I had a conversation with an acquaintance recently. He was seriously considering a “Phase 2” for his life, and a new career. Formerly an executive at several leading technology companies, his sincere interest in personal growth, and experience with mentors and coaches in his life made coaching a likely option in his mind. I shared as much as I could about my journey. This conversion about “How does I become a coach?” is one of dozens I’ve had in the years since I first started my Phase 2 as an Executive Coach for Technology Leaders. 

Reflecting on the conversation in the quiet of a pre-dawn morning (we have a toddler, who blessed us with the gift of spare time by sleeping in for a change!) I figured I’d do what I always do, and write down my thoughts. They turned out insightful (for me) so I’m sharing them publically for anyone who cares.

Writing is thinking, as I’ve learned over the years (h/t to Steven for reinforcing this point in me during my Microsoft years in his organization). What follows is rambling about my journey into becoming a coach and how it has progressed from there. I share the steps I took, what I realized along the way, and how I’ve changed my approach. 

Please don’t view this article as a roadmap for what you should do. Instead, read it to hear my journey, and then see what clarity is arising from within you regarding your next step. 

Note: the cover photo is of a Gazebo at the ashram I attended often as a teen and young adult. I still visit whenever I get the chance to study and explore Vedanta and connect with family.

TL;DR 

Knowing what I know now, I could have achieved the current state of affairs in my coaching practice (income-wise, impact-wise, satisfaction-wise, etc.) within 2-3 years, easily, instead of 6. However, if I had a do-over, I wouldn’t change a thing. Every step was insightful and informs my approach and decision making looking forward. As the great sage, Eminem said, “I guess I had to go to that place to get to this one.” 

Inspiration

In January 2014 I quit my job, a wonderful and high-paying job, to travel the world with my wife and road trip the country with our two dogs. Living out of backpacks, and eventually, our Subaru Outback, for the better part of a year was transformational in many ways. One thing that dawned on us, was the desire to live well, not just work well.

Work, and a great career, always mattered to me from my youngest days. Specifically, I saw work as a chance to explore, create, build friendships, and generally, do stuff with interesting and intelligent people; and get paid in the process. Microsoft was like a playground for me (though at certain times it was more like thunder-dome, I’ll save those stories for another time). 

Priorities are only as good as the context in which they are made. During my sabbatical my context widened massively, clarity emerged regarding the type of life I wanted, including work in a much bigger picture. Three things were repeatedly vital to me. Note: when I say “me” my wife was very much a co-creator in all this! 

• Freedom to be able to work and generate an income from anywhere. I had no plans to remain a nomad. However, I didn’t want to deal with horrendous commutes or limited capacity to take holidays for the next phase of my life, especially with our plan to start a family. 
• Learning was also key. While I was learning a lot in my previous role, it wasn’t what I was wanting to learn. I wanted to dive into and develop mastery over something that I was sincerely interested in. 
• Lastly, I wanted a direct sense of contribution to people’s lives, not the indirect feeling I had in knowing that software we built was used by a billion people (I worked as a “Product Management” leader on Windows, Office, and other broadly-used products). 

Giving this, coaching was a logical choice. I had thought about in years past, had taught yoga for an extended period of time, self-organized a personal development community in Seattle during my mid-20’s and worked with coaches of various types as well. However, prior to my sabbatical it never occurred to me that I could actually “be” a coach. It was in direct conflict with my self-image as a fast-rising tech person. Anything that “smelled” of HR was anathema to my personal identity, even though I highly valued HR and personal/team development to a high degree. This self-image (which was made up, to begin with) dissolved as my mind settled and things starting “clicking” for me on a deeper level. 

Decision Time

As we wound down our travels, I decided that I would jump into a coaching training program. Coaching was (and still is) the wild, wild west of careers. There are over 30,000 certified coaches globally according to the International Coach Federation (ICF). I would estimate there are at least 10X that number who operate as coaches but don’t have a robust certification. Anyone who wants to sell their time calls themself a coach (it’s now more trendy than saying you are a consultant). 

I made the conscious decision to get certified. Yes, I had already worked in a demanding career for 14-years (much of that leading teams). Yes, I had already run the gauntlet of training programs during my corporate career. Yes, I also knew I still had much to learn. I figured that if I was going to make something my profession, I might as well learn the ropes and core principles of the field. Even if I decided to operate differently than my training would teach me, it’s better to be a change-maker having learned a field to some degree, than to just blaze one’s independent path and pretend a field doesn’t exist!

Choosing a Coaching School

There are many coaching schools out there. At the time, in 2014, there were few that really adopted remote learning as the default mode of training. This narrowed down my exploration to a few spots. Erickson, based in Vancouver, seemed to have a robust program, had virtual training options, and seemed to offer a well-rounded and ICF-Certified curriculum.

I attended a free online info session and enrolled. The first few months of classes, I was holed up with my wife (and two dogs) in a tiny house (<200 square feet) surrounded by rescued horses (the owner adopted them from tragic situations and cared deeply for them) in the dead of winter in the interior of British Columba. We spent these two months shivering, watching the horses (Chunky and Joe were mini-ponies who lived right next to our tiny house), nordic skiing, writing, reading, and contemplating our next moves. I used the opportunity to dive into coaching training. 

Fast forward six years later, how much of my coaching is based on my Erickson training or my experiences with Tony Robbins (I attended many of his programs in my 20s) or other coaching-oriented training? 

Very little. 

How I coach now is far more informed by my upbringing, studies, and practices of yoga, meditation, and non-dual spirituality, than my coaching training. However, some of the basic practices of establishing sound coaching conversations are still used. There are also a few coaching “tools” that I occasionally employ to support specific situations. 

This doesn’t mean the training was a waste, it just means that as I evolved as a coach and saw what was most effective, my coaching approach evolved as well. 

There are now many coaching schools and (all – given COVID) have robust virtual training offerings. CTI, iPec and many others for example. If you are setting out to be a coach, explore them, drop into a few introductory sessions (many have them hosted periodically) and take your pick.

I do think an ICF-certified training is the right first step for a new coach (who isn’t already trained as a counselor!) as a first step. Though (as I will share later) much of my coaching education and training since my original Erickson course has been with non-credentialed programs/courses and coaches who are outstanding, but haven’t gone through the trouble of getting certified.

Go, Set, Ready

A yoga mentor in my 20s used to often say to our class, full of experienced practitioner-teachers, “you are ready now” when people were insecure about starting out as a yoga teacher. The context was that the mind often creates distractions that keep one from doing things that have a lot of upside but little actual downside (though the mind will think there is a lot of downside). 

On the first day of my coaching training, the teacher concluded by mentioning that we don’t have to wait until we are certified to start serving clients. If we have something to offer, just go for it. It would be the best way to learn. I ended that training, and something clicked inside of me. I went to Facebook (I was more active on the platform then, than I am now) and posted a note letting my friends know that I was winding down my “gap year” and was looking to start coaching. I asked if anyone was interested in being a “guinea pig” as I started my new venture. I instantly had a dozen people reach out for complimentary coaching sessions. Three of these people then hired me. I was floored!

I’m very happy I enrolled in formal training. I’m also very happy that I didn’t wait to complete the training to get started. The actual experience of coaching clients made my training far more effective and real. I asked better questions to my classmates and instructors. I was able to digest the training and practice what I was learning.

Slowing Down, To Go Fast

I spent an inordinate amount of time in my first 2-3 years of business trying to scale-up my practice. I hired a marketing consultant. I hired a coach. I enrolled in online courses promising clever lead-generation techniques or ways to scale-up fast.

It was a big waste of time (mostly, working with a coach was excellent though!). 

At some point, a few years into my practice, I just decided that I would ditch a bunch of elaborate marketing (lead funnels, webinars, etc.) and just do what I enjoyed. I would blog and engage in social media on my terms. I would let things more organically grow. I would stop fixating on income goals as a “ceiling” and instead just make sure I was doing my best to achieve an income “floor”. 

An “income ceiling” is a pie-in-the-sky income number that is aspirational. It’s how most companies operate as well. Shoot for the moon and you’ll land among the stars, and all that. Now, even the moon isn’t far enough, you need to be shooting for Mars or you’ll get fired!

Instead of this, I set an “income floor”. I knew how much I needed to earn to pay the bills. While I had some savings, I also left behind most of my net worth in unvested stock when I left Microsoft (valued at many millions today). My income floor would cover modest living expenses with some room to spare. It was reasonable and seemed doable. It was a stress-free thing to focus on. 

As I shifted my focus, I slowed down the frantic business-building activity and spent more time serving clients and connecting to people in general. I connected deeply with the local coaching community here in Colorado. It was more enjoying things and far less stressed. Over time, my business was built.

Here is a chronology of the first three years:

• Year 1: The Experiment. Would I enjoy it? Was I any good at it? Would anyone pay me? Yes, yes, and yes were the answers.  
• Year 2: Making a living. Can this pay the bills consistently? Yes. 
• Year 3: Impact. Can I support my clients in creating even bigger outcomes? Were results good enough for clients to vouch for what I do? Yes and yes. 

Giving Up (almost)

Roughly three years into my coaching practice I had an awakening. I almost quit. Something was not right. While my practice was steadily growing, clients were getting better results and referrals were starting to come in, I was having an existential crisis. One factor was my fixation on trying to grow my business. As previously mentioned, I stopped aiming for growth and found a new ease in my practice. This helped dramatically. 

There was another element, however, that was a big factor. 

During this period my coaching approach was heavily focused on creating a clear focus on desirable goals and marshaling one’s resources (mentally, physically, etc.) to align with that desired end. It was a traditional approach used by coaches (successfully), understood in the world of business, and aligned with what clients were looking for. Imagine if someone walked into your restaurant and asked for pizza, and you gave them amazing pizza, that would be a successful engagement, right? That’s like what I was doing. 

The problem was, this type of coaching approach was not creating the well-being that mattered most to me (and also, to my clients, though they didn’t know how to articulate it). The worst moment was when a client called to celebrate a big promotion at a leading tech company, only to follow-up with a somber “What’s next?”. There was no joy, no gratitude, and no peace. There was only a clamoring for the next thing. 

It hit me like a ton of bricks. I was coaching in a way that was helpful, but limited. I was also ignoring much of what I knew about how life works. My upbringing in the Eastern spiritual tradition of Advaita Vedanta, years of practice, and teaching of Yoga, and observations of success at work and life had revealed a much different way in which to navigate things. I had stopped trusting myself and put too much weight on how coaching was “supposed” to work as per my training.

Luckily, this awakening resulting in my shifting, gradually at first, then completely, the manner in which I coach. I found new mentors, coaching colleagues, fresh training, books, and places to look for answers. I unearthed literal boxes of notes and books that I hadn’t opened in years – much of it grounded in ancient philosophy and spiritual teachings, and starting asking myself how to apply these timeless principles to one’s success in work and life. Perhaps one day I’ll write a blog about that. 

Trusting Myself

As I type these words, I’m still a coach. I love what I do. I’m continually realizing how much I don’t know as it’s a field with an infinite learning curve. My business is doing just fine. It’s growing smoothly and happily – with a few fits and sputters here and there (things like COVID-19, you know?!). I’m continuing with my journey towards higher level of certification (ICF “Maser-coach” is the next stop), though, many pieces of training I dive into are not certified. I’m following the certification process b/c I see no downside (aside from some cost and time), and I’m personally interested in the learning that will come from the process.

I see my social feels littered with “build-a-6-figure-coaching-practice-in-90-days” blueprints. I stopped laughing out loud at these pitches. I also am not angry at the people hawking them. People will take the journey they need to take. I personally know “coaches” who built practices that are far more lucrative (financially) than mine, in a fraction of the time. That’s wonderful. I wouldn’t trade my journey for anything. Things take as long as they take. In a world looking to have the future appear NOW NOW NOW, we should remember that. 

I never could have imagined, 6 years ago, that my work (and my life) would be what it is now. It’s not all glory, but I love it. Who am I to say where I need to be in 1 year (or 5 or 10?). Looking ahead, I remind myself of something I often explore with clients:

What would it be like to trust in myself even more than I do now?

That is one thing I can do. It’s a way to navigate from an innate sense of knowing, in a world that seems to be enticing us to be looking everywhere else for answers.