10: Behind the Book: Organizing, Writing and Gremlin-Taming
8 Dec 2025 · 31 min
Jenny Blake walks through her book-writing process: organizing ideas across post-it walls and Google Docs, writing 30-minute daily sessions with a "shitty first draft" approach, and managing self-doubt along the way. Her first book sold roughly 30,000 copies; her new one, Pivot Method, comes out with Portfolio/Penguin.
Questions this episode answers
Spring of 2011.
About 30,000 copies.
A Target order for 15,000 copies (2012) for new-grad displays.
30 minutes every morning.
About five months to get a solid first draft.
Chapters
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Hi, I'm Jenny Blake, your host of the Pivot Podcast and author of the book Turn what's Working for you into what's Next, which comes out with Portfolio Penguin in September of 2016.
In this podcast I talk with peak performers to reverse engineer their most successful career. Pivots interview experts on what it takes to be agile in a rapidly evolving economy and open the kimono on what happens behind the scenes of my book and business. You can learn to capitalize on risk, fear and uncertainty as the doorways of opportunity. My promise is that you will leave every episode with practical tips, tools and tactics. For show notes from this episode, visit jennyblake Me Podcast.
If change is the only constant, then let's get better at it. Here we go.
Part one. You heard about the process of finding a literary agent, writing a book proposal and selling that book proposal to publishers. And also why I chose not to self publish and why I love traditional publishing, books that you can hold in your hand and bookstores. If you didn't listen to that call yet, no worries. Today this second part is going to be about organizing the behemoth task of a book writing my actual writing process and habits, and gremlin taming that goes along with the first two. Naturally, as I caveated in the first call, I'm not an expert. Really important that you know that I and sometimes describe myself like an 8 week old puppy when I sit down to write that I have ADD just like the rest of people who feel like they can't just sit and write for hours upon hours. I don't think of myself as a great writer, just an okay one that has many years of practice. And.
I do love organizing. I will say maybe I'm an expert at organizing, so I can't wait to tell you about that crazy things that go on in my brain to get a book, something like a book organized. And it's getting even more fun this time around because of all the tools that are available real quick. If you're new to me or my site, this is a behind the book deal call from you know I just announced that I got a book deal with Portfolio Penguin for my next book, the Pivot Method, that will come out in early 2016. And it's a blueprint for becoming more agile in work and life. Borrowing principles from Silicon Valley, I will share a three step process for pivoting your career. When you've hit a pivot point, or a point where you feel kind of bored or restless, or as some people describe it, where your job is absolutely soul crushing. So it can run the gamut. My first book, Life After College, came out in spring of 2011 and was published by Running Press.
So a lot of people say to me, I would love to write a book someday. And a lot of people also wrote when they responded, and thank you to all who did, who said, yeah, I'm working on a book or I hope my book someday sees the light of day. And when I talk with people who aren't writers, they'll say, oh my gosh, you wrote a book. It sounds almost impossible. And as someone who did write a book, I kind of agree. You know, even for me, at times it seems and feels impossible, but alas, it is not. It is doable. You just have to break it down into very small steps. One thing is think of the complexity of it as fun. I know that at first it mostly seems intimidating and overwhelming, but the more that I think about pivoting and I'm studying people and talking to people, I realized that the type of person who wants to write a book is usually one who loves a challenge, is maybe you're feeling a little incomplete or it's not always bored, but you just, you want a challenge. So it's the same time that we are intimidated by something like writing a book, there is a part of us that knows, yeah, that's the level of excitement that I'm looking for. That's the level of challenge that I can really sink my teeth into.
Sometimes people also get intimidated. I know I did 100% with life after College about, but you're so intimidated to write the book. And then you're like, but I don't, I don't know how I'm going to sell it. How am I going to sell the book? And you let that get in the way of the writing. There are three very, very distinct processes and I think that they take equal proportion to each other. The first major phase is writing the book. Write a shitty first draft, whether you self publish or traditionally publish, at some point you actually have to write the book. That's big. The second phase is editing. Editing. It shocked me how much time editing took. It for me took as long as writing the book itself. And then promotion is its own gargantuan, amazing, crazy task. And that as well took equal preparation, planning, logistics. Some people have asked, how long did it take you to write a book? I mean, life after college, if you include the book block. The dark days where I wouldn't even open the word file from start to finish, two and a half years. With this timeline that I'm working on for the pivot method, it will be, I'd say, five months to get a solid first draft. I'm not exactly sure how many to edit. And then as soon as I turn in the final book, I'll probably have three or four or five months until it comes out to really focus on the promotion plan and machine. Some people think that they don't like traditional publishing because it's too slow. For me, it is plenty fast, as is now, from the time of this recording, I have.
Maximum a year and a half before the book comes out, maybe less. I'm going to estimate a year just so that I'm on the conservative side. And that's quick to write, edit, figure out the promotion, line up a business model to go behind it. Because this is kind of my. The focus of my. The next phase of my business. That's a lot of work. It is plenty fast. Let me just say that. And so for me, it's really important that I, during the writing phase, for the most part, focus on writing. I tend to take about 80, 20 view of this. 80% of my energy and attention will be on writing and the ideas. But 20%, I do have feelers out for promotion. I am clipping into Evernote things about pre orders or I'm watching what other authors are doing, what kind of bonuses are they giving, how are they launching, who might I partner with, who might be interested in bulk sales? I do have an eye on all of that, but it's not a main focus and I'm not letting it intimidate me right now. So that's how I was with the first book too. You can intimidate me, just not right now. Get back to me in six months. Promotion, so. And then as my brother reminded me with life after college, he said, jenny, if you only sell one copy of your book, you're still a success, you're still an author. And that was such a great thing to hear. We put so much pressure on ourselves to be successful by all these external metrics sometimes. And for me, it is a wonderful reminder that by the time the book is written, I don't have as much control over it as I would like to think. And again, I'm not a mom or anything, but I think of a book like a kid. As soon as it's out, it takes on a personality of its own. And that's how I treated life after college. I didn't want to force it as far as promotion. I felt like if this book is meant to be something in the world, then it will be and people will tell their friends. And it's really going to be readers who enjoy the book who pass it along, or people who buy it as gifts who I've never come into contact with. I don't have to hustle, hustle, grind, do backflips to sell every single copy. Or rather, I don't want to approach it that way. To this day it has sold about 30,000 copies, which blew my mind when I first heard it, and it's published in Korea, Japan, and soon Taiwan. But I got really lucky. Target in 2012 in a deal I had nothing to do with that the distribution company made. They said they wanted to buy 15,000 copies for display in their new grad section of their stores with three other books. That was a huge win. I had nothing to do with it, but it's an example of the book kind of getting its own legs and taking on a life of its own.
All right, let's get down to brass tacks about organizing. I know I said at the beginning, I'm not an expert. This is just my crazy method. If it works for you, awesome. You might think it's way too much overkill. But basically, before I ever even tried to outline the book, I did this crazy post it wall on the back of my front door. I can't wait to show you pictures. And I put these headings across the top in post its. Of course inspiration, books, skills and vocabulary, processes, stories, my own and others and quotes. And then I filled the whole door with post Its. Of course they're in color categories and I let there be blank post its all over my door. And then when I was feeling inspired or motivated or an idea came to me, I would just go to the door and jot something down. So if it was a personal story that I remembered, if it was a book that inspired me or that I would want to reference in the pivot method, I included that. If it was a quote that I liked, I would write that down. I even thumbtacked a rubber band to the side of the door and would hook the pen on onto it so that the pen was always right there as well. And this was a lot of fun. And it was also really fun to see the book visually coming and going. So it was constantly reminding me this is here, this is happening. And you know, I didn't add to it every day, but I just made a point to have a collection bucket for when I had good ideas. And there is a post it applies by the post it company by 3M is freaking incredible. You take a picture of as many post its fit in the view of the camera and it scans them all. It is so incredible. It scans the exact visual of how all your post its are arranged. It's incredible. So if you're someone that wants to start with handwritten, but eventually you want it backed up to your phone or available to you on your computer, that can be done with the post it applies. And hat tip to Brad from Skilled up who told me about that one. So thank you, Brad.
Kind of at the same time as I did the door post its. Then I also started my Evernote collection buckets. At first it was.
Five or six. Let me read them to you. I don't know exactly. I had Pivot articles, Pivot Models, Pivot Quotes, Pivot People, Pivot Books, Pivot Feedback, Pivot Fun and Media, and Pivot Book Marketing. Those are all separate notebooks, so they're all named actually 5a/, 5b, 5c underscore so that they're all in the same place. This allowed me to clip articles using the Evernote web Clipper very easily that I might want to cite as research while writing my book. Pivot models are usually other models from, let's say, leadership or health and fitness or anything that I might reference. Pivot quotes I have within the notebook. Then notes for things like fear, courage, dreaming, hard work, innovation. And whenever I come across a good quote that I like, it goes into the relevant note. Pivot people, there's a note. One is the. I call it the collection bucket. It's an ongoing running list of people I might want to interview. But then I also will save notes if there's a specific story from a specific person that I hear or I think I might want to include, or once I've conducted an interview that they get their own note with the name. Pivot books are ones that I might want to reference. Pivot Feedback is ideas or things I hear from other people. Pivot Fun Media, that's like videos. I clipped the one from Silicon Valley. The show where the skinny, tall, skinny guy character is like, pivot. We have to pivot. So I clip things like that. And then book marketing, I am using the web clipper to grab good examples. When I see other authors who have done interesting launches, I save when they email about pre orders. I just got my little feelers out to see what other people are doing. And if I come across anything that maybe it's not another. Not another author, but it's an idea that I have about how to market the book that will go in there as well.
Okay. That is how I initially set up Evernote. Then it was time to outline the book. And I kept getting overwhelmed. I kept doing this in a Word document. Oh, I'll talk about Word versus Scrivener versus Google Docs in a second. But I kept trying to outline in a Word document, and I was getting so frustrated, I couldn't wrap my head around it. It just never.
It just didn't feel complete. Even what I turned into the publisher and what ended up getting a deal was by no means complete. The structure was kind of there, but I could not wrap my head around it. So I live in a studio apartment in New York City. I have minimal wall space. My dad's art is covering most free wall space that there is. I found this half.
Sheet. Goodness gracious, what's the word? I have like half a wall, not a big one. I have a little window in my kitchen that looks out, and it's beneath the kitchen window, but there's blank wall space kind of next to my couch.
Point is, I started outlining with Post its once again. So across the top, I just have intro, part one, part two, part three, and end. And then down the left. For each of those parts, I would include the chapters that I thought that I wanted to have. Then across. And I'll have to show you a picture of this too. But then across, I would have little topics that might go within that chapter. And I started taking pictures of diagrams that I had sketched out in my notebook. I uploaded them all to one Evernote called diagrams, and I started labeling those sketches D1, D2, D3, D4. So on my wall now with my Post its, I can also add a post it D4 next to the chapter where I think that diagram might go. What was nice about this was that I could once again visually see things, move things around, handwrite, add to these post its. I then did scan them using my Post it app. But it's nice. It's right behind my desk so I can Swivel my chair around and actually look at them if I want to. But once. And what's nice is now when I'm sitting on my couch in the morning having coffee, I can also just look over to my right and see this wall of the book outline. And it's good. It kind of prompts me as well, like, oh, what might I want to write about this morning? And so then thanks to Shane Snow, who's one of my favorite new authors that I've discovered, he just wrote a book called Smart How Hackers, Innovators and Icons Accelerate Success.
That book is so awesome. Just side note, I read it in one day. I literally couldn't put it down. I read it while walking hardcover. So I'm that annoying person that's not walking while texting. I'm walking while reading a hardcover book. But I loved it. That book was fantastic. There's a ton of overlap, actually, to things I'll be talking about in the Pivot Method. Shane One of his bonuses if you buy the book is his writing process. And he described how he outlined the book in a Google spreadsheet for tracking and then set up a Google document for each chapter.
Hallelujah. That has been the first thing that actually feels like it's working for me. I had a Scrivener for file. Scrivener is like Evernote but for writing a book. And it will. It's like there's little notes. You can organize them in a timeline. It can export the whole thing into a Word file for you. But it was too clunky for me and it was not syncing. It doesn't sync across all my devices. And I would have all these ideas on the go and I would email them to myself or put them in Evernote, but then I had to get them into Scrivener. Likewise, when I was out and about, I couldn't just open Scrivener from my phone or my iPad. It just wasn't working. And it was too big and overwhelming. And so then Word, forget about it.
I don't use Microsoft products if I can help it. They're all. They're just so clunky, slow to load, hard to search. They're just. I don't like them. I don't like the formatting. Okay, so Google Docs, Shane Snow, you're my hero. If you are listening, make it this far. They're fantastic. I have now a folder in Google Docs called the Pivot Method. I have then subfolders for each part of the book and Then within each part folder I have one doc per chapter. The chapter is like the big concept. So one part of my book is Foundation. Do not pass go without this foundation. One chapter is Mind Body. So within mindbody chapter I'm putting all my writing about Mind Body Optimization. Another chapter of foundation is Financial Foundation. So what are the financial nuts and bolts that you should have in place for a pivot? And another example of a chapter is Systems. How do you get organized when you're getting ready to pivot?
So that is how Google Docs is set up. Now this has been so helpful. I then also set up Evernote notebooks for each part of the book. So I have the following Evernote notebooks. And again, these are all labeled with the same like 04_, 04_ so that they're all listed in the same order. I have a catch all notebook that's for any random tasks or notes or things I haven't filed yet. I have intro, I have part two, which I'm.
It'S going to be kind of like the emotional rollercoaster of a pivot. Part three Foundation. Part four is the actual pivot method of a three step process that I'm going to describe. Five is a section for leaders and companies and managers. Six is the end. The end includes things like glossary, acknowledgments.
References, any additional resources.
Then within each notebook. So there's a notebook for each part. Then I have lots of notes. Some chapters have multiple notes. But now when I'm on the go and I'm walking and I have an idea, I can file it right into the chapter or the kind of note that relates to that topic, it's already in the right place. So when I sit down at my desk, I've been trying to write for 30 minutes every morning. It's not a lot, it's usually less than a thousand words, but it's what I can do. Right now. I'm trying to prove to myself that during my busiest time of year I have a ton of speaking and travel this month, that I can still do something. And I'm so glad that I'm doing it, because at first it felt torturous and it is now slowly getting easier and I am seeing my word count accumulate. But when I sit down in the morning to write, I can dig in to any Evernote folder, find any note that still has text in it, and then I go write it in the appropriate Google Doc. And when I have done my writing on it, I remove it from the note in Evernote so that I know anything that's still sitting in these Evernote notes is like to do, essentially. And what I love is that I don't have to do this all in any order. I'm kind of like, I write all over the place because I don't. I. I don't know, I get inspired to talk about different things at different times depending on what's going on in my life right now. So that's been working very, very well for me. And.
The writing itself, brother, let me just say, you just have to be willing. My motto every day is, shitty first draft, shitty first draft. Oh, my. It's. Oh, it's so rough. It's so rough. But.
What are you gonna do? I think sometimes it's easy to get very intimidating reading other authors books. But it's like that. It's like the quote that people use in reference to Facebook, don't compare your insides to somebody else's outsides. It's like, don't compare your shitty first draft to someone else's finished product on your shelf. And every author now, when I read their acknowledgments and they're like, to my editor, this book would be nothing without you. To my husband, thank you for being by my side through the torturous ups and downs of the writing journey. It makes me feel more human. And so my goal every day is just sit and write. Minimum of 30 minutes, let it be as shitty as it needs to be. And I will edit later. I will. It is right now. It's very wordy. Some of it's really stupid. I think there's more than probably I'm going to end up with a lot of crap to cut out. Okay with that? Because if you try and write it perfect from the get go, it's just paralyzing.
Some of my favorite advice has come from my dad. My dad wrote a book called the Bliss Engine. It's available on Kindle. I helped him edit and get that up there with Melissa Ansmann, who helped us format. In any case, my dad gives great advice. He has great metaphors on this stuff. So I'm going to read you a few of them just because they're so great. When he said, think of it like you're a winemaker and you have a field of 100,000 grapes, which are ideas that will make a case of wine, which is a book, he says, each grape is a thought. Gotta pick them one way or another, Put them in a big tub, mash them together, then let the juice sit for a while, fermenting. Then second draft time, then third draft, then the final will write itself as it speaks to you, asking for clarity, of expression, of ideas that have reached fruition. I love that. And I think it's very true that the book kind of writes you as much as you write the book. There will come a point where it kind of starts to take on a life of its own. And one of the other authors I read, maybe it's Nassim Taleb, said if I was ever feeling bored or feeling like he wanted to procrastinate when he was writing, he simply did not write that. Because why would a reader want to read something that you were bored writing? And I try and remember that too. If there's an idea that I'm procrastinating, fleshing out, or writing, maybe I should ditch it. Because.
Who would want to read that if I don't even want to write it? And I am having so much more fun when I write things. And I'm like, oh, yeah, that. That's really something. Okay. My dad also has this advice. Try to separate the harvesting of ideas from the writing of the ideas. Writing is the rational, clear part, but the thinking is the most fun, interesting, and challenging. Thinking and writing are two different mind processes that often get confused. Sometimes they happen at the same time, but often they are separate brain activities. Maybe for a few weeks or months. You are simply recording your thoughts and not writing. Save the writing for later when you have a group of thoughts assembled. These will give the actual writing an urgency and clarity. My first draft of the Bliss Engine was written longhand, printed carefully with a double zero rapidograph using India ink, a very slow device that allowed me to think as I was writing.
He also said, if you hit a roadblock on a particular day, while at your desk at home, do the tour where you walk through the city to at least three of your favorite coffee shops and do a bit of thinking or writing at each one. Take index cards for ideas raining down between stops. When you return home, you have some new juice for actual book text. And that's so fun too, because he's right. At any time, we can just get out of our comfort zone, get out of our house, get out of our own head, go talk to people. And while you don't have to share every detail of what you're working on, it's so fun to get people's feedback. Or for me, I'm so fascinated when I meet people, I want to know their story, their pivot story. And that's how I know that for me, this is a great topic because I'm genuinely curious about it. I recently met a man, very successful, very high up in his career. He was at the FBI for 24 years and he pivoted 13 times to different roles within the FBI. So while he was at the same company and now he's working at a Internet security startup company. And so I'm going to interview him for the book and I can't wait to hear his story about how he decided to make those changes and why he's now at a startup. Last piece of advice from my dad, he said Another metaphor that occurred to me was a series of horse races like our big three, the Kentucky Derpy, the Kentucky Derby, the Preakness, and the Belmont Stakes. If a horse wins all three, it wins the Triple Crown. Imagine 12 horses in the race, but not necessarily the same ones. Your current basic ideas racing in the Kentucky Derby, your mind, they jostle for position in your idea stream. Then the second race a few months later may have the same horses, maybe several new ones and so forth. At the third race, maybe only 3/4 of the original horses. Subject headings, ideas come and go. No big deal. They all help one another. That is so cool. That's how I felt when I got the book deal with Penguin with Portfolio, because I had told myself I was going to start writing about two months prior. But honestly, I was so distracted by the proposal and pitching process that I there's no excuses, but I simply didn't write. I was not writing. I think it's partly because I wasn't disciplined about it, but also I was just focused on trying to get the deal. So by the time I knew and had that comfort that this is happening, we do have a publisher partner, I felt like it was time to write. And I felt a little. I felt like I had all these racehorses lined up, just like bursting out the gate, you know, ready to. Ready to go. And it was like, where do I even start? There's so much to capture. I've been thinking about this in my head for years. And so I love the idea of whatever outline, whatever you do come up with, that's your first Kentucky Derby. You don't know who's going to win and who's going to stay in the game, but you just go with that set for a little while and then you revise. And honestly, the thing I'm most nervous about is what if I don't feel done? You know, like with life after college, there were some great ideas that came to me once I had already turned in the final manuscript. And there's nothing really we can do about that. I think that those of us who are writers or thinkers, we will think and write for the rest of our lives. And at some point the book has got to ship and go to press. But I'm more nervous, like, oh my God, I have to have all my best ideas captured by April. And what if I have good ones after that? Maybe that's, you know, it's a good problem to have to have more ideas, but I just want to somehow feel really solid and complete in what I put together. And.
It'S just interesting to see how much a text does change from month to month, or ideas or a process. And so, once again, that's why I do not feel that traditional publishing is too slow. I think it's just right because I want to give these ideas time to marinate and have the good stuff rise to the top and have time to really edit out stuff that isn't needed. Tim Ferriss in the four Hour Work Week he suggests he gave his book to his friends and he said, just circle where you get bored. He didn't ask for other feedback. He just wanted people to indicate as they're reading, any point where they got bored. I think that's brilliant. I'm definitely going to do that. And if any of you are up for being my. Let me know when you get bored readers, let me know. Michael Larson, my book, one of my earliest book angels, as I'll call him, who I mentioned in the first podcast, he said, when it comes to feedback, you should say to people, don't spare me, spare the reader. Don't worry about hurting my feelings. This is going to go into a book for the rest of time. Like, please, please hurt my feelings. Like, don't spare me, spare the reader, spare all the people who are going to hold this in their hands and help me make it really awesome for them.
The final piece, I promised I would talk about Gremlin management. Just I would say, get ready. If it's a task as big as a book, the gremlins are going to come out in equal proportion to the task. That's how these things work. I have come to accept that you're gonna feel all the things you're gonna feel, all the feelings that you're not good enough, not smart enough, too young, too old, too unqualified, too many ideas, too few ideas, not a good enough writer. I mean, everything under the sun, you're gonna probably think and feel it. And if you don't, kudos. Thank you. I'm amazed. And let us know your secrets for everyone else who does like me, I mean, I even will figure out as I'm writing, I'll be like, oh, yep, Amazon one star review is gonna come in on that paragraph right there. They're gonna pluck that one out and they're gonna use it and they're just gonna skewer me. And the funny thing about getting one star reviews with life after college is that they didn't kill me. Shockingly. For as afraid of them as I was, what do you know? I'm still standing. And the thing is, the satisfaction of tackling such a huge project and conquering a very scary goal diminishes what those 1 star reviews could take away from me. I felt like, who are you, guy? One guy told me that I'm so something. Like I'm so unhinged. I probably, I'm so unqualified to write this book. I probably go sit in a corner and cry when I'm at home. Bullshit line like that. Anyway, it's like, what are you doing, guy in your living room? Show me your book. Show me. Did you go to coach training? Did you work on these things at Google? Like, what have you done? What makes you qualified? So the part of me was just laughed. And then there's another review that is like, oh, the number one most helpful review of my book. It's a one star review and.
It'S funny that just I have so many positive reviews, but this one people have rated up so high. And he's like, she's just, you know, advocating for the man and corporate America. And at that time I was, it's not a life after college was not a book about entrepreneurship. And even if I was an entrepreneur, I was writing it for the majority of college grads who are not going to be self employed. They will be working for companies. So I wanted to help them be successful at that. However many, much of his feedback is valid. So when a one star review comes in, there's part of me that I will often agree with it, you know, or secondly, or it's not meant for that person in the first place. One of my one star reviews was from a woman. She said, I walked into the bookstore and I picked this up to consider giving it to my son. And there's no substance here. Okay, lady, the book's called Twitter meets what colors your parachute is how I describe it. But she didn't even read it. She Just flipped through it, put it back down, did not buy it, and gave it a one star review. And the point is, it wasn't written for you. So it's like if you're worrying about your critics while you're writing, there's no point because you can't please everyone. And I have some of the thinnest skin on earth. I'm very sensitive. I do not like criticism. I. I don't handle it very well. For the most part. I can't stand the thought that if someone doesn't like me or they're mad at me. But I get. I get over it. And I think when you find a project that is very important to you, and then at least the excitement of that will override the gremlins. And hey, think of it as good muscle building for dealing with your own shit, because it will all come up. And, you know, I'm trying to stay really positive about this time around. I don't want to just assume, oh, it's going to be a slog. Book writing is such a roller coaster. My mantra is let it be easy, let it be fun. I'm going to keep looking for ways that this can be easy and fun. And if I hit a dip, that's okay. I understand, I expect it, but that it's all part of the process. And in the end, it will make for a richer book because I'll have more to bring to the table. And that's certainly been true of the last few years of my own torturous Pivot. It's given me a lot of good gristle for the book itself.
Thanks so much for listening to this episode of the Pivot podcast. To learn more and get in touch, visit jennyblake Me, where I blog about systems at the intersection of mind, body and business. Or find me on Twitter @jennyblake. And remember, build first, then your courage will follow. Hasn't it always.
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