An Entrepreneur's Diary
~On fear, humility, perfectionism and learning
in any creative endeavor~
I’ve written a piece below about my entrepreneurial journey over the last 15 months launching my latest business. It’s divided into four chapters. My hope is that you find threads that mirror your own risk-taking ventures, and also find validation in the time it takes to get a new project up and running, the many failures to learn from along the path, and the inner grit required. This piece is more personal than most because, in a facilitation-based business like mine, I am, in a sense, the product. And as I write that, I wonder how much my thinking has been influenced by capitalism and, of course, by schooling—a few good rants about which are contained below. I hope you enjoy and, as always, I’d love to hear any reflections this piece brings up for you.
Chapter 1. Profound relief: The joy of leaving a job you have outgrown.
This is the happy moment when a person regains that most valuable of commodities: time. For me it means escaping the Kryptonite-inducing effects that traditional school has on me, thanks to a confluence of factors that have enabled me to buy the freedom to work on my own passion projects for a limited period of time. In other words, a super broke and anxiety-ridden sabbatical called solopreneurship. I have “chosen my discomfort,” as Blake Boles says in his piece “You Don’t Have To Go To Work.” And goddamn do I love it. I dive in.
Chapter 2. When the muse visits.
This phase, for me, feels like: action (partnering with the muse) and fear (oh god); upping my fear management practices and thickening my skin; repeating cycles of action and fear management. I believe that this stage is highly dependent on several factors, including one’s proximity to power; trauma history, cultural background, and personality. Growing up in Iowa as an extremely shy and sensitive white queer girl who inherited a strong dose of unprocessed family trauma, even creating a website in my name feels like a whole lotta hubris. For those of us in this camp, fear management is part of the deal in creative ventures and that shit takes time to attend to.
From the outside, this phase looks like being on the cusp of and actually implementing several big ideas and projects. In my case, I complete several chapters of a book; have a podcast on simmer in the background; and begin to do restorative justice in schools. My main project is to create an online course based in restorative justice, deschooling and racial healing work using somatic and land-based practices, poetry, and meditation, which I run three cycles of over a period of many months. Throughout this process, I begin honing in on my niche, which, as those fellow entrepreneurs out there know, is everything.
Subchapter in which I talk about my niche and go on a big ole’ rant about school.
It took me a while to remember that my love prior to restorative justice was self-directed learning. I loved her so much that I co-founded and ran a self-directed learning centre over a span of five years before she crashed and burned like so many enterprises that serve as bridges to a new world (who funds those?) I realized that my niche lies at the intersection of self-directed learning and restorative justice—you know, where all the money is— by helping to further decolonize and heal alongside people who already know that schools need to be radically transformed because the very structure of their coercive and hierarchical way of being is a part of what is putting us on a path to our own extinction—and taking down millions of other species along with us.
I recently heard the phrase "Truth and reconciliation are sequential" and it went straight into me. We can't reconcile ourselves to the fact that schools need transforming until we explore the truth of them and the profound impact they’ve had—and have—on all of us. Among many other hidden lessons from school, it teaches us to constantly seek permission from others, deny our bodily impulses and passions, and to find the one right answer; it tells us that rules are more important than relationships, and to be the best in a made-up pecking order hell-bent on reproducing itself generation after generation. Yes, children do manage to learn things in school, even though a recent Yale Study found that nearly 75% of students’ self-reported feelings toward school were negative. Yes, many teachers are wonderful even though they have the highest burnout rate of any profession in the U.S. Learning and relationships happen in spite of a system that relies on carrots and sticks to keep its often less-than-joyful inhabitants in line.
I’m not here to convince you of this. Get involved in the education liberation movement and we can deschool together. I’m tired of, as my mother would say, pussy-footing around. One thing I’m sure of: Restorative Justice is one key to a new (old) anti-colonial, rewilding, relational way of being together on this planet.
End of rant.
Chapter 3. Putting time and money into learning the structures that will increase the odds one’s project will succeed and living at a sane pace while doing so.
For me, this looks from the outside like upping my marketing and business development know-how in the form of courses and trainings. Internally, it means realizing I need to take things slowly and with a good dose of humility.
Unlike the glorious love child of my first entrepreneurial venture, with Education Liberation I'm learning how to make my business last. Passion and taste unfortunately do not come with a matching set of business know-how and virtuosity, a gap that Ira Glass talks about here, a useful reminder for anyone launching a creative endeavor. To put it bluntly, in the first—and sometimes years long—phase of any creative project, we learn by trial and error. This, too, is part of our unschooling, as avoiding “failure” is deeply ingrained by schools, to tremendous cost to our culture in the form of un-acted-upon dreams. Usually eschewing perfectionism, I tend to jump in and learn as I go. Fortunately, I found enough brave souls to populate the first three cohorts of my online course, particularly given that it promised to explore our murky inner worlds, terrain actively avoided by many*. We left our circles altered by having co-constructed a space together that was strong enough for difference, vulnerability, and yes, experimentation.
*A master-avoider of anything smacking of vulnerability over my teen years and early adulthood, I would have been quite fine continuing in the same vein until I shed this mortal coil. However I was far from fine, particularly given my trauma-laden background, which is precisely why I started down the path of inner healing. That I am in the business of collective inner work is only because I am so utterly convinced of its usefulness as an under-utilized superpower to heal our world. And because of my relationship to vulnerability, I need to take care of myself along the way. It’s in continuing to soften that we make change, not steeling ourselves and plowing ahead as a lone saviour.
Chapter 4. When it’s time to get off the full-time solopreneur/single mom ride for a time and get a part-time job.
When you’ve been in harsh entrepreneurial winds for a while, the word “paycheque” has never sounded so reassuring. I've had the immense privilege to work on my own business full-time for the past year and a bit and live at a very human pace while doing so. To be able to do what you were meant to do in this life is a glorious gift—one that mass schooling pounds out of most of us. Of course I'm nervous about time spent at my new part-time job affecting my ability to keep moving my business forward. At the same time—because there’s not one right answer here—my new position closely aligns with my life’s work and includes a much-needed measure of community care and security.
My next projects include co-facilitating a girls’ circle with four generations of women, using the One Circle curriculum; creating a series of ‘tiny courses’ on deschooling, which will be available on my website soon; leading training for self-directed learning centres and other alternative educational spaces; and starting another online course of Education Liberation when it feels slow and right.
