Write While True

It’s been a while. Episode 46 came out in late January of 2025 and I’m recording this now in mid-December, so it’s been about 10 or 11 months. When I last left off, we were in the middle of season 4, and I was telling you about all the things I was learning as I was writing my book, Swimming in Tech Debt.

Well, I’m happy to say that I finally finished Swimming in Tech Debt, and it came out in September of 2025, a couple of months ago. And then the print book came out about a month and a half or so later, and I’ve learned so much about the book publishing process that I want to share with you.

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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.

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But even with all of that new writing, a lot of the ideas and content are drawn from my blog. That’s what I want to talk about today — How I started this project by reviewing and gathering my work.

My first step, at the end of 2023, when I decided that I wanted to write a book, was to immerse myself in my own writing, so I just read my blog. I just read all of the posts.

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My intention after episode 43 was to follow along the process of writing the book and share what I learned along the way. But, a few things happened that derailed me (in a good way).

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There’s a hole in this process, and we need to fill that right now. This only works if you’re doing the lead activities consistently, and if they really do build up to the end goal. It’s true that working on the book is intrinsically fun and interesting. And if that’s all that happened, I’d probably be okay with it, but I really do want a book in the end.

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As I mentioned in the past two episodes, I’m trying to write a short book, and I want to share the process as I’m going through it. For example, to help me structure my time, I’m using the book The Four Disciplines of Execution.

In the last episode, I shared how I’m applying the second discipline. I defined an activity that I could do every day and a lead measure, a metric of that activity, that I could have as a goal for every week.

The idea is that if I constantly achieve this lead measure, I believe that the larger goal will be achieved. My weekly goal is to spend at least one hour a day on five different days working on the book. It’s a goal that resets every week. That way, a bad week doesn’t derail me. Every Monday, I have a chance to try to win that week. But I have to remember to do it. Keeping this lead measure top of mind is what the third discipline is about. And that’s what I want to talk about next.

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My wildly important goal is to publish a fifty page book on a topic in my industry by the end of 2024. I defined it using the SMART goal format (S. M. A. R. T.), which means it’s specific, measurable, achievable, relevant, and time-bound. This is a good way to define goals, but the issue with SMART goals is that even though you can easily tell if you have reached them, they don’t drive day-to-day activities. That’s where the 2nd of the four disciplines comes in.

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For season four, which I’m starting right now, my plan is to take you through my process as I try to write a short, focused book. I expect it to be about 50 pages. I call this kind of book a pamphlet.

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The white pastel can draw white on top of the charcoal, so now I can make white marks, which can also be smudged and mixed. It’s giving me a range of values I couldn’t get before. Throwing white highlights onto a dark drawing is a way of directing attention and makes it more interesting.

Black and white, on a drawing, are the extreme values. If I try to apply this idea to writing, it should also be a juxtaposition of opposite extremes.

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I’m reading a book by Stanley Fish called How to Write a Sentence. I found this book by Googling that exact question because I wanted to find anything that might be a fit for what I’m podcasting about this season.

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