I work with a lot of coaches.
This is an understatement, because I am surrounded by coaches in both my professional and social life. They are my clients, but also my friends. I do technical production for probably the best coaching school teaching enrollment (CFJ Coaching Success School), and I both worked for and graduated with a Master’s Degree from the University of Santa Monica, a school famous for turning out powerful coaches for the last 30 years.
I have been coached upon occasion by powerful coaches – but I have never actually had an extended experience of one-one-one coaching. Until now.
On one of the online coaching groups I am part of, an unusual post caught my eye a month or so ago. Drew Tupper, a coach in Victoria, British Columbia, was offering his home for a few people to gather, unplug from their devices, and experience his beautiful home and the surrounding area, and to receive his coaching.
The offer felt clean and airy, like crisp new sheets, and there was a spaciousness around the concept; pictures were included of his home, cool, empty rooms with lots of space…and wood, lots of wood. He described the area he lived in, and spoke about walking on the beach and being present with what was there, in real life, beyond the screen. No devices allowed.
Almost impulsively, I replied, thinking I could just submit and inquiry. I connected with Drew – and he met with me. A focused, smiling man with a childlike eagerness coming forward through clear communication and some obvious coaching mastery, my first session indeed brought forward at least one powerful awareness.
My own path has taught me to be very present and aware of the messages I hear from Spirit and the world – this is part of a practice going back 25 years, and I acted on my inner calling by committing to this retreat. This was still a somewhat impulsive decision; my situation was unstable at the moment, due to an ongoing medical diagnosis and uncertain business circumstances that had taken a downturn the peceding month. At one point, I sent him an email panicked about money, and uncertain if I could make it to the retreat. Our conversation gave me a glimpse into the very issues I needed coaching support with: intentions vs. commitments (I knew this one, but dropped the ball because of the other issues), financial challenges (I had just bought a business asset I was trying to launch, as well as deal with unexpected medical bills and one of those common downturns businesses often have, and that should be ideally prepared for in advance), and a sense of personal disempowerment in regards to my own power in making decisions in various areas of my life.
All of these things were intimately interacting, so that the medical issues were entirely intertwined with the personal and financial, and I was to a great extent, aware of this. I had a lot of training, and a huge commitment to my personal development, but, as they say, “stakes were high”.
Drew held space, but you can see he was a little surprised by my vacillation. He worked with me, and our call was somewhat an establishing of our relationship, and a clarification of our agreement.
My business took an upturn, and I decided to honor my commitment, first and foremost because it began as a commitment, and I knew the value of keeping this as such. I made plans to go, for the first time, to Canada – from Los Angeles on the Amtrak railroad and the ferry to British Columbia from Seattle!
This inimitable adventure was exquisite when it arrived. If you have not traveled up the Coast of California, Oregon and Washington by train, you are missing, in my opinion, one of life’s great experiences – and also an opportunity to be an a train for a day and a half for all of your personal and creative work. I wrote blogs, website copy, poetry, letters to family, sales funnel copy, and designed workshops. Most of all, I stared speechless at the great banquet of life outside my North Hollywood studio unfolding in a phantasmagoria of beauty, one gift upon another, a bald eagle soaring, a community of houseboats and a lone egret perched above them on a tree, impossible homes, graffiti, migrant camps, mighty, mighty rivers, majestic bays, and the oldest of the old school rail yard buildings of small towns, Eugene, Portland, mountains, volcanoes, shipyards, sheep like clouds come down to earth, and the Pacific Ocean keeping pace right beside you.
After a night in Seattle at my business partner’s home, I embarked a ferry crossing to Canada, where I arrived in Victoria, an exquisite city that revealed itself as nearly utopian in it’s perfect combination of small town vibes and old world cosmopolitan flavor, exploding with flowers and gardens and seaside riches. I am largely a man who is highly attuned to beauty; this personal wealth is perhaps my greatest treasure; I am overwhelmed quite frequently by even something as simple as a flower, and when nature presents true beauty, I am transfixed.
I arrived at Drew’s beautiful craftsman home in an area of Victoria I could categorize as trendy would that not contradict my impression of Victoria itself. One of the best moments of the retreat was where he flung the door open and I was greeted with pure welcoming excitement by both Drew and Irina, the only other person at this mini-retreat. I immediately felt special and at home.
Over the next three days, Drew revealed a well-planned retreat experience that he communicated as kind of a pilot, an experiment. It unfolded with grace and some spontaneity and adjustment. It seemed that he chose Irina and I because we were coachable, and he seemed to have an ideal scene in mind with this workshop as he brought forwards suggestions, projects and ideas, in the context of nothing being mandatory, but with some agreements in place. I would like to keep a lot of these in my pocket; if Drew continues and expands this to an ongoing workshop, and you find yourself attending, then you will have some surprises.
What I feel called to express is what it is like to be coached in a way that gives you an idea of what is possible in your life, and that activates, through shared experience and the coaches own expertise, the areas of your daily living that are ripe for change, that are begging for you to drop the heavy rocks of your past patterns and blind spots. My challenges that were right before me on the breakfast table were financial anxiety (already under impressive transformation working with Kamin Samuels, a money coach, in a 3 month workshop), people pleasing, a challenge in my straightforward, courageous and authentic expression as a leader and partner, and health and wellbeing manifested in my daily workday (this also was riding on the heels of the powerful coaching I received in still another workshop, the L5 with Stephen McGhee).
As a matter of fact, re-reading that last paragraph brings a smile to my face, because one of the challenges Drew brought forward was to not name drop the coaches and people I have worked with in my communications (both Irina and Drew were coaches, and I was a facilitator and have coached before also, so naturally personal development work came up a lot in conversation), but to own my own knowledge and mastery and speak with my own voice, not preface it as what I have learned from others. This was interesting because the underlying reason was a habit I had formed of using this practice to give myself “creds” with clients – I worked with so and so, I learned from so and so – and even though I wasn’t actively pitching or selling to Drew and Irina, it was an ingrained practice of “making myself worthy”…
You see a bit of how this works? With the idea and concept of coaching and those who enjoy it’s benefits, it’s easy to just roll your eyes at what some people see as a relentless and exacting self-examination protocol and lifestyle – of making yourself flawed and needing to fix yourself – but done correctly it is not about being endlessly self-corrective, but having a sense of fun and humor about the whole thing, and knowing that every second of this life is a precious opportunity to shine as brightly as you can. This is the essence of expert coaching.
Drew also worked with us on owning all aspects of our lives as valuable building blocks for our future, challenges, trauma, damage and all. Irina and I were both game; we each had a lot to work with, to say the least, in our respective histories. There were exercises that gave us opportunity to really step into our mastery and leadership roles. But here’s what really stood out to me through these suggested activities, which were well thought out, insightful and coming from a place of fun and spontaneity; they were the product of a distinctive joy in the art of coaching.
Drew was vigilant; he was so overtaken with how much he loved what he was doing that you could see his wheels turning as he evaluated “is this an opportunity? What can I bring into what they just communicated to open up an awareness, to create an a-ha moment, to create power and growth?” And, it was all about us. You could feel the love. It wasn’t love for us personally, it was a universal love of both Irina and I that was also a love of all humans and the art of coaching itself, which brings to mind, as Kahlil Gibran said, “love is work made visible”.
Because I can own that I am adept at my own process, I brought that in, my own skills and techniques, but also stepped into a great open space beyond technique – I even set a primary intention to, “as an experiment” Drew said, leave behind personal development initiative (having to be better, damnit!), and what that really meant was to give a rest, just for awhile, to continual and internally systemic self-criticism (what my ego thinks it needs to motivate me) – and just practiced “being” without agenda. This created some powerful and very direct emotions. They showed up as the device free, distractionless retreat progressed; as if masked behind my usual “doingness”. They flowed easily into powerful and almost unendurable moments. I remember walking by the beach sobbing with joy over the gifts that I had been given the last few days…each part of my trip, and a coach who just wanted to love and serve me…this transitioned into grief for a father experiencing dementia…and the emotion was intense and cathartic. To be so emotionally fluid is a gift on so many levels, and the direct result of personal development and coaching.
At a certain point, and this is how many might experience such powerful coaching, I almost had a “coaching hangover”…I remember sitting with Irina and Drew and thinking, can I just escape for a few minutes into something mindless and funny and stupid? Those who know me know I joke, and often it doesn’t land well, because I have a bit of a penchant for the inappropriate. And, I joke to blow things up a bit, even as light self-sabotage, which I picked up on a bit even in this retreat. I wasn’t missing the devices or distractions as some might, but feeling a little too “real” for my ego’s comfort.
When a seasoned and skillful coach catches you on patterns of behaviors like this, or anything you are doing that is an opportunity to examine that behavior, the way they bring that forward is truly something to behold – cushioned in very precise language that is pointedly non-shaming but at the same time inherently a challenge. The work then becomes for you not to police yourself around them, but to actually bring forward stuff that can be worked with. I can only imagine how much time is wasted by clients trying to show up as totally together for their coaches. And I bet I do it too in ways I’m not altogether aware of, still. At the root of it for me, it turns out, is a underlying belief in my own incapacity and worthiness, one that is even quite primal in its origins.
Drew made an observation, in response to an inquiry by Irina, that in choosing a coach, you might look for someone who has solved what you have on your plate, that is “a few steps ahead of you” – but maybe not way evolved beyond these problems, because it is an “in” to relatability. Drew only brought to the table his own “stuff”, upon occasion, only in context of revelation and support for what Irina and I were working with. This way of being presented, to me anyways, as mastery, and also was significantly appealing personally.
I think to choose a coach, you want to find someone who in many ways is an embodiment of your ideal of how you want to show up in the world, and also you really want to spend time with. I believe the successful nature of this coaching had a lot to do with me being with a man who had what I want, and who presented the way I saw myself as an idea. I experienced Drew as a model for me in the areas of self-care, intimate relationships, and the intersection and harmonious nature of money and work as they manifest through your heartfelt dreams.
In the weeks that followed my retreat, I kept my media and screen consumption confined to work and short interludes of curated film, TV and comedy while I ate, and have been doing well with it. I brought into action the work Drew had given me, had important conversations and made decisions based on my understanding of the greater power that flows through us all, and I truly felt at peace with this.