How Bestselling Author Ann Handley Writes

The Transcript

How Bestselling Author Ann Handley Writes

Voiceover: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at RainmakerPlatform.com.

Kelton Reid: These are the Writer Files, a tour of the habits, habitats, and brains of working writers, from online content creators to fictionists, journalists, entrepreneurs, and beyond. I’m your host, Kelton Reid: writer, podcaster, and mediaphile. Each week, we’ll find out how great writers keep the ink flowing, the cursor moving, and avoid writer’s block.

In this episode, I’ve invited digital marketing pioneer Ann Handley to chat with me about her writing process. She’s a Wall Street Journal bestselling author, a brilliant keynote speaker, the world’s first chief content officer, and a prolific digital content creator. Ann Handley appeared on the written interview series last year and stopped by again to share her methods of madness with us, including her art of productive procrastination, why your writer’s block may be a research problem, how hard deadlines help writers to ship, and the secret to what makes a good writer truly great. Let’s get into the file of Ann Handley. Welcome, Ann.

Ann Handley: Thank you so much for having me. I’m really excited to be here with you today.

Kelton Reid: Who are you, and what is your area of expertise as a writer?

Ann Handley: I am Ann Handley. I am the world’s first Chief Content Officer as far as I know, and no one’s challenged me on that yet. I am the author of the bestselling book Everybody Writes, the co-author of Content Rules, which is also one of the bestselling books on content marketing, and the chief content officer of MarketingProfs.

Kelton Reid: What are you working on right now?

Ann Handley: What am I working on right now? I’m kind of in between projects right now. I was talking to somebody last week who said, “Everybody Writes is now six months old. What are you working on next?” I was like, “Are you kidding me?” My heart and soul went into that book. I need to have a period of rest and recovery before I can think about doing any other big project like that, because it takes a lot out of me.

Right now, I am just working on my ongoing projects. I write a monthly column for Entrepreneur magazine. I blog regularly at my own site, AnnHandley.com. I do some writing for MarketingProfs, and I’m also working with folks here, folks internally at MarketingProfs, on developing a workshop based on Everybody Writes. All that stuff is keeping me pretty busy.

Everybody Writes: An ‘Elements of Style’ for the Digital Age

Kelton Reid: I will just add that I love Everybody Writes, and it feels like kind of an Elements of Style for the digital age. I’m a huge fan.

Ann Handley: Oh good, thank you. Yeah, as you know, that’s exactly how I hoped it would be embraced, and I’m really gratified to feel that. For the most part, I get super great feedback on it, so that’s awesome. Thank you for saying that.

Kelton Reid: We’ll drop that in the show notes, of course, for people to find. Let’s chat a little bit about your productivity if you care to share. How much time, would you say, per day do you read or do research?

Ann Handley: Yeah, I was thinking about this. I think I do an inordinate amount of research on everything that I put out there. I think my background as a journalist instilled that in me. That’s true whether I’m writing a column, whether I’m writing a blog post. Pretty much anything sensitive I’m putting together, I do a lot of research. I’d say for every hour of writing, I probably do between two and three hours of research on whatever it is I’m putting together.

I spend a lot of time wandering around back alleys and down corridors that I don’t know when they’ll end to try to figure out, first of all, as much as I can about a subject, and then how I feel about it. It does take me a long time to actually sit down to physically write because I spend a lot of time researching what’s already been said and researching any information I can find.

Kelton Reid: Before you start to write, do you have any pre-game rituals or practices that kind of get you into the mode?

The Art of Productive Procrastination

Ann Handley: I am a terrible procrastinator, so I spend a lot of time not writing before I start writing, which sounds funny, but it’s so true. I can spend many, many hours kind of distracting myself. So I’ll eat all the snacks in the house. I’ll wash and fold all the laundry. I’ll answer all my work e-mails. I’ll do every other task that’s in front of me that’s on my to-do list before I’ll actually sit down to write, because I’m always looking for ways to not write.

I spend a lot of time distracting myself from actually writing before I write.

Kelton Reid: That sounds familiar. Do you find that you have a most productive time of day and/or locale for getting into the flow?

Ann Handley: Yeah. Right now, I am speaking to you from my tiny house, which I built in my backyard. It’s kind of a writer’s studio — or it is a writer’s studio, essentially. It’s very, very simple inside. The only thing I have in here is an Internet connection and electricity and a heater, which you heard before we started recording, which is incredibly loud. My ritual is to come in here. This feels like almost sacred space to me in a way, which I know sounds kind of goofy, but it really feels that way. It’s the place where I feel the most creative.

In terms of timing, I would like to say that I spend every morning writing, and when I’m working on a big project that’s absolutely true. But when I’m not working on a big project, like I am right now, I tend to spend my morning sort of easing into the day, so goofing around on Twitter, or looking at Facebook, or sort of warming up through writing small things. That’s not true when I’m working on a big project, but right now that’s definitely true.

Kelton Reid: Do you listen to music or do you prefer silence while you’re writing?

Ann Handley: No, I hate listening to anything while I’m writing. I really, really need silence. If anybody is home and breathing in my house, I ask them to stop because I find it really distracting. Right now as I’m talking to you, the guys just came up to mow the lawn, and I’m a little bit annoyed because after we hang up I was planning on writing, so I don’t know how this is going to work. I might have to shoo them away. I like total silence.

Kelton Reid: Do you find that you’re putting in a certain number of hours, excluding that kind of warm-up stuff? Are you disciplined, in other words?

Ann Handley: Yes, I do think I’m disciplined. I have a strong work ethic. I have a feeling that I will never disappoint anybody who is relying on me for something, whether that’s a presentation, or an article, or a book, any of those things. I’d say that if I’m not working on something, it’s probably an hour or two a day that I spend writing, either things for work or just for me personally.

If I’m working on a project that’s much lengthier than that, I tend to work through an entire weekend, for example. I will easily spend probably 20 hours in a weekend just writing and then during the week anywhere between five and six. I get up early, and then I’ll do my job, and then I’ll write after my job. It’s a much more aggressive schedule, I guess, which is in part why I don’t relish jumping back into it too soon.

Kelton Reid: In your book, you do talk about kind of the writer-as-athlete metaphor and working those muscles and staying limber. Do you write every day?

Ann Handley: Yes, I absolutely write every day.

Kelton Reid: Do you believe in writer’s block?

Why Your Writer’s Block May Be a Research Problem

Ann Handley: I don’t, actually, and I talk about this in Everybody Writes. I quote a journalist — and I’m totally blanking on his name right now. I should have looked that up. I quote a journalist who says, “My father never got truck driver’s block,” or “my father never got plumber’s block,” and no one ever gets ‘speaking block,’ for example. I do think that writing is the same way. I think that writing is nothing more than a way of communicating. I do believe in procrastination, as I just said, but I don’t believe that writer’s block is a real thing.

That said, there are times when I’ll sit down to write, and I’ll think, “I don’t know what to say.” Usually, that’s more of a thinking and a research problem than it is an actual writing problem, so that’s typically a sign to me that I need to do some more thinking about something, or do some more research before I think about what my own particular take on something is going to be, you know what I mean?

Kelton Reid: Absolutely.

Ann Handley: Yeah.

Kelton Reid: Why don’t we get into talking a little bit about your workflow? What hardware or typewriter model are you presently using?

Ann Handley: Does anybody actually use a typewriter model to write?

Kelton Reid: I have no idea.

Ann Handley: Wow, that’s interesting. I use a MacBook Pro. I’m waiting for them to bring back the 17-inch. So far, it’s been a pretty long wait, because this 17-inch MacBook Pro that I have, it’s my life. It seems like Apple is going smaller and smaller, and I don’t think they’re going to bring it back, so I am a little distraught over it, honestly.

Kelton Reid: Do you have special software? Do you have a set of software that you use most for writing and your general workflow?

Ann Handley: I use Word, and when I’m writing a big project like a book, I’m a huge fan of Scrivener for that just because it’s such great tool to help you organize your writing more than anything else. Otherwise, I’m pretty simple in my tastes. Just a simple Word doc is really fine for me.

Kelton Reid: How do you stay organized? Are you using Evernote, for instance, or are you traditional — note cards and sticky notes?

Ann Handley: I will tell you, this is my weak spot. I am terrible at Evernote. I’ve tried it, I don’t know, six or seven times now. Every time, I feel like I’m going to make a commitment to it. I’m going to make it work, and I don’t know — I just can’t. I don’t connect with it. I’m like allergic to it or something. It’s just not for me.

I’m very old school in the way that I keep myself organized in terms adding to my internal editorial calendar. I keep a written list in a simple Moleskine notebook. I am trying to use Trello consistently as a way to keep an editorial calendar of myself and keep my projects aligned, and as a visual of what it is that my month looks like, for example. But as I said, this is completely my weak spot, so I’m sort of casting in the dark a little bit with this one.

Kelton Reid: I definitely lean pretty heavily on Trello, so I’ll drop that into the show notes as well.

Ann Handley: Do you? Okay, that’s cool.

How Hard Deadlines Help Writers Ship

Kelton Reid: I know we talked about procrastination before. Do you have some best practices for beating procrastination when it comes down to the wire?

Ann Handley: Honestly, I lean into it. I lean into procrastination pretty hard, and then ultimately, it’s always my work ethic that saves me. I think the most important thing is to show up, to ship when you say you’re going to ship, to show up when you say you’re going to, and not to disappoint people. People start to lose faith in you after a while if you do that consistently. I never miss a deadline, but I will say that I do go right down to the wire, and the only thing that ultimately saves me is that I have to get my ass in gear and make sure it happens.

Kelton Reid: At the end of a long day of writing and overcoming procrastination, how do you unplug?

Ann Handley: Wow, it feels weird to think of my day as hard days. My life is relatively soft, really, when I think about it. I think about my grandparents, for example. They had hard days. My grandfather worked all day at an asbestos mill, and then came home and took off his clothes and breathed in all that horrible stuff, so that’s a hard day to me. I feel like my days are relatively soft by comparison, but what I do is probably the same as a lot of people.

I end the day by taking my dog for a walk, typically. I walk her in the fields, and it brings me such joy to watch her run through the fields, and it sort of melts any of that stress away. Then I make a nice dinner for my family. We eat together. Then, usually I’m obsessed with something on Netflix, so that caps my day. Pretty boring, I know, but that’s when I’m home but I do travel quite a bit, so I really do treasure those moments when I’m around.

Kelton Reid: Just a quick pause to mention that The Writer Files is brought to you by the Rainmaker Platform, the complete website solution for content marketers and online entrepreneurs. Find out more and take a free 14-day test drive at Rainmaker.fm/Platform.

Let’s talk about your creativity. Can you define creativity in your own words?

Why You Have to Find a Way to Shape Your Ideas for Sharing

Ann Handley: I think creativity is really about finding a way to share your own ideas with the world, or maybe not share, but finding a way to shape the ideas that you share with the world. I think that’s important, and I think it can take place in whatever your art is. For some of us, it’s writing. For others, it’s a different kind of art, but I think that’s really what it is. I think it’s about really shaping your ideas and sharing them with the world.

Kelton Reid: Do you feel like you have a creative muse at the moment?

Ann Handley: What inspires me is reading really good writing. You asked me earlier about how I end my day, and one thing that I was just thinking is that after Netflix, after all of that stuff, I always end the day by reading a really good piece of writing, and typically that’s fiction, or it may be some creative non-fiction from the New Yorker or something like that. I’m always really inspired by reading incredibly good writing.

Sometimes it makes me anxious, the sense that, “God, I wish I wrote that,” but it really is inspiring to me to read people who can take you on a journey with their words. I don’t think I have a specific muse as much as many, many muses who speak to me in different ways.

Kelton Reid: When do you feel the most creative?

Ann Handley: I think when something really strikes a nerve in me. There’s almost a sense of, “I can’t not say something.” When something is kindled inside of me, I almost feel like it ignites, and I have to figure out a way to get it out. Otherwise, it literally will consume me. That’s where my best ideas come from. We were talking earlier about Everybody Writes, and that book really did come out of this feeling that I can’t not write it. It’s like, I didn’t know what else to do because it was just something that I felt had to be said, and I let it kindle for a long time inside of me before I was like, “Alright, I just need to do this.”

I think that’s actually the only reason to write a book, is because you can’t not write it. But I also think that’s almost the only reason not to do any kind of writing. It’s when you can’t not say something — that’s when you should say it.

The Secret to What Makes a Good Writer Great

Kelton Reid: What makes a writer great in your opinion?

Ann Handley: I think it’s a realization that you are never really the best writer you can be. That’s something that you’re always evolving into. I almost feel a little sheepish sometimes when I think of myself as a writer when somebody calls me a writer, because it feels like I’m still working on that. It’s like when someone says to me, “You’re a great speaker.” It’s like, “Really?” Because I feel like I’m just evolving that.

I think that’s what makes writing and speaking and communicating so interesting to me, because I don’t feel like I’m ever going to be a master at any of that, and I think that’s true of the best writers. You look at Hemingway’s early stuff and then you look at his later stuff, and it’s very different. It’s the same for any great artist in whatever their media or medium is. I think this willingness to evolve is really what makes a great writer, makes a good writer great.

Kelton Reid: Evolution.

Ann Handley: Yeah.

Kelton Reid: Do you have a few favorite authors at the moment?

Ann Handley: Yeah. I have some writers who I’ve read every single thing that they’ve written, and I’m scared that something will happen to them and they won’t produce any more work. That writer for me is David Sedaris, which is funny because everybody knows David as a humorous writer, but he’s also a really great writer. He’s incredibly soulful. I think he’s very talented, and he’s almost sold short sometimes I think as a humorist. It almost feel like it diminishes his work, but I think his work is really, really subtle and really wonderful. He’s probably my all-time favorite author.

I also am a huge fan of E.B. White, not just because of the Elements of Style, but also, I’ve read everything he’s ever written, from his children’s books like Charlotte’s Web, and Trumpet of the Swan, and all that kind of stuff, all the way up to his letters. He’s somebody that I really love. I feel very connected to him, and I think he’s an amazing writer — or was an amazing writer.

Joan Didion is another favorite of mine. In the business world, I read almost everything that Seth Godin writes because I think he’s a really brilliant and interesting mind. Right now I’m reading a book of short stories by Amy Bloom, and I really love the way that she tells a story as well. Like I said, it’s almost anybody. It’s almost whatever book I’m reading now is my favorite book because if I don’t love the book that I’m reading, then I don’t keep reading it.

Right now I would say it’s Amy Bloom, but I wouldn’t say she’s necessarily the one for the long term. My heart belongs to David and to Joan and to E.B., but Amy, right now, she’s a fantastic writer.

Kelton Reid: I know that Everybody Writes is just chock full of what I call ‘writer porn.’ It’s got so many great quotes in there, but can you share a best-loved quote for the podcast?

Why Your Audience Is Key to Effective Writing

Ann Handley: Yeah, I have two. One is … I’m not sure if it’s actually in Everybody Writes or not. I’ll have to think about that. I’ll have to go back and look at it. But it’s, “Write with the door closed; edit with the door open.” It’s a quote by Stephen King, and what I love about that quote is that what’s inherent in there is that you write for yourself. You just sort of barf it up, and you get it all out, and then you write with your audience in mind. You almost swap places with your reader at that moment.

That’s a thing that I think if any writer keeps in the back of their minds — and by writer, I mean anybody who writes — I think it ultimately makes your writing so much better. Because you really are putting the audience first, which makes you respect the audience. It makes you think of, “I know what I’m saying, am I communicating it clearly?” I think that is ultimately, especially in the business world, the biggest key to really effective writing.

My second one is in a completely different realm, by Eleanor Roosevelt, and it’s something that I live all the time, and she says, “Do one thing every day that scares you.” I do something maybe not every day, but pretty often. I do many things that scare me all the time, and so I think of that a lot.

My first impulse when anybody asks me to do anything is typically to say no. Maybe not this podcast — I was actually okay with this, but to travel to an event because I hate to fly, to do anything that puts you slightly outside of your comfort zone, my feeling is always to say no first. If I can just sit with that and then remember that Eleanor Roosevelt quote, I — more times than not — will ultimately opt in to do it.

Kelton Reid: Let’s do a few fun ones just for kicks. Who is your favorite literary character?

Ann Handley: A lot of my favorite literary characters are from my childhood, essentially. They’re people that I feel like I grew up with in a way. Way back when, my first, probably my first favorite literary character was Laura Ingalls Wilder. When I was a little girl, I read all of those books. There was some tell-tale signs that I was going to be that kind of obsessive-compulsive reader, and so I read all of her things. She’s not quite a literary character because she’s a real person, but there’s sort of this literary character-esqueness to especially her younger books. Encyclopedia Brown was another one. Do you know the Encyclopedia Brown books at all?

Kelton Reid: Of course.

Ann Handley: Yeah, I always wanted to be him. I always wanted to be this super clever kid who functioned outside of normal childhood who did these amazing things. He almost had a super power. Almost any character invented by Roald Dahl, another one of my favorite authors, so Willy Wonka and Matilda, any of his characters, I think, are really brilliant and really different.

Kelton Reid: Do you have a writer’s fetish? I know it’s kind of an interesting question because ‘fetish’ has a couple different meanings. One of my fetishes is vintage typewriters, as I mentioned in an earlier episode, but I think I also have others that are weirder and more esoteric that I kind of keep around my office, but I won’t mention what they are for fear that I’ll be ostracized.

Ann Handley: Oh, they’re real fetishes then, huh?

Kelton Reid: Yes.

Ann Handley: I have a couple of vintage typewriters. I have three, and they’re right behind me in my tiny house right now.

Proof that Paper Books are Pure Writer Porn

Ann Handley: I think my biggest fetish, if you can even call it that, are paper books. I feel sad that ebooks are taking over paper books. I love the heft, the feel, the smell, the experience of paper books. I can count on one hand, literally, the number of times I’ve read an ebook, and half the time, after I’ve read an ebook, if I like it, I’ll go out and buy the paper version of it, because I need it. It’s like I need to have it on my shelf. They become my friends, which I know sounds incredibly weird, but since we’re talking about fetishes, what the hell?

Kelton Reid: Who or what has been your greatest teacher?

Ann Handley: My parents, for sure. They gave me all the freedom to be whoever I wanted to be, and they also gave me a really fantastic work ethic that I mentioned before. That came from them.

My second greatest teacher, I think, has been the many, many, many mistakes that I’ve made. I get this question a lot: “Which mistake do you regret the most?” The answer is zero. I regret no mistakes, only because I’ve often learned a lot from any big mistakes that I made. Sometimes it’s saying no to opportunities, as I mentioned previously, that used to be my default answer: saying no to opportunities.

Sometimes it was just being young and stupid about something. They’re mistakes that we’ve all made, but they’ve taught me so much, ultimately. My big effort in my life is to let my children make those mistakes too. My children are now teenagers, and my son is a young adult in his 20s. It’s like I want them to make those mistakes, too. It’s so hard as a parent not to control it, to warn them away, but at the same time, I think they need to make their own mistake because it is your greatest teacher. I think mistakes are your greatest teacher.

Kelton Reid: On that note, can you offer advice to fellow writers on how to keep the ink flowing and the cursor moving?

The Value of Patience

Ann Handley: Patience. I think patience is the biggest thing. It can feel like you just want things to happen fast. I think it takes a while to find your voice. At least it did for me. You or your listeners may be a faster learner than I ever was, but I think it takes a while to really hone your voice. I don’t think you’ll ever stop, so I think it’s just giving yourself permission to take longer than you think it’s going to and enjoy the process.

It’s easy to say that because while you’re in it, sometimes, it can feel really horrible, but I think it’s wonderful. When I go back and read something I wrote five or six years ago and I can see the difference — like I wouldn’t say things in quite that same way — it really does make me appreciate where I’m at now and my evolution as a writer. So I think it’s giving yourself permission to be a patient person.

Kelton Reid: Thank you so much for your patience and wisdom and honesty. Where can fellow scribes connect with you out there?

Ann Handley: You can find me at AnnHandley.com. It’s a site where I write most often about content and marketing but I also write about my life, or in person I will be at Copyblogger’s Authority Intensive 2015, which I am super excited about. It’s one of my top events of the year. If you’re going to be there, I’d love to meet you there as well.

Kelton Reid: I will also be there, and I really look forward to hearing you speak. I don’t know if I can say the name of your presentation now, but I know that Ann is going to be dropping some wisdom for us, and it’ll be outstanding regardless of what the name of it is. Thank you so much.

Ann Handley: Thank you.

Kelton Reid: In the words of Ms. Handley herself, “Think before you ink.”

You can see Ann Handley live at Authority Rainmaker, a carefully designed live educational experience that presents a complete and effective online marketing strategy to help you immediately accelerate your business.

Ann will be speaking about creating content that makes a difference for your business objectives by showing us how to create content that is empathetic, useful, and inspired. In addition to Ann, you’ll have the opportunity to see Dan Pink, Sally Hogshead, punk legend Henry Rollins, and many other incredible speakers live. Get all the details at Rainmaker.fm/event.

For more episodes of The Writer Files and all the show notes, or to leave us a comment or a question, drop by at WriterFiles.fm, and please subscribe to the show on iTunes. Leave us a rating or a review, and help other writers find us. You can find me on Twitter @KeltonReid. Cheers. See you out there.