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How the blog-to-book experiment is going: challenges and thoughts

by Tom Johnson on Jun 15, 2023
categories: creativity writing

In this post, I explore the challenges of transforming a blog series into a book. The process proved to be more complex than I thought, and I had to deal with inconsistencies around tense (present vs past tense), time management, momentum, and more. Trying to read through 70,000 words to see if it had the shape and arc of a book was no small feat, and is one I'm still wrestling with.

Origins of a writing model: continuous exploratory digging

Since graduate school, I’ve had an idea about writing that I’ve experimented with off and on: start with a topic (anything, really) and ask yourself 20 questions about it, then answer the questions. From the most interesting answer, ask another 20 questions about that particular answer. From the most interesting answer of those questions, ask another 20 questions. Keep on digging like this and see where you go after about 20+ iterations.

Following this pattern, I’ve found that despite any starting point, it doesn’t take long to get deep into topics of psychology and philosophy, and things become interesting. Also, to follow this pattern, I usually need to expand my knowledge by reading books about the topics.

Back in graduate school, the essays I wrote using this “continuous exploratory digging” technique had a mad-genius tone to them. The essays didn’t cohere well, though, and seemed unbalanced but with interesting nuggets here and there. So I mostly shelved the technique and just used the questions technique as a means of brainstorming about topics.

On my blog, I’ve often followed similar writing trajectories. Instead of a list of 20 questions, I decide to write a post, then another post, then another post, all following a single theme. If you look at the Series tab, you’ll see that series-type posts are what I generally like to write. I’ve often thought that perhaps a good series of posts could lead to a book at the end, or at least a collection of thematic essays. This approach is sometimes called a “blog-to-book” model.

With my Journey away from smartphones series, I wrote 20 posts on the topic. Each post led me to the next. I also discovered that reading about the topic allowed me to continue to the next level.

Results of the blog-to-book experiment

After 20 posts in the smartphone series, I compiled the content into a single document and read through it to see if the series had enough coherence to feel like a book, or at least an essay collection. Reading through the smartphone series, the answer was mostly a yes, but there were problems.

Tense. First, the tense in most blog posts was present tense, like a diary. I found the constant present tense tiring. Books work much better in the past tense. So I revised everything into past tense. This revision was difficult because some blog posts contained musings or thoughts, which sounded odd in past tense.

Arc and conclusion. The conclusion lacked substance. The series didn’t reach the key epiphany and turning point that makes for a good story. So I added another chapter, attempting to give it more arc. Overall, the number of words is around 70,000, which is a good length for a collection of essays.

Images. Another problem was what to do with images. About half way through the series, generative AI tools like DALLE and Midjourney came out, and I started adding lots of images to the posts. These images seemed superfluous when reading the blog posts as a book, so I stripped them out. But later I reinserted them because I also want the content to have a life on the web, and plain text with no images seemed too dry. I’m still mixed about the inclusion of the images.

Too much detail. While reading some posts, I grew bored in places and decided to drastically trim or summarize the content. In some sections, I got more detailed than I needed to be (such as in summarizing Nicholas Carr’s book, or in describing how to sideload APKs onto a feature phone). I used my own interest level in deciding what to keep or discard. If I got bored reading it, then I trimmed it down or removed it. Better to mention a point briefly and get to the good stuff faster.

Language editing. I also wanted to fine-tune the language. I pasted each post into WordTune and fixed many of the grammar errors and other style issues that WordTune flagged. This was the most tedious part of the process and took weeks of mind-numbing editing, jumping from one paragraph to the next to try and judge whether the edit made sense or if would break the flow.

By looking at the suggested edits in WordTune, I realized that I have a wordiness problem. WordTune helped me express my ideas more directly and concisely. I include far too many modifiers and weasel words in my writing.

I then reinserted the content back into my blog and converted the posts from random date-based posts into a Jekyll collection (which is a unique set of pages), consolidated in the same subfolder. I also numbered the articles. I configured PDF generation for the smartphone collection and generated an output (using Prince), which I made available as a link at the top of each page.

Finding time. One challenge has been finding time to edit and work with the content. Last month I started experimenting with a new model for my newsletter, including lots of news snippets, especially following AI news. I thought the newsletter summaries would be something I do on the side, but no, it turns out I have a limited number of writing hours per week (about 5 hours of blog-writing time). If I send out two weekly newsletters that take 2 hours each time, this leaves almost nothing for other blog writing, and my series and efforts on the book lag. I decided the newsletter pivot wasn’t worthwhile and didn’t want to spend my limited personal writing hours focused on ephemeral news at the expense of my more significant writing projects. So I paused that newsletter effort.

Long-term momentum. I have a terrible habit of starting projects and then abandoning them when I get immersed in some other work. (I prefer to write new content instead of editing already written content.) But I didn’t want to leave this project/series unfinished. I’ve abandoned so many major writing projects that I’ve only half finished. My attention tends to shift into other projects. The problem is that if I let a project sit for more than two months, I lose all context and momentum to even know where I left off and what needs to be done, making it harder to pick back up. The ability to continue hacking away at a problem long term, especially if it may require several years to complete, requires a strategy and vision that I haven’t mastered.

This is where I’m currently at in the process.

Next steps

As for next steps, I want to read through the output again from start to end to see how it all holds up, as well as whether the language edits helped speed up the prose in good ways..

Whereas I thought that writing a book would be mostly a matter of stringing together the posts and editing them a bit, I found that it’s a lot more work. It’s hard to shape these 70,000 words into something that feels book-like.

Larger problems

I’m running into more challenges beyond mere finding time and editing. Some of my takeaways and rules for smartphone use, etc., have continued to evolve. Most troubling, I’m reverting more and more to my old ways, and reading less. This troubles me, making me feel like the whole experiment was a kind of flowers-for-algernon transformation. Why am I backsliding? Should I keep iterating on the themes to address where I’m currently at? Why can’t I make meaningful life changes that stick? (Queue the whole self-help genre and why I’m not reading Atomic Habits.)

My larger vision is for this essay series project to put in practice a life philosophy of sorts: to write a collection of essays following a specific theme every year. The way I envision my life, I want to pick a new topic every year and write about 20 essays on it, yielding an essay collection by the end of the year. I found that writing the smartphone series was fulfilling from an intellectual and personal point of view. Focusing this way gave me something to think and experiment with in a sustained way. The project allowed me to select books and texts that deepened my knowledge of the topic and provided points of interest from the activities and ideas I was writing about.

If now I were to find that the whole blog-to-book experiment doesn’t actually work, that it leads to a fragmented, incoherent collection of posts that don’t ultimately fit together into a thematically consistent story arc, and that any changes or experiments tend to fizzle and my behavior reverts, then what becomes of my life experiment and philosophy? Do I abandon the yearly essay collection idea and become a one-off blog post writer instead, only capable of single articles following random themes?

No, the life experiment has to work. So I’m doubling down to refocus on the smartphone book. Perhaps at this point, I need to reexamine my life to understand why I’m backsliding out of reading books again, and why. I need to examine what has truly worked vs what has proven a temporary fix only. I need to figure out what micro-goals will support the long-term goals.

More than anything, I want the collection of essays to provide meaningful change in my life, whether it’s change in perspective or habits or other actions. If I can’t actually change anything about my life, what’s the point of writing? Fundamentally, writing should lead one to uncover new ideas and to put those ideas into meaningful change.

Long-term focus

I recognize that writing a book might be a multi-year battle, and that I can’t just knock it out in one round. Sometimes ideas need to percolate on the back burner while I get more distance, maturity, and perspective. This is why I’ve chosen to rotate between two series. The other series I’m working on is the fizzled trends series, which morphed into systems thinking. I also hit a roadblock in that series, finding that big picture thinking that crosses multiple organizational groups gets little budgetary support. So I’m working through that problem as well.


I’d like to wrap this post up by explaining how I overcame all of these problems and finished this whole smartphones project, but the truth is that it’s still unfinished. This is more of a mid-way checkin point. If you have feedback on this project, feel free to share it with me.

About Tom Johnson

Tom Johnson

I'm an API technical writer based in the Seattle area. On this blog, I write about topics related to technical writing and communication — such as software documentation, API documentation, AI, information architecture, content strategy, writing processes, plain language, tech comm careers, and more. Check out my API documentation course if you're looking for more info about documenting APIs. Or see my posts on AI and AI course section for more on the latest in AI and tech comm.

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