By the time you read this I'll have over 100 LitReactor columns under my belt.
There have been some successes, some failures, and a whole lot to learn for someone new to the freelance writing game. Some of the lessons are about writing, pitching column ideas, productivity, and a good portion are about Demolition Man.
Let me narrow it down to the 100 most important things. Which are in a particular order: the order in which they came to me.
1. tl;dr is the realest shit ever.
2. Don't rail against tl;dr. Time is in short supply for most folks. Whatever you’re writing, make it worth someone’s time.
3. Like all rules, tl;dr is good to keep in mind, but it's not the end-all, be-all. If you're tackling something longer, go longer.
4. Make introductions as short as possible. By the time most people hit your column online, they have an idea what they're getting. That’s what brought them to your column. Get on with it already.
6. There’s an important difference between creating an enticing title and making clickbait. The difference is in whether the article fulfills the promise of the title.
7. Clickbait titles also tell the reader how to feel, not what you're going to provide.
8. Titles and one-line descriptions are the hardest parts. Do those last.
9. Making a list of "Best [blanks] Of All Time" is the fastest route to hearing, “No, asshole! What about X!”
10. Every writer sort of hates social media, sort of feels like they need it for promotion, sort of has a guilty enjoyment of it. It’s a confusing world.
11. It’s going to be a column you never expected that gets you the most notice. Which means you’d better do a good job on all of them.
12. Neil Gaiman is right with his advice for freelancers: be on time, do good work, and be liked.
13. Neil Gaiman is also right in that you only really need to do two of those things to get by.
14. If I was ranking them, to get a new gig, I’d go 1.Be Liked, 2.Do Good Work, 3.Be On Time.
15. If I was ranking them, to keep an existing gig, it’d be 1.Be On Time, 2. Do Good Work, 3.Be Liked.
16. At my day job we deal with potential book bans. One of the questions you’re supposed to ask someone who’s looking to ban a book is whether they’ve read the entirety of the material. This is also a great thing to ask anyone who has a problem with your work.
17. People you haven’t spoken to in decades will read your stuff. Be prepared for that.
18. Learn to take a compliment. They come sometimes, and taking them well will help you remember compliments better.
19. There’s something very rewarding about connecting two disparate worlds, like bodybuilding and writing. It gets your work into a new realm.
20. And it brings atypical people (bodybuilders who write) out of the woodwork.
21. And it makes those people feel less alone.
22. There’s an entire book out there in finding out what the deal with Wild Animus is. Or maybe a Best Worst Movie sort of documentary.
23. In fact, I'm going to do that. Forget I said it.
24. You are going to lose a column here and there. You’ll close a tab, you’ll delete a file. It’ll happen. Be a grownup about it.
26. When every fifth column you write can be about poop, you’ve found the right place to write.
27. Making a little money for writing is REALLY different from making no money for writing.
28. People who like your stuff will “offer” you the chance to write for their site for free. There is no such thing as exposure equaling pay. Do you hear me, HuffPo? This is a much-debated thing, but I'm telling you, you are being exploited when you let someone take your work for free.
29. By that same token, don’t shit on writers who work for free. We’ve all done it, we’ve all been in a place where we didn’t have other options. It’s not the fault of writers.
30. All that said, doing work for yourself for free can be better than working for someone else for pay.
31. When you’re doing some freelance writing, ask about your rights to reprint or republish your work at a later date.
32. Keep copies of your stuff. If you work for a site that goes under, you might want that material.
33. If you think Ms. Marvel is like a 7 out of 10, just keep your mouth shut. It’s not worth it.
34. Lots of people read articles to confirm what they already believe. Lots of people read articles to get mad at what someone else believes. A very small number of people read to challenge their own beliefs, to ask themselves a question, or to explore something they're not sure about. These are the people you’re writing for. Never forget that.
35. Find a running joke for yourself. Squeezing a Demolition Man reference into a column is a great motivator.
36. In all seriousness, Stallone is a personal hero of mine. People make fun of that dude. They say he’s a moron. He wrote Rocky. We should all be so stupid.
37. Stallone turned down a huge offer for the Rocky script because he wasn't going to be allowed to play the role of Rocky Balboa. He hit big by first doing something great, then believing in that thing's greatness.
38. No matter how weird you might pride yourself in being, Max Booth’s shit is way weirder.
39. Don't get into arguments about the right to have your own opinion. It’s not about rights. It's just that it’s generally okay to have your own opinion.
40. Want to get your writing done? Take your social media off your phone. That’s probably the easiest thing you can do to reclaim a good half hour of every day.
41. You will never, ever win a Twitter argument no matter how right you are, and it’s a waste of your time to try.
42. When someone shits on your work by hitting the part you’re most proud of (sense of humor, grammar, etc.), those ones will hurt.
43. Keep track of all your column ideas in ONE PLACE. Keeping track of the ideas you have is almost as important as writing them.
44. The ideas you were most excited about pitching will be the ones you most often regret pitching. I don’t know why it works this way, but it totally does.
45. Keep track of the ideas that don’t make it through. They're not always bad ideas. Sometimes it's just the wrong place or the wrong time.
47. Learning a lesson about writing and applying the lesson are two very, very different things.
48. If you’re going to start writing as a gig, you need to sit down your loved ones and explain that this is work. It’s not just a hobby. It’s a job. There will be times you need to sacrifice other things to get it done.
49. Jeff Garlin gives some of the best artistic advice:
Take what you do seriously, but don’t take yourself seriously.
50. When you start to figure out the difference between taking what you do seriously and taking yourself seriously, you'll be better off.
51. That said, there will always be those who don't understand this separation and think you're a clown.
52. Remember, if you’re writing for Outlet A, when you start writing for Outlet B, you’re starting from scratch. Outlet B doesn’t give a damn about the good rep you built with Outlet A. You can't get away with as much nonsense right off.
53. If I could do it all over again, I’d make my author bio really, really short. Maybe two lines.
54. Because a good bio shouldn't be about you. It should be about what you make.
55. My favorite author bio is Chip Zdarsky’s Amazon bio:
Straight up? I've never been scared of spiders. You come at me with a rubber spider and I'll just be, like, "so what."
It tells me nothing about him and everything about the stuff he makes.
56. Everything on Pinterest is 1000 times harder than it appears.
57. Sometimes you’ll write something deeply personal and it’ll seem like nobody heard it.
58. Sometimes you’ll write something deeply personal and it’ll work out. Just depends.
59. The point being, don’t write something deeply personal if you're concerned with being heard. Just write the thing. There are no guarantees other than the guarantee that if you don't write it, no one will read it.
60. Revisiting stuff you loved as a kid is almost always a disappointing experience.
61. There’s a rumor about Guillermo del Toro doing something completely fucking awesome like every 3 months. Almost none of these things will happen.
62. All writing software is pretty much the same. Which is to say, you will get out exactly what you put in.
63. “First thought, best thought” is the biggest crock for a columnist. Proof your shit. Rewrite. Think twice. Think five times.
64. When you’re starting out with a new outlet, saying Yes is the way to go. Even if something sounds a little out there or not exactly suited to your interests, screw it. Say yes.
65. You’ll get better column ideas if you leave the house. When someone suggests you come along and do something that's not up your alley, consider doing it just for the sake of getting out of the house.
67. I've never started a column and then backed out because it wasn't going well. Plowing through and writing something difficult will give you tools to use when you hit the same wall again. Which you will.
68. Sometimes you’ll have an idea that’ll cost you a couple bucks. Go for it. Do it. Do a bunch of these and then decide if they're generally worth your while.
69. You won't miss those few dollars months later.
70. In fact, set aside a couple bucks every month for a “column supplies” fund. If you don’t use it, just buy drugs!
71. If you want to save money, learn to cook.
72. You want to save money. The less money you need, the more time you can spend working on stuff you like.
73. There's a lot of debate about writing as a profession versus having a day job. I think both things and any mixture of both works. What you really want is to be in a position to say No to anything that you don't want to do, whether it be in your day job or writing gigs. Being able to say No, that's the goal.
74. Take the time to set up an email for yourself through your own site (pd@peterderk.com, for instance). Everyone will be fooled into thinking you’ve got your shit together.
75. A remembrance column about someone recently deceased does not need to bring up their problematic aspects. Someone's death is a great time to apply the rule about saying something nice or saying nothing.
76. A column never turns out worse when you write it by hand first.
77. If you're going to write something, read things in that style. If you're going to be a columnist, find a few columnists you like online and keep up with them through whatever they do.
78. Don't forget to read those other columnists AS a columnist. Don't finish and say, "I liked that." Find out what you liked about it, how the writer accomplished their goal, and figure out how to apply all that to your own work.
79. When you don’t get a gig somewhere, check out who they DO hire. See what it is about their work that made them the better choice. Learn something.
80. The second you start writing freelance, keep track of your stuff in a CV format. You'll be glad you did.
81. Keep track of columns that really generate a lot of hits, or columns that turn out really great. You'll need these when you're making other pitches, and it's a lot easier if you've got these ready in your back pocket.
83. I don’t give a damn what your list is, books or authors or whatever, you need a non-white, non-dude person on there. If the lineup is all white men, that will become the most important thing about your list.
84. Try to work it out so you can leave your computer at home when you go on vacation. The hassle of hacking out a column early is way easier to manage than the hassle of carrying a laptop through the airport. Twice.
85. Also, if you’re visiting someone, they probably have a computer you can use.
86. You don’t have to write exclusively about things nobody’s written about before. When you’re covering an oft-covered topic just make sure you bring something new to the table.
87. On that note, don’t avoid reading articles about topics similar to yours. Just because you don’t KNOW that what you’re working on has already been written doesn’t mean others who read won’t know.
88. Give yourself a break on your Work In Progress when you spend a couple hours on a column.
89. If you don’t like your column, nobody will.
90. If you do like it, that’s still not a guarantee that anyone else will give a hot damn.
91. In fact, whether or not you like your own work might be the most important thing. There’s only one person you can guarantee pleasing: you.
92. Transcribing an interview is probably the most tedious, difficult thing you’ll end up doing.
93. Plus, if someone is willing to do an interview via email, they will "sound" more the way they want to.
94. It’s tired, old advice. Read your stuff aloud. You’ll catch a hell of a lot more mistakes.
95. This method is the only productivity method I’ve found successful. It does the most difficult things: maintains focus, creates hierarchy, and it takes no time to start using it. Plus, no shit to buy.
96. After writing a couple columns about it, I’m 100% convinced that the perfect gift for writers is something unrelated to their writing.
97. It wasn’t that long ago that typing in a coffee shop was a show-y, weird thing to do. Now, you’re almost a throwback if you’re on a laptop in a coffee shop and using a word processor.
98. If I’m pitching to an editor, I try and do it with the same ideal that I do when recommending books to someone. I'll pitch one column that I think is very closely aligned with things they like, one that shares a mix of similarities and differences, and one that seems totally left field but my gut likes it.
99. If you’re making a debate of some kind into a column, see if you can be neutral on the topic at the start and make your decision at the end. It makes things a lot more interesting.
100. Don’t commit to a number of things for a list. Just pitch it as “X things that…” Otherwise, you'll make a list of 100 goddamn things.
About the author
Peter Derk lives, writes, and works in Colorado. Buy him a drink and he'll talk books all day. Buy him two and he'll be happy to tell you about the horrors of being responsible for a public restroom.
