August is for innovation, or escaping the scary freelance financial life cycle

August has been flying by, faster than I'd like, especially because on Friday I'll be heading off for 9 days and am not quite ready. This is my month for two big new projects that are both exciting and a little panic-inducing: prepping my first self-published anthology (a reprint/expansion of 2007's Sex and Candy, whites now out of print), and preparing the launch of my first new set of online classes. I was going to say "self-hosted" online classes, but that's not strictly true; I'll be doing them through Teachable, which is a whole learning curve unto itself. I want to start with three classes, so that's a whole lot of writing and video content to create.

Both are a lot of work for zero money upfront; in fact, the anthology will cost me at least $2,000, and that's just for author and copyeditor payments, not the actual costs involved of getting it online. The Teachable classes has required me to buy a microphone and likely will require dozens of hours of my time, but doesn't cost anything to upload; they take a small percentage of course fees. I'm doing these things not just so I can "feel like a businesswoman," but so I can slowly wean myself from the gross, needy, helpless feeling that being a freelancer produces in me. Everything I do requires someone's approval in order for me to get paid: with my books, it's my publisher's approval and then, of course, readers' approval; if nobody buys my books, I make nothing (I get a small advance on each anthology but almost all, and sometimes more than that advance, gets paid to authors and copyeditors and also my assistant, who helps me with promotion). With freelance writing, whether my pitches are accepted or not is at editors' whims, then whether I get paid in a timely manner or not remains to be seen. Those are stress-inducing situations, where from one month to the next I don't really know how much cash I'll have on hand. Sure, right now I have a weekly copywriting job, but as a freelancer, that could end at any second.

So I chose August as my month to set these new projects into motion. My goal is to release the self-published book in September and hopefully launch the first of my classes then too, and add some more in the new year. Meanwhile, I'm also reading everything I can about marketing and trying to learn how to get my books and audiobooks into the hands of new readers and listeners. I'm trying to think like a beginner because there's really no point in pumping out anthologies if the sales are stagnant, if I'm not reaching new readers, if I'm not innovating. I don't want my forties to go by and just feel like I repeated my thirties ad nauseam professionally, and even more, I don't want my forties, as I inch ever closer to retirement, to go by and not have stacked up a good amount of savings. Obviously, both these projects are gambles, albeit small stakes ones. I could invest my money and time in them and they could bomb, hard. But I don't think they will. Rose Caraway is going to be recording the audiobook of the Sex and Candy reprint, and her audiobooks earn me more in royalties than my print and ebook titles. I trust that her podcast listeners will enjoy these sweet and luscious stories. And I've asked some of the alumni of my classes if they'd be interested in the first few topics I'm planning, and they are.

I even have a cool new fishnet stockings logo I'll be sharing here soon (if you want to see it first, subscribe to my newsletter). I'm excited, but being your own boss takes a great dose of vision and belief in yourself, and I don't possess that every day. Yesterday I got really down on myself, wondering what the hell I'm doing, whether I'm in over my head technically, whether it's worth it or if I should just stay with what I know. I keep returning the realization, though, that I want to try something new, even if it fails, because either way I'll learn. Both of these new systems will mean I'll see sales data in real time, which will enable me to change things like book covers and prices as needed. That's the part I'm most excited about: feeling in charge, rather than passively waiting around, fingers crossed (or more like, nails being bitten to shreds). I'll be sharing more about these projects as they get closer to completion, but for right now, this month I'm in the thick of learning and exploring and trying to take a little bit of control in such an unpredictable career path.