts in mindset, or building up new ways of leading or working (more in a future post on other ways to go towards your most alive life…). Your path will not look quite like anyone else’s - I want to help you find & own your unique version of success through living the truest expression of yourself.

• I’ve trained my coaching skills with the Co-Active Training Institute and Positive Intelligence, completed over 700 hours of coaching experience, worked with more than 50 paid clients, and connected with many like-minded coaches and people around the world.

• I’ve designed my life around self-connection, community connection, travel, creativity, and play.

• I am working on letting go of some other societal “should”s (more on that in a future post).

• I made very difficult but important personal decisions.

• And even when things are hard, I am accessing a sense of freedom and empowerment.

Living this way does not mean life feels easy. It just feels meaningful. Alive.

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If this story resonates with you, I’d appreciate a like, comment, or subscription. I’ll be sharing more of my journey, as well as insights and frameworks from my coaching work. And if you want to explore 1:1 coaching with me, please check out my website here or book a free consultation.