Playing the Long Game

When I started writing with the idea of selling stories, I was 20 years old, going on 21. When I sold my first story, fourteen years had passed. I wrote intermittently during those years. Sometimes pouring out stories, other times going months without writing a single word. Funny thing is, from the very start, I felt as if I would sell each story I wrote. It was years before I began to think of writing as a practice, and more years before I began to realize that the only way to improve was through that practice. And believe me, I needed a lot of practice. The lesson I drew from that is the answer I’ve given to many writers just starting out who ask what the “secret” is to selling stories: Practice, I say. Lots of practice.

I’ve been thinking about this for three reasons:

  1. I’m re-reading Stephen King’s novel Bag of Bones the main character of which, Mike Noonan, is a writer. That has me thinking about writing, naturally.
  2. I’ve felt like I’ve had writer’s block for the last several years. Indeed, reading about the (fictional) Noonan’s own experience with writer’s block was helpful, because it reads so much like my own. I want to write, but I am afraid to do it.
  3. We are beginning to plan for retirement, and that has me thinking of the passage of time.

I turned 49 this past March. Our current plans will see me retired from my day job when I turn 59-1/2. Call it ten years from this coming September. Ten years is still a long time, but given that I’ve worked at my company for nearly three times that (27 years this fall), it is conceivable. If there are no big surprises between now and then (a big if, of course), I’ll retire after 37 years with my company. Not too shabby in a time when five years at a company is a lifetime for many people in tech. Add to that 4 years I worked in college, and 3 years I worked through high school. All told, that’s 44 years of work.

Once retired, what then? I’ll still be (relatively) young. The natural thing for someone in my line of work would be consulting. The idea of consulting, however, makes me shudder. When I began writing I was a junior in college. I had to write “in the margins”; that is, I wrote in whatever little gasps of time I could find. Once I graduated and got a job, it was the same. I worked all day, and wrote when I could. I’ve often dreamed of what it would be like to really have time to write. When I retire, I told myself, I could do that.

And that is, more or less, my plan. But I have also always been pragmatic about my writing. It’s something that I enjoy, but it is something that I am also paid for. The money I’ve made from my writing has never been much more than pin money. It bought me a laptop. But I couldn’t live for a month on the total money I’ve from my writing so far.

Maybe retirement can be different. Maybe I can actually supplement my retirement with writing income. Of course, to make more than pin money as a writer you have to write books–for a fiction writer, this means novels. I’ve written a single novel draft in my life, back in 2013. Moreover, your novels have to be good enough to sell. They don’t have a to sell particularly well–we wouldn’t be planning to retire at 59-1/2 if we couldn’t afford to–but it would be an added bonus if they did.

Thinking about all of this recently, I wondered how I could get to the point where I’d be able to write a novel well enough to have a decent chance of selling it. And I had a kind of epiphany, courtesy of Mike Noonan (or maybe, Stephen King). In Bag of Bones Noonan’s writer’s block is hidden from everyone for the first four years he has it thanks to a trick he had up his sleeve. Over the course of 10 years of writing novels, the fictional Noonan wrote 2 novels in 4 of those year and put them in a safe deposit box. He was playing a long game. It was these 4 novels that gave him breathing room when his writer’s block set in.

My epiphany came from the fact that Noonan was expected (as most mid-list writers are expected) to write a novel a year. And he did this for ten years. Ten years. That’s just about how much time I have before I retire. As in most of my own stories, one idea isn’t good enough. It has to collide with another idea before there is chemistry. The idea this collided with was my advice to new writers: the secret to selling stories is to practice.

I’ve always been a short story writer. It took me a while to get to the point where I felt I understood the form and could write a story that would sell. If I had to do it all over again, I’d practice more, trunk stories that I knew were junk after learning what I could from them, and then move on to the next one. Many writers I know had not only written many short stories before they began to sell, but many novels too. I’d never done that.

Looking at it now, maybe I am finally in a position to play the long game. I have a little over ten years between now and retirement: if I could write a novel a year for the next ten years, that should give me plenty of practice. Ten novels is a lot of practice by any standard. The more I thought about this, the more I realized that this really may be a thing. Not only does it give me a target to write to, but it also:

  • Allows me to try things without much risk. For instance, I plan to experiment, writing different types of novels to get a feel at what works best for me. Maybe some s.f., maybe some mainstream. Maybe some mysteries. Maybe some thrillers or horror. Why not? I’ve got ten tries. I should explore, right?
  • Gives me a framework to figure out how best to organize my time. I don’t want to spend every waking moment in retirement writing. We have other plans, too, which includes travel and doing all of the things we didn’t do because we were saving for retirement. So figuring out when to write, how much is reasonable, etc. is the part of the practice.
  • May result in a novel manuscript ready to submit when I do retire. Assuming, of course, that with practice, I will improve somewhat each time around, maybe the 9th or 10th year will produce a story that I can actually sell, thus giving me a little head start when the clock rolls over into retirement time.

For some reason, this idea has caught fire with me over the last few days. For the first time in a long time, I actually feel like writing. I’m not quite ready to write. I’m still thinking through the overall logistics of my plan. And I do need a plan. That is one thing I’ve found that helps me focus. A novel is a big task. Breaking that task down into small steps makes it feel much more manageable to me.

Is it possible? It is possible that when I retire, I can write and begin to sell novels? I think it is. I’m not deluding myself into thinking I’ll be anything more than a minor writer, but I have two things in my favor that I think give me a big advantage: (1) I’m willing to work hard, and put in the practice necessary, even if it means throwing most of those drafts away; and (2) I’ve already proven that I can write fiction well enough to sell it in short form.

So when does all of this begin? Like I said, this is a new idea for me, and the plan is still germinating in my mind. (What does write a novel a year mean? Does it mean write a draft and throw it away? Does it mean write a draft, set it aside for a while, and then write a second draft–my usual practice for short fiction?) Right now, I’m thinking of trying to have a plan finalized before the end of the summer. That means I’d begin carrying it out sometime in September–just about exactly 10 years before my planned retirement date.

I am playing the long game here. A lot can happen in ten years. But I am exciting at the thought of attempting this. I am excited at the thought of actually trying to write again. And I have a fictional writer to thank for the inspiration. That seems almost poetic to me.

About Jamie Todd Rubin

Jamie Todd Rubin writes fiction and nonfiction for a variety of publications including Analog, Clarkesworld, The Daily Beast, 99U, Daily Science Fiction, Lightspeed, InterGalactic Medicine Show, and several anthologies. He was featured in Lifehacker’s How I Work series. He has been blogging since 2005. By day, he manages software projects and occasionally writes code. He lives in Arlington, Virginia with his wife and three children. Find him on Twitter at @jamietr.

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