For the last two weeks I’ve written over 60,000 words and officially finished the first draft of my upcoming book “Creativity For Sale.” I wanted to give a behind the scenes look of the last two weeks and how I got so much writing done in such a short period of time. I also want to preface this post by saying I have no clue how much of my first draft was actually good (hah!). The editing, rewrites, and organization start this week. And if you didn’t already know, I’m keeping a visual author journal (updated daily) on Pinterest.

My Writing Schedule

As you can see from my Google Calendar above, I dedicated as much time as possible to writing my book during the week. This was the first week of writing. I still had plenty of other calls, meetings, followups, interviews, etc, but I tried to keep them to an absolute minimum. Once it was confirmed that RTC was going to be helping me write my book, they became a priority on my schedule (hello “Lizzie”). Each morning started with a call to my book writing coach Lizzie to talk about what writing I was going to do that day and how I was feeling about it. In the afternoon we’d hop on a Skype call (more below) and talk about how the day had been going.

One important thing I did each day while writing was to eliminate as many distractions as possible. I closed the Facebook tab I normally always had open. I closed Tweetbot. I closed Mac Mail. I put my phone on silent and out of sight. You’d be shocked how much more you can get done without notifications popping up left and right! This was crucial for me to stay focused on writing nearly 5,000 words per day.

(Side note: I used to have the biggest FOMO  when it came to social media, but I’m slowly letting go and it feels great.)

While I’d love to tell you I did a perfect job of sticking to the schedule laid out on my Google Calendar, there were always things that came up. Phone calls, trips to get (or make) more coffee, walking my dog, realizing I hadn’t showered in days, etc. And even if  I tried to stick to my calendar, there were many times I didn’t feel motivated to write anything. However, it was good that I scheduled the time on my calendar because it made me feel like I had to push through and write during those times. Keeping myself accountable through my Google Calendar was critical for me.

Lizzie, My Awesome Book Writing Coach

Everyone this is Lizzie, Lizzie this is everyone. Lizzie works for RTC (the company that sponsored the back cover of my book) and is my book writing coach. The photo above pretty much sums up most of our relationship: Me being confused and her listening and un-confusing me.

I didn’t know Lizzie before we spoke on the phone about a month ago. I’m not even sure she’d heard of IWearYourShirt before she found out she was going to have the task of helping me write my book. I’d also never worked with someone in a “coaching” capacity for any of my projects or businesses before.

I had no idea what to expect. 

Could I be my normal goofy self or did I have to be Business Jason? Could I share stories that were tough for me to talk about with a complete stranger? Could I tell her things no one knows, but that I wanted to write about in my book? Would she rip every word I wrote to shreds and make me feel insignificant because the extent of my writing was limited to these blog posts and 140 character tweets? Would my story bore her to death??

The first thing Lizzie and I did was to establish a working schedule. As I mentioned earlier, I would call her each morning and let her know what I was writing about that day and how I was feeling about it. Then, in the afternoon, we’d get on a Skype call together and talk about what I’d done so far that day, again how I was feeling, and any other thoughts/questions/concerns. Lizzie seems kind of like a therapist huh? I guess you could say she is. And you know what? She’s a badass one! 

From day one I’ve felt really comfortable talking to Lizzie (especially about our passion for unicorns). If there are things I’m not comfortable writing about, but want them to be in the book, I’ll share them with her and she’ll help me fit them in. She’s been incredibly helpful in asking me questions that help pull information out of my brain, which can be a tough place to pull information from.

I’ve come to realize the first draft phase of writing a book is kind of like the honeymoon phase in dating. I don’t get penalized for writing something dumb. Lizzie hasn’t put any pressure on me. It wasn’t an easy process, but there was no editing involved, just writing. As we move from first draft to second draft I’ll be sure to let you know if Lizzie’s true identity emerges and she turns into some crazy fire-breathing-Microsoft-Word-editing dragon! 

My Emotions While Writing

The photo above shows just a handful of the emotional states I was in while writing (in no order whatsoever). On the first day I felt great. I was so jazzed to start writing. Then on day two I had to write Chapter Two twice. I don’t even remember why, but I know it sucked (that’s the image of me pulling out what little hair I have left). Each chapter has seemed to bring about different emotions for me, both in how I felt while writing and digging deep into my memory banks for stories or failures. 

On the ninth day of writing I seemed to hit a mental wall. It probably didn’t help that the previous evening was a private dinner where I ate too much delicious food and drank too much tequila. I didn’t feel hungover or sick, but every time I tried to start writing my brain felt like mush. That entire day was spent writing a paragraph and taking a break after each one. It was grueling! At one point during the day I made it through writing two paragraphs, but then I couldn’t concentrate or think clearly for about three hours. It was honestly a really weird feeling. I remember talking to Lizzie on Skype during the middle of the day and she had this smile on her face. She reassured me that those feelings were completely normal and that I needed to give myself a day off from writing. I didn’t understand why I needed a full day off.

While talking to her I made the connection to something that made complete sense to me: playing basketball. In a normal game of basketball, I never play every single minute of the game and there’s a reason for that. While I may feel like I can physically play every minute, if I don’t rest at some point, I won’t have energy for the end of the game (which can be the most important part). And also for me, if I kill myself physically to play an entire game without rest, I’m usually much more sore for the next game. This analogy may or may not make any sense for you at all, but it helped me in my time of mental struggle!

It’s certainly been a roller coaster of emotions these first two weeks, and I’m sure that will continue going forward. 

The Writing Process

You know, I’m not exactly sure why I used Microsoft Word to write the first draft of my book. I know I used it to write my initial outline and Lizzie has based all of her feedback on that Word document. But to be honest, I hate Microsoft Word and it feels terribly unintuitive. (Lizzie, can I use Google Docs or something else?)

Anyway, Microsoft Word has been fine for the writing process itself. Not surprising, the application has crashed and not saved some of my writing. With the Auto-Save feature and my propensity to save religiously (due to using Photoshop) I haven’t lost much work at all. That being said, I find Word’s inability to keep a document formatted the same way a huge bummer. However, the “Tracking Changes” feature is fantastic. Truthfully, I didn’t know that existed before two weeks ago – no joke.

One thing I’ve tried to do while writing each day for the past two weeks was NOT to stare at a blank Word document. I learned this about myself when I started writing blog posts for IWearYourShirt in 2009 (which I wrote daily for nearly 4 years straight). If I leave any type of writing document blank, I’ll stare it and let myself get distracted. Instead, I always add an image or copy+paste a paragraph of text into the document. Luckily with my book writing, I had an outline I’d already written with comments from Lizzie. So each day I’d just copy+paste the first paragraph and start writing. I never once stared at a blank document watching the little cursor blink. 

Also in the writing process I’ve kept two notebooks at my side. One of them is my all-around notebook and one is dedicated solely to Creativity For Sale. My lovely girlfriend Caroline bought me a cool vintage notebook for Christmas and it makes me feel like a real writer because it’s weathered and unique. I take notes from calls with Lizzie, thoughts that pop in my head, quotes that inspire me, and keep my daily post-it notes (image at the top of this blog post) in the back of this notebook. I’ve even drawn a random dragon in my notebook. This was partly because of something you’ll find if you read my book, but also because it was an exercise that took my mind off writing one day when I got stuck.

My writing utensils are exactly what you see above. I guess my laptop should be pictured here, but you get the gist. It’s weird, but I like a mix of different style pens when taking notes in my notebook or writing things on my daily post-its. Call it weird habits or just that I like different writing utensils, either way it seems to work for me. The badass real-wood pencil is great in theory, but once it gets dull it’s a pain in the ass to sharpen. Oh well, I feel cool using it!

Even though I put my phone on silent, I keep it near me in case I have notes or need to search something quickly. I find that if I search something on my laptop while writing on my laptop I’ll inevitably end up browsing Facebook, reading my tweets, or checking my email. Keeping the distractions to a minimum was very important!

These are the three places I’ve sat the most while writing. The yoga ball was week one. The outside (green) furniture was one Saturday when it was beautiful outside (although it didn’t work out because it was uncomfortable to type with my laptop on my actual lap). The yellow chair is at my dining room table, and while not that comfortable, it was a nice change of pace from my office. I also tried writing from a coffee shop and a car dealership, neither of which were great environments for writing. They were terrible actually.

Because I want my book to be creative and I want to write the best content possible, I knew I didn’t want to write in the same place the entire time. Moving around has definitely helped and we’ll see where I end up writing this week. I’ve got my eye on a desk in our second upstairs room.

Reading While Writing

I’m by no means an avid reader. I have a bookcase that contains about 50 books, but the majority of them are business or marketing related and I’ve never read them. However, when I do read a book it’s very thought-provoking for me. I’ll often read a chapter from someone’s book and it inspires me to write a blog post on a similar (or opposing) topic. Because I knew reading other books got my mental wheels turning I decided to read a book a week while writing my book. 

The books you see above are the books I’ve already read. Pam Slim’s Body of Work was the first book on my book-a-week journey and it was the absolute perfect place to start. It’s full of knowledge and amazing soul-searching lessons and stories from Pam. The second book was Austin Kleon’s Steal Like an Artist. I found out about Austin’s book by seeing it on my girlfriend’s nightstand. I really enjoyed the story Austin wove throughout the book, but I even more so enjoyed the creative layout. Paul Jarvis’ Everything I Know was the third book I read. Paul’s book is a very easy read, but also very motivational. Paul doesn’t sugar coat things and shares his own personal failures and successes, which are very relatable (I hope I can do similar things with my book). David Gaughran’s Let’s Get Visible is the latest book I started and it’s all about learning how to best get exposure for a book in the Amazon Kindle Store. Very niche right? Well, I figured it wouldn’t hurt to learn that stuff, since I know a huge percentage of book sales these days are Kindle (or e-versions). I won’t lie to you though, it’s pretty damn boring.

Last but not least in the photo above is Wreck This Journal by Keri Smith. This book is less of a book and more of a journal with creativity-inducing exercises on each page of the book. It’s not a book you “finish” in one sitting, but it’s fantastic for overcoming small mental blocks and stretching my mental legs. My sexy, sexy, mental legs…

The books I’ll be reading next are Everything That Remains, The $100 Startup, The Suitcase Entrepreneur, The Power of Less, and APE by Guy Kawasaki.

Taking Breaks From Writing

Even though my schedule was jam-packed with writing the past two weeks, I also made sure to take lots of breaks. I’ve overworked myself on a few occasions before, and I didn’t want that to happen with my first book. Lizzie reassured me that this was a great mindset to be in, so, bonus points for Jason!

The photo you see above is my 1948 Chevy 3100 pickup truck named “CLIFFRD.” I’ve always been a car guy and going for a cruise helps me clear my head. Especially in my 1948 truck which doesn’t have working windows, functioning AC, is extremely low to the ground, smells like exhaust fumes, and takes effort to drive it. When I’m driving CLIFFRD I tend to be very in the moment with it. I don’t worry about anything else outside of driving. I think about things like how much stopping distance I need for a 66 year old truck to come to a complete stop (hah). Or why something made a weird noise when I went over a bump. Or maybe just how awesome the weather is and how fortunate I am to be driving around this antique truck while taking a break from writing my own book. Either way, I’ve driven CLIFFRD more in the past two weeks than I have the past four months. 

Besides driving my old truck, I’ve also taken breaks to do projects around my house. I haven’t had any big projects, but just little things I know I can start and finish (I call this process “the power of completion“). I’ve also been trying to force myself to go to the gym, even though I’m tired or I feel like I need to keep writing. Disconnecting myself for short periods of time has kept me sane and happy while writing nearly 5,000 words per day for 14 days straight.

Eating [Well] While Writing is Important

The first few days while I was writing I noticed myself putting off eating and refilling my water bottle because I was in the “writing zone.” By the end of the first few days I was extremely tired and I also noticed it was harder for me to wake up the next morning. Once I realized I wasn’t eating on my normal schedule I made sure to be more cognicant of eating like I normally do. 

For those of you who are wondering, my diet is fairly simple. It’s typically 4-5 meals a day that consist of meat and vegetables. I will admit that for the past few weeks my girlfriend and I have been buying sourdough bread loaves from a local farmer’s market. (It’s some of the best damn bread I’ve ever eaten!) Aside from that though, I try to stay away from dairy and processed foods. I’ve also tried to be better at my portion control. Even though I eat reasonably well, if I eat too much I know I’ll slip into a food coma. Food coma’s are terrible places to be when you need to put your brain to work. 

As far as alcohol goes, I don’t drink a ton normally. I enjoy a craft beer now and again, but lately I’ve really been enjoying a red wine called Apothic Red (thank you Clay and Julia for the recommendation). I find that having one glass of wine a night helps me take the edge off of an entire day’s work and stress. Don’t get me wrong, I’m not super stressed out right now, but it certainly helps to enjoy some wine and wind my brain down a bit (even if I plan on writing later in the evening). 

Oh, and the image above is a mason jar I have on my desk filled with “creativity pills” aka red skittles. A few months ago I joked with a conference organizer that I wanted red skittles waiting for me on the podium when I got up to speak (he knew it was a joke). To my surprise when I got home from the speaking gig I had a bag of red skittles waiting for me in my mailbox. Hilariously awesome. Since then I’ve kept this mason jar full and when I’m feeling mentally stuck I eat a small handful of my creativity pills. While enjoying these delicious little red treats, I can feel myself figuring out a tough writing section or remembering a story I wanted to share. This little placebo actually works for me, so I’m not going to stop doing it! More red skittles!

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That’s pretty much been the last two weeks for me and I’ll find out later today what the next two weeks look like. I’m keeping an open mind about this entire writing process. If what I did the first two weeks helps me going forward, great. If I need to completely change my habits and my daily schedule, I’ll do it.

I can’t thank Lizzie enough for all her help so far, as well as my girlfriend (although Caroline hasn’t read a single word of what I’ve written yet!). 

Thanks for taking the time to read this. I’ll be sharing more updates with the SponsorMyBook Email Listand daily photo updates on my visual author journey Pinterest board. I hope you enjoyed seeing behind the scenes, and feel free to ask any questions about this process in the comments below.