Fifteen minutes long, because you're in a hurry, and we're not that smart.

15.01: Evolution of a Career

Your Hosts: Dan, DongWon, Mary Robinette, and Howard

Season 15 is going to be a bit broader than the previous seasons have, at least in the abstract. We’re going to focus on your questions. In this episode we tackle the topic that dominates our collection of these questions: CAREER.

Liner Notes: It hasn’t actually been 15 years. It’s been 12. Writing Excuses launched in February of 2008, and the first five seasons were not full-year seasons. 

Credits: This episode was recorded by Bert Grimm, and mastered by Alex Jackson.

Homework: Whose career do you wish you could have? Research them, examine how they’ve done it, and then ask if that’s still what you want.

Thing of the week: Follies, by Stephen Sondheim.

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As transcribed by Mike Barker

Key Points: This season is going to be organized around topics taken from questions from the audience. So this is what you wanted to know! Starting off with the evolution of a career, goal setting for a career as a writer. How do you choose a book for early in your career versus saving it for later? Work on what you’re most excited about. Start with something simple, tell it well, tell it clearly, and tell it straight. Sometimes you want to push yourself, set a challenge for yourself. When you look back on first projects, you are sure to think you could do it better now. But that opportunity cost comes with everything you write. Pick an area to improve, but focus on the things that give you joy. If you have an idea, you’re excited about it, it’s ambitious… Go for it! Even if it doesn’t work, you will learn. Don’t worry about using your best idea too early, you will have more and better ideas later. The path you expect, the path you plan, is probably not the path you will follow. Grieve for the untaken path, but rejoice in where you are walking now. You always learn from experience. How do you plan for the next stage? Have a plan, but be ready to toss it. Look for options. Avoid closing doors. Don’t brand yourself by your first project. Do a couple of books to prove you can do it, then do something else. Leave breadcrumbs for your readers to follow. Pay attention to what your readers like. Think about who is this book for. Brands evolve. As you plan your career, make sure you have a plan, and make sure it’s something you love.

[Mary Robinette] Season 15, Episode One.

[Dan] This is Writing Excuses, Evolution of a Career.

[Dongwon] 15 minutes long.

[Mary Robinette] Because you’re in a hurry.

[Howard] And we’re not that smart.

[Dan] I’m Dan.

[Dongwon] I’m Dongwon.

[Mary Robinette] I’m Mary Robinette.

[Howard] And I’m Howard.

[Dan] Awesome. We are very excited to have Dongwon with us for this, the very first episode of 2020. We are doing something a little different than we’ve done in the past with this new season of our show. Mary Robinette, this was your idea. Can you tell us what we’re doing?

[Mary Robinette] Well, we realized that the podcast is 15 minutes long, this is 15 years long at this point, and we’re not that smart, but you all are. So we decided that rather than trying to come up with a topic, what we would do is go to you and see what things you wanted to know about. So we’ve collected a bunch of questions, and we’re using them to guide the season this year. So you will not, in most cases, hear a specific question from an audience, but the topics and the questions that we’re trying to answer for you have all been generated by you.

[Dan] One of the things that we saw a lot of, and this shouldn’t have surprised us as much as it did… Maybe a third of the questions we got in were all based around career. What does a career look like as a writer, and how does it change over time, and how do you decide what you’re going to do? So, since we’ve got Dongwon with us, we wanted to talk about the evolution of a career. How do you set goals for your career? So let’s… Let me actually start with this question that I think is really interesting, and I’ll throw it to Dongwon first. When you’re starting to look at your writing as a career rather than just a thing that you do, how do you choose a book that is very good for early career versus one that you might want to save for later on when you’re better or more established?

[Dongwon] It’s kind of a tricky question. Because… The thing that I always, always, always tell people is when it comes to you picking the project that you want to work on, work on the one you’re most excited about. That said, I do talk to a lot of writers who at some point will say, “I tried to do this thing and it was too big for me at this stage. I didn’t know how to do this, I didn’t know how to do that.” So sometimes, when it comes to that first novel, and a lot of debuts… Often times, you can read a book and know that this was a first novel, that this was a debut, that this was the first thing you did. Because it has sort of a clear, sort of straightforward through line. It tends to be A to B to C. It tends to be much more straightforward, in terms of how we naturally as people tell a story. Right? So sometimes what you want to think about for that first book is keep it a little simpler, right? Don’t try to do the 15 POV’s with complicated tense things, complicated structure. Focus on telling the story that you already know how to tell. Tell it well, tell it clearly, and tell it straight.

[Mary Robinette] I sometimes talk about this with my students as setting things on the easy setting. There’s nothing wrong with an easy setting. Like, you can do beautiful, beautiful work if you are dealing with things that you are confident in. So sometimes I think about that, like, waiting until you have the writing chops, or picking one aspect of the novel that you’re going to put on the difficult setting and everything else is well within your comfort zone. I also want to say that having a practice novel as your first novel is… There’s nothing like wrong with saying I’m going to write this without the intention of publishing it. If you finish it, and you’re like, “This is publishable.” Potentially. Sure. But we don’t say, “I have picked up the violin. I’m going to go to Carnegie Hall…”


[Mary Robinette] “With the first thing that I’ve learned to play.”

[Dan] Yeah. Well, I do want to emphasize that there is absolutely nothing wrong with setting yourself a challenge that is kind of beyond your level. That’s how we push ourselves. That’s how we learn. But I do agree that when you’re sitting down and saying, “Okay, I’ve got a few books under my belt. I think it’s time to do one that I’m going to really try to get published.” Maybe back off on that difficulty level, like Mary Robinette was saying, and do something that you know you can really hit out of the park.

[Howard] Sorry. At risk of overthinking things, there is nothing in the first five years of Schlock Mercenary that I couldn’t go back now and do an infinitely better job at. There are no first projects that later you is going to look at and say, “Boy, that… I really only could have written that as an early career thing. I’m not ready to write that anymore.” No. You’re always going to be leveling up, you’re always going to be improving. There’s a story in the second year of Schlock Mercenary where I start telling the story from the point of view of the bad guys, and Schlock is the monster. I decided to use marker art for it. It was all hand-lettered. I… This is me… This is in 2001, 2002, I think, that I’m telling this story. I remember thinking at the time, “Yeah. There’s no way I could have told this story or illustrated this story when I was first starting out.” I looked back at that now and I think I was not ready to tell that story then.


[Howard] I could do such a good job with it now. But now it’s done. Now I’ve told it. Now I can’t tell that story again. There is an opportunity cost associated with that for me. But that opportunity cost is associated with everything you write. You don’t get a do over. You know what? Life is grief.


[Howard] Just own that. Own the fact that your first project is always forever… It’s going to be your first thing. We all had to do that.

[Mary Robinette] My… So, the first novel I published, Shades of Milk and Honey, is the fourth novel that I wrote. When the UK edition came out and they asked me if I wanted to do anything different, I’m like, “Well, yes, in fact.” So that novel, the UK edition is two chapters longer than the US edition because I had a better idea of how to do endings. But every novel I do is an iteration of like, learning where my weakness was. So I think that’s the thing… Like, when I say do the easy setting, I don’t mean for the entire novel and don’t… But what I mean is pick something… Pick one area. Just one area to improve, when you’re thinking. Like one area to stretch in, and focus on the things that make you… That give you joy. Chase that. Rather than doing the thing that I see a lot of writers do in their early career, they put so much effort… Focus on “I gotta have an original idea. It’s gotta be original, it’s gotta be new and exciting.” So, as a result, the emotion that they’re trying to evoke in the reader is that writer is clever. Which is… That’s like wanting someone to say, “That person is funny.” Instead of trying to…

[Dan] Instead of trying to make them laugh.

[Mary Robinette] Right. Yeah.

[Dongwon] One last point I want to make on this, and to contradict myself a little bit. I do really want to encourage people, though, that when it comes to writing that first book, if you have an idea and you’re excited about it, and it’s an ambitious project, swing for those fences, right? Like, go for the big thing. Don’t go half measures. Kind of talking about Howard’s point a little bit, resolve to not have a regret about it. Just do the thing! If it doesn’t work out, you still learn so much in that process. Then it’s on to the next book. Right?

[Dan] Yeah. Given that we’ve raised the specter of the opportunity cost, I do want to point out, the more you practice this, the more you do it, you’re going to have better and better ideas every time. So don’t worry that you’re burning your best idea too early. Because 10, 20 years from now, you’re going to have such better ideas than that one, and so many other cool things to do.

[Dan] Anyway, we are going to stop now for our book of the week. Which is actually a musical theater production of the week. We were… Mary Robinette and I were absolutely just geeking out about what turns out to be one of our shared favorite musicals of all time. Mary Robinette, what is it?

[Mary Robinette] Follies, by Stephen Sondheim. I love this musical so much. The idea is it’s an old vaudeville house… Like a Ziegfeld follies kind of thing. It’s shutting down, and all of the old performers are coming back for a reunion. So the whole thing is told in present day and flashbacks. You get to… They have cast present day elderly actors and their younger selves. It’s a fascinat… It’s like beautiful and heartbreaking. Some of the singers can’t hit the high notes that they used to be able to hit anymore. But the depth of their performance is so much more. So it’s… When we’re talking about the evolution of a career, this thing that we had just been geeking about is a beautiful portrait of that.

[Dan] Yeah. One of my favorite songs in the show is called The Story of Lucy and Jessie. Where it is a woman singing about how now she is older and more experienced and much more interesting, but she doesn’t have her youth and energy, whereas the youth and energy person was such a bland, boring person that nobody wanted to talk to, and how she can never be happy because she can never combine those two parts of herself. The way that it looks at age and youth and early career and late career is stunningly cool.

[Mary Robinette] So that’s Follies by Stephen Sondheim. You can find it on many different forms of media. I am a big fan of the original cast. Dan is a fan of the new cast.

[Dan] I do prefer the original cast, although the new cast does have Bernadette Peters on it. She really hits it out of the park. So. Awesome.

[Howard] I arranged music for an a cappella group, when I was [hhhhh] 25 years younger than I am now. They did a song called Don’t It Make You Wanna Go Home. Nine guys. At the end of the song… One of the guys was a contra tenor, who just killed it. Squeaking up there in the stratosphere. Another guy who was a… one of the sons of the university’s music faculty. Amazing voice. End of that song, they are scatting and noodling around. The two of them duel very briefly with notes that most of us can only admire from a great distance. It was an amazing and beautiful thing. I caught up with the other singer a few years ago, and found out that… Boy, not five years after singing that, he developed vocal nodes and could no longer perform at all. But now works as music faculty. I have the recording that I was present for, where he was… I almost have guilt, because I wonder if the things that he was doing to his voice to hit those notes that the other guy was just born to hit might have been part of the problem. But that thing that he was able to do in that portion of his career will always be with me, will always be with him. It always exists. But he had to take a different path. When we talk about the evolution of careers, we have to recognize that the path that we think that we are on, the path that we have laid out for ourselves, is not the path that we will be on 20 years from now. It is going to change. We can’t hit it regret free. There will always be… I said, life is grief.


[Howard] You get to grieve for the path untaken. You get to grieve the expenditure of what you thought was the best idea when you couldn’t write it as well as you could now. But you also get to rejoice in where your feet are right now. You’ve got to be agile and keep them moving.

[Dongwon] The thing I want to say about that, though, is also there’s no wasted time. You always learn from that experience. You can take so many lessons from a moment that… I’m a big believer that the only way, literally the only way we learn new things is through failure, right? You hit that wall and you learn lessons from how you hit that wall. You pick yourself back up, and then you keep moving forward. Right? So. Even if it doesn’t work out, take the lessons from it, right? Examine it to see what other things you could have done, how you could have pivoted from there, and do that next time.

[Dan] We… I don’t want to spend too much time on this specific topic, because we’re going to dedicate an entire episode to it later in the year, called Rebooting Your Career. But for now, we’ve talked about the early stage of your career, let’s talk a little then about career planning. So another question I’m going to pitch right at Dongwon. Once you’ve got that first book, maybe you’ve made your first sale you’ve done some self-publishing and found some success. How do you plan for the next stage?

[Dongwon] This really is one of my very favorite topics. It’s one of the things I love most about my job is working with writers to help them strategize about how do we want their career to look. What are we planning for this first book, for the book after that, for the contract after that, for the contract after that? Right? So, roughly, generally with most of my clients, not necessarily everybody, with most of them, we have a sense of here’s what we’re doing now, here’s what we’re doing in five years, here’s what we’re doing in 10 years. Right? Now, the thing is, publishing is a system that is designed to be extremely random. Right? What makes a book work is highly unpredictable. What makes a book tank, also highly unpredictable, right? So when you’re thinking about this… There’s two things you need to keep in mind, is, always have a plan. Always know where you’re trying to get to. But also be ready to throw that plan out the window at the drop of a hat. Often, what we’re doing is, when we’re planning for those decision points, right? You’re looking at… We have contract one, contract two, contract three. Then, what you’re doing is, at each of those junctures of when we’re deciding what are we going to write next, the thing we’re solving for is having options. Right? We’re not solving for we will do A to B to C. What we’re doing is solving for, okay, once we do this, what are the three moves we can make at that point? How do we make sure that the first move we make doesn’t close doors for the next move we want to make? Right? If we get that movie deal, then we can do this. If the book sells five copies, then we can also do that. Right? So you’re keeping all those things in your mind, and trying to build out a little bit of a decision tree. But you will go completely mad if you try to map the whole thing. So you pick your path, but then you’re ready to know, we can pivot wherever we need to. Right?

[Mary Robinette] This is a really important point that you… Having those options open. One of the things that I see writers do at the beginning of their career is that they pin their identity and their… They brand themselves around their first project. That is, let me just say, a mistake. Because the first project is unlikely to be the first one that takes off. If George RR Martin had done that, we would all be looking… His entire brand would be vampires on a steamboat.


[Mary Robinette] Because that was… Fever dream.

[Dongwon] It’s a very good book.

[Mary Robinette] It’s a very good book. It’s not what he became known for. I did a lot of Regency stuff, but one of the things that I did, very consciously, when I was… This is, speaking of closing doors. We sat down and talked about book 2. It was a sequel. But the classic sequel in a romance is that the sister of… Or the best friend of the main character now becomes the POV character in the next book and does… It’s another romance structure. We made the conscious decision not to do that, because had I done that, I would have… That would have put me on the romance path very, very firmly. I like romance, but I didn’t want that to be the only thing I did. So we made the conscious decision to not do that. That’s the kind of thing that you’re looking for.

[Dongwon] My general rule of thumb, strategy, is you have book 1. You do book 2 in a way that’s similar to book 1, either same category, similar voice, similar topic, to prove you can do it, you can do it again, and then in book 3, prove you can do something else. Right? That’s generally how I think about it. It’s not always that pattern, but it’s why… If we’re going to do a series, I like duologies, I like linked standalones, I don’t like a seven book series. Right? Because if you have a seven book series, then you’re trapped in that for seven years of your career at a minimum. Right? So if you’re doing track… So, what you want to keep is maneuverability. You want to keep the ability to jump to something else if things go wrong. Or even if they go right, sometimes the right move is to jump to something else.

[Dan] Yeah. I want to… Excuse me. I want to jump in on this because I very specifically went maybe much farther over the line then I should have with my second project. My first thing was first person, modern day, contemporary horror. Then the second project was third person, post-apocalyptic science fiction. Multiple viewpoints instead of one, female protagonist instead of male. Like, I made it as different as I conceivably could because I wanted to not be pigeonholed. I wanted to present myself as the person who can do anything. Which has had both pros and cons. It is very difficult for a giant audience to follow me book to book. Because not everyone’s interested in the same things that I am. On the other hand, I’ve got a historical fiction that came out last year. Everyone was like, “Oh, okay. That makes sense. Of course he’s going to jump out of the other four genres he does into a brand-new one, because that’s the brand he’s established for himself.”

[Mary Robinette] I looked… So, when I was… When we were first talking, it was like, “Do I want to do a Tad Williams career, where every single book is different, or do I want to do a series, genre, where you are doing a series?” I write all over the map in my short fiction. So the thing that I have been doing is I’ve been doing the same, but different, path. So like book 1, straight up Re… Austen pastiche, book 2 is a courtroom thriller… Or is a wartime novel, spy novel, disguised as a Regency romance. Like, the same is the set dressing and the characters. That is my same. My plot structure shifts. When I got to Ghost Talkers, I kept a plot structure that was similar to one that I had already done, and I stayed in historical, but I jumped forward by 100 years. I also knew by that point that what people liked in my books was that I had happily committed couples. So I stuck with that. With the Lady Astronaut books, it’s science fiction, but it’s still historical. That, again, it’s like that is a very conscious choice. The book that I have coming out this year is another Lady Astronaut book, but the one that I am working on for next year is… It’s straight up science fiction, but I am deliberately giving it a 1920s noir feel, in terms of the aesthetic, to retain that sense of familiarity, to make it easier. So, I think of it as leaving breadcrumbs for my readers to follow me. Which has…

[Dongwon] I mean, really what this is is having a brand.

[Dan] One of the things we talk about a lot, and that new writers hear all the time, is don’t chase market trends. Don’t try to write what you think people want. This advice sounds like it’s the opposite of that. Because you’re saying, I know what my readers like. But it’s because they’re your readers. You’re not trying to chase an entire market. You have found your people and you are giving them what they want. Which is a very different thing.

[Mary Robinette] Yeah. I am looking at expanding out of that, because I’m like, I don’t want to stay just with the historical Regency. Which, obviously, I love my Regencies. But I… Like, how do I bring science fiction in? How do I bring mainstream people in? Like, I’m trying to add each time without losing my core.

[Dongwon] I talk a lot about how all of publishing is reducible to one question. That question is, who is this book for? Right? So what you’re doing isn’t writing to the market. It is being very intentional about who this book is for. You know this is my current audience. I want to grow my audience. I want to push my audience to also follow me to these other places. So, sometimes when you make the big jumps, as Dan was talking about earlier, it can be hard to hang onto that audience even though you know who the audience of the new stuff is, right? So in terms of transitioning and growing, I think there are two very different strategies that can work really, really well.

[Mary Robinette] I did lose people when I didn’t do the traditional romance structure for the second book.

[Dongwon] I mean, you always will, right? Because you take risks when you write a new book, otherwise, why are you writing a new book? So, there are chances you will lose people, but you will also gain people, hopefully.

[Howard] When this episode airs, I’m six months away from ending the 20 year Schlock Mercenary mega-arc. In terms of career decisions, that is a conscious decision built around… Big surprise, making money. The two words…

[Dan] That’s a good career goal.

[Howard] Schlock and mercenary…


[Howard] Either of those words should suggest that I’m all about the art. When you reach the… When you get to the bookshelves and you are holding something and you see that it is the first book of three, or the third book of 10, and book 4 isn’t out yet… There is a group of people who won’t spend money yet. Well, I’m right now, in print is book 15 out of 20. I need to be able to say, “The end.” And have everything in print, because there is a group of people whose money I don’t have yet.


[Howard] That is…

[Dongwon] There’s 10 of them. You’re going to get them.


[Howard] I’m coming after all of them at once.

[Mary Robinette] I’ve never bought one of your books.

[Howard] That’s just fine.

[Mary Robinette] I mean, you keep giving them to me, so…

[Howard] But this… So, this decision, I need to be able to say the end. There are people who are asking me, “So, what comes next?” No matter what the answer is, there’s a group of people who won’t be satisfied with that. The most important person for me to satisfy right now, and Sandra and I have had this conversation several times, is me. What do I want to do next? Part of what I want to do, and this is the sort of thing that’s dangerous to put on the Internet in a recorded permanent sort of format. One of the things that I would love to do is no longer be putting out a daily comic strip. Because there are things that I can’t do while I have that deadline pushing down on me. But the thing that has set me apart from almost every other comic strip out there is that it has been daily and has updated without fail. So, am I sacrificing my brand in order to do the thing that I want? Or am I making the right career decision? As of this recording, I don’t have a good answer to that.

[Dongwon] I mean, but this brings up a really important point, that the thing about strategy is that brands evolve. Right? They have to evolve. If you remain static over time, you don’t have a strategy, you have a pattern. Right?

[Mary Robinette] My brand when I began was the puppeteer who was also Regency. Right now, it is the writer who can talk about tea in space.

[Dan] Yeah. Which, there’s a huge market for that. Who knew? We… Excuse me. We have let this episode run a little long because it is the very first one and we wanted to introduce the whole year. I do want to end on the point that Howard hit on. Which is, first of all, as you’re planning your career, a) make sure you have a plan, but b) make sure it’s something that you love. Because otherwise, why are you doing this? Goodness knows, there’s not enough money in it to make it worthwhile. But if it’s something that you genuinely love to do, that is what is going to see you through everything else that happens to you.

[Dan] So, we want to leave you with some homework. Let’s get that from Dongwon.

[Dongwon] I think the homework is, a lot of times when I talked to a writer I’m considering working with, I’ll ask them this question of whose career do you wish you could have if you look out in the market today. When I asked that question, I’m not asking who do you want your books to read like. It’s not about the style of the books, it’s not about the voice of the books, or even the subject matter. It’s look at their career. Look at how fast they publish, what kinds of book they publish, kind of who they’re publishing for, are they doing YA and adult, are they doing like all different genres, categories, and things like that? So, take a look around at the market and really pick one or two authors. Really examine how have they published. What years… What was the pace of that, when did they start taking off, and those kinds of things. Consider, is that the life that I want, or do I want something else? Then that will help start helping you inform a decision about the career choices you’re looking over the next year, five years, 10 years.

[Dan] I would add to that, look at the other ways they spend their time. Are they the kind of person that does a lot of news stuff, a lot of convention appearances, do they make most of their money speaking rather than on their sales? Kind of look at all of that peripheral stuff as well.

[Dongwon] Are they doing a lot of school visits? Yeah, exactly. What’s their lifestyle like, too? Do you want to live that life? Right? Do they have a day job? Or, all they are, are chained to a desk, putting out books every six months?

[Dan] Awesome. Well, great. This is been a cool episode and we’re excited for the rest of the year. Please join us next week when we’re going to have Brandon Sanderson and our 2020 special guest, Victoria Schwab. We’re going to talk about theme and subtext. It’s going to be awesome. So, for now, you are out of excuses. Now go write.