Typically on Wednesdays I’ve been reposting old Sudbury content, especially my 2009 posts as a guest blogger for This Wednesday I have no business posting at all, as I’ve been in bed for all but about two of the past twenty hours. But I thought, why let illness get in the way of checking in and sharing a few thoughts on my quest to make passion-pursuing sustainable?

Tonight, it occurred to me that, much like a middle-aged celebrity, my life these days is one of reinventing myself. Far more than a mere geographic relocation or career shift—or even the effort to make money doing what I love in a place that feels like home—I am engaged in redefining who I am and what I’m capable of doing.

For example, despite the many times people have said I’m brave for making this leap, I don’t feel very brave at all. On the contrary, I’m often anxious over whether this grand scheme will work, whether I should have leaped at this time and to this place. As you might imagine, the constant novelty and uncertainty is very exhausting. But this gambit requires confidence and boldness, so I must play the part.

I come by my cautiousness honestly. As I’ve probably mentioned before (and will probably repeat), I was not programmed for a life of defying norms and venturing outside the mainstream. In the world where and when I grew up, the idea was to find a career and stick with it. So these past fifteen Sudbury years, and especially now, I’ve not only been taking risks with my financial and material security, but going against my training.

My training, and my nature: while an obstinate, determined streak is absolutely part of who I am, more often than not my drive has met its match in second-guessing and hesitation. This part of me can’t believe I gave up the best job/school I’d ever known, along with the best choir I’d sung in to that point, to chase after a crazy dream of building up CASE, as well as securing more of the “money, mission, mate, and home” mantra I’ve decided is my personal vision of the good life.

To some extent, then, my current quest plays out an internal struggle between, on the one hand, the part of me that wants to play it safe, sticking with familiar territory and tasks that offer a reasonable chance of success and praise; and on the other, that part of me driven to seek out the situations most challenging to my desire for security. I’m reminded of my going to college in Chicago despite growing up in a small town, and of the many times I’ve found myself on stage, making music, acting, or speaking, despite being a textbook introvert.

I’m also reminded of when I left a secure teaching job for a second round of grad school, and then when I left grad school for my Sudbury career. In other words, this is not the first time I’ve leaped: but it never seems to get any easier.

Making CASE into a going concern involves sailing into uncharted waters, where I can rely on some strengths, but for the most part have to forge ahead despite not knowing what the heck I’m doing. Making a new life in Austin requires a willingness to be new and disoriented, as well as overcoming the impatience I typically mask with stubbornness and a refusal to give up. Although I don’t really enjoy gambling, I feel as though I am playing craps with not only my savings, but my even more precious and limited time.

Often this quest does not feel the least bit safe or smart. Who do I think I am, taking risks like these? It can be difficult to ignore the voices that tell me I should be scared, that I’m not capable of pulling this off or doing what it takes. Why, these voices ask, didn’t I just stay put, where even though I didn’t feel at home or have much long-term security, at least most things were familiar and a couple things quite good indeed?

At times like these, I try pattern myself after the Sudbury alumni I know, who seem incredibly self-assured, boldly pursuing their dreams despite levels of uncertainty that would scare many of us conventionally raised people out of our proverbial boots? I also fall back on my limited Zen training. Understanding the limits, distortions, and transience of our self-images, I try to remember that ego is malleable—that I can reinvent myself.

And so this Halloween, I can choose to go as a better version of myself, one who is confident even when he’s scared, even when doing things at which he’s new or not particularly good. Tonight I can vow to keep plunging into the unknown and uncertain, to lean into the fear even as I trust that my deepest, truest self really does know what it’s doing.

I’ll be honest: this quest of mine for “a viable life of mindfulness and creativity” is much more daunting than I’d anticipated. Doing what you want with your life is often far more frightening than the best horror movie or the most convincing haunted house. I can only hope that the rewards are equally thrilling.

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