Countless lawyers have said, “I’m going to write a novel some day.” I am included among them. There’s something innate, particularly among litigators, that compels us toward storytelling. But Robert Dugoni has actually made the transition and written not one, but more than 20 novels.
In Episode 12 of Lawyerpreneur, we sit down with best-selling thriller author Robert Dugoni and talk about his writing career. He shares real, practical wisdom about making career choices and gets personal about when he knew he had to make a change from litigation to pursuing his vision for himself of being a writer. Finally, Dugoni discusses how succeeding at writing requires the same diligence and perseverance as in a legal career, and what that looks like on a daily basis.
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Today’s show is sponsored by ALPS, the nation’s largest direct writer of lawyers’ malpractice insurance. Right now you can get 25% off one CLE seminar from ALPS. Go to alpsinsurance.com/cle and use promo code LAWYERPRENEUR upon check-out.
From Litigator to Thriller Author with Robert Dugoni
Jeremy Richter: Welcome to Lawyerpreneur, where we discuss the alternate paths that allow lawyers to engage their entrepreneurialism and distinguish themselves from others, because being a lawyer doesn’t have to mean doing business as usual. I’m your host Jeremy Richter.
My guest today is Robert Dugoni, the internationally best-selling author of more than 20 books. His most recent book, A Cold Trail, was released in February of this year. It’s doing really well. Welcome to Lawyerpreneur.
Robert Dugoni: Thank you. Thanks for having me. I’m going to warn you that I have some construction going on at my house where I’m in, you know, confinement, with the stay at home order, so if you hear little explosions going on in the background, it’s not….
Jeremy Richter: I’ll likewise put a warning in. I’m doing this from my car. It’s about 120 degrees in here. And so we’re doing the best we can today and we’re going to chalk this up to example, you know, 674 of learning new flexibility in this brave new world that we’re in.
Robert Dugoni: Exactly sheltering in place, I’ll tell you.
Jeremy Richter: That’s right. So we’re recording this on May 28. I’m in Birmingham, Alabama. We are not sheltering in place anymore. Things are pretty open right now with some restrictions, but like my law office, for example, I think everybody’s back in. We’ve just brought in our summer associates. So things are really busy, and everybody seems way more comfortable with that than I am. But you know, we’re doing the best we can. What’s it looking like for you?
Robert Dugoni: You know, we are not yet really open. There are some things opened. I started golfing last year and the country club has opened again. So you know, I’m able to at least get out of the house. But here in Seattle, most of the businesses are looking at like June 15, I think is when the second phase will come due. We got hit, as you know, we got hit very hard very early on. We were sort of the center of the pandemic, and it was actually not far from my house at a retirement center, sort of just a few miles from my house. So it’s still going to be a while, and all my family have adapted and adjusted. And as I’ve said several times before, I really feel more badly for the young people more than for myself. It’s a whole new world for a lot of them, you know. No graduations no senior proms, no accolades. It’s just sort of they’re done. So anyway, I cannot complain at all. Yeah, blessed that, you know, I get to do what I love to do and I can walk down the hall to my office, which is normally quiet, and I’m grateful for that.
Jeremy Richter: Yeah, we’ve got a five year old and a two year old, but the five year old kind of knows what’s going on and the two year old doesn’t. And you know, he said to my wife just this week, they went on a Target pickup run where somebody just brought it out to the car and he said, “I’m ready to be for Coronavirus to be over so I can go places again.” And she just felt terrible for him. Because it’s been months since he’s been anywhere. You know, it’s been like 10 weeks, and he’s just ready for something different.
Robert Dugoni: You know, you wonder what the world’s going to be like for that generation. You know, I mean, you and I are of the generation where you could go through the airport without having to go through any security or walk right up to the gate and you’re good to go. And that has changed for forever. Yeah, now, you know, he’s just wandering what’s going to happen with this whole thing, whether we’re going to have to wear masks and when we go into public places or movie theaters, and it just remains to be seen. It’s an interesting issue for authors because you know, are you do you include the pandemic in your next novel? Do you not include it? I have not included it in the novels I have coming out next year. And I haven’t mainly because I’ve had so many people thank me because they have been blessed, really, with being able to have their mind taken off it.
Jeremy Richter: I was listening to a podcast with Joanna Penn, who is The Creative Penn, and she was saying the same thing that at this point, she doesn’t have any intentions to write that into her novels, because it’s just people need an escape. And right now she’s going to hold off on it as long as she can.
Robert Dugoni: Yeah, I think that I think I’m going to do the same thing.
Jeremy Richter: And that’s even transitioned into, like, what I’m reading what I have intended to read, like I was going to read — Bob Iger has a new book that came out recently. He’s the CEO of Disney. And I was going to read Cal Newport’s Deep Work. But I found that when I have time to read, I just want something that takes me away from everything, even just like analytical self-assessment, and just lets me escape to a different world and enjoy a different thing for a while.
Robert Dugoni: Yeah, absolutely.
Jeremy Richter: All right. So I was doing some homework on you. And it seems from what I was reading about you that you knew from an early age, that you were a writer and wanted to be a writer. How did that manifest itself in your educational and early career choices?
Robert Dugoni: Well, you know, literally it was seventh grade, I had to give a speech on slavery in school and I just, you know, it went really well and I just really loved the whole experience and writing was something that writing came easily for me. Writing well doesn’t necessarily come easy. And then, you know, when I got into high school I did what kind of a lot of young men do, which is try to pursue the athletic career and success on the gridiron. And unfortunately, I wasn’t really blessed with the athletic gene. I have some weird factors I’ve learned as I’ve gotten older. You know, like, I wasn’t good. I wasn’t going to be a long distance runner. Let me put it that way. You know, probably the best advice I got was from a high school basketball coach who told me, I’d make the team but I probably would never play, and the alternative was that the head of the newspaper department really wanted me to be the editor in chief for the newspaper. And so I had a choice to make. And it really was an easy choice. And I chose the newspaper and that was kind of off and running.
Robert Dugoni: I thought I’d be a journalist. Got out of Stanford University. Worked for the LA Times for a brief period. Was asked to stay but had friends going to law school and was always told as a young man, by my parents to get as much education as you can while you’re young, so you don’t have to go back when you have a family, etc. So I went to law school and became a lawyer.
And as you know, the law is not a job, it’s a profession. And you don’t go to work nine to five, you go to work at seven and at five, you get off and that’s when you start trying to find new clients and do all those other things and you join an organization. Anyway, it’s a profession. It’s like being a doctor. You devote your career and your life to it. And you know, for me, Jeremy that was just that was never really my calling. It wasn’t really what I wanted to do. I enjoyed it, I worked at what was a young and up-and-coming medium-sized law firm in San Francisco, where everyone was about the same age, so it was like being in college again. Everyone had the same interests, the same ideas about fun. We just had a great time, really a wonderful firm. But in the end, I had one of those epiphanies we all have in life where, I realized I’m not getting any younger. And I’m not doing what I had set out to do. So really a number of different factors came into play, but the biggest one was – I wanted to do what I love to do, so I left the practice of law and started trying to write novels.
Jeremy Richter: Was there a transition where you were doing both or was it like you up and quit and decided I’m doing this other thing now?
Robert Dugoni: There was a transition. There wasn’t necessarily intended to be a transition. But what you learn very quickly, what you do not know. And even though I could write, I did not know how to write a novel. And so no one really sits you down and says, here’s how you write a novel. In fact, even people that go through the MFA programs, they’re not necessarily told, this is how you write a novel. And it wasn’t really internal. I started to realize what I didn’t know that I began to understand what I needed to know. And I could find the books on the craft that would put me in a place to move forward. And really, I always tell people, because I know a lot of times you’ll get young authors or new authors on your podcast, and so the big one for me was Christopher Vogler’s book The Writer’s Journey. That was a book that taught me what it how to create a plot. And from there, I read Saul Stein’s book on writing, which talked about developing characters, and, you know, it was just sort of one thing after another. And once I was able to really understand it, like writing a legal brief, you know, once you sort of understand the format, I was able to then devote my resources to making my characters and my plots interesting. Knowing what elements of the story I needed to hit and so.
During that period of time, to keep my family afloat and all that, I worked part time as a lawyer up here in Seattle, where I wasn’t licensed. So I couldn’t be a full time lawyer and I couldn’t go into court and do all those things. But I could do a lot of the behind the scenes work for lawyers. I could write briefs for them. I could analyze files for them. I could prepare them for depositions, so I made a decent living doing that while I was trying to get my writing career off the ground. And then in 2013 you know, I really struck paydirt. I wrote a book called My Sister’s Grave, which I was very blessed to have a publisher at Thomas and Mercer, Amazon publishing that really understood the book and understood what I wanted to do and bought it. And it’s been, I’ve just been off and running ever since.
Jeremy Richter: That’s really great. And I can identify with the difficulty in writing fiction, because at this point, I’ve written three nonfiction books. They’re all about law practice, and related things. And a couple years ago, I sat down – I’d had a couple of ideas for novels – and sat down to do it. And, you know, got 10,000 15,000 words in and it was I was really enjoying it. But I was also learning like, these are not the same things. And this is so much harder than any nonfiction thing I’ve ever written.
Robert Dugoni: Yeah, yeah, it is. There’s a lot of balls in the air to juggle and a lot of characters to juggle. And I often tell young writers – I teach writing – and often tell them it’s a lot for me anyway. I don’t outline. And so it’s really more like the way that an impressionist painter would paint. You don’t try to paint one corner of the painting all the way to completion. You really start with the whole canvas and you put down that first layer and then you go back and you put down another layer and a third layer and a fourth layer.
And for me in writing, what I mean by that is my first draft is – nobody gets to read my first draft but me. Period. And because I live by that, I’m much more free and open to write anything I want. Even though I know as I’m writing, it is probably not going to make the final draft. But I tell students don’t let anything get in the way of your creativity in that first draft. You know, you obviously want it, once you learn story structure and you learn the way a story is supposed to be told, and you learn the beats of a story, you can go back and then edit out some of that stuff. And some of that stuff may become another book. You just you never know. So I say of that first draft, just focus on being creative. And then the second draft maybe focus on your characters.
I’m in the process of writing a story that involves a young man in Vietnam. It’s not a Vietnam book. It’s a coming of age book. But I have multiple scenes which take place in Vietnam. And one of the things I had to realize was that I had made him a combat photographer. And yet after the first few scenes, there wasn’t a lot about photography in the book. And so you know, one of my last passes through my draft was to just go through and make sure that that thread of combat photography was finished so that the reader didn’t say, wait a minute, I thought he was a combat photographer. What happened to this? What happened to that? Because readers are really perceptive. So each draft that you go through, you can add a little more and take out a little more.
Jeremy Richter: Going back to your journey. Was there anything particular that triggered that decision to commit to writing and to pursue the dream and the passion for that, as opposed to what, at that point, was probably the easier path of just staying in your legal career?
Robert Dugoni: Yeah, the one thing I can remember and for what it’s worth – I can remember getting up one morning and putting my feet on the floor. And I was involved in a very difficult case. And not only was it a difficult case, I had a very difficult client, which every lawyer knows can be really emotionally draining. And I put my feet on the floor and I just realized, you know – what am I doing here? What am I doing with my life? This is not the path I had chosen. How did I get here, you know, getting up every morning and really not being very satisfied or being fulfilled. And, you know, I just, I said to my wife, “I can’t do this anymore.” And, you know, from behind me, she said, “Then we won’t.” And that’s really all I needed to hear was that it was okay. We would be okay if I wanted to go down this other path.
And the other thing really that happened, Jeremy, was again, I was in the shower one morning, and you know, call it whatever you want, but all of a sudden, I was just in tears. I was just in tears. Because, you know, I had always planned other things for my life, and I wasn’t pursuing that. And I know that there are a lot of people out there that go through these moments in their life. And they don’t get the opportunity – they’re not blessed to be able to do what they want to do. And I understand that. And I think that’s why I always give thanks for the fact that I did. I was able to do it.
I’ll never forget the time this young man came up to me. He was in one of my classes. And he said, “I’m a lawyer and I want to do what you do. And I just find really difficult time to find time to write.” And, you know, like a jackass. I said, “Well, you know, if you really want to do it, you’ll find the time, you know. You can get up at four in the morning like JK Rowling and you can ride on the train and you could write when you commute you” And he looked at me and he said, “I have four kids under the age of eight.” And it really made me realize that we’re not all the same. And we’re not all in the same position. And we can’t all sit there and say we’re going to do this or we’re going to do that. Everybody’s different.
And I looked and I said, you know, “God love you. This is not the right time for you. You have your obligation to be a husband and father. “You have basketball, plays. You have all these things and you don’t want to miss out on those. You don’t want to look back on your life and say, you know, my kids are grown and I didn’t get to spend time with them.” And I said, “Here’s what you can do,” and I gave him a list of five or six books on the craft of writing. I said, read these and study these in your free time in your spare time before you go to bed. Whatever you have, so that when you when your life does settle down a little bit and you do have more time, you’ll be ready to hit the ground running
Jeremy Richter: Yeah, that’s really good that. There are seasons of life where we are able to pursue certain things, and others where maybe our own personal dreams have to be put on hold for the sake of our family, or whatever events that we’re dealing with. Yeah, I think it’s really good.
I saw that you started writing novels in 1999. You told us that it wasn’t till 2013 that you really had a big break. And that’s a lot of time. And I know that a lot of people think people are overnight successes, but in a lot of interviews that I listen to with authors, they’re like, yeah, I’m an overnight success that was 20 years in the making. What did that journey look like for you?
Robert Dugoni: Well, there’s a couple things to keep in mind. One is, I don’t know that we know a lot when we’re in our 20s. You know, I don’t know that we’ve had enough life experiences. So there are writers out there certainly in their 20s, I guess have been are very talented. But you know, in my 20s I didn’t know anything. I hadn’t been married; I got married in my 30s, early 30s. I didn’t have kids. It was a completely different life. Like you said, a completely different season. And I think you’ll find a lot of writers find success as they get older, because they can write about things with a certain authority they couldn’t write about when they were younger, because they had no experience with it.
And I’m not saying you have to write what you know. I think that’s a fallacy. I’m saying you write what you what you can learn and what you’re interested in learning about. I certainly didn’t serve in the Vietnam War. But after 15 first-hand accounts in books that I’ve read and 15 movies I’ve watched, etc., when I have experts I can write pretty well about what happened in the Vietnam War. But again, you know, I don’t think we really know a lot until till we get a little bit older.
And so in 1999, I had this idea for a novel. Yeah, but I didn’t know about story structure. I didn’t know about character development. I didn’t know about three acts. I didn’t know so much that it’s kind of a fallacy to say, well, I was a writer back then. I was an aspiring writer. And so for me, it was really – I look at it as both a blessing and a curse. You know, I had my first book published in 2004. That was a nonfiction book called The Cyanide Canary. And it was right up my alley. It was about a trial. It required a lot of newspaper skills, etc. And that book hit The Washington Post best books of the year and that got me my foot in the door and it got me an agent, a really good agent. And I started writing my novels and things were sort of underway for me and I had five or six novels out, before I got let go by a publisher for a lot of reasons that are really not worth getting into. But that really pushed me into a corner where I had to sort of reevaluate where I was and what I was doing, sort of like I did when I was practicing law.
And I really took the time to take better hold of my career. What was it that I did well? And what I did well was I wrote novels. And when I found Thomas and Mercer at Amazon Publishing – well, they found me I should say. What they said to me was, we think the best thing that a writer can do is write the next novel and leave the promotion to us. And that was music to my ears. And since 2013, I think I’ve written 12 or 13 books, something like that. But it’s because I’m doing what I love to do, and I’m doing what I’m good at. And I think we can all as we get older, we can all relate to that – do you want to go out and build a barbecue in your backyard? Or do you want to pay somebody to do it? Well, I could go out and do it, and it would look like hell, and probably not be very good. Or I could pay somebody that does it well, and in the interim, I could write novels, which is what I do. So for me, it was really finding that sweet spot. And that sweet spot was understanding what I did well, and focusing my attention on what I do well.
Jeremy Richter: Was there a time when you knew that it was going to work out as a career? That writing was going to be something you were able to continue to do and make a living at and take care of yourself and your family?
Robert Dugoni: I never really doubted myself until I was let go by a publisher. But even then, I wasn’t willing to give in. I’m one of those people that I’m stubborn and I’m a little bit of a pitbull, and I was not I was not willing to give up. I was not willing to give up. And I keep going forward, and there’s always going to be issues, and there’s always going to be problems. There’s always going to be pirating of your novels. There’s always going to be people trying to give away your novel for free. All those things have become a potential issue that writers and musicians and other artists have had to deal with. But, you know, again, I could sit there and I can worry about all those things. But then I’m not really doing what I love to do, and which is to write novels. So I would say that I knew I was going to be able to do it full time, and that I was going to be okay. When My Sister’s Grave hit, and I was able to really walk away from the law entirely, and just devote my time and my attention to it – teaching writing, writing novels, going to conferences, doing these kinds of podcasts, and all those things.
Jeremy Richter: There’s a lot of people who want to be writers and want to be authors that think that all you have to do is write. But you’ve talked about here, how you have the writing, the speaking, you have multiple streams of income. Do you enjoy the other aspects of teaching and speaking, getting in front of people? Is that fulfilling to you?
Robert Dugoni: Yeah, Yeah, I do. I enjoy those very much. But you know, that has changed for me, obviously, in these conditions. And so one of the things you want things to bear in mind is we’re going to be constantly evolving, and one of the evolutions has been Zoom conferencing. And so I’m doing a lot of Zoom conferencing and book clubs and rotaries and all those things. But I’m not traveling anywhere. And I used to travel a lot. I used to travel to a lot of different conferences, and I had a lot of things planned. I was going to South Dakota this year and Texas and Florida and really all over, and everything’s come to a halt. And while I really enjoy doing those things, I enjoy getting out meeting people and going to new places and seeing things. I also have to say that there’s been something sort of nice about being able to just be home with my wife. My kids are home; they haven’t been home in a while, and they’re home and we’re just enjoying each other’s company. So I really enjoy those other things and I hope that we are able to get back to doing them because it’s much more satisfying when you do it in person. But you know what, time will tell.
Jeremy Richter: Well, being home is something that my wife and I have talked about a lot too. We’ve got a young family, like I mentioned. And we’re not really ready – we’ve been really fortunate. And she’s a nurse here in Birmingham. So she’s got her job. My job has been fine. And so we’re really blessed to be in that position. And we’ve been home with our kids so much more. I’ve been able to work outside watching the kids play, answering emails and drafting things and all that, that normally I would be stuck in my office for 10 hours a day. And I’m getting all this extra time with the kids. And we’re not really ready to quite give that up yet. It’s been really amazing.
Robert Dugoni : Yeah, I hear you. And, you know, again, I know this has been really a tragedy for a lot of families. And so it’s something that I hope we past and we get through. But I have enjoyed certain aspects of it.
Jeremy Richter: So you’ve been really prolific since 2014. What is your daily writing process look like?
Robert Dugoni: You know, I’m one of those OCD lawyers, right? You wake up thinking about a case. You think about a case in the shower. When I’m writing, when I have a story going and I really like the story, it’s hard to keep me away from the typewriter. I will say that I have gotten better about taking weekends off. I really try not to work at all on the weekends. I may have a notepad where I have thoughts come to me and I’ll note those and things like that. But I really try to keep my weekends free.
And other than that, I go to work every day. I try to get to my desk early. Not going for workouts in the mornings, because I can’t. So I’m doing online workouts, but I put in a good seven, eight hours a day, either working on the novel and working on editing the novel that’s already been completed. Doing copy edits, doing it developmental edits, answering emails, answering Goodreads questions, doing all those things. So it’s a full day. I’m not one of those authors who, you know, works two or three hours and then goes in and goes to Starbucks. I work every day. And I put in a full day, which is why really I think, you know, I have been able to be prolific.
The other thing is I come from a background where you have to learn how to write quickly. As a as a journalist, you need to write succinctly and quickly. And as a lawyer, there’s many times where you get a pleading in that you’re not expecting and if it’s an ex parte application, for instance, you got to write a response within a couple of hours and get it back to the court or reply to an opposition motion, or whatever it is. And so I’ve learned how to focus my attention and my thoughts. And when I come in to sit down, I’m pretty good about keeping the focus, not getting distracted by phone calls. Not getting distracted by emails or text messages, and really just writing. And I don’t have young kids at home right now, so I’m unlike you and other people. I’m not running off to Little League or any of those places. And so I feel pretty blessed that I get to do what I love.
Jeremy Richter: Well, let me ask you this, whether it’s writing, whether it’s some other endeavor, what advice would you have for lawyers who want to pursue something outside of their practice? And whether it says, you know, a side hustle that they do adjacent to their law practice, or something that they’re looking to get out of practice altogether? Yeah, for people looking to do that …
Robert Dugoni: You know, I would say the same energy and skills that lawyers put into becoming lawyers can be transferred to other areas. So one of the things that good lawyers are good at is being able to multitask. Because they have to. They don’t just have one case, they have six cases that they’re dealing with, and they’re getting phone calls all the time from on a different case. And then a new case comes in. And so what I would say is, handle whatever that thing is that you want to do, as you would handle your law practice. And what I mean by that is – plan for it, put together a business plan, put together a checklist, put together a list of things that that you want to do. So for instance, if you think, I really like to write novels is something I’d really like to do, but I don’t have the time right now. I have a trial coming up. I have a trial following that. You know, you realize sort of what your limitations are, then go out and find the books that speak to you, that teach the craft of writing, the craft, the storytelling, of plotting, of characters, and begin to sort of work your way through those. If you have an idea for a novel, begin to jot it down. Just outline it, even if you’re not an outliner, because at least that makes you feel like you’re sort of pursuing your passion. You’re pursuing what you’re what you’re passionate about.
And you know, lawyers and doctors and a lot of professions out there are filled with people who know what it means to work hard, who know what it means to put in long hours. And so you just have to understand that there’s going to be a rhythm to this thing, but you don’t have to do it all at once. You can plan for it. If you have a partner, your wife or whatever, you can you can sit down together and say, okay, you know, this is what I would like to do, how am I going to make this happen? You know, one of the things that really helped me out was that we when we moved to Seattle so I could pursue this – well, we moved to Seattle because my wife’s family, her grandmother had remarried. And she was in her in her 80s. And so her the home that she originally had was basically being rented. It was all paid off. And so I could come up to Seattle and I could live very inexpensively, very cheaply. And that gave me the freedom to not feel like I had to have a job right away. My wife made money and we were able to sort of budget – okay, here’s what we’re doing; and here’s where I’m at; here’s what I’m trying to do; and then once you sort of get a novel written or then you got to find an agent. There’s just a lot of different things you can do, but I know some people that have done a really great job of planning it. And I think that’s what you need to do. You need to plan the stages of the profession that you’d like to be involved in, and then take it one step at a time.
Jeremy Richter: I like that. I think it was a really practical, helpful answer. Alright, if people want to follow you connect with you, where’s the best place to do that?
Robert Dugoni: You know, my website, robertdugonibooks.com, and you can sign up for my newsletter on there. I won’t spam you. I only get out a newsletters a year, usually when some big news comes like when I sell things to LA to Hollywood and those kind of things. And other than that, I’m on Facebook. I think it’s at Robert Dugoni (Facebook link). And I’m on Twitter. So I’m on sort of the normal social media channels.
Jeremy Richter: Well, I really appreciate your time. Thanks for coming on the show.
Robert Dugoni: My pleasure. Thank you. Thank you for having me. I’ve been down to your state a couple times for book festivals and I enjoyed it very much.
Jeremy Richter: Well, hopefully we can all travel again soon. Maybe you can make it back this way.
Robert Dugoni: That would be great. If I do, I’ll let you know.
Jeremy Richter: Great. If you’ve enjoyed the show, you can support it by writing it on Apple podcasts or wherever it is you’re listening. And make sure to subscribe so you don’t miss anything. You can also support the show on Patreon at patreon.com/lawyerpreneur. Thanks for listening.
