I’m Lou Franco and this is episode 46 of Write While True.
Write While True is an infinite loop, and that’s because I think of writing as an infinite game. A game I’m playing for fun and to get better at it. Like a game of catch.
So in each episode, I’ll tell you something I learned about writing, and then I’ll throw you the ball with a writing challenge or a prompt.
Episode
This is the 7th episode of season four. I started this season in January of 2024. My intent was to document the process of writing a book. But even though this season is over a year long, there have only been 7 episodes, and that’s because I took a 9 month break. I want to talk more about what happened during that break, and how I was derailed from my plans, and how I recovered.
Here’s a brief timeline.
I started thinking about writing a book in late 2023, and so I read all of the posts in my blog to see if I could find some idea in them.
To write the book, I designed a book-writing process based on the ideas in the book “The Four Disciplines of Execution”. The fourth discipline is about accountability, so I had to have some kind of accountability meeting. But I was working alone, so I thought that doing this podcast would help with that. So, I started season 4 to share this process. My plan was to give updates all along as a way of holding myself accountable.
But I realized that that wouldn’t be enough, so I joined the Useful Books community, which has a few writing accountability meetings during the week. The Useful Books community also includes access to a book sharing platform called Help This Book. The members encourage you to use it to share your work in progress, which I did.
So, things started out great. I wrote a few thousand words in January and shared them. Then, I wrote a few thousand more and shared that in March. Then I went on vacation for a few weeks in April. At that point, I had shared the first four episodes of the podcast of this season, but I was taking a planned break.
About a week before my flight back I got a message from Gergely Orosz from the Pragmatic Engineer newsletter. He’d seen my draft and asked me to propose an article based on it for his newsletter. So, I wrote an outline and a proposal, which he accepted, and he sent me a writing guide that described his newsletter’s audience and the style that he wanted.
With that guide and his approval of my draft and outline, I felt very confident that I understood what Gergely wanted, and then I proceeded to write seven thousand words that he hated.
That sounds strong (and it is), but he read the first few paragraphs and got so frustrated that he stopped and asked me to start over or give up—but, in a nice way. He told me he wanted to hear about my personal experiences and what I had learned from them. Not abstract tips and generalizations.
I skimmed his comments and dashed off an email where I told him that I would submit a new draft. Then, I tried to read the comments in depth.
Even though his feedback was short and to the point, it took me days to read it. I kept stopping. My self-doubts about my writing, my imposter syndrome, my worries about failing in public — they literally made it hard for me to read more than a few words before I would just CMD-Tab away from the document. It was like touching a hot stove. I would instantly pull back.
I spent the next six weeks wondering if I should even write this book. Every time I tried to write, I felt like I was going to fail again. I couldn’t figure out how to fix the article, which meant I couldn’t fix the book because they were so similar.
So, I started a new article from scratch. I pulled in some paragraphs from the online draft that had prompted Gergely to message me in the first place. And I got to about 2,000 words in mid-July, less than half of what the article needed.
It was taking a while, so, Gergely wrote to ask me if I was going to submit something else or if I just wanted to quit.
After I read that, I almost quit right there. Not just the article, but the book too. If I couldn’t write an article on this topic for this audience, I obviously couldn’t write a book.
But, instead, I told him that I was about half way done, but I was having trouble. I said I would spend a week working on it, and then send him a new draft. I made this deadline before I had a plan, but I needed to do something to get me going. Having a week meant that it would require about three to five hundred words a day, which is doable if I actually sat down and wrote.
I realized that the only way to move forward was to really understand the feedback. So, I forced myself to read it slowly and methodically, taking notes along the way. It was direct and kind, but still, like I said, hard for me to read.
But I read it, and I read it again, and I internalized the central message he was trying to tell me. He wanted me to tell personal stories where I used the techniques I was writing about and show what happened. Instead, I had submitted a draft where the advice was not motivated by relating it to my personal experience. My draft was abstract and he wanted something specific to me. I hadn’t done this because I was afraid of admitting my failures, but that’s exactly what he wanted.
Around this time, I talked to a software developer friend, and I told her what happened. About my first article and about the feedback and all of the troubles I’d been having rewriting it. I told her that that I was anxious about writing in a personal style so publicly—that I would embarrass myself. First, she reminded me that I often try to get points across by telling stories from my career, and that this was just like that. Then she said: “If you don’t write the book that only you can write, then why do it at all?”. I had nothing to say—it was clear to me that she was right.
Soon after that, I reread “On Writing Well” [affiliate link] by William Zinsser. This is a classic book on writing non-fiction. Here’s an excerpt where Zinsser writes about this same issue, and how to solve it.
Writers are obviously at their most natural when they write in the first person. Writing is an intimate transaction between two people, conducted on paper, and it will go well to the extent that it retains its humanity. Therefore I urge people to write in the first person: to use “I” and “me” and “we” and “us.” They put up a fight.
“Who am I to say what I think?” they ask. “Or what I feel?”
“Who are you not to say what you think?” I tell them. “There’s only one you. Nobody else thinks or feels in exactly the same way.”
“But nobody cares about my opinions,” they say. “It would make me feel conspicuous.”
“They’ll care if you tell them something interesting,” I say, “and tell them in words that come naturally.”
It’s weird, because on my blog, I do write as myself (and this podcast is also my point-of-view on what I am learning about writing). I’m telling you a story right now about my failures. I have no trouble being vulnerable about my struggles here and I frequently wrap it all in personal stories that show how I learned the practical tips I include.
But my blog and podcast are mostly for self-development. I am trying to transform myself into someone that writes and who can speak coherently. I hope that my audience learns something, but mostly, this is practice for bigger things.
But, in my first draft of that article (and in early drafts of my book) I stopped writing as myself. It made it harder to write, and (based on feedback) harder to read. The irony is that I used my blog and podcast to practice writing, and almost all of that practice was writing in first-person with my point of view, and then as soon as I tried to write something longer, I abandoned it. It took me months to figure out that even though I was writing for myself, I wasn’t writing as myself.
So, I gave in, and it’s gone a lot better. I can still say what I want to say in the book (the tips and practices I think will help people), but wrapping them in stories makes the book easier to understand.
By the way, in order to do this podcast I had to go back and read my first draft and all of that feedback that I got. I hadn’t looked at it since last July, but I decided to refresh my memory by looking it over. I read through the correspondence and feedback to make sure I got the details right. All of the emotions I had at the time came rushing back, even though I did eventually write a well-received article and currently have a draft of the book done. Implementing the feedback and having success did not make it easier to reread.
I don’t know if you have this issue, but if you do try to write something in the first person. Use that as a prompt to be yourself with your spoken voice. I find that when I do this, the words flow out better. Whenever you start to give an opinion, relate it to your personal experience, so that the reader can understand the context where it might apply. It’s hard, but it helps to talk about failures too and how you overcame them.
Thanks for listening. This has been Write While True, a podcast where we love infinite loops, as long as they’re fun.