Tag Archives: windmill-tilting

Missionary Positions

A friend and I occasionally joke—and by “joke” I mean commiserate, laughing at ourselves—about our being reluctant windmill-tilters. I’ve spoken before about this tendency of mine toward passion-driven crusades, this compulsion to dream impossible dreams. The reluctance comes into play with my textbook introversion and general aversion to conflict.

DonquixoteEven taking a bold, controversial stance, appearing to know something with some assurance, is a challenge, which makes it a wonder I found myself in a career where I promote an unorthodox (I prefer the term “cutting-edge”) model of education. That said, this paradox has been an unmistakable, recurring pattern in my life: I’m a private person, yet I reveal a great deal online; I’m self-conscious, yet I often fling myself into the limelight of musical performances and public speaking.

This split personality has its liabilities, for sure. For example, the past couple months I’ve taken up a daily Twitter habit, venturing boldly into that arena of self-assured soundbites. Even more frequently than with Facebook, here I find myself cringing and/or deleting posts that seem too strident, sighing with exasperation at the umbrage and audacity of others. Every day, it seems, I dance this endless tango of assertiveness and self-restraint.

Fortunately, my well-developed diplomatic side tempers the missionary zeal to which I’m prone. In the seventeen years I’ve been associated with Sudbury schools I believe I’ve become considerably more reasonable and pragmatic: more capable of respecting divergent perspectives on what, to me, is a vital issue; less likely to press my convictions on those with whose views I profoundly disagree.

This wasn’t a quick or easy process, however—and it wasn’t without costs. Continue reading


Filed under Sudbury

Hacking at the Root

“There are a thousand hacking at the branches of evil to one who is striking at the root.”

~ Henry David Thoreau

Blogging often seems to me the height of hubris or faith. What a series of assumptions are required to continue this silly activity, flinging words at the digital void: the belief that I have something worth saying; that my words will find an audience; that I might somehow parlay my ramblings into sustainable work.

Yet I persist because some part of me knows, deeper than knowing, that if there is such a thing as a calling or vocation, mine lies in the direction of word-driven windmill-tilting, an adolescent’s passionate idealism persisting into middle age. As you know (if know me at all), my primary professional passion is Sudbury schooling, a way of revolutionizing and humanizing education to become truly empowering and aligned with how people learn.

Even so, I sometimes wonder whether I’m tilting at the right windmills. As deeply as I believe in Sudbury, would my energies be better directed at something like climate change? After all, if we no longer have a planet (or one on which life as we know it is sustainable), what will it matter how our children are educated? What about political issues like campaign finance reform? (If the system is broken, how can anyone advancing real reform hope to succeed on a broad scale?) Poverty, violence, disease, overpopulation…there’s no shortage of potential windmills, worthy causes greatly in need of support.

In my more mindful moments, I realize that what’s more pressing than any particular issue is the overall level of consciousness in the population at large. In other words, the fundamental problem is not this or that issue, but the fact that far too many of us are either oblivious to real suffering or believe there’s nothing much we can do about it. This is one reason Zen holds so much appeal for me, as a means of developing mindfulness and compassion. This is why I often wonder whether I should give up what I’m doing and immerse myself in efforts to wake myself and others.

But regardless of whether I pursue Zen, or education reform, or political or ecological activism (or some combination of these causes), the real question—the ongoing thorn in my side, a relentless source of confusion and anxiety—remains how to make this work Continue reading

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Filed under My Quest

Write Livelihood?

Ah, just like old times: blogging on consecutive days. Seriously, though, after yesterday’s post I’m keen to keep at this question of what sorts of things I can do now—not later, now—that both I and my bank account would find fulfilling.

What I really want to do is spend my days reading, writing, networking and otherwise advocating for CASE. For years I’ve been longing for this to be the focus of my working life, not crammed into the odd margins of evenings and weekends. I want to build CASE into an active clearinghouse and catalyst, bringing people and ideas together to support the cause of Sudbury schooling.

As the executive director, I want to spend hours and hours each week cultivating CASE’s online presence: posting content (and moderating user-generated content), as well as seeking opportunities to comment on external sites. I want to secure funding, brainstorm new forms of collaboration, and pursue additional strategies for marketing the Sudbury model to an ever-growing audience. I want to see more people aware of, talking about, and working together to raise the profile of Sudbury schooling.

Yet the obstacle of startup funding remains. My intention has been to use the savings I accumulated over the past few years to lay the groundwork, put things in place to which I could refer potential donors. However, I’m currently overextended with staffing at Clearview, as well as choir and Zen activities. So there’s one problem. There are also the mysteries of how much infrastructure to create before seeking donors, and where to look for these people.

With my board members and collaborators very busy and geographically dispersed, the rate of CASE’s development remains much slower than I’d like. And my Sudbury colleagues and counterparts are unlikely to become less busy—indeed, one of my main motivations in launching CASE was the realization that Sudbury advocates are typically too busy to attend to all that could (and needs to) be done.

So I understand that CASE may not yet (or even soon) be in a position to support full-time, paid work. In general, the sort of work I find most engaging and worthwhile—passion-driven, world-changing, and all-around empowering—seems rather difficult to find, create, fund, and sustain. Given all this, I need to consider how I might supplement my CASE activities with non-Sudbury jobs that suit my talents, interests, and personality. Continue reading


Filed under My Quest, Sudbury, Writing

Do You Think I’m Asking Too Much?

I’ve explored the wisdom of navigating terra icognita by relying on one’s sense of what’s appealing or compelling at a given moment, and of skipping ahead mentally to one’s preferred life and working backwards until a path’s in sight. Perhaps it’s time to apply those models a little more closely to my own situation.

Recently I’ve begun applying the navigation-by-inclination approach to my current situation, surveying various activities that seem both appealing and capable of generating income. In this post, I’d like to start delving into my personal vision of an ideal work environment and see what that turns up in the way of options.

On the most general level, I know that I crave meaningful work that enables a modest, yet comfortable, lifestyle—in other words, the “mission” and “money” elements of my mantra, leaving aside for now the aspect of “home” (though I will say that paying work I can find not tied to a particular locale would seems to maximize my flexibility).

Speaking of flexibility, I know this is an important quality in whatever work I pursue, along with a great deal of discretion or latitude in setting my agenda and deadlines, plus ample amounts of quiet solitude. Being able to spend time outdoors and travel would be a bonus.

Given all this, as well as things mentioned in recent posts, it would seem my niche lies in nonprofit management, promotion, building, etc.—entrepreneurship with a cause. As I’ve said before, I feel absolutely driven toward work that truly makes a difference, that will leave the world a better place: reducing suffering, cultivating compassion, empowering people.

Yet I wonder how to go about finding this kind of work in a form (or forms) that enable me to cover my basic expenses. The world for which I was prepared and conditioned—one of full-time employment in stable, extended careers—seems long-gone now. This appears especially true for the sort of crusading, windmill-tilting work that calls me, work whose relative tenuousness and low pay isn’t all that new.

So once again, the core question of this blog looms: how do I, a middle-aged man with ancient teaching credentials and modest freelance writing experience, create a life of meaningful, enjoyable and creative work/play, sustaining and sustainable? Continue reading


Filed under My Quest