My Coaching Journey (so far)

I recently realized I announced my recent career transition on LinkedIn, on Facebook, and have even been interviewed about it on the Corporate School Dropout podcast, but somehow forgot to talk about it on my own blog. Oops. The summary is that I left Google in July after working there for almost 11 years, to grow my coaching business named Too Many Trees (riffing off of the idea of not being able to see the forest for the trees).

I shared my personal development journey in last year’s introduction post, where I said that my passion for coaching was borne out of my personal growth; I wanted to help people free themselves from the habitual patterns that were keeping them stuck, so they could unleash their potential. But I’ve had a few people ask me how I got into coaching, and how I made the eventual decision to leave Google despite having a dream job there, so this post will cover that journey.

Let’s rewind three years to 2016, when I broke my neck in a bike crash. While recovering, I spent time reflecting on my life and whether I was making the most of it given how easily my life could have ended if things had gone slightly differently. I went to the 2016 Overlap retreat despite still being in a neck brace, and while there, I complained to a new friend that I felt that my job wasn’t measuring me on the things that mattered. My new friend asked the obvious follow-up questions of “So how do you want to be measured? What are the things that matter?”, and I was stumped.

I spent several weeks considering my response to those questions, and wrote about it here with my posts on choosing action over identity, and practicing gratitude and generosity. I realized that what I found meaningful and energizing was helping people to figure out their path and move forward towards their potential (choosing action). In particular, I had always enjoyed mentoring colleagues and friends, and I realized that the part of my Chief of Staff job that I found most meaningful was being a thought partner to my VP, not the business operations work that was how I was being measured. My Overlap friend said “Hey, that sounds like coaching – have you explored coaching?” and a new possible direction was identified.

In the second half of 2016, I told friends that I was interested in doing more coaching and mentoring, and had several friends take me up on the opportunity to get my perspective on their situations. They all appreciated my insights, making me feel like I could add value as a coach/mentor. I also realized that the few hours I spent in these conversations each week were my favorite activities of the week, and I wanted to get more coaching into my life.

So in the fall of 2016, I went and interviewed five professional coaches, who all generously shared their time to give me advice on how to get started as a coach. They all said to get trained and certified; one noted that even if I were a natural coach, the rigor of a coaching program would give me a formal structure to fall back on when my instincts failed me. Two of the coaches I talked to had gone to New Ventures West and a couple months later in January of 2017, I started the Professional Coaching Course (PCC), a year-long training and certification program.

I chose New Ventures West is because not only was it highly recommended, but the way it described its work it made me the most nervous. The webpage of CTI, another coaching institute, is full of results-based language like “world-class experience” and “the gold standard of coaching training”; it felt like if I went to there or the Hudson Institute, it would be a set of classes teaching coaching techniques and practical applications, which I felt I confident that I could handle given my classroom excellence. New Ventures West, on the other hand, describes its brand of coaching as “an ongoing, evolving methodology intended to be the most comprehensive response to human life. Its practitioners reach deeply into the past, gathering wisdom from East and West, while still staying current with the frontiers of new discovery in cognitive science, genetics, and other disciplines.” When I first read that, I was like “What the heck are they even talking about?!” It felt very California hippie “woo woo”, which challenged my practical “objective” worldview, and I felt nervous that I would not fit in with this program at all. So, leaning into my Personal Operating System slogan of “If something scares you, try it”, I signed up.

The year I spent in the PCC of New Ventures West was personally transformational; I feel that I emerged in March of 2018 a different person than when I entered. I found new depths of stability and groundedness within me, and learned new ways of connecting with others. And, yes, I am more hippie “woo woo” than I was before, as evidenced by my last post on spiritual bikepacking, because I have more direct experience with new ways of being. Rather than having to understand everything intellectually, I can trust that my own experience is real, even if I can’t explain how that experience happens. Another way of putting it is that one of my goals for the PCC was to transition from being default head first (thinking through everything logically) to the possibility of being heart first (trusting feelings), and the feedback I get from others who meet me now indicates that I have accomplished that goal.

One example is that in the first and last weekend of the PCC, we did an exercise where we stare into a classmate’s eyes without speaking for several minutes. The first weekend, I found it to be profoundly uncomfortable, and I spent most of the time panicking in my head about what I was supposed to be feeling or sensing or doing. At the end of the program, I was able to stay present with what was happening rather than getting lost in my own reactions, and was able to pick up waves of emotion from my classmate despite not a word being exchanged. I could try explaining that via micro-expressions or auras, but the proof was in my experience. Coaching feels present and experiential for me, rather than intellectual, and I can’t really explain how I do it; when I’m doing my best work, I’m totally tuned into my client, helping to find what might be blocking them, and to create the space for them to unfold.

During the time I was doing the PCC, I also signed up to be a “Career Guru” at Google, which is a peer coaching program that offers career coaching in one hour sessions to anybody at Google who signed up. I did about a session a week and was rated five stars by the 80 or so Googlers who met with me. I loved doing those sessions; I had people contact me a few months after a session telling me how our conversation had changed the course of their career and showed them new possibilities that they hadn’t imagined. It was so inspiring to feel like a one hour conversation with me could help to change a life, and gave me an idea of how this work could “scale”; I couldn’t reach millions or billions while coaching, but the effects of a change in somebody’s life could ripple outwards in unexpected and powerful ways.

With these encouraging signals, I took the next step in the summer of 2018 to create a coaching business, Too Many Trees, including incorporating as an LLC, setting up a business bank account, etc. This was in part to gain more experience as a coach, but also to use Cal Newport’s test to find out if I had accumulated enough “rare and valuable skills”, where the test is whether I was creating enough value that people were willing to pay me to coach them. And the answer was yes!

By the spring of 2019, I had several regular paying clients who were starting to refer others to me. I was also at a crossroads in my Google job as Chief of Staff – I had hired somebody to help me with the process and operations portion of my job in the fall of 2018, and they had handled things impeccably when I took a couple months of leave this spring. But the process and operations portion of my job was set to grow enormously, and I wasn’t excited about doing more of that work when coaching was feeding my soul. I had some savings built up to give me some time to build my client base, so I gave notice in June, and my last day at Google was July 12th.

I share this story for a few reasons.

  • Friends and acquaintances have been curious how I took such an abrupt turn from a fast-track business strategy and operations job with a great team at Google to dropping out and becoming a coach. Admittedly, those who have known me longer through my previous transitions from physics to software to business may not find the unexpected career change as surprising.
  • People sometimes think that if they really have a passion, they should just quit their job and figure out how to make that passion their work. I tend to be cautious, so I prefer to use small steps and experiments to figure out what works, and you can see that in how I approached this change. I first tried it for a couple hours a week with friends, then I interviewed people who could give insight into the path ahead. These were low-effort low-cost ways to gain more information before I committed to the cost and time investment of the year-long training program. After I finished my training, I still didn’t quit, but built my coaching business on the side to work out some of the kinks. I only made the leap after I had proof of my value in the form of paying clients. Yes, it took three years to make this transition, but as a result of my more incremental approach, I felt confident by the time I made it.
  • And even though I felt confident, it was still difficult for me to walk away from a high-paying prestigious job at Google. In American capitalist culture, where more is better and there is no such thing as “enough”, it felt like a crazy irresponsible thing to do – why would I give up the kind of job that others spend their lives trying to get? I had to spend some time this spring to articulate my values and re-align myself to say that making more money was not the purpose of my life. Reading The Soul of Money by Lynne Twist helped, as did reminding myself that this step was reversible in that I can go back to work in tech if this doesn’t work out. But it was still very difficult mentally and emotionally to make this leap, so I wanted to share that context.

I hope that sharing the story of how I got here will help others see the possibility of making changes in their own lives to align more closely with their values, even if it starts off as only a slight tweak in how you spend a few minutes each week. I am happy to answer questions about my experience, and of course am available to work with people who want help making such a change in their lives. Regardless, I want to share love and possibility for all in finding their way.

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