Gary Bloomer | SHAKING THE TREE # 343
Dear Ben,
I don’t know if you will get to read this note or not. But if you do, know this: the books that leave the longest lasting impressions on us aren’t the ones that hand us a neat, pre-packaged set of rules or a checklist to help us manage our day. They are the ones that quietly, almost effortlessly, strip away the artificial constraints we’ve spent a lifetime building around our lives in order to protect ourselves from the things we would otherwise prefer to ignore.
For me, the book you and Ros wrote—The Art of Possibility—was precisely that kind of catalyst.
When I first encountered it, I was well-acquainted with what you describe as the “world of measurement.” It was the default operating system of my life: a relentless, high-stakes game governed by scarcity, competition, comparison, and my quiet, persistent fear of trying again and again while only ever feeling I’d come up short.
Working in graphic design, writing, and brand strategy as I have these last 40 years, that mindset acted like a slow poison. It convinced me that space was limited, approval was scarce, and every mistake or rejected pitch was a black mark against my creativity and my character. I was not playing to win, i was playing not to lose.
The Art of Possibility hit me like a bucket of cold water dropped from above because it dismantled my entire mental architecture in a few swift moves. It reminded me of a simple, liberating truth: the rules I treated as absolute physical laws were often nothing more than invented stories. Constructs. Fictions designed to keep me trapped. I realized that if I was the one inventing the narrative keeping me stuck, I also had full agency to invent a better one.
Of all the practices in TAOP, three in particular completely reshaped how I approach creative work, business, and human connection.
The first was your concept of “Giving an ‘A.’”
I am not an academic and I don’t have any students, so I decided to give myself an “A” grade on specific, personal challenges. Because I’m now leading with trust in my own voice instead of groveling for feedback from others, over the last 12 months I’ve given myself the latitude to write two books: a fiction piece about a World War II veteran and his grandson, told from the point of view of the latter, looking back as an adult. And a second, nonfiction work about self-determination and the search for personal sovereignty. When I began giving myself an “A” upfront, I instantly removed the paralyzing anxiety of having to prove any degree of worthiness to other people. I skipped the defensive posturing I’d been hiding behind for the better part of 30 years, and I stepped into the act of doing real, uninhibited work.
The second was learning to say, “How fascinating!” That single linguistic shift helped me reframe my mistakes into pure data. In design and copy, iteration is everything. The second I stopped viewing a flawed draft or a wrong turn as an indictment of my talent, that failure transformed into useful feedback. In my writing, it’s helped me understand the importance of first, second, third, and fifth drafts. I’ll skip over the fourth draft, it was simply too sad to deal with.
Finally, there was the shift toward “Being a Contribution.”
The moment I pivoted from performance to contribution, the imposter syndrome that had plagued me for years lost its grip. Now, whether I am writing an essay, pitching a campaign, or sitting across from a client, the work is no longer about protecting my ego and has become entirely about delivering authentic value to the human being on the receiving end.
Ultimately, your book became an operational framework for my creative freedom. It challenged me to stop treating my life and career as an obstacle course to be survived and it helped me begin treating life as a canvas to be painted.
Before I left England to come and live and work in the United States in the spring of 1999, I had spent the previous 35 years trying to measure up to other people’s expectations. Now, at the age of 63, and having lived here for almost 28 years, I have stopped trying to measure up and instead, I’m inventing and building from a place of contribution. As a result, my view and vision have gained focus, and my work has become clearer, bolder, and infinitely more satisfying. Thank you for putting that framework into the world.
Respectfully,
Gary Bloomer
As always, thanks for reading.
—Gary
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ABOUT THE AUTHOR: Originally from the U.K., Gary Bloomer is a writer, branding advocate, marketing specialist, and an award-winning graphic designer.
His design work has been included in Creative Review (one of the UK’s largest design magazines). Since 2009, he has answered over 5,000 marketing and business questions in the Know-How Exchange of MarketingProfs.com, placing him among the top 3% of contributors. He lives in Wilmington, Delaware, USA.