Write Road P.S.

Today’s post came to me as in a dream—or rather, insomnia.

Waking up in the middle of the night, I realized I’d left one or two things out of yesterday’s post regarding what I don’t know but need to figure out as I go about reviving my dormant freelancing work. Rather than hastily scribbling notes (I’m not sure why I didn’t), I rehearsed this thought-kernel to myself before resuming my on again, off again sleeping, then and each time I woke until morning, when I opened my browser and typed what was still with me.

(Incidentally, I’m quite pleased to have posted on three consecutive days, and that I haven’t had to schedule or make time, haven’t had to scrounge for topics or push myself overly much. Seems like a good sign, a really good one.)

“What I Don’t Know” could fill volumes (increasingly so, the older I get): in this instance, it includes all the concrete practicalities of building a freelance business. After sixteen years with Sudbury schooling, I’ve developed a deep appreciation for entrepreneurs, for those who create and grow their own businesses. This is no accident, as Sudbury schooling very much embodies a start-up mentality—and not simply because our schools are small businesses. In my experience, Sudbury fosters a willingness to jump in before you fully comprehend what you’re doing, and then just keep doing it—whatever it is—learning as you go, becoming expert enough in all the many, varied skills required for success.

Or as an Alpine Valley School alum once said during a panel discussion, in the context of starting her own business, “We kept telling ourselves, ‘We’re smart people; we’ll figure it out.'” It’s no surprise to me that so many Sudbury alumni go into business for themselves: self-motivated individuals used to taking initiative, persisting past obstacles, confidently calling their own shots—Sudbury is one of the best preparations for entrepreneurship I can imagine.

I, however, only came to Sudbury as an adult, so I still have a lot to learn (and un-learn): in particular, confidence in the face of the unknown remains a challenge. Among the things I’m daunted by these days are questions of structuring a business, accounting, and taxes. Should I set myelf up as an independent contractor, or create a sole proprietorship or LLC (and what do those categories entail, exactly?) What’s the best accounting software—what do I need to account for, and can I manage it myself or should I look into hiring someone? Should I consider taking some Small Business Administration seminars? Where do I start in sorting all this out?

Beyond these basics, I’m still very much the novice when it comes to blogging and social media in general. How frequently should I post, on what platforms, and how do I go about generating a following? And, harking back to yesterday’s post, how do I balance this push to make money through wordsmithing with my desires to participate in my local Sudbury school and build my Sudbury nonprofit?

Even with all these questions staring me down, I remain mindful that I do possess some talent here, some traits and some experience that should serve me well in this quest. For one thing, even with all my circumspection, I’ve rarely shied away from taking a big, bold leap when that seems the thing to do. And from studying, teaching and practicing the art of writing, I know that the only way to get into doing something is to start doing it.

Now.

Refine later, hurl myself into it…

now.

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