When I left my last salaried job, a little over 10 years ago, I did so knowing that the world I wanted to help create was more likely to be found in the ventures that I and others have co-conceived and co-founded than in existing organizations or companies. The status quo is, by definition, backward looking, inert, and resistant to change. And so it stands to reason that for people like me, who have a strong internal compass and what these days is called “moral ambition,” the challenge and opportunity lies in forging our own paths and not expecting to find resonance in existing institutions.

As is the case with so much Millennial re-discovery and re-branding of concepts that have been around for a long time, “moral ambition” has its antecedents in an experiential pedagogy made familiar through the Outward Bound movement. Its founder, visionary German educator Kurt Hahn, famously believed that “There exists within everyone a grand passion, an outlandish thirst for adventure, a desire to live boldly and vividly through the journey of life.” The adventure in question is internal, the overcoming of imagined limitations and shoulds that stand in the way of being your authentic self. I was lucky to attend the first boarding school founded by Hahn in Germany after World War I, and later one of the United World Colleges he founded after World War II. I never attended an Outward Bound course, but that kind of hands-on experience in nature was part of our daily curriculum—as part of “Sea Service” at my school in Canada we were a Coastguard substation and frequently the first responders on the scene. That’s a topic for another day, but the whole expeditionary and experiential pedagogy that Hahn espoused can be summarized in my German school’s motto, Plus est en vous! ~ Which roughly translates to “There is more in you [than you think].”

So, generally, I don’t expect my raison d'être to be reflected in job descriptions that come across my electronic transom. I have also never really applied for a job. Towards the end of my graduate studies, I did two informational interviews that led to my first consulting project and a project director job, respectively. The latter turned into almost 15 years with the same organization, which I left as President 10 years ago. 🤷‍♀️

And yet. Every once in a while a job description pops up that speaks to me and sparks an imaginary conversation with the job poster—first in my head, then on paper, then on screen. More often than not these positions are mediated by a recruitment firm, which is another circle of hell of maintaining the status quo. But I find it useful to take job descriptions at face value, and to engage with them from my point of view. So I essentially end up having a one-sided conversation with the entity doing the hiring about what they could do if yours truly had a say in it, using the cover letter as a literary form of short, speculative, non-fiction. In two pages or less, cover letters afford me an opportunity to use the hiring entity as a foil for articulating to myself and them the systems patterns I see in their job description, and the opportunities for overcoming them should they be willing and interested.

On a recent visit to Pendleton, OR to visit a friend I got to meet the city manager, and was reminded how pragmatic these folks have to be. When you work for a city, who have to solve real problems in real time, and there is a whole slew of opportunities to be creative and innovative—at least in theory. I had a lot of fun re-imagining how I would approach the economic development portfolio of my hometown in a cover letter to its economic development agency for some high-up job. As a major landowner, there is so much potential for leveraging real estate and other assets in productive, new economy ways; and to use the purchasing, political and positional power of the agency to crowd in old and new sources of capital from inside and outside the city; work with local companies of all different sizes to imagine new clusters of industries; and do so from a perspective that centers community and entrepreneurs. Who better than an actual entrepreneur to lead such an agency? Alas, there is a revolving door of lifer economic development sector experts who make the rounds across the country, and track record is valued over ingenuity. While not every economic development agency might be able or willing to bring outside-the-box thinking inside, there is an encouraging and growing interest by such agencies large and small to work with the likes of me on a consulting basis to create more integrated and innovative capital ecosystems. More on that as it transpires.

While I generally take a pretty dim view of the philanthro-industrial complex, it is illuminating to contemplate what I would do differently inside a large foundation, and those jobs give me more pause than most when they come across my transom. I was particularly intrigued by a job at a foundation that sat at the intersection of principled technology, movement building, and senior nonprofit management. Here is my one piece of (unpaid) advice for this topic: When you are 3 for 3 in a role description, you should definitely apply!1 In that cover letter, I went on an exploration about using the foundation’s market position and power as the owner of a major technology product and community to shape the ecosystem we need for more democratic, publicly controlled technology over and beyond nonprofit and / or open source projects. This was just a little bit before it became apparent just how toxic Silicon Valley style technology has become—now that it is eating our democracies, our children’s mental health, and the environment. They hired a phenomenal woman of color, who I worry will be ground down by the slog that was the subtext of the role: managing a founder transition against the backdrop of diminishing revenues. Founder transitions have at best a 50% chance of success. Been there, done that.

On the topic of technology, another fantasy of mine is doing good things from inside the beast. So when a social impact position at one of the big AI behemoths came across my desk, I threw my hat in the rink. Hilariously their prompt for the 500 words on why you wanted to work for them included the instruction to not use AI. I wonder if they were warding off against today’s digital natives and early adopters of all things AI who can’t imagine doing anything without it anymore? 🤔 For a position like this, having a principled stance would be incredibly important, and I had fun succinctly articulating the hard-won design principles that we adhere to at the impact tech company I co-founded. How great would it be if a major AI company adopted them? It would certainly be an acceleration of my life’s mission!

And finally, my most recent cover letter went to a family office masquerading as a social enterprise. They, too, wanted original writing and warned off against the generic cover letters that I imagine are endemic these days when job seekers “spray and pray”, and people report applying to hundreds of jobs. In this one, I was intrigued by the internal disconnect of an organization wanting to catalyze a whole ecosystem of organizations that bring about the new economy, but framing the job as a glorified fundraising position for their signature product and programs. 🤦🏼‍♀️ You can’t hope to create ecosystem effects if you are narrowly concerned with only feeding your own organization. There was also a marked lack of tie-in to the trustees’ considerable overall wealth and how it is currently managed, creating another layer of dissonance in making the organization look deceptively small when the underlying ego and opportunity are anything but. Pointing out these tensions and articulating ways to address them was an illuminating exercise, and increased my compassion for ultra high net wealth people who want to do more of the right thing but run into the inertia of the internalized narratives about how to go about it. As well as their staff and advisors, who are all just managing to a set of incentives that keep them gainfully employed and relevant.

All this to say that in 10 years, I have been intrigued enough by a whopping 4 job listings to write a cover letter that took the particular role as an opportunity to have a conversation between my authentic self and their corporate persona. I am pretty sure that’s not how you are supposed to engage with the recruitment process as a job seeker. But this kind of short, speculative, nonfiction it’s a lot of fun to write and I find it illuminating as I plod along my life’s course. Plus, I like the idea that just maybe I might find alignment with an entity that’s willing to pay $250,000 and up for my expertise and experience. I mean, life would be soooo much easier! 🤣