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Episode 77: Conquer Writer’s Block – Become a More Effective Writer with Gary Kinder, New York Times Best-Selling Author, Lawyer and Founder of WordRake

Guest: Gary Kinder, New York Times Best-Selling Author, Lawyer and Founder of WordRake

Episode 77: Conquer Writer’s Block – Become a More Effective Writer

Sharon:   Welcome to the Law Firm Marketing Catalyst podcast. Today, my guest is Gary Kinder, a New York Times best-selling author, lawyer, entrepreneur and founder of WordRake, the first editing software for professionals. He’s taught legal writing to lawyers and judges throughout the United States. Today, he’ll give us tips about how to conquer writer’s block and be a more effective and persuasive writer. Gary, welcome to the program.

Gary:       Hi, Sharon. Thank you for having me on your program. Glad to be here.

Sharon:   So glad to have you. Tell us about your career path. Did you always know that you wanted to be a writer?

Gary:       No, I did not. I was not one of those kids who had the neighborhood newspaper back in second or third grade. I had no intention at all of becoming a writer until after I had graduated from law school. I enjoyed writing. If I ever had a choice between taking an exam and writing a paper, I always chose writing a paper. I won a writing contest while I was in law school, but that was the extent of it. I taught in the legal writing program for a short while after I graduated, but after passing the Florida Bar, I decided I didn’t want to practice law just yet. I had never seen snow before, and I wanted to live out west in the mountains. I ended up in a place called Sun Valley in Idaho, and I loved it out there. It was so different than where I grew up in Florida. While I was in Sun Valley, I actually worked as a bellman for a few years and I really enjoyed that. I skied a lot. Some people would laugh if they heard me say that, but I learned a little bit about skiing. Then I started writing as a hobby six months or a year after I got to Sun Valley. It just surfaced, and I started writing more and more. I loved writing. Finally, I decided that I wanted to devote my career to writing. I gave up on the idea of practicing law and started writing in national magazines and then eventually went to books.

Sharon:   You work with a lot of lawyers. How was it that you came to—I mean, you’re a lawyer and you taught legal writing, but how did you circle back?

Gary:       Responsibility. I had two very young daughters, one year and four years old, and they were going to be starting school soon. Living in Sun Valley was a great place to be and my books were doing all right, but I needed more money to raise a family, so I moved to Seattle. When I came to Seattle, I wanted to continue writing, but I thought I could become an in-house writing editor, a writing consultant for a big firm like Perkins Coie out here. It seemed so natural to me. I’ve got two editors in New York plus my agent, and every time I write something, they go over and over it, plus it’s pretty decent writing to begin with, pretty tight. I assumed that lawyers with millions or even billions of dollars could certainly use an editor, but I discovered that the lawyers didn’t want an editor. They didn’t want that extra layer of time involved, and they didn’t know how to charge a client for me. So at Perkins Coie, one of the lawyers said, “Why don’t you come in here and teach us how to do what you do?” I created this writing program for Perkins Coie. That was in 1988, and that was right about the time when MCLE was coming online in those states. It took off. I was writing as much as I could, but my day job, so I could put my daughters through school, was teaching writing programs around the country to lawyers.

Sharon:   Wow! Tell us about your books. You’ve written at least three books. Tell us the names and what they’re about. They all sound very interesting, but I think the first one got a lot of attention in terms of the subject.

Gary:       The first one came out in 1982. That was called “Victim: The Other Side of Murder,” and it was a story about a mass murder. I’ve confirmed this since then—it was the first book ever written about a true crime from the victim’s perspective. There was “In Cold Blood” that told it from the perpetrator’s perspective, but this was the first one to take the victim’s side. It’s a touching story. It was a hard story, difficult for some people, I think, but a very touching story.

The second book I’m not very proud of. Frankly, I don’t think I did a good job on it. I didn’t take the time to understand the story, but it’s called “Light Years.” It was about a guy who lived in Switzerland—these are all nonfiction, researched, Tom Wolfe, new-journalism-type projects—and this was a Swiss farmer who claimed to have had contact with extraterrestrials. It was an investigative piece. I tried to determine how this started because he had examples of metal from spaceships; he had recordings; he had thousands of pages of notes. He had photographs and film footage of flying saucers. I think it all could have been debunked. I didn’t know how to go about telling the story properly and I was going to can the book, but my editor said, “Let’s see if we can’t sell it to a pulp house and get some of the advance back.” When I finished, he said, “Just knock it out as fast as you can,” and I did that. When I finished it, he showed it to some other editors and they liked it, so they published it as a long book.

My last book came out because of WordRake. I had been working on that for a very long time, but it came out over 20 years ago. That was called “Ship of Gold in the Deep Blue Sea,” and that is the book that I’m very proud of. I was proud of the first one, too, but “Ship of Gold” was a difficult story, a very complex balancing of telling two stories, first how a ship sank in 1857. It was a big side-wheel steamer. I didn’t even know these things existed before I started “Ship of Gold.”

A lot of people who went to California for the California Gold Rush in 1849 and throughout the 50s had walked across the country, literally, and it took five months. People know that story, but what most people don’t know is that a lot of those people returned and eventually would travel to California via ship, and it was these big, side-wheel steamers. They would leave from New York and go down to Panama. About 500, 600 passengers would cross over the isthmus, get to the steamer on the other side and then take it up to San Francisco. One of these ships, called Central America, was carrying about 500 passengers, 100 crew and many tons of gold coming back. All these ships carried a lot of gold when returning to eastern banks. The ship hit a hurricane and it went down. It was 200 miles offshore, but through a bizarre set of circumstances, all the women and children were rescued. Most of the men perished, went to the bottom, and along with them went tons of California gold.

The rest of the story, which is about two-thirds of the story, was about a young man named Tommy Thompson who had graduated from Ohio State as an engineer. For some reason, all treasure hunters come from the middle part of the country, but he was really a scientist and an engineer. He was far more interested in engineering than the challenge of working in the deep ocean, but he selected the Central America as the target to develop technology, a remote-operated vehicle, that could work on the bottom of the deep ocean. He found the Central America and was able to carefully recover the gold and other delicate artifacts, which had never been heard of at that time. The guy who was head of the Navy’s salvage operation, a guy named Bill Searle, told me—and he told Tommy at that time—that what he was about to do was impossible. It could not be done, and Bill knew because he had been involved in every deep-water recovery attempt. The gold, the ship, the wreck site was in about 8,000 feet of water, and Tommy Thompson figured out how to go down there. Not just go down there and look, like you could do with the Alvin years earlier, but actually work there on the bottom of the ocean. He recovered that gold, and it’s a thrilling story.

I was exhausted. It took me 10 years to finish that book, along with all the teaching I was doing for law firms, but again, I’m very proud of it. I was completely worn out and had no intention of writing another book for quite some time. I started wondering if we could take some of the things I taught about editing and put that into algorithms and create software that could help lawyers edit their own work. That became WordRake, and we’ve now been out almost eight years.

Sharon:   What does WordRake do? You put your work, whatever you’re writing, into the black box of WordRake, and then what happens? How does it work?

Gary:       It’s a black box and as the engineers say, “This is where the magic happens.” It’s an add-on to Microsoft Word and Outlook. It will work in Mac, in Word, and you just install it. It takes 30 to 60 seconds to install, and then whenever you write something, when you’re finished—it’s not going to edit as you go because I think that’s too distracting—it will look for words that are unnecessary. That’s what all of our algorithms do. I determined over the years that there are certain patterns of writing that can be improved, and if you know how to recognize these patterns, it will highlight these for you.

When you are finished writing your memorandum or your brief or even before you think you’re finished with it, you start the editing process by turning on WordRake. Once you install it, it appears in the ribbon right above the Microsoft ribbon. You just click on that to open it. It ripples through what you’ve written very quickly, and it will highlight in-line. One thing I insisted on with the engineers is that they make it look like a live editor with a red pen. It’s all right there in-line, but you cannot accept all the changes at once. You have to go through it and say, “I like that one. I like that one. This one I’m not sure about. Maybe it changes the meaning,” and you hit the reject button for that one, and the others you hit the accept button.

It will point out everything that it thinks you could improve or get rid of. It’s a wonderful way to start your editing process. I tell people this all the time—I don’t think they believe me until they use it—that no matter how good you are, it will point out things you did not see in your own writing. No matter how many times you’ve edited it, no matter if it’s a big case, if you’ve got six lawyers working on it, outside counsel working on it, it will still point out problems that you could improve.

Sharon:   Has it been accepted by the lawyer clients you have or when you show it at ABA programs? Are they resistant or do they say, “Oh, that’s fabulous”?

Gary:       They usually gasp, and I mean that literally. The first few times I showed it, there would be a roomful of 50 to 100 people and they would ask me to demonstrate it. I would take one of their briefs and push the Rake button, and it would start rippling very quickly, a thousand times faster than humans can think, and people would burst out laughing and gasp, “Oh my god,” and then they would look. I could always tell who was in charge, because everybody in the room would turn and look at the person, saying “We’ve got to get this.” I see this when I teach first-year associates at a big firm—I’m still teaching, by the way—and when I demonstrate WordRake at the end, often they’ll turn and look at the trainer in the room and with their eyes ask, “When are we going to get this capability?”

Sharon:   It sounds fabulous. You work with all kinds of professionals. Have you found different challenges working with lawyers? It sounds like they’ve accepted WordRake. We find sometimes that lawyers are tied to their own words and work, and they’re resistant to editing out.

Gary:       Lawyers are good writers. You don’t get through law school without knowing something about writing, but I made a living for 30 years because there are enough lawyers out there who have realized they could be much better than they already are. They’ve been really willing to accept my teaching as well as WordRake. It helps them. Once they see it, it makes life so much easier for them.

Sharon:   Everybody wants that. It’s a life hack.

Gary:       It is. The courts over the years have been shrinking page and word limits, and it’s gotten to the point where it’s difficult for a lawyer to have a brief. In their mind, it’s “Oh my god, I’ve got to include all this stuff. I’ve got to include this issue and this issue and all these cases, and I don’t have room and everything’s too important. I don’t know how to cut it down to get within that limit.” If you push the Rake button, it will show you where to start cutting down. If you’ve got a 20-page brief due and you’ve got to get it down to 20 pages because yours is 22 or 23 or 24 pages, I can’t guarantee that pushing that button will eliminate 10 percent of that brief and bring you under that limit, but it will jump-start the editing process. We figure that roughly 95 or 96 percent of the changes we suggest through WordRake are acceptable to most writers, and if you accepted all of those, it’s going to take out 5 to 10 percent immediately.

When I teach, I teach them how to look for words they can get rid of even if they don’t have the software, but WordRake also helps people see things in the sentence they can make better. Even if the algorithm won’t point anything else out, you will see these things once the editing process starts. You use WordRake and it will correct something. You get rid of four or five words in a sentence, and now you’re looking at that sentence and thinking, “You know what? I could write this even better,” or “I just need to get rid of the whole sentence. It doesn’t say anything.” It draws your attention to these weaknesses. Even once you’ve made some of those changes, there are things you can do to improve. It is a huge benefit when you’re trying to get a brief under a certain page or word limit.

Sharon:   It really sounds like something that can make life a lot easier. I’m sure this is something you’ve faced, having written books and having to sit down in uninterrupted blocks to write. You have a 21-minute method of conquering writer’s block.

Gary:       Guaranteed.

Sharon:   Can you outline that and fill in the gaps if there’s more you want to say?

Gary:       Sure. This is no big secret. Most of us have read about the left brain/right brain dichotomy. A neuroscientist would cringe to hear me talking about this because they know that every time we make any kind of a decision, the whole brain lights up in different places and all of it interrelates. But over the years, we’ve gleaned that there is a left side of thinking, which is more structured and organized, and there’s the right brain side of thinking, which is looser and not as concerned about details. Based on that—and this goes back 25 or 30 years ago—I started teaching how to get over writer’s block, and like everything I teach, I try to break it down into building blocks. You see why it’s a problem. You see what you need to do to correct that problem when I teach the editing techniques. You can go back to your office after lunch and immediately use it. You don’t need to sit and study anything.

It’s the same way with conquering writer’s block. I broke it into three steps and three rules. The first step is to converse. I tell people to imagine a conversation with a real person. It can be a parent, a spouse, a friend, a teacher; it could be the partner or client for whom you’re writing this brief. It could be after work, you’re having a glass of wine or kombucha, talking to your friend, and the last thing this person says is, “Tell me about this case you’re working on, assuming you can talk about it.” You start talking, and I tell people to imagine that conversation in that setting because you will not sit there and stare out the window. You are going to respond to what that person asked you, and it’s not going to be great. It’s not going to be perfect. You certainly wouldn’t say this to a judge in court with no preparation. But you’ve been researching this thing and you understand what this case is about, so you start making it interesting, and all these facts are fascinating to your friend. Now, the facts are all over the place; there’s nothing linear about the storytelling. I tell them as they’re doing this, they should become a third party and observe themselves and this friend and start taking notes. Everything you say, write it down in any order; it doesn’t make any difference. As writers say, you just want to get black on white. Rule number one during this step is no research. You don’t want to get out your research and put that on your desk. All that is going to do is confuse you. This is just the first draft.

One thing I have taught over the years—and this was like getting hit by lightning, I guess; I’ve never been hit by lightning, but I was hit by intellectual lightning. I was teaching a program one day, and it occurred to me in three words what the problem is. The problem is creativity, and we lawyers are creative. Creativity requires failure. That’s what the whole creative process is. It’s just a series of failures. Each time, you get closer to something good, so you don’t want any research in front of you. You just want to write down whatever pops into your head and realize that it’s not going to be good. It’s not supposed to be good. It cannot be good if you’re doing it right.

I’m working on a piece of a book right now, an epilogue to the last book, actually, and I’m throwing stuff in—research off the top of my head, ideas, half-sentences, a word or two, somebody’s name I need to check a quotation from. It’s a conglomeration of stuff, but it’s like I was talking to somebody over a glass of wine after work. Once you get that, you will realize it’s allowing the right brain to fail, to run with it. This method of conquering writer’s block, the 21-minute brief, is just a way of holding the left brain at bay while the right brain does what it does so well. It will tell you when it’s finished. You just run with it for four or five minutes. It’s like popping popcorn in the microwave. You will slowly run out of new ideas and at that point, you stop and set it aside and come back to it later. We often don’t get half a day or a day to work on a brief. It’s only 20 minutes here and there, or it may be an hour or two if we’re lucky and lock the door, but you can work on this in increments.

The next step is to organize. You look at what you’ve got this mess on, a couple of pieces of paper because you’ve typed as fast as you can go, and now you start to organize. You realize some of these ideas are connected. You put them together and arrange the groups of related items in a logical order. You can label them A and B or one and two or symbol. It doesn’t make any difference; however, you want to organize it—you can mind map it. I’m going to skip rule two for now and I’ll come back to that in a second, but then step three is to write.

We’ve got things rearranged in a loose form—and remember, this is another failure going forward—but rule number two, now that we’re writing, is don’t stop writing. This is how you keep the left brain out of it. If you stop writing at any of these earlier points, even when you’re conversing or organizing, as soon as you stop, that left brain is going to kick in and start to criticize and analogize and analyze and assess, and that’s what you’re trying to keep away from. You can’t stop writing. Now, you’re going to make mistakes. There are going to be typos, and most of us can’t stand it when we know we hit the wrong key; we have to go back and change it. That’s why we have the rule to not stop writing. Whatever thought pops into your head, you put it down on paper.

The third rule when we’re engaged in the writing step, the third step, is go all the way to the end of the rough outline you created in the first step. Don’t stop to go sideways on a case you want to talk a lot about. Finish talking about it as much as you can think of, but don’t sit there and try to analyze it and make it better. It is much, much better to do several drafts quickly than it is to do one laborious draft, and believe me, you are hearing that from the person who is the slowest and most purposeful writer in all of publishing. I want to go sideways on everything, especially in the early stages. Before I get down to the editing and refining, I’ll fly right to the next step and keep going. It’s worked wonderfully for me.

Sharon:   It makes a lot of sense. I often get stuck halfway through the organizing draft and then say, “OK, now I’ve got to start again.”

Gary:       Right, you just want to constantly improve that nut you started with.

Sharon:   Now, is that 21 minutes, or what more do we have in your 21-minute method?

Gary:       To break that down into numbers, the step one conversation happens in about four minutes. Then it’s a lot easier to run with something and try to organize it. The organizing is the easiest part of all of it. The organization takes about two minutes for step two. It’s much more difficult to get something down on paper. So we converse for about four minutes; we organize for a couple of minutes, because that’s the easy part, and then we give ourselves about 15 minutes to write, and at the end of around 21 minutes, you will have that first draft.

Now, that first draft might be two pages of what’s going to eventually be a 17-page brief, but you’ve got something to work with. When you come back to write draft two, that might take a little longer—you might spend 30 minutes on it—but you cannot wait to get in there and change everything you know is waiting to be changed. That’s part of the key; that’s the energy you bring to it. You can’t wait to go back and start tearing it apart and making it better, and that will happen every time you come back through.

Sharon:   When you talk about conquering writer’s block, I have this image of you. It’s like, “Kapow!” through the bricks of writer’s block because at least when you’ve done this, you’ve overcome the anxiety and fear of writer’s block.

Gary:       Right.

Sharon:   What are your top one or two writing tips when you walk into a classroom or when you talk to lawyers? You often hear, “You write like a lawyer.” We read a lot of lawyer’s articles and you can tell it’s writing like a lawyer. What would your thoughts be in terms of top tips?

Gary:       It’s funny. You and I have not talked before this interview, but one of the things I tell them, especially if they’re new at this, is that writing like a lawyer is the problem. You don’t want to write like a lawyer. You want to write like a warm, logical, intelligent, fair-minded human. If you can get over that and write like a human, that is a huge step. The problem is in law school we read stuff written by lawyers and judges, and we think that for anybody to take us seriously as a lawyer, we have to write like a lawyer. We adopt bad habits of saying “assuming arguendo.” We like to stick a little Latin in there, and it’s unnecessary to do that.

The really fine writers—you can ask at a firm who is the best writer there, and they will go right to one person. Almost everybody will mention one person, and that person has usually been around for a while. You will find that this person’s writing is so clear, so concise, that anybody could understand it. That is when you’re getting at the very top of your game. I’ve heard this about artists, that when we’re four years old we just scribble stuff. Yet an artist, once they mature, will work for the rest of their lives to try to get that creativity, that mindset they had when they were four years old and not inhibited by anything. I think the fine lawyer writers are the ones who can simplify and make it intelligent. You’ve got to discuss all of it, and there are legal principles that in themselves are difficult, but you have to explain these in a clear, logical way so another human can understand them clearly and concisely. Judges get so much garbage, so many poorly written briefs that it’s like a breath of fresh air. I’ve talked to a lot of judges about this. They see this as a godsend for them and the work they do. It’s a way to make a real impression.

I’ll tell you how to do this in a mechanical way. I know a lot of people use word limits, but I’ll use pages for now. If you have a 20-page limit in federal court, 98 percent of lawyers—and I’ve actually tested this by talking to judges, clerks and other lawyers—will produce 19 ¾ pages. They do this because they say, “Wait, I’ve got another quarter of a page. I could stick something in here,” and often that’s what they do. Or, let’s say an associate is a good writer and gets his message in early on and turns in a 16-page brief. The partner they give it to is often going to say, “Well, we’ve got four more pages. You could stick something in here,” and that’s what they do. Then the judges go, “Wait, they had everything covered. What’s all this other stuff?” A judge or a clerk will always do what the rest of us do whenever we have something to read, and that is, they’ll turn to the last page and see how many pages it is to see how much they have to read. If they see a 16 or 17 on that last page, they will turn back to page one assuming you know far more about this case than your opponent does and that this is going to be a good brief. They haven’t read one word yet, but that’s the assumption if they see you’ve come in under the limit they gave you.

Sharon:   Interesting. It’s like when people are told they have three minutes to speak, nobody rehearses it because they think, “Oh, it’s easy for me to say what I have to say in three minutes,” but it takes much more time, effort and thought to say something worthwhile in three minutes than it does in 30.

Gary:       It’s easy to ramble. You’re right.

Sharon:   I was thinking while you said this, you know how you see on newsletters or articles that it only takes seven minutes to read? Maybe lawyers should start putting that at the beginning that it only takes three minutes to read.

Gary:       I’d look forward to that.

Sharon:   Gary, thank you so much. This is great information. It’s useful and actionable. It’s very valuable.

Gary:       You pushed all of my buttons, Sharon. I just started talking. I apologize. I think I cut you out most of the time.

Sharon:   No, this is great. Everybody wants to listen to you, not me. We’ll have links to WordRake and your information in our show notes. To everybody listening, if you like what you heard and you’d like to hear more, you can subscribe on iTunes or wherever you download your podcasts, and please rate us. We’ll be back next time with another thought-provoking guest who can be a catalyst for moving your firm forward. Thanks so much for listening.


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