Apple-Obsessed Author Fella

Some Thoughts For You Mid-Career Writers Out There

Writing advice online is generally geared toward the new writer. It makes sense — most recipes online are catered to people who can cook but who don’t have a stable bank of techniques on which to trade. Sex advice, on the other hand, is often very different — it moves well-beyond INSERT TAB A INTO SLOT B and THIS DIAGRAM SHOWS A HUMAN PENIS and goes into some trickier business. It assumes you’ve done it and know what you’re doing, and so you start to get things like HOW TO INCORPORATE VEGETABLES INTO YOUR LOVEMAKING or HOW TO FUCK FOUR PEOPLE AT ONE TIME ON PLAYGROUND EQUIPMENT AND WHY THAT GETS YOU CLOSER TO YOUR INNER GOD. Sex advice goes right to the Kama Sutra (“monkey steals the plums”!) while writing advice is very frequently 101-level stuff (“how to put words next to each other”).

I find really one of the things that is missing from discussing of a writing career is talk of what a mid-career writer should do. Nobody talks much to the writer who’s already doing what she wants to do, with a handful of books already under her belt. But this is necessary stuff. You get to a certain point in your career and it starts to feel like you’re in a one-man washtub boat out on the ocean with no sign of shore and only the glimpse of islands in the far-off distance. The easiest thing to do is just to float, but the best thing to do is to pick a direction and paddle —

Problem is, what direction?

I’m in my “mid-career” now, I guess — which is to say, I’m not a beginner, not at all, though I certainly haven’t mastered my Authorial Kung Fu, either. Though I’ve only been publishing books since 2012 or so, I’ve had quite a few put out into the world (cough cough sixteen /humblebrag), and I’ve also been writing professionally for about two decades (haha oh shit wait I got old). I’m no chump, I like to hope, but I’ve also not had anything really really break out, and I still find myself wandering this career path without a map and a torch.

Given that I am at this point, I probably need the advice, but nobody’s really giving it. So I’m going to do the next best thing — I’m going to offer up my own advice and pretend I know what I’m talking about! This is the Internet, after all. It is the only way!

So, here are some thoughts on being a mid-career artist — aka, HOW TO FUCK FOUR NOVELS AT ONE TIME AND HOW THAT GETS YOU CLOSER TO YOUR INNER ART GOBLIN.

Or something.

(As with all posts here, this is very YMMV. And certainly some of what follows repeats things I’ve said before. As such, take it not just with a grain of salt but a whole salt lick.)

Good Time To Reevaluate Goals (Present And Future)

Forget loftier questions such as who are you as an author and what satisfies you the most as an word-chugging art-monkey, and go straight to the most practical one — the one that has to do with output, the one that has to do with practical application:

What do you want to write?

Maybe right now you’re writing the thing you want to write. Maybe you’re not. Maybe you like what you’re doing now but you think it’s time to try your hand at space opera, or mystery, or you really have a hankering to write about the long-simmering adventures of Gibblins McKink, an erotic dwarf detective. I will say the advice now applies as it did when you were a new writer, and it will apply in 30 years when you’re a writer on his death bad for having huffed printer ink for too long: write what you want to write. This career is not so lucrative generally that it’s worth writing things you don’t like. There is, of course, nothing wrong with writing just for money and just to the market — you do you, but I personally find it unsatisfying, and further, the market moves both so slowly and so unpredictably that I wouldn’t even know how to manage it. It’s like trying to thread a needle held in somebody else’s trembling hand. It is vital to note that satisfaction in a creative career is a very good way to stave off burn out and to ride out the DARK TIMES, and so for me it matters to be writing what I want to write.

Thus, I factor that into my overall plan.

And my plan looks a little something like this:

I try to figure out what my next year looks like.

And the year after that.

Then, five years.

Then, ten years.

This isn’t just about what books I want to write. It’s about where I want to be in my career. It’s about what kind of money I hope to be making, how I might evolve myself as an author, what sassy dance moves I might perform if I am ever mistakenly given an award. Really, you can have nearly any goal you’d like, reasonable or not — “I want to be published by Rangdom Panguinhaus. I want a short story published in Corklin’s Literary Salon. I would like to write a comic book or a video game or the marketing copy for a sex toy company. I would also like to quit my full-time job, be a bestseller, and have a trained marmoset to fetch me my feather and quill every morning!”

(Note: it’s better to have goals you can control rather than goals you can’t.)

(Note: it’s still fun to mentally identify goals about things you can’t control anyway.)

The long-looking plan works like this, by the way —

The first year is pretty much what you’re going to do now. It’s what you have on deck. You likely have some irons in the fire in terms of deadlines and contracts, so do those.

The second year for me may have more deadlines, but it’s also likely THE PRECIPICE — meaning, somewhere in the year after this one my career is going to again fall off the cliff and down the side of a mountain and into a hole where it will be eaten by rats because really, the writer’s career is pretty much always in danger of this. You’re always trying to negotiate the upcoming cliffs. An art career is peaks and valleys — but it’s both creative peaks and valleys and financial ones. Worse, those peaks and valleys don’t line up well. A financial peak sets you up for new creative deadlines — and then you fulfill those deadlines and have no more and suddenly you’re back in the hole and something something rats. It is the constant act of trying to juggle SELLING WORK and WRITING WORK, and sometimes that work is on spec which only further confuses the issue. Oh and then there’s also PROMOTING THE WORK which is a whole other thing I’ll talk about later in this post. A post that is likely to be epic in length and I’m sorry about that.

So, the second year is about evaluating how you’ll stake out temporal territory to plot and scheme what comes next — either a brand new novel that you’ll write or a pitch for a new novel that your agent will attempt to sell. (We’ll talk about agents shortly.)

The fifth year is a bit of wish fulfillment, sure, but it’s also the garden you envision growing up out of all these seeds planted. Looking five years down, you can start to see that what you want then needs to start now. It’s a good impetus for getting all your quacking author-ducks in a row. I find that my career is very much about these seeds. And I ask myself every week — what seeds am I planting? How am I moving toward my goals, even if in only incremental ways?

Ten years? Well, you’d be forgiven if ten years down your only goal is TO NOT BE DEAD, or TO BE CLINGING TO THIS WRITING CAREER WITH AT LEAST THREE FINGERS. But for me it’s also about bigger, loftier goals — positioning of oneself as an author, predicting potential career pivot points, considering larger and stranger diversifications.

Also Good Time To Revaluate Agents

I know quite a few professional mid-career writers, now.

And several of them have done the thing where they break up with an agent.

At the start of your career, this is unthinkable. You’re just happy to have an agent. It could be an agent who lives in a garbage can like Oscar the Grouch and you’re like, WHATEVER, PLEASE JUST SELL MY BOOKS, GLORIOUS TRASHMONGER. This isn’t the greatest way to be, of course, and sometimes it leads writers to a fracture in the agent-author relationship. The agent says she won’t — not can’t, but won’t — sell your latest novel. Or he tells you that he thinks you’d be better off writing [insert genre you don’t really like to write]. The agent offers up a view of your career that isn’t your view of your career. And some writers? They go with it. They see themselves as lucky to have an agent at all and so they follow the river where it takes them.

Do not do that.

Do not be that author.

This is a very good time to reevaluate your agent. The wrong agent is worse than no agent at all. Let me tell you an agent’s job — an agent’s job is to help you, the author, sell the books you write. The agent represents not a single book but rather, the total author. The agent also represents authors, not publishers — though some seem more interested in helping the publisher, instead. The agent is there to bring out the best career for you, and as a result, get both of you to make some motherfucking money in the process. If the agent does not see the potential in you, the total author, the agent should not represent you and you should not want the agent to represent you.

The agent-author relationship is a partnership — both financial and to a degree, artistic.

That’s not to say you shouldn’t trust your agent’s judgment. But those judgments should be again toward helping you realize the version of the career that you envision for yourself — not the career the agent envisions. (This is similar to the editor’s job, in a sense. An editor helps make your book the best version it can be. An editor doesn’t turn your book into somebody else’s book. So too it is with an agent and your career.) You do not work for your agent. To a degree, your agent works on your behalf, though not “for” you in that she’s not your employee just as you aren’t hers. It is a mutually beneficial relationship. SYMBIOSIS. If that symbiosis fails, well —

You may need to break up with your agent.

It’s okay if you do. Lots have, and they’ve survived.

Some of you may think you can get by with an attorney or a manager instead of an agent. This is true if you’re a screenwriter… but to my mind, less true if you’re an AUTHOR OF BOOKISH THINGS. In publishing, agents are both vital in their contract skills but also valuable in the relationships they have with editors. They know the history of a publisher, they know what can be gotten and what can’t, whereas most attorneys do not possess a familiarity with the industry beyond the contract you put in front of them.

(Er, just in case my own agent is getting wide eyes reading this — ha ha, no, I’m not going anywhere. You’re stuck with me! And my daily neurotic emails! Sorry!)

Cash Money (And, Should You Quit Your Job?)

A career as an author is about a lot more than money.

…and yet, it’s also a whole lot about money.

What this means is:

a) You should be getting paid. Any of that “for free exposure” bullshit better be over and done. Writing has value. Art has value. You are not a zero, and so your fee is not zero.

b1) You should be thinking about ROI — return on investment. Anything you do in service to your career needs to be considered with a return in mind. No, not every return is financial — some returns are about happy-making vibes or relationships or some other abstract metric. But financial matters. Planning on traveling in service to your work? Doing cons and festivals? Buying tech upgrades? Whatever it is, make sure you’re not putting out more money on it than you’re bringing in. (If it costs you a lot of money to sell not a lot of books, that’s a problem.)

b2) That said? “Creative ROI” is a thing. Sometimes you plant seeds in a new format or genre for less money in the aim that this garden will grow in a specific direction and offer up new bounty.

c) If quitting your job to become a full-time writer is a goal, think hard about it. Save up. Get ready. Don’t built a parachute on the way out of the plane. Keep your job as long as you can. For me the metric of when to quit your job in service to your writing is this: you cease to have time to do both. You have enough contracts and deadlines than either the day-job goes, or the writing gig does.

d) You should be having financial discussions with your agent. Not just creative ones.

e) You should be on a budget at home. The money that comes in from writing is unpredictable-ish — I mean, you can peg certain payout periods given your contracts, but the point is, the money fails to be steady. Budgets will help you figure that out.

f) Taxes are their own special fun. Have an accountant or book-keeper or MAGICAL MONEY HOBO to help you. Do not do it yourself unless you are well-trained in this dark art. Be advised: you can totally write-off lots of awesome and actually vital things as an author. Books are tax deductions. If you don’t think that’s totally awesome then I’m not sure we can be friends.

On Royalties And Advances

Information on this subject is often veiled behind shimmering clouds of bewilderment, like it’s all a state secret – for the most part, royalties and advances are hush-hush. Again, an agent brings value to this equation — they have enough experience ideally to pierce that veil of secrecy. They know the score. They know what’s gettable. And they’ll push to get it. Royalties don’t often budge, though it’s best to get royalties paid out on list/cover price rather than net, because net will vary depending on discounts and other price variations. Further, contracts can offer escalators that change your royalty or offer bonus payouts if certain sales targets are hit.

Advances are tricky, too — note that once you start to get those vaunted low six-figure payouts, you’ll feel like you made it. And those payouts are a helluva lot better than, say, five grand. Just the same, budget accordingly. One novel a year at ~$30k a year is nice money, but it’s not always livable money depending on where you live. Hell, if you live in New York City, that money will pay for four minutes of rent. (Oh, that reminds me, mid-career authors — it might also be high-time to reevaluate where you live. You can write from pretty much anywhere in the country, and all you need is reasonable Internet and proximity to an airport. Otherwise, you can extend your Publishing Ducats considerably by living somewhere with a lower cost of living.)

Hey, By The Way, Keep As Many Rights As You Can

Publishers will want to take rights from you.

Fight this with tooth and nail. There are exceptions, of course, as there are to every rule. But generally speaking, at this stage in your career, scoop up foreign rights and audio and film/TV and shove them in a box and then lock the box and then set a cranky badger to guard it.

Translation: Read Your Contracts

That header says it all, but really, no foolin’ — read them. If something is vague, ask your agent or the publisher. If you don’t understand something, ask the question. You don’t need to be a contracts lawyer, but read the contracts, learn about the clauses, realize what it means. Non-compete clauses can kill you if they’re too strict (though at the same time, publishers also don’t want you running around publishing 47 different epic fantasy novels because bookstore shelves have finite space for that shit).

Your “Do Not Die” Plan

Know your exits.

On an airplane, in a movie theater, in your writing career.


I am aware at any point the floor could fucking fall out from underneath me. The publishing industry could poop the bed or my books just won’t sell anymore or something cataclysmic and unpredictable could happen. Have a plan. Know what happens if that happens. Do you get another day job? (For me, that gets tricky, because my skillset has narrowed to the point where I’m good at writing things, less good at, say, sitting in a cubicle and doing cubicle things.) Do you seed opportunities in game design or comic books or marketing sex toys? What about Patreon? Or journalism? IS THERE A PYRAMID SCHEME YOU CAN SEIZE UPON TO EXPLOIT YOUR FAMILY AND NEIGHBORS? Lack of pyramid schemes is what killed the dinosaurs.

Have a plan. Be prepared for the meteor. Know how to evolve and, well, not die.

Survival May Mean Diversification

Being able to write in different media, different genres, different formats, different voices, for different age ranges — it matters. Different publishing models are an option, too. Writing diversely is a skill. It’s like having a Swiss Army knife out in the wilderness in case some shit goes down. With a Swiss Army knife, you can cut kindling, you can open wine, you can do a favor for a grizzly bear and punch holes in his belt if the belt is too small — okay, you know what, I’m getting the feeling here that Swiss Army knives actually aren’t that useful. Never mind that metaphor. Point is, get savvy writing lots of different things. Get ready to stick and move. It will make you a better writer and help you survive.

Something-Something Self-Publishing

Let me be so bold as to say, you should be self-publishing something. Maybe it’s your dominant mode, maybe it’s a side project. But self-publishing offers an opportunity to control the total content and have something out there that earns you slow but steady money. (Maybe more if you get lucky, but in a writing career, never make “GET LUCKY” part of your overall plan. No form of publishing is a lottery, so don’t treat it like one.)

Authors with devoted fanbases can use self-publishing (or other variant publishing models like Patreon) to deliver new stories to those readers — and, duh, make some coin in the process.

Financially, when I talk about gaps in payment, two primary ways to bridge those gaps is with:

a) royalties


b) self-publishing.

(Note, self-publishing does not pay “royalties” no matter who calls them that.)

That money softens the edges, and sometimes can do more. Maybe it pays for dinner, maybe a car payment, maybe more. But it’s meaningful.

Multiple Publishers

I have multiple publishers. Some authors do; others are locked into one by contract, by choice, or by the inability to provide fresh novel-length work for multiple outlets.

The advantages of this: you are diversified automatically, and you can write across different genres. Plus, you get experience with multiple editors and marketing departments. You start to zero in on what works, what doesn’t, what you like, what you don’t. And you foster relationships that matter, and not just relationships in a narrow way, but more broadly. Across an industry.

The disadvantages of this: publishers will want their own earned space on the release slate (meaning, on bookstore shelves), and that can be competitive and tricky. Also, deadlines may shift and suddenly work will back up and clog your creative pipes.

On The Subject Of Pseudonyms

A publisher may call upon you to take a pseudonym. OR NOT.

Advantages: you get to be a debut author all over again and that gives a boost to that particular book. It also lets you ditch any particular baggage you may have with your name, especially if your name is associated with something weird like a book about a guy who cornholes goats or something. Plus, maybe you get to write for a different age range or genre.

Disadvantages: you don’t get to be you and you have to handle two names and any work you’ve done for your own self-promotion doesn’t carry over and also you have to adopt a second personality and then that second personality becomes a serial killer.

Wait maybe not that last part.

Note, that I’m finding pseudonyms are often expected of women more than they are of men. This is likely because of sexism both in an audience (they won’t follow a ‘romancey’ author to a new genre because ew girl germs) and because of sexism in the industry (the same industry that leads to very distinct gendered book experiences which is frequently bullshit).

Branding And Platforms And — *Barfs*

I’m going out on a limb here and say that, as an author grows into a career, that author starts to realize that a lot of the branding and platform talk he listened to early on is at least half a sack of monkey shit. What I mean is this: your writing career is predicated on writing books — it’s very seductive to believe that Our Every Movement Online will somehow be The Crucial Detail that sells our books. So we curate a persona and work very hard to say the Right Things and not the Wrong Things and to Demonstrate Our Social Value As A Content-Delivery-System but at the end of the day people want a book they like. They want a book they enjoy for whatever definition they have for “enjoy.” The author matters, but the author is secondary to the book. It has to be that way. You’re not an online personality. You make stories for a living. And it’s tantalizing to assume the story you should be making is YOUR OWN, but I find that at the end of the day, it’s a very big distraction and will pull you away from doing the thing you should really be doing.

Two rules here prevail:

Don’t be an asshole (and if you are, try to fix it).

And be the best version of yourself online.

That’s it. Beyond that, write books. The best you can.

Also Something Something Marketing And Self-Promotion

Another myth that gets shattered is that the author is somehow fully responsible for turning her book into a smash-bang hit. The marketing is on our shoulders and we should be self-promoting to hell and back and if we’re not then our book is doomed to the Hell that is obscurity.

We should self-promote, yes. Author Stephen Blackmoore just said it very well on Twitter — “All we can really do is make people aware of it. We’re not moving used cars.” A writer can sell 10s or 100s of copies of his book. Selling 1000s is a marketing job that requires more than just getting on social media and waving your arms like a drowning swimmer. It’s the publisher’s job, really, to move that number. (Note: if you self-publish, you’re now the publisher so you should be treating marketing like its very own department inside your brain.)

Here’s where it starts to matter — it starts to matter in the industry. Your self-promotion isn’t always about reaching an audience of readers, but also about reaching a community of writers, editors, publishers, buyers, agents, bloggers, reviewers, and so forth. (Bemoan gatekeepers all you like; they exist everywhere, and are often not appointed to the role.) Now, to be clear, “self-promotion” here is not the narrow view of SELL YOUR BOOK, but rather, SELL YOURSELF BY BEING A COOL, UNSHITTY PERSON TO TALK TO. MAYBE EVEN FUNNY OR SMART OR INTERESTING. It’s not about shoving your book in a cannon and pistoning it into people’s faces. It’s about you being nice and useful and connected to that world.

That’s not branding. It’s not about platform.

It’s just about being you.

This is also necessary outside social media.

Take meetings.

Introduce yourself.

Go to festivals and cons and parties — not like, all the time, because again your role is BOOK WRITER, not LITERARY GADFLY, but meeting people matters.

Bookstores Still Matter, Too

Meet booksellers and be nice to them. (Librarians, too.) Meet book buyers and library buyers. Again, not just for the crass BOOK-PEDDLING, but because these people are vital parts of the book-to-reader ecosystem. Physical book sales are up (though don’t trust anyone who tells you e-sales are down, as those metrics fail to recognize sales from self-published digital releases).

Support bookstores and libraries. Go to them. Be awesome to them. They are the drug dealers peddling your narrative narcotics. Ignore them at your peril.

Your Authorial Community Is Extra-Meaningful

Networking has its limits. The writer’s career is not all that. And yet —

The community of authors around you is super useful. I don’t necessarily mean the sum total of it, but Jesus on a bicycle, get some friends who are writers. Here’s what that nets you:

– Commiseration and celebration.

– The sharing of information that may otherwise be difficult to come by (info on advances, royalties, contract clauses, publishers, editors, agents, whiskey, that one jerk on Twitter, whiskey, more whiskey, and coffee).

– A community willing to back each other up, whether that’s regarding publisher disputes, contract issues, or again, that one jerk on Twitter.

This is also one reason to join a professional writer org. (In genre, SFWA is an example.) It’s not a necessity, but it’s one way toward that community.

Your Books Might Not Sell

Every week a nuclear megaton of books drops on the reading audience — it is a lot of books for not a lot of audience. A great many of books sell less than we’d like. I’ve had books sell really well. I’ve had books where you look at the numbers and want to ask, “Shouldn’t there be another zero on there?” And the publisher quietly shakes its head and then pushes you down an elevator shaft.

Your book may not sell.

Many of your books may not sell. Or they’ll sell well but not well enough. Or you won’t earn out — “earning out” is of course a wonderful thing where sales outpace your advance and then you start getting those precious royalty checks, which often begin embarrassingly small (“With this check I can afford the gas it will take to go cash it, huzzah!”) and then ideally begin to climb in number and begin to represent a slow-but-steady roll of incoming quarterly cash.

If your books aren’t selling, there is only one piece of advice that is true, I’d say:

Keep writing.

Books do not sell for an unholy host of reasons. It might be you. It might be the publisher. It might be the marketing department of the publisher. It might be the audience, or the retailer, or the fact that your genre is overloaded, or the fact it’s a weird genre, or, or, or. Some books land well. Many land nngyeah, okay. More than a few are flung bricks landing in puddles of shit.

Some authors drop three pooch-fucker books and then the fourth comes out of the stable like a magnificent stallion. Some authors hit big on the first and then sales descend every book thereafter. Others build a slow and steady career over decades. It’s rarely ideal, but you can almost always make it work. If you do one thing: survive.

All you can do is hang on. Be like the little cat dangling from the branch — just hang in there, delicate writer kitten! BECAUSE WINTER IS COMING AND YOU ARE A VULNERABLE LITTLE THING AND SOON THE SNOW GOBLINS WILL HUNT YOU FOR YOUR TENDER MEAT.


Survival is the most vital success an author can engineer for herself. Simply staying in the game — emotionally, mentally, productively — is huge. It counts for a lot and it is the way to a stable writing career. Again: this is a career of peaks and valleys. A lot of writers love the peaks but can’t hack the valleys. Learn to love the valleys for their ability to let you rethink and reframe your careers and give you a new peak to which you can look forward.

This Is Only The Tip Of The Iceberg

Sweet crickets, I could keep on going.

And I probably will — but in another post. This one has gone on too long.

At the end of the day, the most fundamental advice is the same as it is for anybody: don’t get mired in drama, do your best work, sell it for what it’s worth, and try to improve with every iteration. Do not base that improvement purely on sales or reviews, because both of those are the result of a thousand wildly spinning compasses. Sometimes it’s on you, sometimes it’s on the publisher, sometimes it’s on the fates themselves. You control what you can control, which is the work. Write. Edit. Publish. Repeat. Survive. Look to a career that is not just the few books and the few years you’ve invested but is an ongoing carousel of the weird wonder that is a writing career.

* * *

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Writer’s Digest