Episode #16: Workshopping & Outlining (Intro to Book Writing Mini-Series, Part 3)

In today’s episode, we’re bringing you the third of our 3-part mini series on an introduction to book writing. We’re taking you on a deep dive into the meatiest (and perhaps most challenging?!) part of book writing: workshopping and outlining! We then finish the show with a weekly actionable tip.

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Welcome to Driven; a show about business, life, and wellness from two confident, curious women who are pulling back the curtain on what it’s like being an entrepreneur. Each week, join hosts Diane Sanfilippo and Cassy Joy Garcia talk about being your best, showing up for your dreams, and kicking self-doubt to the curb.

Diane is a business whisperer, best-selling author, and plant-hobbyist based in San Francisco. Cassy Joy is the founder of www.FedandFit.com, best-selling author, and casserole enthusiast. She calls San Antonio, Texas, home.

Diane Sanfilippo: In today’s episode, we’re bringing you the third of our three-part miniseries on an introduction to book writing. Today we’re going to take a deep dive on the meatiest and perhaps most challenging part of book writing; workshopping and outlining. We’ll then finish the show with a weekly actionable tip.


  1. What’s on my plate [2:24]
  2. Shop Talk: Workshopping [10:51]
  3. Shop Talk: Outlining [32:27]
  4. Tip of The Week: talk to somebody [47:07]

Cassy Joy: Today’s show is brought to you by the Nutritional Therapy Association. The NTA trains and certifies nutritional therapy practitioners by focusing on bio-individuality and the range of dietary strategies that support wellness. The NTA emphasizes a whole-food, properly prepared, and nutrient dense diet as the key to restoring balance and enhancing the body’s innate ability to heal.

Throughout their programs, students learn a wide-range of educational tools and techniques to identify and correct nutritional imbalances and deficiencies in their clients, and to launch a successful career in holistic nutrition. The NTA produces like-minded practitioners and consultants that we endorse and consider colleagues in the health and wellness space. Registration for the February class is now open through January 31st. And seats are already filling up quickly. You can learn more, and save your seat by going to www.NutritionalTherapy.com. Don’t forget to mention our name, The Driven Podcast, on your application.

1.  What’s on my plate [2:24]

Cassy Joy: What’s on My Plate. In this segment, we talk about what’s happening in our businesses, and in our lives this week. Diane; what’s going on in your neck of the woods?

Diane Sanfilippo: Well, I’ve got a few updates. So this episode will air December 2nd, so we will just have wrapped up a big week of a Black Friday sale. So I’ll share more on maybe how that went later, when we actually have that information. But really exciting. We all know that this time of year is obviously a big time for shopping and gifting. And it’s actually a big time for new customer acquisition. I noticed with a sale that we did several months ago, when we looked at the ratio of new customers to returning, we actually brought in a lot of new customers with a sale that we had. So I’m super excited to be able to look at the data from this week from the Black Friday sale for Balanced Bites for both spices, and we have an offer that we were giving out for meals as well. So I’m very excited to look back at that. But that will just have wrapped.

The Balanced Bites team retreat is actually happening this week, as of the airing of this episode. So we will definitely give you a little recap on that, as well. And for those of you who follow on Instagram, I did this little succulent wreath workshop at The Sill. We all know I’m so obsessed with The Sill. Hello, if you work for The Sill and you’re listening, please sponsor our podcast {laughs}.

Cassy Joy: {laughs}

Diane Sanfilippo: But I did this really fun succulent wreath workshop. And I thought; well, maybe this lovely woman who is teaching the workshop could come to my house and teach it with the members of our team. So we’re going to be doing that as part of our retreat; a little fun team building exercise.

Cassy Joy: Fun!

Diane Sanfilippo: Yeah. I always feel badly when I’m doing stuff like that, and I know that the team sees it, and they’re like; we want to do that too! So I’m super excited about that. And two other business-y updates. We’ve got a video editor in testing mode right now, so I’m very excited about that. We’ll see what happens. She’s going to be working on something that’s a bit of an example kind of demo. And I think this is pretty common; maybe not for every type of role in companies like ours, but for creative types of roles, especially. And I think we can probably talk about this when we do a little miniseries on hiring. I’m sure we’ll be able to do that at some point soon.

But, I am so much more interested in seeing what someone can do than seeing what they have done in the past. A resume is relevant and important; I need to just take a look at that and see where you’ve been. But when I give you a task to do, that’s where the rubber meets the road. Because I don’t care what your resume says; if I ask you to do something, and what comes back doesn’t really align with either what your resume said or what I need, it’s not going to be that helpful. So, she’s working on a little example, and we’ll see what happens. So that’s exciting.

And the last new, we’ll actually be kicking off probably in January 2020 is we have secured a branding firm to work with for Balanced Bites. We’re getting some new branding, and I found a company that I think is going to be a really good fit. They also can work on a Shopify site, so we do have two Shopify sites for meals and spices. Each have their own. So if we decide we do need help changing what’s going on with the sites, they can help with some of that. And they have an illustrator who they work with who, his work seemed to be a good fit for what I want for some new branding for Balanced Bites. I’ve got a really; I mean, I think it’s a fun and creative idea, in mind. So we’ll keep you guys updated on some of that going forward. But it’s going to be totally different. Because we have never really had an illustration, or an icon, or a company mascot. And I’m really inspired by what Siete foods has done with their branding over the last several years. They’ve really up leveled. So yeah. I’m just super pumped about that, and finally going to be moving forward with it.

Cassy Joy: That is so stinking exciting! {laughs}

Diane Sanfilippo: Cassy’s face did indicate the excitement before she said that. So. I love being able to see your face while we’re recording. What’s going on over in San Antonio? I know you always have so many fun updates.

Cassy Joy: Yes. So, I’m about to admit a mom thing that maybe most people don’t talk about out loud. But I’m going to go there. So I’m pregnant with my second child, and I’m in my 17th, almost 18th week of pregnancy. So I’m almost halfway through. And with Gray, my daughter, I was aware that I was pregnant just about every minute of the day. Right? It was something; it was always top of mind. I couldn’t wait for the next doctor’s appointment. I thought; man, these doctor’s appointments are too few far in between. And with this baby; I forget. I forget that I’m pregnant.

Diane Sanfilippo: {laughing} Second child, uh…

Cassy Joy: Is that what’s going on? Is there just so much work going on? I find myself forgetting. Anyway, I say all of this because I’m in this season now that I can start; I have another anterior placenta. I just threw out the “P” word on a business podcast. {laughing} But I have another anterior placenta, which is what I had with Gray. Which means that the placenta attached; it’s essentially between the baby and if I have my hand on my belly. It’s between me and the baby. So it acts as a buffer, a pillow. So I can’t really feel the baby kick a whole bunch with it in that position.

So now, but I can feel the baby now. And it’s just nice to now have a reminder throughout the day. Baby will kick and I’ll be like; there is a little human in me! That is so sweet! And then I just; anyway. I don’t know what that admits or not but if you’ve ever forgotten in those instances, I’ve got your back.

Energy is high, speaking of pregnancy. It’s second trimester, and if you’ve ever been through it; the first trimester, for my pace of how I approach life, I was at a low. I was not feeling great. I was tired. I don’t nap, I’m not a napper. And I would fall asleep on the couch at 3 p.m. It was really bizarre. And I was rested. It’s not like I wasn’t sleeping at nighttime.

So, anyway. Energy is high, and it just is the best dang feeling in the whole wide world. I’m like that; that manifesting generator in me is like; oh yeah. Let’s kick things back into gear. It’s nice to be able to have this season. Honestly it feels like a blessing. Such a blessing. Because I’m about to dive deep into the book world, right, and kind of leave my team high and dry. Not really, but I feel like I’m leaving them high and dry to keep the Fed and Fit website afloat while I’m lost in book world. And then, I’m going to have a baby. And then, I’m going to have a maternity leave. So it’s just so nice to be able to really get in there and really generate some work with the team and grind with them, so it’s been great.

We’re doing holidays a little bit differently at Fed and Fit, if you haven’t noticed already. But we are focusing more on quality than quantity in this season of gifting. In the year’s past, there was this pressure as a content creator to want to just check all the boxes. If I heard of a deal, then I felt that it was my responsibility to tell you about the deal. Right? No matter what it was, or where it came from. Because maybe you like those number two pencils, and I just found out they’re two for one right now. I don’t know what it is; a terrible example because I’ve never seen a deal on something like that.

But, I just felt compelled to want to give all the deals. And we are really focusing on quality. And I think that our readers are growing up with us as content writers, because they’re looking for more quality instead a curated list, here are the five or the seven things to focus on. Get up early; and this time will have already passed, like Diane said, by the time this episode comes out. But the plan is; get this email in your inbox on a Black Friday at 5 a.m., sit there with your cup of coffee, and you’re done. You’re done in 30 minutes, if you want to be done. It’s not this endless array and just line up of deal after deal. So that’s going to be exciting. We’re also doing more sustainable gift guides. Homemade gift guides. Things like that that hopefully add more meaning to the holidays.

2.  Shop Talk: Workshopping [10:51]

Diane Sanfilippo: Now it’s time for Shop Talk. The whole reason we created this podcast. In this segment, we talk about topics that are on both our minds and yours. We’ll cover all sides of the issue, and hopefully land somewhere concise, actionable, and helpful.

Cassy Joy: Today we’re talking about workshopping and outlining your idea for a book. So just to recap, in case you missed it. We really encourage you do start at the beginning of these miniseries if you’re jumping in fresh. Rewind to; let’s see, episode number 14 would have been the first episode in this miniseries on book writing. We talk about the whole book writing process. And then Diane and I do a deep dive on pros and cons; and we’re very honest. Brutally honest.

Diane, I don’t know about you, but I had some friends message me that are currently working on a book, had recently signed contracts and were like; oh no! Did I make a mistake? {laughs} I was like, no you got this. You’re going to be great.

Diane Sanfilippo: I had someone who has just turned in her manuscript who was like; yep. Agree. On all of that.

Cassy Joy: {laughing} Oh man. And then our second episode, we also did a deep dive on the proof of concept phase. And in hindsight, we thought we would squeeze that in with also workshopping. But in hindsight, it really did deserve its own episode. Because it’s such an important crucial stage of the project if you want your book to be a success. And of course you do.

So today we’re chatting about workshopping and outlining. And this is arguably, could be some of the most challenging part of the entire book writing process. And we want to call that out; it’s all a challenge. But this is where you transition; kind of like Diane and I were having a conversation before we really started the episode. So if you’re familiar with; what is the personality test? It’s the Manifest generator?

Diane Sanfilippo: Human Design?

Cassy Joy: Human Design. Thank you. So I am a manifesting generator within that context. And I find that’s why this is so challenging. Because you go from the manifesting stage of the book process to having to generate. And I do; I think it’s a big pill to swallow. And a big gear to really shift into.

So workshopping your idea is what we’re talking about first. How to workshop the idea further. And then we’re going to talk about some of the nitty gritty examples. But I want to quickly highlight; when we were talking about proof of concept. Remember we said in that episode that during a proof of concept, you want to cast as wide of a net as possible. And get as much feedback as possible. This is where, if you have a website, or an email list, and maybe some social media presence, you want to talk about this idea to all of them. And you want to see where it lands. You want to see what kind of feedback you get, because you just really want as much data as possible.

Now, once you’ve done that, and you have a better idea of where the concept needs to go and how you need to evolve it, you’re going to workshop it. And you’re going to do that with a smaller net of people. This is when you focus. You create a focus group; you create a beta group. You really dig in with a smaller number of people.

Diane Sanfilippo: So at this point, what I’ll do is jump in and talk about the ways that I workshopped a couple of the books that I have written. Because it has been a similar process, but different for some of them. So going back to Practical Paleo, my first book. And, even thinking about the 21-Day Sugar Detox. When I wrote the 21-Day Sugar Detox as a program, it was an eBook. So that was kind of; it was casting a wide net, but that was actually a bit of a smaller net because people did need to pay for that. So I’ll back up to Practical Paleo as the first one.

I was blogging, which was the wide net. I was posting on, at the time, Facebook. Instagram didn’t really exist. And Twitter, just kind of helping people answering questions about what is paleo and how to help them make that transition. But when I decided to write Practical Paleo, it was after I had actually been physically workshopping, teaching workshops. And I think, for anybody is teaching information or has a service-based business, anytime you can do things where you will have not only some free content, but a way to say; will people pay for this?

If people will pay for it in a workshop, where they’re coming to sit with me for three, four, or eight hours, and they’re going to pay anywhere from, let’s say, $35 to $45 up to $100, $115, to be there in the room for the day, then that’s a great proof of concept. And, when I’m in the workshop, I can actually get that real time feedback of; ok, which topics are they really excited about. Which ones do they need more information about? Where am I not going deep enough. Which topics are not best served for this format? I’m like; hey that’s going to be great in a book because I can really detail that. Which do they seem just confused about?

So really it’s about paying attention in that moment, too, when you are workshopping, essentially it’s testing. Right. So you have this proof of the concept being of interest to people and does it work? But now you’re really getting into the nitty gritty, the N=1. Did this person try your method and it worked for them? Did this person come to your workshop, your class you were teaching, and they learned what you wanted them to learn? Did they walk away with what it was that you were trying to teach?

So that’s something that, also at the end of each of these classes that I would teach, I would always have a feedback form. And it’s not always the easiest to end the day and read those forms. And I used to be like; Liz, let’s read the forms! And she’s like; really, Diane? We just finished this class. I’m like; yeah! Give me all the criticism right now. While it’s fresh, I want to hear everything. So I would read those, and it was really helpful to know; ok, somebody expected to learn more about this thing. Or they didn’t expect to learn this and they loved it. It was their favorite.

And really diving deep on what are those topics that you can discover you didn’t realize; wow. That was new to them. I thought this was old information; I didn’t think going deeper on this was going to be valuable. But it was. And maybe I’ve explained it in a way, or I’m presenting it in a way that they have not heard before. That reflection and that response and feedback is so valuable. Because I think; often we’re in a bubble, or we’re even talking to our peers, or we’re working with just the people who are giving us feedback when it’s free. And that’s not always the most valuable feedback. You want the feedback from somebody who is potentially either paying for something or maybe they opted into your email list. That’s still a payment. Someone’s email is still a payment in a way. It’s not just floating out there on the internet for free.

So that’s what happened with Practical Paleo. I was teaching workshops for a couple of years. I was also working with one-on-one clients, which was workshopping the hands on of the meal plans, and how does this work, and is it practical? Can they make these recipes? Is this easy in their lives? And I think remembering that we’re there to solve problems with our book, whatever it is. Whether you’re solving a practical, in real life, saving time type of problem or saving money type of problem. Maybe you’re solving emotional problems or thought pattern problems. Right? Some self-help books and just kind of sharing about your life. And I think whatever that is, we need to make sure that it may have worked for us, but it has to also work for other people to then move forward.

So that was kind of what happened with Practical Paleo. And then with the 21-Day Sugar Detox, it was a similar thing but not with the workshops. I had written an eBook that was not free. People had to pay $21, and hundreds and then thousands of people went through that program. So eventually knowing that writing a book would be valuable and people would get a lot out of it and be able to complete the program successfully and have the results that they wanted, and that we expected, obviously it had that initial proving ground of; we have actually run this program in this way through the eBook, and now we’re just taking it bigger, expanding on it, giving them a lot more recipes and putting it into a book.

So what would you say about this process, for you, maybe initially with Fed and Fit and then moving on from there to Cook Once?

Cassy Joy: Fed and Fit is a much easier, succinct way to talk about the workshopping stage because it was a nutrition program that I was really trying to iron out. So I went from the proof of concept phase, was really me blogging, talking about it, trying to see what language resonated with people. What problems were they actually facing? And then, of course, in my one-on-one consultation business and just seeing what trends emerged. That was kind of that period.

Now, when I came up with the Fed and Fit Project, which was essentially a way to help people figure out how to design their own healthy lifestyle. Which is in Fed and Fit the book, you can still access all of that information. But when I decided that I wanted to build this program, I workshopped it with a genuine beta group. I opened up applications to my email list. I said; you guys have heard me talking about this. You know I’ve been working on it. My community is always in the know of what I’m doing; sometimes three, four years in advance of me actually going live with it. Because I don’t believe in secrets. I really don’t. Maybe that’s a marketing fail. But I would just rather everybody know everything. And be along for the ride. I really value transparency in that regard. So folks knew.

And I said; hey I’m going to open this up. It is rough and tumble. Don’t expect a pretty eBook. Don’t expect pretty downloads. In fact, I don’t have any of that. And I’m going to run the whole thing in a private Facebook group. And I’m going to write it as I go. So what I did is I opened it up; I had 25 spots that I wanted to open it up to. So remember, small net. 25 women applied. Sorry; more than that, but I wound up settling on 25 people who were ready to dig in, and it was just apparent in their application that they were familiar with the concept and ready to do the work. Because it’s work. The Fed and Fit Project is work. There’s a lot of journaling and a lot of reflection.

And I will forever be grateful. We call them the beta girls. I will forever be grateful to these people who came in and really helped me put the four walls around this concept that I had dreamt up. But I did; I workshopped it with them in a Facebook group. Every single day, I would post the new piece of content that I wanted them to have for that day in Facebook. I would write it that morning, on this private group. They would all reply with their feedback; what they were doing, how they were learning from it. And I would use that and improve it.

And by the end of the first 28 days in this Facebook group, I knew by then that I wanted to have a 28-day track; I knew that I wanted to have a 3-month track; I knew I wanted to have a reintroduction phase that was more grace-filled than necessarily technical. I knew I wanted to focus a lot more on mindset, because that’s where folks were struggling the most. And I never would have had those answers; I never would have had that clarity if I had skipped this stage. If I had just written the program.

So it was crucial. It was crucial. And the Fed and Fit Project has been wildly successful for the people who have put in the work for it. So like I said, I will forever be grateful for that.

For Cook Once, Eat All Week, it was different; this phase. Because it’s a meal prep concept. So the workshopping on that; proof of concept, like I said on the last episode, was more around the website, the web series, putting it out there on the blog as a free download, and then just the wild acceptance and excitement around this brand new way to meal prep was what told me. Because that was the wide net, right? Was what told me; ok, we need to workshop this further.

And then what we did is I just followed up with really just our core team. I workshopped it; at this point, I had the luxury of a Fed and Fit team, and I could dig in with them. And we sat there and we brainstormed and we fine-tuned, and we asked tough questions. We ruffled it up. We reshuffled the deck. We were tough on ourselves to make sure we were making this the most concise product possible.

So that was the difference between those two in terms of this workshop stage. But I had this thought, while you were chatting, Diane. And I want to highlight it before I forget. If you’re thinking that you want to write a book; and maybe you do. Maybe you are writing a book. And you get to the next part; the outlining stage, and you are looking at that paper, and you’re thinking; gosh. I wonder what to put on here. If there is some mystery around what you’re going to include in your book, and if there’s some mystery around the problems you’re solving and what sets you apart and what’s going to be of service to people; if you don’t have those things locked down before you sit down to write your outline, you skipped this step. And you need to go back. Because it makes the rest of it easier. It really does.

Diane Sanfilippo: Yeah.

Cassy Joy: This might sound tedious. It might sound superfluous. Did I use that word correctly?

Diane Sanfilippo: {laughs}

Cassy Joy: It might feel superfluous in terms of the whole effort, because when you’re chatting with your book agent and your editor, this is not a part of the process that comes up in conversation. But it’s going to make a world of difference.

Diane Sanfilippo: Well I think, too, sometimes what happens is people take the proof of concept stage as enough, and often it’s actually not even their own proof of concept. I was just thinking about this, too, for Cook Once, Eat All Week. That was your own proof of concept. But just the concept of meal prepping being something that people want is not enough. This stage is so necessary because it’s a deep dive on your solution. Your particular approach. Your particular take on something.

So I wanted to throw a couple more things out there on this workshopping thing. Because as we ran people through the 21-Day Sugar Detox back in the day, part of what came out of that. I mean, again, it is the workshopping. It’s not the proof of concept anymore. We discovered; and I say we. Myself, and at the time, probably one team member, maybe two. That people needed to know what to expect. While they went through the process; yes, people can have a list of what to eat and what not to eat. Yes, recipes are going to be really helpful.

But we learned along the way that the best thing we could give people was a bit of a roadmap of, here’s how you can expect to feel days 1 through 21. And then we also got the feedback of; how am I going to feel before and right after too? And if we could give them that, it would actually help them be a lot more successful. So that’s part of the value of the workshopping. It’s like; if you don’t have people actually test your concept and go through it, you’re not going to find the holes. Because you know the whole thing. You know what I mean?

You know how to take your Cook Once shopping list and make it work, etc. But when someone else goes and tests it out, and they’re like; actually, I wasn’t clear on this. Or it was missing this. Or I needed more instruction here, etc. I didn’t know what to do in this spot. That also helps you build confidence. Because when somebody identifies that something is missing; oh my gosh. You actually feel so much better because you realize you could never have thought of that on your own. You wouldn’t have seen that missing piece. And you know that that one person represents hundreds or thousands or tens of thousands more people who would have had the same exact question.

So then what we ended up doing with the 21-Day Sugar Detox Daily Guide was extrapolating that out into even more. Because as we watched more people go through the program, I was like; you know what? The single deciding factor to the success of most people on that program is whether or not they are prepared when day 1 comes. Because you can’t decide today that you’re going to start a 21-Day Sugar Detox tomorrow. For most people. Because you won’t have the right food in the house. And inevitably, by day two or three. Whatever you did have in the house that was suitable for the program, is now gone. So if you haven’t prepared, then you’re going to flop. And that’s not what I want. And it’s not what you want.

So what I did is I backed it up, and I said; I’m giving you a pre-detox week. I want you to prepare. It doesn’t mean you’re cooking 7 days that week to prepare. It means, the first day you’re reading up. You’re getting your head on straight. You’re understanding and wrapping your head around these different concepts of; there’s going to be people who don’t agree with what you’re doing. It’s just really getting your mindset right, and then starting to get into some of the practical stuff as well, so that you have that chicken broth made. Or that sauce that you want to use. Or whatever it is. So that day 1, you don’t just slam yourself into a brick wall of; oh my gosh, this is so hard, I can’t do it.

The workshopping also; you’ve gone through this now with Cook Once, Eat All Week the first one. Now you’re doing the next one; that book itself has been part of the workshopping, I’m sure, for this next one. You’re seeing where there might be some minor holes, right? Because we can look back and be critical and say; ok, I can do this part a little bit better. We nailed this; and this part we can improve on. So that’s kind of what we learned with the 21-Day Sugar Detox and being able to do that in a new book.

And I’m just going to back up a little bit, too. When it came to Keto Quick Start, and the way that I workshopped the piece of that book that’s really unique in terms of problem solving, for those who aren’t familiar. Most people who tell you to eat a keto diet; all they really do is say; you need to eat this many grams of carbs, don’t go over that. Sometimes people will say limit your protein. I do not believe that’s the right approach to take.

But that being said, when I followed a keto diet, or a keto way of eating, over the last, I don’t know, almost 8 years, multiple different times, the way I did it was different than the way most people do it. So my workshopping on that initially was a bit of an N=1. Just me; I was the experiment. Where I took something that was a proven concept that people used elsewhere, of sort of macro counting, sort of blocking nutrition. So for people who have come from the CrossFit world or you followed the Zone diet and people counted blocks of food. Ok, I’m eating a serving of chicken, whatever it’s going to be.

I kind of combined these approaches in what I was doing for myself, and then what I did in this workshopping phase is I really passed it to a handful of people. It was maybe 5 to 10 people. For that specific element of the book. And I said, I want you to follow this plan, and tell me not only how does the plan in the book work for you in terms of crossing things off and counting and all of that. But how does it actually work for you in terms of results.

The whole book itself wasn’t perhaps the same approach to workshopping; right, because I don’t need to workshop the keto diet. I wanted to workshop my specific approach to what will lead to success for people. So it was a bit of a smaller net, but that’s because I was really only focused on this one element of the book. So I think that’s something that might be worth considering for some people. You might not need to workshop the entire concept of your whole book; cookbooks exist. You don’t need to workshop, does somebody want a cookbook? But there’s a certain element of it that you might want to workshop.

Cassy Joy: Yeah. Whatever problem you’re trying to solve is definitely worth testing to make sure you have the solution you think that you have.

Diane Sanfilippo: Mm-hmm.

Cassy Joy: And to give you some actionable ideas of how can you use this concept; this workshopping concept, depending on where you are. So you can do it; really, you could do N=1. That’s definitely an approach you can have as far as workshopping. You can do this in a private Facebook group, like I said before. If you have your core group of people. When I think about, who do you invite to this core workshop group? These are your superfans of the product. Right? These are the people who saw you come out with this, when you were proving the concept in a very public way, and they were your biggest cheerleaders and your biggest supporters. And maybe also some of your biggest critics. But they were the most vocal. That’s who I’m inviting into this workshop. The people who are going to really dig in with me and be excited to be a part of the process.

So I think a private Facebook group is great. You can do it with an email list. You can do this all via email with 12 people. You can do this in a private Instagram chat. And that’s actually what I did to workshop book three. I have this, gosh, what is it? I went on and created a private chat on Instagram. And I said who wants to dig in with me? I want to know all of the holes that you see with Cook Once, Eat All Week. And I want to know; where can you see room for improvement?

And I already had an idea of where I wanted book three to go. But they really helped inform some of the specific directions. You can do web calls. Webinars. Those are places to do it. So you take your superfans, a smaller group of them, and then you really dig in and you start working the pieces of the concept that you really see are your signature solutions. Is that fair?

3.  Shop Talk: Outlining [32:27]

Diane Sanfilippo: Yes. Alright, so next we’re going to dive into outlining. And this part; I think it’s more challenging for some people and less challenging for others. When we were chatting briefly earlier about the difference between being a manifestor, manifesting generator. We’ll get into that in another episode; I don’t think either of us are extremely well studied on Human Design, but we’ve definitely tapped into a little bit, because we’re just obsessive about knowing ourselves better and trying to work with our strengths and not against them.

So, I think that because a lot of folks actually tend to be generators more than manifestors, I think a lot of people won’t have as much trouble with this part as maybe I do. Whereas kicking off and just starting an idea and having an idea and having that gut feeling of what to do next and how to get it on; throw it against the wall. I think a lot of people will be able to dig into this part. Whereas, what I see out there at large is; what should I even write about? What is even the idea? And I think you and I are both like; we have a lot of ideas all the time. Never the problem is the idea. It’s just kind of sometimes the next part.

But, anyway. In this part, you are fully detailing what it is you’re going to write about. This does not have to be set in stone, of course. You can scratch this out on paper. You can type out a draft. But I think it is important to start to give yourself a bulleted list of; what are the main topics you want to cover. What are the breakdown points from there? And the way that I usually address it, is; what are the questions that you’re answering.

Because if you go to write a chapter; I have a chapter in my most recent book, Keto Quick Start, about fats. And look; there’s a lot you can write about fats. So you have to decide; what are the questions? What are you teaching the reader? And what are you answering for them? What are they thinking along the way?

So, the notes that I have here. What are the main topics you want to cover, and what are the questions that you’re answering, in each of those topics? I would love for people to think of the content a little bit like a presentation, but in a linear fashion. Where you’re not going to obviously repeat yourself the way you would when you’re speaking. When you’re speaking, repeating yourself is a way to emphasis and remind people what you were talking about. Obviously, if they’re in the room with you, they don’t have a transcript right in front of them. So you have to bring them back there audibly, to that other note that you had. But when you’re writing in a linear fashion, they will be able to reference that backwards.

So you want to start with foundational information, and basics. And layer on from there in terms of complexity of ideas. The reader is obviously going to be starting at chapter one and learning as they go. So, if for example, I was teaching about fats in chapter 5 of that book, and I’m going to start talking about elements of why we’ve been told to eat this and that, and here’s what we should eat instead. It’s like; I should lay the foundation for, why were we even told that? Somewhere, way back in the book, I should be talking about what we’ve been led to believe and all of that. So by the time I get into the deep dive, they’re not just thrown, literally, into that deep end and don’t understand the foundations that I need them to understand.

And then you can go deeper and you can kind of layer on from there. And this could also happen a little bit if you end up writing other books where you can potentially expect, and maybe this is something you’ll do with your new Cook Once book; I don’t know what the details are yet. But you can kind of expect that folks have started with book one. Of course, you don’t want to throw them into the deep end either way. But, there can be a little bit of an expectation when people are coming in. It just depends. If this is your first book and you need to get that foundation out there, you can expect people to know what keto is or what it means. Or know what a paleo diet is or what it means, if you’re writing about that type of topic. Does that make sense?

So if you’re writing about female hormones, you can’t just talk about solving the problems. You actually have to start at the beginning, and expect that your reader actually knows nothing. And give them that foundation. So those are some things that I like to give people as far as how to start outlining. And I think it’s going to vary depending on the type of book that you’re writing. I don’t know, maybe you can give us your concepts on this.

Cassy Joy: So for outlining; and I agree with what Diane said, and I think that’s really great advice. It makes me think, actually; back when I wrote Fed and Fit there are 100 pages of nutrition science, and explains my philosophy on health and wellness and mindset and sleep and hydration and fitness and food. And I was like; I have to write this! I have to get this out there. I had to set a foundation. I had to have a reference, in case anybody says; what is your nutrition philosophy? Because I’m eating smoked oysters on seed crackers for lunch on Instagram stories with a squeeze of fresh lemon. Or I’m talking about daily water needs. I needed to have a reference point. So that’s a part of the reason why I did put that there, and I think that’s a really valid point.

So, what I do when I’m outlining a book. Let’s say; Cook Once, Eat All Week is a little bit different. This is definitely a; it was not my foundational, here’s the introduction to Fed and Fit, the brand. Right? It was; here, now we’re solving a more specific problem that a lot of people are seeing. And it’s under the umbrella of what we at Fed and Fit do.

So what I do for outlining is; the way my brain works, I will sit down and almost do a stream of conscious. Is that how you say that phrase? {laughs}

Diane Sanfilippo: Consciousness?

Cassy Joy: {laughing} I sound real smart.

Diane Sanfilippo: Pregnancy brain?

Cassy Joy: Nope. {laughs} I wish I could blame it on that. {laughing} So I will sit down, and I will write out every problem that I think I’m going to solve with this book. Right? And these are things, of course, that I’ve tested. That I’ve worked with the audience on. These are topics I want to address that I feel I can deep dive on, and I can outline and I can build out. And I write them all down. I write all the headers down that I’m going to touch on in this book. And I just have to get them on paper. I have to get them all on paper, and then what I do is after I get what looks to be all of the headers that are going to show up somewhere in my book, I’ll go through and start seeing what groupings are emerging. From a bird’s eye view, I’m able to see the forest for the trees a little bit easier, and determine what are the sections. And then I create section headers. And then I file them where they need to go. All of my ideas. All of the problems I want to solve. All of the important points I think I want to make, I start putting them in each section.

And then I want to talk about one quick pitfall here. Because I think it can be really tempting to have a little bit of an analysis paralysis when you’re thinking about; what goes where? What kind of a concept goes where? What’s worth a little sidebar mention and what’s worth an entire chapter? It’s easy, I think, to fall into this analysis paralysis when you are building out the outline in this stage. And I say; just get it good enough on paper and you will answer those questions in the process of writing. You and your editor or team of editors will work together to really help you answer that. You’ll be more equipped later on.

But just remember that in hindsight, you’ll be able to more clearly determine things. So for example; on Cook Once, Eat All Week we had reheating instructions, for example. Reheating from frozen and from refrigerator, and storage instructions. I had that as a thing that I wanted to include in the book.

And that’s also; speaking of the workshop stage, not something that I was going to include in Cook Once, Eat All Week. I was not going to include reheating instructions, or storage. Because I thought; doesn’t everybody know this? Surely everybody knows how to store food. And surely everybody knows how to reheat from frozen or reheat from their refrigerator. And it’s not. I was woefully wrong. So we decided to include it in the book because it was a clear problem that we could solve for our readers.

And originally, we had all of these; I had all of those instructions on every single recipe. And it wasn’t until hindsight that I was done writing the book, that I could look back at the body of it and say; this makes more sense as its own section at the front. So don’t get caught up in the minutia, or the details of where certain topics go. My advice, if you’re feeling like you just don’t know how to get started on this process. You don’t just write roman numeral one and then start writing your outline in order. Outlines aren’t written that way.

Diane Sanfilippo: Yeah. And when you were saying like the brainstorm; definitely. I will write down what a main topic is, and what questions I’m answering. But I have no idea of what order those are going in. I have no idea if I’m going to come up with another question later, to your point. You’re like; that actually fits better over here. Right?

Cassy Joy: Exactly.

Diane Sanfilippo: That’s all just scratching notes.

Cassy Joy: Exactly. That’s how you outline. I think that before you go through it, you might have this romantic notion that you are going to sit down in Word. That’s where I write, in Microsoft Word. That’s a question that we got that we’ll address in the next episode. But I will sit down in front of Microsoft Word, and I will start my Roman numerals. Or I’ll be tempted to start my Roman numerals and write everything in order. But really, what’s going to make me work through this part of the project the fastest and the most effectively is to do bullet points. And just get them all on paper. And like Diane said; give yourself the freedom to go in and edit and add later.

Diane Sanfilippo: I think also, there might be some people for whom the concept is very clear and they can put it down in order. And they do know. Especially; if you have workshopped something very closely for a long time. When it came to the first version of Practical Paleo; even in hindsight, I’m like; I don’t know. The order of that book; I don’t know if that made sense to people. When I was teaching in a workshop that was like; ok, we’re going to teach this part now. And I think that makes sense to do first. And then we’ll talk about the history, and what we were led to believe. Then I’m going to talk about blood sugar regulation. Then I’m going to talk about digestion. These are the things that I want to talk about, and I think they’re important in this order.

Sometimes you do just kind of have to decide that. But when I went to write my most recent book, Keto Quick Start, I had a conversation with the publisher, actually, at the time. And I was very much resistant to writing the book. And it was like; well, here’s what you’re going to cover. And I was like; oh, ok. And of course, that wasn’t, we write down an outline day one and that’s what actually comes out. But sometimes somebody else might have that 10,000-foot view for you to say; well here’s what you cover in the book. And then you’re going to fill in a lot more details. Or you might even say; actually, you wanted me to fill this part in but that’s beyond where I really want to take this book. So I’m not going to do that.

So somebody else might actually have the ability to help you with that outline. And it really depends, too, on the type of book that you’re writing. Are you working with an agent, and a publisher, and people who actually have; there are going to be some of you listening who are just doing your own thing. But some of you may get to a point where you’ve got someone who says; can you write this book? They might actually come to you and say; can you write a book about this thing. And they might have more ideas for you than you realize.

So there are different approaches to that, as well. And I think if you’re somebody who is obsessed with doing things in a very detailed; I go A to Z, then you can do it that way. You have to do whatever is going to get the ideas out of your brain and onto the paper. That’s the most important thing.

Cassy Joy: Yes. And I think a theme is emerging from hearing you talk, just now, for this entire miniseries on the book. I think it’s so easy to look at a book and think; my name is going to be on the cover, so I need to go at this alone. This is my work; I’ve got to just hammer this thing out. I’m going to do it. I’m going to do the author thing. And at the end of the day, the best works are a team effort. Whether it’s your audience pitching in.

You get as many people involved in this project as possible, from your entire audience and your; gosh, what is it? Proof of concept. I wanted to call it point of view. In your proof of concept stage, you’re getting a smaller focus group together in your workshop stage. And then when you go into to outline, to Diane’s point, work with people on it. If you’re feeling stuck, talk to your editor. Talk to your publisher. Talk to your agent. Talk to people who can really help you mold and get this thing on paper.

Because if you think about it, a book is a community resource. And I think it’s silly and narcissistic and totally egotistical to think that you can come up with the perfect resource for the community all on your own.

Diane Sanfilippo: Yeah.

Cassy Joy: And unless you’re, I don’t know, a novelist, and you just have this beautiful story already perfected in your head. And I don’t even know that all novelists work alone, even. I think that very rarely is that the case. And I think that if you really want the book to be helpful, then get more people involved.

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4. Tip of The Week: talk to somebody [47:07]

Cassy Joy: Tip of The Week! In this segment, we give you one tip that you can take action on this week to move your life or business forward. So riffing off of what I just said about how the best books are a community; it’s a group effort. It’s not something that you create all on your lonesome. So our tip is to get out of your own head and go talk to somebody about your book. I want you to call up your business mentor. The person who you’ve been working with and you bounce ideas off of already. Call them up and tell them about the book idea you have. And just get the conversation started.

I want you to call up somebody who; maybe it’s your business partner. Somebody that you’ve been working with in work, and you’re like; you know what? I do want to have a more dedicated conversation around us writing a book together. Maybe you have an editor already. Maybe you have a publisher that you’ve been in conversation with. Go ahead and start talking to them. And know that it’s ok to get information from all sides. It’s ok to collect information. It’s ok to not commit to everyone’s ideas. But in this information scrappy stage, data is everything. And you’re just trying to get thoughts out of your head, bounce them off of other people, so you can start this process really mindfully and meaningfully.

Diane Sanfilippo: That’s it for Driven this week. If you liked this episode, be sure to subscribe in Apple podcast, on Stitcher, Spotify, or wherever you listen to podcast. Follow us on Instagram @TheDrivenPodcast. Cassy is @FedandFit and I am @DianeSanfilippo. Tune in next week for our listener Q&A episode all about writing a book. We’ll see you next week.