Show Me the Money

I’ll admit, I’m getting a little nervous.

Why so? Well, six months into this grand experiment, seeking passion-driven work that’s viable and sustainable, I’ve as yet found only the tiniest trickles of income.

Granted, this dry spell was part of the plan: prior to leaping, I’d saved up enough money to go more than a year without income. Even though choosing a negative cash flow runs counter to my conditioning and personality, it seemed necessary to clear out a great expanse of time in order to find…well, something. Myself? A new revenue stream, a new groove in my career track?

Regardless of whether you buy into the equating of time and money, currently I feel as though I’m running low on both—which begs the question of why I’m writing here, now. Shouldn’t I be working on a plan of some kind, or simply job-hunting? Polishing my resumé, updating my LinkedIn profile, scouring Craiglist for freelancing writing and editing work?

To tell the truth, I’m a little afraid of blogging: afraid it’s a waste of time, that I either won’t have anything to say or won’t be able to shut up (not that those are mutually exclusive, of course). Who knows, though: as I’ve written previously, it’s surprisingly difficult, if not downright impossible, for me to ascertain whether a given activity is an utter waste of time or an investment in the future. Is what appears to be downtime a necessary break? Is there learning or networking going on beneath the surface?

Getting back to the subject of this post, a more personal, pressing question these days is why I seem so allergic to income.

Am I just not suited to salesmanship, to the entrepreneurial life? I know that, whatever my natural predisposition, being forced to sell all manner of crap for every single activity or group I joined growing up (from wrapping paper to cheese and sausage to magazine subscriptions and much, much more) turned me off from most forms of fundraising. Still, that’s no excuse: I also know that for things in which I believe, I am a fully capable, passionate salesman.

What’s more, I have all manner of ideas for projects and schemes (which I intend to describe in a future post), some of which could very well generate revenue. So what’s stopping me from pursuing any or all of those? Surely not laziness, or a lack of persistence or self-discipline. So did I acquire other bad habits at some point, tendencies of which I’m as yet unaware? Or am I actually right on target for realizing my vision, yet somehow unaware that I’m doing just fine?

Another thing I’d like to explore in a future post is the way I feel caught between my conditioning for a single, stable career and my craving for meaningful, unconventional work. As much as I’m drawn toward pursuing my passion and making a difference, carving out my own, unique path, something else in me hesitates to wander so far out of sight of the known and familiar. I’m compelled to leap, even as I remain fearful of where I’ll land.

I’ve also written previously that “I like to imagine that I’m living my retirement now, while I’m still young enough to enjoy it.” Really, I feel as though I’m at a point in my life where, as ridiculous as this may sound, I need to do absolutely nothing for a very long time—not nothing, exactly, but rather an extended, apparently aimless, wandering (wondering as I wander, of course). Yet how viable is this (he asks, as his savings steadily dwindle)?

Winter Break from my current school gig is a great opportunity to reflect on these things. (It’s also been, as you may have noticed, an easy excuse to fall off the regular-blogging wagon.) Although I don’t make New Year’s resolutions as such, I’m finding myself, in this fortnight of reflection, with renewed resolve to finely craft my life, bringing it into ever closer alignment with the purpose and path that I actually can, if only dimly, sense.

Skeptical as I am—in the best sense of that term, questioning everything—I do believe this: that we all have access to a way of deep knowing (call it intuition, if you will; no metaphysics required), if only we can manage to get out of its way now and then. For me, it’s becoming increasingly clear that I must learn to trust myself more fully. In true Sudbury style, I need to understand that the best course is always to go with what drives me, what I enjoy (and want to spend my time) doing. It does not serve me to shy away from the unknown, what I’m not (yet) good at. Somewhere, some part of me knows exactly what it’s doing.

I just need to keep that part of me in the driver’s seat. Meanwhile, I wish I were as fearless as the Sudbury students and alumni I’ve known. (Another future blog post, perhaps…) And I hope substantial clarity and income show up before I have to surrender this time of open wandering for a more restrictive source of financial support.