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When I started writing my book, How Are You, Really? it wasn’t the traditional way. I don’t really do things in the traditional way. My podcast was birthed in the front seat of my car while parked in a freezing cold garage. Most of the episodes are recorded in a closet. And of course, when I finally decided that I was going to write a book, I didn’t follow the rules. So I started my book with a Google Doc and the Google Doc was titled “I’m going to write a book”.
Writing a book is a very daunting thing. If you’ve ever considered it, if you’ve ever thought about it, there are so many things that you want to figure out before you start the actual writing, which is really just a really fancy way of procrastinating. I’ve done this in so many areas of my life, where I take the planning stage so far that really I’m just using it as a means to procrastinate, which is holding me back from actually making any progress.
So with that blank Google Doc I was committed. I was all in on just getting started. And I started writing.
In this episode of the Goal Digger Podcast, I wanted to give you an off the cuff discussion of why I didn’t write a book about business despite having been an entrepreneur for the last 10 years (and counting). I haven’t done an episode like this in a while – just me, a microphone, and a few notes sharing a behind the scenes look at easily one of my biggest projects to date.
Doing It Backwards
I approached the book process completely backwards. I said I would never write a book for so many years. And so I wanted to challenge myself, like if I am going to commit to doing this project that is going to take up two plus years of my life, I want to make sure that I’m in it for the right reasons and that I’m willing to do this when nobody’s watching, when there aren’t likes or comments, when there’s no feedback. I wanted to basically write and not tell anyone.
I didn’t ask for advice. I didn’t take an online course. I didn’t even start with a proposal. I just started writing. I wanted to like to do the actual art and not just the things around it. And so one thing that is super fascinating is that because I did everything backwards, I didn’t have a book deal. I didn’t have a book proposal. I didn’t have an agent or an editor. I didn’t have a publisher. I just started writing.
Overcoming a Mindset Block
So I didn’t have any of the traditional things that people have when they start writing a book but I did have something… A massive mindset block.
When most people introduce me, it’s about this podcast or the marketing world or the strategies I’ve taught. I love business. I love marketing. I love strategies. All of those things come natural to me. But when I really stripped down why I am so passionate about those things, it really comes back to the fact that the reason why I personally love entrepreneurship is that it affords me freedom and flexibility.
One of the things that I really leaned into in the book writing process is looking at how we as human beings put ourselves into boxes and how we do so at the convenience of other people. And when I look at how I started writing a business book, I was doing it to myself. I was literally boxing myself in as the “business Jenna”, when I am so much more than that.
Evolution of My Book
When I finally decided to write a book, the stories poured out of me. I wrote the entire manuscript and I didn’t tell anybody. I didn’t tell my mom, my sister didn’t know. I didn’t tell my college best friends. Part of the reason why I said I would never write a book in the first place was because every time I entertained the idea of writing, someone would tell me what book to write.
I wrote an entire manuscript and I kind of created an outline as I went. I only let one person in, which is Brooklyn on my team so that someone could check me, question me, and join me on this journey to hold me accountable.
When I finally got an agent and started that formal process, I sent the manuscript that I wrote over to my agent Margaret and Margaret told me she had a lot to work with and she would begin pulling chapter to include in the book proposal.
What I realized was that Margaret was pulling out the non-business chapters, the chapters about life and family and loss and identity. When the proposal was sent out to editors, I noticed that while people loved that I was a business woman and entrepreneur, there was a theme that kept coming up, that the book and the message were so much bigger than just speaking to entrepreneurs.
I remember on one of my editors calls, they said, “Close your eyes, Jenna. Imagine walking into Barnes and Noble. Where do you see your book on a shelf?” Spoiler: I didn’t see in on the business and entrepreneurship shelves.
More from this Episode
There’s so much to this story of my first book, How Are You, Really? I hope you’ll hit play to hear my off-the-cuff reflections from the last two-plus years of my life while I worked on this book in secret, with nobody watching, so I could create the book I’m so proud of today.
I want to leave you with this question: Where are you boxing yourself in? How are you believing that you can only show up in a certain way or only bring a part of yourself to the party? Where is there an opportunity to invite your whole self to show up and to show up proudly and excitedly? How can you bring your whole self into your life more? And lastly, how can you get quiet enough? To ask yourself an honest question, but to lean on into yourself and to answer it.
If you need help with any of those things, I sincerely hope that you order my book, How Are You, Really? wherever books are sold.