How My Journey of Freelancing Began

And where it’s taken me...

Leap. It’s the word I chose to help guide me through 2018. My theme for that year.

I knew I was going to pick this word way back in the summer of 2017 when I was sitting out in the yard at my mother’s house, watching two baby owlets learn how to fly. I remember one of them skidding across the metal roof of the pole barn, then crashing into a juniper branch. I remember the other watching him, and then making her own clumsy landings from one branch to another.

It was such a beautiful gray and gold spring evening and I was filled with a sense of delight that I hadn’t experienced in a very long time.

These beautiful creatures just leapt with abandon, no matter how badly their previous landing had turned out. Inevitable crash? Don’t care. Keep going.

At the time, I wanted terribly to quit my job. I had wanted to quit pretty much from the day I began, actually. It’s not that it was a bad job — it was helpful to the community, relatively interesting, and I worked with people I genuinely adored. But the stress was overwhelming in ways I cannot even begin to describe. And…

…it wasn’t writing.

The truth is, what I’ve wanted more than anything since I was 10 years old was to be a full-time writer. Anything else has been just something to get through until I achieved my dream.

I don’t know if I ever really believed I could financially provide for myself as a writer. I mean, I knew it was possible to make a living as writer — there are countless examples of successful career novelists in this world. But could I do it?

In my own circle, there was too much resistance to it. People seemed to characterize it the way they would have if I had said I wanted to be a movie star. Sure, that seems like a far-fetched dream, one that might take endless perseverance and a couple vials of Felix Felicis.

But was becoming a successful writer really comparable to achieving movie stardom? I’m not so sure — though I definitely think it takes the same kind of endless perseverance and maybe more than a couple of vials of Felix Felicis.

In general, the message seemed to be: Get a real job. Maybe you’ll become a writer someday, but just get a backup job until then.

All this loving advice was, of course, delivered with a tone that indicated “someday” would probably never come.

I wrote like a maniac in my twenties, starting novels every few months and sometimes finishing them. But I rarely sent them in to publishers or agents. For one thing, it was the 90s. Things in the publishing world were vastly different back then and despite my well-worn and regularly-updated copies of Writer’s Market, I really didn’t have any idea what I was doing. I was so young and hopeful — I just wanted to write.

But I also didn’t have much confidence in myself. I knew I was a good writer — but great? Good enough to be published? I wasn’t sure and didn’t want an agent to tell me that I sucked. So I wrote for my own pleasure.

By my thirties, I had put aside my “childish dream” to be a writer. I finally surrendered my will and spent $25,000 to earn my master’s degree in teaching. I actually didn’t really want to be a teacher — not unless I could be Jo March, Mistress of Plumfield. Anything else seemed so dreary. And sure enough, I knew I had made a mistake the moment I started student teaching.

After ten years, I didn’t want to teach anymore, but due to some major life changes, I needed to find a job, and fast. So I ended up with the job I had on that fateful evening when I was watching the owlets fly.

By the time I took that job, I was in no mood to keep skipping around the truest love I’d ever had: writing. Suddenly, I was halfway through my life and I had spent most of it settling for work I didn’t want to do because what I really wanted to do seemed just too far outside my reach.

I didn’t want to settle anymore or be mildly unhappy most of the time. And so when I watched those owls leaping about and knew that that would be my word for 2018, I already knew, somewhere deep in my heart, that I was going to quit my job.

Though once the year began, I barely thought of it and was shocked when I hit an impasse that autumn that basically forced my hand and left no option but to quit. Looking back, of course I see it was orchestrated by fate and my desire to change course.

And the owls, of course. The owls inspired it, or at least foretold it.

Then came some of the hardest months of my life. As I write this, I’m still mid-flight. Mid-leap. Over a year later, I don’t know what’s going to happen from one hour to the next and have no idea where I’ll end up or where my next paycheck will come from.

I hit my financial limit in July, and incredibly, miraculously, I found a few outlets, including Medium, that helped me patch together just enough for me to make it one more month. And then I was able to make it one more month after that. And then another…

It’s been hard, I admit. Much, much harder than I ever expected it would be, which is saying a lot, because I expected it to be grueling. I work nights and weekends and I never stop thinking about work. I’m probably averaging $1/hour for all these long days that only bring in just enough to barely cover (or almost cover) the bills.

But for now, I’m okay with the struggle. I’m exhausted, but I’m happy. I love my work and I am so grateful to the people who love it, too.

I don’t mind leaning on my gift, asking it to help me pay my way in the world. I know Elizabeth Gilbert cautioned against that in her brilliant tome, Big Magic, but, with the hope that I don’t get struck by lightning for contradicting that beautiful sorceress, I disagree. She’s right…but she’s also wrong, which is the beautiful paradox of any creative practice.

Life is too short for me not to ask my muses to make big lifts for me. It’s too short for me not to engage with my writing as often as possible and to use it as the container for my ideas to alchemize into the structures of my physical survival in this world.

I get why Liz (can I call her that?) believes that this reliance on our writing can smother our creativity and make it harder to receive the flow of inspiration. This certainly can be true. But honestly, I find that the blocks I encounter due to this kind of pressure keep me from producing good writing less often than the time constraints of my former 9–5 jobs. Good point, right?

So that’s where I am right now, asking my writing to support me. Though I have a long way to go…

When facing similar struggles, what would my owls do? They sit very still and listen. Sometimes I envy the seeming simplicity of their survival. Listen. Find mouse. Eat. Repeat.

The world is filled with mice. There’s no end to that abundance, and likewise, our world is filled with opportunities for us, as well. It’s not really the mice so much as the energy it takes to get them. Like us, owls can become exhausted by the effort of feeding their families. But they keep going. They have to.

Simple as it is, I can relate to that. I can do that. And like them, I must listen. And focus.

Beyond that, I simply do not know. Do I have to return to the pursuit of backup jobs that I don’t really want? Do I have to surrender to low-grade unhappiness so I can pay the bills?

Or is it possible that I can actually make it as a writer? Is it possible that I can pursue the things I truly love?

Is it possible to pursue passion over practicality?

I guess there’s only one way to find out…

© Yael Wolfe 2020