[Upon further reflection (by which I mean obsessive retooling). This "20 Ways" article will be "30 ways." Because there are just that many ways for writers to be miserable. -Ima Lister]
11- Don't write for yourself. Follow trends. Follow the market. Listen to "what will sell." Write "what's being published." It doesn't matter if you really want to write hard boiled detective stories with a magical unicorn investigator who solves grisly murders, and then rides a rainbow back in time to prevent them from ever happening by giving everyone hugs. Instead let market trends convince you to write erotica about a sparkly vampire sex maniac who likes having sex with teenage girls without their consent. This is a double dose of misery. Not only will the market be flooded with "trendchaser" clones before you ever get done, rendering your effort completely futile, but a writer has to work for years, maybe even decades before developing an audience or getting published or making a penny, so you'll also spend years doing something you aren't passionate about. Bring on the misery.
12- Fetter yourself to other writers. Don't develop your own voice. Do you honestly think you have something useful to bring to the world? You??? When we first start writing, the advice of the greats can be so useful. It can give us ideas. It can mold us. A Hemingway binge can make our writing short and declarative (and downright evasive). After a lot of Woolf, we find ourselves writing in a barrage of layered sensual details and loving subordinate clauses folding image upon image with a peppering of simple sentence descriptions to fill in the scene. It's like how we learn to talk by listening to others, but then one day we have our voice and our word choice and our own accent and we stop judging the way we talk against others. But if you want to miserable, don't develop your own writing voice and style. Shoehorn your voice into someone else's because you have nothing to offer.
13- Expect it to be easy. Nothing will make you more miserable than having no fucking conceptual grasp of how much unrelenting, pulse pounding, ass kicking, WORK it is going to take to achieve your goals. If you think you can write a book in a month, you will be mortified to learn that it takes more like a year (or more). If you expect to be able to do a mere grammar polish on a first draft and then pop it off to a publisher, it will be a harrowing experience to discover that the publisher you sent it to is of the opinion that the last time they had too much Mexican food (with way too many margaritas) and ended up taking a massive dump in the urinal (because the stalls were full and it was zero hour), that the splatter patterns of poop on the wall all around were a more compelling than what you just submitted. It will horrify you to learn that you probably need to rewrite the manuscript at least once more (probably twice), revise it at least two more times (or more) before you even think about things like grammar polishing that festering turd. Maintain a naive sense of the industry and how much work successful writers give writing and don't do any fact checking on your expectations--that way you can be miserable every time you get a glimpse of the truth.
14- Internalize rejection. If you get a rejection letter or a nasty comment, don't contextualize it. Certainly don't dismiss it. It's not about that person. It's not about their foibles. It's not about the theme of the issue you submitted to. It's not about a bad fit. It's not about a stylistic difference. It's not about taste. It's not even about something you maybe sent out a bit too soon and could use another pass or two. It's about you, asshole. It's all about you. You are being rejected as a person. You are a fuck up. You suck. Don't have a good cry and move on. Be miserable. They hate you. They really hate you. I hate you! Everyone hates you. Your parents probably hate you. Why would you think you could be a writer?
15- Don't take care of yourself. Treat your body like a garbage disposal. Eat crap. Don't exercise. Get insufficient sleep. Remember that your brain is an organ inside your body. If you treat your body well, your mind will follow. You will end up in a good mood and not suffering and your art will fall to shit. Let your neural pathways degrade from lack of sleep and fill the space in between with sour cream, grease, and extra cheese. (I recommend Taco Bell Nachos for every meal to hit the trifecta.) You'll be miserable in no time. Stay away from vitamin B (6, 12, 18, 36...whatever). To a bad mood, that shit is like garlic to a vampire. No walks for you, the combination of exercise and fresh air could undo all the misery and suffering you've worked so hard to achieve. You've got this.
16- Let "real" shit get to you. You know those "real" jobs where people make "real" money? They're doing something "real" that makes a "real" difference. Let all that shit get to you. Your fake money and fake job and fake life aren't valid choices. Those people are more real than you because they drive a nicer car and wear designer jeans. Art isn't a real thing that makes a difference in peoples lives. When did writing ever change someone's mind or affect someone's life? You should be fixing pipes on toilets or grooming dogs or something that really makes a difference in this world. Miserable yet? Good!
17- Compare yourself to other writers. The beauty of this one is that you can be miserable almost no matter how you choose to do it. If you compare your career to someone further along than you, you can feel like you're behind. If you compare them at your age to you now, you can feel like you aren't making enough progress. If you compare their writing quality to yours, you can feel like you'll never be as good--or maybe that you're so much better than they are and deserve so much more success. There's virtually no way to not end up miserable if you go this route. Just be careful, the one person you don't want to compare yourself to is you from yesterday. That will lead down the path of improvement and before you know it you'll be happily achieving goals and not even slightly miserable.
18- Hold back. Don't give it everything. Treat your creativity as a finite resource. Keep your best ideas for when your career "really takes off" because you know you're never going to think of anything as good as that again. That's the best idea ever. Hold off that awesome story for when you have an audience to adore it, and are really able to tell it. Work only on your second and third rate ideas because they don't involve a risk. You'll sacrifice your life on work you don't really believe in. You will live at the corner of Misery Way and Suffering Street in Anguishville.
19- Be afraid. Be very afraid. You might get a bad review! Someone might tell you that you're not a good writer. They may not gush about how genius you are. You may not get money as fast as you think you will. God there are some truly scary consequences out there! (Maybe not...like....quite as scary as dirty bombs or smallpox, but we can let any fear consume us if we give it enough power.) Live your life in terror of all those really horrible things that might happen if you take risks as a writer. Because lord knows a plane crashing because the pilots have been killed by millions of spiders (which are now swarming the cabin) as you fall from great height into the shark filled ocean has to at least be as bad as finding out a literary review doesn't want your short story. And as Yoda can attest to, fear leads to being a great artist.
20- Sulk. Like complaining from Part 1, sulking has the benefit of combining with any other misery trigger and enhancing its effect. You can sulk about how hard it is. You can sulk about how you don't compare to others. You can sulk about how you don't make "real" money. Any situation can make you ten times more miserable for ten times as long if you sulk about it. If you sulk and complain you're just about guaranteed to be able to ride that wave of misery and suffering until the next misery trigger comes along. You never have to feel not miserable again. Then you're a real artist!
On to part 3---->
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