Monica Leonelle

8 Questions with Monica Leonelle

Sean:  Hi there and welcome to Eight Questions. Today I’m talking to Monica Leonelle who I have just mountains of respect for. I actually found your first email to me just the other day and it was totally coincidental because I was looking for something else and had nothing to do with anything, and it was from like early 2013, like February, 2013.

And you’re saying oh, my friend, Matt Gartlin, has been talking about you. I just wanted to introduce myself, and you have like a little list of goals. I said oh, that’s fantastic, so good to meet you.

(If you prefer audio, you can listen to this episode on the 8 Questions Podcast)

It’s almost three years later and Monica is just a really impressive person who has done like quite a lot, and we’ll talk about that, but Monica’s a good friend.

Monica is like on the outskirts of the company, on the very fringes of the company and has done a lot of work with us and for us and she’s just a really, really smart person. And welcome.

Monica:  Thank you so much. That’s an amazing intro. I feel like I need to live up to that intro.

Sean:  You will, you have eight questions to prove yourself.

Monica:  Okay.

Sean:  Let’s start with – this is one that all of us at Sterling & Stone can really identify with. You straddle the line between non-fiction and fiction, right, much like we do. How hard is that to do and do you find that constant tug of war between the two worlds?

 Monica:  Yes, definitely. It’s hard.  I think the other thing is that the non-fiction I’m doing right now is really focused on just like whatever I’m learning right now, that’s what I’m talking about in my non-fiction essentially.

So of course what I’m learning right now is about writing and building a fiction business. So there’s like a meta part of that, like you’re writing about writing essentially.

Sean: Do you find yourself teaching yourself, like it’s almost like getting it out of your system. So the very first book that I wrote, I really, really wanted to write fiction, but I had to write Writing Online. I almost like had to.

Like I didn’t even enjoy the process really, but it was a book that I couldn’t start focusing on stuff like Available Darkness until this book was done, out of my head, and I feel like okay those lessons are now out of me.  Is it like that at all?

Monica:  Yes, I think whenever I’m struggling with something, I have to have a framework for it. It’s like I just can’t move forward without deciding how I feel about every little aspect of it, and having like my little set of rules that I follow to go forward.

So I think a lot of the stuff that I’ve done so far, almost all my books have frameworks. That’s kind of how they start. It’s like here’s the framework that I use and having that kind of helps me.

It’s almost like an affirmation. It’s like when you say I’m successful, and then it’s like you start to believe it. I feel like the books are kind of like an affirmation of the way I think about things, definitely.

But yes, I think non-fiction is interesting because it’s definitely something I want to expand in as well as fiction. My team and I we were talking about like how can we do that going forward.

So right now I’m writing just to authors, like how can I expand that non-fiction to like artists, which is really similar to what you guys do. But to other people who are trying to build creative careers and then how can I expand.

Sean:  It’s hard too because then you start diluting your message.

Monica:  Exactly.

Sean:  We’re really finding that with Iterate and Optimize, and we actually wrote it to be broader than Write, Publish, Repeat and to hit more creatives than just authors.

And we’re actually revising it now to shrink down the message because it just got watered down. It’s like oh, we’re talking to painters and musicians too. We’re not actually servicing the ideal reader of this book and it’s hard.

We have an idea for next year, that broad book, but it’s hard. You know your stuff when you’re talking to authors.

Also you’re such an infovore too. I read Nail Your Outline and you’re talking about how you have 40+ books on craft and you’re just consuming, consuming, consuming, and then okay, well, I’ve absorbed all of this and then here’s my interpretation and now I can move on. Right?

Monica:  Yes, yes, that’s exactly it. That whole book, that’s exactly what that book was about. Yes, it’s basically like okay, I’ve thought about this a lot and here’s what I think.

And yes, I think that does help me move forward. Definitely as far as how I do a fiction story. What I put in Nail Your Story, that’s how I do them now. And that’s kind of going to be my process for a while probably.

Sean:  Do you get more enjoyment out of one or the other, or is it just a matter of I’m doing this thing right now, so it’s what I enjoy and I’ll do the next thing later?

Monica:  Yes, I think I love fiction more. And when I think about the project that I’m passionate about right now, like it’s definitely a fiction project, and it’s one that I’ve been trying to do since like 2010.

Sean:  That’s a long time in.

Monica:  Yes. It’s kind of like I started it many times and I mean it’s gotten pretty good feedback so far, but it’s really like I just haven’t been ready to do it.

So I feel like Nail Your Story, actually having that done made me, well, I hope it made me ready to do this next project.

But I definitely think that I’m probably more passionate about that. And I was trying this year to figure out what is the one thing that if I died on like January 1st, 2017, what is the one thing I will have wanted to do in 2016? And the project is Waters Dark and Deep, which is a fiction series.

So I definitely enjoy doing the non-fiction, but I feel like most of the time – so I was listening to Big Magic by Elisabeth Gilbert this week and she talks about this in this book. She says that a lot of her non-fiction, and maybe because it’s more of a memoir, but she says a lot of that is about figuring out her own life, or kind of processing something that’s happening in her own life, as opposed to necessarily like trying to help other people.

When that books goes out, it resonates with people and that’s why she’s had some big bestsellers like Eat, Pray, Love and I think several of her follow-ups.

So I think for my non-fiction, I think a lot of it is me processing my own life or processing something that’s happening in my life usually. And it’s usually about what I’ve been learning.

So it’s just a very different thing than fiction. Fiction I feel like I’m writing that for myself but also for others to enjoy.

Sean:  How hard is it to follow through on your ideas?

Because you’re clearly an idea person, like at the highest level, right. It seems that the idea is as exciting, if not more, than the execution, right.  So how do you reconcile that with your day-to-day?  So in other words, how ideally would you like to spend your time? Is it doing the things that you do now, or would you like to build out a team so that you’re really almost like a show runner and you’re coming up with ideas and then having other people articulate them?

 Monica:  Yes, I’m definitely an idea person, 100%. For example, when I was still working in corporate. I would be able to get these major jobs, jobs that I shouldn’t have even gotten because I had all these great ideas and I could pitch those ideas and get hired very easily.

But then it was like the execution kind of wasn’t as great basically. So then people were kind of pressured, understandably, and I understand that.

But yes, I would say as an idea person the best thing that you can do is build a team of people around you to execute your ideas. And a lot of people kind of frown on oh, you’re an idea person, not a doer. And people want you to be a doer, but I do think there’s a place for it.

Sean:  Hey, having ideas is hard! I think that is doing.

Monica:  Yes. I think that I felt bad about being an idea person for a while, but I have a team of three now and it’s a very, very new team. This is all like in the last six months, but they are all doing stuff and we’re moving really fast now because I have a lot of good ideas and they’re kind of like executing them. So that’s how I would balance it.

Sean:  So ideally how would you spend your time? Do you have a picture of an ideal day or do you just kind of let that constantly evolve?

 Monica:  Yes, so my ideal day – I feel like I pretty much live my ideal day at least like several times a week.

But my ideal day right now is really taking care of myself health wise, so I’m doing like a Pilates Yoga challenge right now. So I do that every morning. I take a walk pretty much every day either with my dog or by myself.

I have like three buckets of work right now. One is my passion project, which for 2016 is the Waters Dark and Deep series, so I try to spend an hour on that every day.

And then I have my work writing I guess. So it’s like projects that I’m excited about and I’m happy to do but like at the end of the day it’s still a job. And I know that. It’s an amazing job and I’m very lucky to have that job, but it’s stuff like continuing the Maddy Raven brand, continuing the Prose on Fire brand. It’s like the books that I know that I need to write.

And then my third one is I call it like Asana time, but it’s really like project management time. It’s like filling in our project management tool with tasks for people to do basically. Trying to express like my ideas for marketing or whatever else it might be, and just kind of getting that organized.

That’s what I do every day. The first one I spend like an hour and then the other two I spend like two or three hours, and then I do all my workout stuff. That’s pretty much all I do.

I cook dinner at the end of the day and I spend time with my fiancé and my dog, and that’s pretty much it.

Sean:  You write really fast, which clearly I’m a huge fan of, and you’re experimental in the way you write fast too. Like you’re always trying to push it and you do a lot with dictation, which I also think is great and a nut that I swear I’m going to crack this coming year. It’s my year to get dictation because I think I should. I’m verbal. I think it’s just a muscle I have not trained.

But clearly you don’t think that hinders your quality.

In what ways do you think that writing fast has helped you become a better writer?

Monica: Well, I do think that writing fast it just leads to more practice, which leads to more quality.

I was reading something, but I don’t have the details of the article, but it basically kind of said this. It said there were two groups, one was told just create a huge body of work and then the other group was told create this perfect piece of art.

And the group that was told create a huge body of work, they actually had improved their skills significant by the end of this experiment. And I would love to have the link for you but I just don’t have it.

I do think that quantity leads to quality, when it comes to art at least. And practice leads to quality. So I definitely think having written so many books, I definitely think has made me much better at writing books.

Are any of my books perfect? Not at all, but I think that I’m moving toward that excellent book that I think some people spend ten years trying to write. I think I’m probably moving toward that faster.

Sean:  Yes, I imagine you’re definitely moving faster towards that. And that’s the thing. That’s always been part of our model. I would rather work on ten different books a year than that one book that you just go over and over and over and you may send out an extra few percentage points on the way to perfection, but to my mind, it’s at the sacrifice of all the other practice that you have building new worlds and new characters and new dialogue and new rhythms.

Every time you start a new book on page 1 you get a fresh chance to do something amazing and to really accelerate your growth.

Monica:  Yes, exactly. I mean you learn something new from every single book that you write. So it just makes sense, write more books.

Sean:  I totally agree.

So what’s the biggest mistake you’ve ever made and probably the more interesting half of this question, what do you think the indie industry is getting wrong right now?

 Monica:  Wow. Biggest mistake, I don’t know. I think getting married for the first time. I know that has nothing to do with writing, but I’ll kind of tie it back to writing.

Sean:  That’s part of your journey though.

Monica:  Yes.  So, I think if you want to make art your career in any way, you’ve really got to have a great support system, and you’ve got to have somebody, especially your spouse and your kids, they have to support you or else you’re just not going to make it.

The person that I married, we just didn’t see eye to eye on the whole art thing, and I think that held me back for several years. And unfortunately it kind of led to the end of our relationship. But kind of the second time around with my new spouse, he understands what I’m doing and he’s very supportive, and I think that has helped me tremendously.

I don’t think I would be where I am without his support.

Sean:  Yes, I for a fact wouldn’t be without that support. I don’t know how anybody does it if they don’t get that push from their creative or I guess their life’s other half. It’s really hard to find that in yourself.

Monica:  And honestly so your book Writer Dad, I know I’ve told you this personally but I just want to say it on this podcast because it’s my very favorite book in the whole Sterling & Stone catalog.

I think reading that book really made me realize like this support thing is so important. Because it’s just so clear from the book that without Cindy and your kids, you wouldn’t have made this leap.

Sean:  No, never.

Monica:  And I just love that about the book. But I think, and I’m sure you get these emails too, where people are like oh, I want to write faster, I want to write more but you know my spouse is just not on board and you can feel it.

Sean:  It’s such an uphill battle.

Monica:  Yes, you just feel so bad because you know it’s kind of like well, you’ve got to get your spouse on board or else you ditch art or you ditch the person. I don’t say that to people but you know that is sometimes…

Sean: But there is a reality there. Yes, it’s a very lonely existence if you don’t have the support. And that doesn’t mean your spouse has to be like the biggest fan of your work or artificially inflate you in that way. But they have to support the dream.

They have to believe that it’s worth your time, even if you’re not going to go make a million dollars as a writer, it’s worth feeding that something inside you, and they can’t be jealous of it. They can’t be envious that oh, he’s spending this time, she’s spending this time behind a locked door with a computer.

It’s not a competition. It’s something that makes you a bigger whole person.

Monica:  Yes, exactly.

Sean: But thank you for saying that too. It’s always nice to hear and just thank you. That’s a book that I almost never published. In fact I probably wouldn’t have if Johnny hadn’t pushed me to. It seems so personal.

Monica:  Yes.

Sean:  So what do you think is something that indie industry as a whole is kind of doing wrong?

Monica:  Well, I mean one thing, I don’t know if this is the indie industry as a whole, but I do notice that people do a lot of promotion but they’re not building like systems. So that’s kind of something that I’ve been thinking about a lot is just this idea of building a system to bring people into your series, like get them through the series.

And I think people focus just so much on that initial part, almost like the top of the sales funnel, like I’ll just get people into the first book or whatever, but they focus less on nurturing their fans and just kind of keeping people even moving through the series.

Because you kind of assume like, okay, someone read the first book, they’re definitely going to read the second or they’re going to read the third. And it’s like there’s a lot of stuff that can happen there.

Sean:  Right.

Monica:  Because like they could forget about you. They could miss your launch.

Sean:  Very easily.

Monica:  Right, like there’s so many things. They could just not really care that much after the first book.

Sean:  Especially as congested as it is right now. There’s so many authors and everybody’s screaming for attention. It’s not just that your book has to be exceptional, you kind of have to tell the reader what to do and where to go and how and really lay it out step-by-step.

Or like you said, there’s just too many things in their way.

Monica:  Yes, and I think about that a lot. I’m thinking right now about the whole entire sales funnel of like how do I turn someone into a reader, and then a reader into a fan, and then a fan into an evangelist.

And just like what pieces of marketing I guess need to be in place for that.

And I think there are a number of things that I wouldn’t be doing otherwise, like social media for example. I’m kind of investing more in that because it’s really about activating current readers.

There’s not really a sale to be made there. It’s more about just like activating my current people and then they kind of spread the word a bit more.

But I’m seeing a lot of that type of stuff and I think that’s where authors are kind of missing the boat.

Sean:  What book or movie, I know you’re big on TV and film and that’s eventually where you want to go, so what book or movie or TV show do you wish came from your brain, you wish you would have written it?

 Monica:  Oh, man. I know nobody is going to agree with me on this, but there’s a show on the CW called The Vampire Diaries and I actually think it’s like brilliant.

It’s in its seventh season right now and it’s a teen drama so I know that most people listening to this haven’t seen this, but the way they reinvent the show every single year. Like to play to a teen audience for that many years and to make the show feel fresh and new every time, and just to have all these different villains, just the show runners are like masterful with the way they do it.

Sean: Have you read the source material for that?

Monica: I mean I’ve read some of it. I’ve read like the first book, so I haven’t read the later books.

Sean:  I heard the show runner on a Nerdist writer’s panel and it was really fascinating. It made me want to watch the show. I have not watched the show still, but it did make me interested in it. It sounded awesome what they were doing.

Monica:  The show runner, she took these villains on the show and she turned it into a whole new show. The spin-off of that show is called The Originals. So she’s got essentially two hours of vampire teen drama on the air right now and I think The Originals is in its third season.

To take a villain to make them the protagonist, that is really frickin hard to do.

Sean:  Yes, that’s pretty awesome.

Monica:  And these villains are immortal, and there’s kind of like no way to kill them, but she comes up with new ways. It’s really impressive to me.

I mean Shonda Rhimes is the only other, so like all her shows I love, which is Grey’s Anatomy, Scandal, How to Get Away With Murder.

I’m obsessed with everything she does right now. And I would love to be her, so.

Sean: When you grow up.

Monica:  When I grow up I want to be Shonda Rhimes.

Sean:  How easy is it for you to stick to a genre?

Monica:  Oh, that’s impossible. I’m all over the place. I like stuff in a lot of different genres, and more so in television than books. I’m trying to improve my book reading.

But yes, I like stuff in every genre, and I like writing in all different genres.

Sean:  Are you more inspired by real life events, television, books or movies?

 Monica:  I don’t know. I would say probably all of them. I guess real life events. I don’t know, it’s hard to pick.

Sean:  Depends on the project, right?

Monica:  Yes. I mean sometimes it’s fun to give something like that glossy feel of like this would never really happen in real life, but it’s kind of created to make you think about this aspect of life more. So I think television and movies do a very good job of that.

Real life events, I’m obsessed with celebrities and their lives. I don’t know why. So I think definitely stuff that happens with celebrities that always kind of inspires things that happen in my books for some reason.

Sean:  What do you want your legacy to be?

Monica:  Yes, that’s hard.

Sean:  Come on, you had to know that was coming.

Monica:  Yes, yes, I probably should have.  So right now, I don’t know.

I guess I want to be a storyteller above all things. I want to work in different mediums, not just be an author. I want to be an entrepreneur and I want to be known as somebody who really built an empire and didn’t just write a series or something. Like wasn’t just one thing.

Kind of like how Oprah, she’s not just a television show host.

Sean:  Yes, she very easily could have been and decided that she was not going to settle to that. She had way bigger eyes.

Monica:  Exactly. Yes, like I would love to be in the magazine business or in the television business. I’d love to tell stories in lots of different ways.

I’d love to be an investor for start-ups and have that entrepreneurial thing as well.

But right now, there’s one series right now, the Waters Dark and Deep series where I feel like just right now, if I write that series and finish that series, that will feel such a huge accomplishment to me and I’ll be very happy with that legacy for the short-term.

So that’s kind of where my focus is right now.

Sean:  Well, that’s a very good answer and I’ve no doubt you’ll accomplish all that. Your head is just so in the right place and you think big and you’re unafraid. And even if it takes you a while to get the doing done, you’re always going forward and you’re always trying to teach yourself something new, and do something new and that’s just such an admirable quality. Especially when set against the things that you’re trying to accomplish. You just have so many arrows in your quiver I guess.

Monica:  Yes, thank you so much.

Sean:  You are very welcome. Where can people find you?

Monica:  You can find me at and that’s where my Growth Hacking for Storytellers series is.

Sean:  And I would, for anyone listening to this, I’ve read all of Monica’s non-fiction and it’s all great. You can’t go wrong with any of it. So pick it up. And I think it’s all in Select at this point, right, at the time of this recording, so if you’re in Select you don’t even have to pay for it and she’ll still get paid. It’s awesome.

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