Write While True

Brian: I’m Brian Hall. And today, I can’t wait, we’re talking about writing tools, talking about your writing stack. And we’ll actually spread this out over two episodes. Today we’re talking about the idea phase, outlining, collecting notes, and drafting. So just the writing part. We’ll save publishing, editing, collaboration tools for a future episode. Write While True Episode 2: Small Bits of Writing How to Take Smart Notes [amazon affiliate link] Obsidian Roam Research Notion Scrivener Transcript

Lou: Today, I would actually like us to look back two episodes where we talked about reader profile, so writing towards a specific reader, and to maybe double-click on that a little and talk a little bit more about the archetype readers that you might be writing towards. So a lot of the way I’ve come to think about this came from Amy Hoy. If you don’t know her, Amy Hoy, she’s one of the proprietors of the 30×500 e-course and methodology of product making. Her idea is that if you have a $30 per month product, and you find 500 customers, that that would be enough to build a small business. And the way that she wants you to get towards that product is by creating educational content for the audience that you intend to serve with the product. And then you’re going to, along the way, find your product after having done this educational content. Stacking the Bricks (Amy Hoy’s site) Write While True Episode 53: Pick a Reader Write While True Episode 5: Audience and Message Transcript

Brian: Today we’re talking about negative feedback. Lou: Oh boy. Brian: Yeah, yeah. No, this one’s gonna hurt. When you write something and you share it, and then somebody tells you that it’s absolute trash in some manner or another, and there’s really no avoiding it. Transcript

Brian: And I’m Brian Hall. And today we’re talking about reader profile, the person or people for whom you are writing, which is a really powerful concept to spend some time on, preferably before you start writing, at least if it’s a big project. I think this came up in the last conversation and your example was, I do B2B SaaS. If you’re in gaming, things might be a little different, something like that. I just want to talk more about that because of how useful it is to make those distinctions.  And I guess the basic point I want to make about reader profile, and we’ll get into what it is and how you do it, but it should make your writing easier to produce. Write While True Episode 5: Audience and Message Transcript

Lou: Hey, Brian. I wanted to start this episode by doing a little bit of a follow up to episode 48, where we talked about starting a collaboration. One of the things we ended with was doing a simple collaboration by just getting feedback on something you’re writing. And I wanted to talk to you about your thoughts on what to do with feedback. Brian: Yeah, let’s do it, for sure. And to begin, the assumptions here are that you’re working on a piece of writing that you intend to iterate on. You’re going to revise this writing, you’re going to improve it. It might be a book, newsletter, blog post, something you care enough about to spend time on after you first put it out into the world for feedback. Write While True Episode 48: Start a Collaboration Transcript

Brian: I’m building up my ability to do that by spending my mornings and my first sip of coffee, learning this framework. And at the same time, you got to watch out because learning a JavaScript framework is not writing per se. So that’s what I’ve been up to. And it’s felt productive and like it works toward my ultimate goal, my ultimate writing focused goal, but I haven’t been writing. So I’ve mixed feelings about that.  And I guess I want to say, Lou, you went through the whole process of blogging for a long time and then taking on a book project or multiple book projects, writing the book, editing the books. Now you’re in the phase where you have to be marketing the book. I hope you’re marketing the book. Talk to me about writing goals in different phases of projects. Transcript

Brian: I’m Brian Hall. And today we’re talking again about habits. In the last episode, we both set out some intentions to change our writing habits and establish a daily practice. Let’s check in on that. Lou, how did it go for you? Lou: Not great, Brian. I did the habit none times. Brian: Okay, not great. Remind us what you were going to do and tell us what happened. Write While True Episode 49: Tiny Habits Transcript

Brian: And so just getting yourself in position and getting started in this way tends to lead to more powerful, robust output. I guess I’ve reached the point where just by starting consistently every morning, I was cranking out a blog post a day for quite a while. And I guess that’s the other thing I’ll say too, is habits can come and go. You can lose a habit and it’s probably not helpful to beat yourself up about that because you can also regain them. If you’re in the middle of a sprint, you might write every single morning and you might produce quite a bit. And then you might finish that book or reach the end of that series of blog posts. And maybe you abandon your habit. It’s there to be reclaimed, I guess. Write While True Episode 1: Training to Unblock Yourself Write While True Episode 19: Prompt Your Morning Pages Tiny Habits [ad] by BJ Fogg Transcript

This is the beginning of season five, episode 48, and I’m going to tell you about something that we’re doing a little different now. This has always been a podcast where I, a software developer, talks to you, who I think are also software developers, about what I write and I’m trying to share with you tips and techniques for writing for people like us that want to write. And in this season of Write While True, we’re going to start something new. Write While True is now a collaboration between me and another software developer who writes. His name is Brian Hall. And throughout the entirety of this run of podcasts, I’ve talked a lot about the kinds of things I write, blogs, and I wrote a book, and this podcast. Write While True Episode 43: Accountability Groups Write While True Episode 47: Write Useful Books Transcript

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. Write Useful Books [affiliate] The Useful Authors community Transcript

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. The Four Disciplines of Execution [affiliate link] On Writing Well [affiliate link] by William Zinsser Swimming in Tech Debt (my book) Help This Book (book sharing platform) Useful Books Community Transcript

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. Season 4 started with The Four Disciplines: 1, 2, 3, and 4 The Four Disciplines of Execution [affiliate link] Write While True Episode 13: New Ideas where I talked about … … A Technique for Producing Ideas [affiliate link] Morning Pages Write While True Episode 1: Training to Unblock Yourself Write While True Episode 19: Prompt Your Morning Pages Smart Notes Write While True Episode 2: Small Bits of Writing Journals Write While True Episode 21: Dedicated Journals Write While True Episode 22: Harvesting Journals Assembling first drafts Write While True Episode 3: First Drafts Transcript

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). The Four Disciplines of Execution [affiliate link] Write While True Episode 23: Take a Break Taking a Successful Break Swimming in Tech Debt Follow-up on my Tech Debt Article in The Pragmatic Engineer Newsletter transcript

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. Write While True Episode 40: Let’s Write a Pamphlet Write While True Episode 41: The Lead Measure Write While True Episode 42: Keeping Score 4DX: Applying the Fourth Discipline Useful Books Community Transcript

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. Write While True Episode 40: Let’s Write a Pamphlet Write While True Episode 41: The Lead Measure How I am applying The Four Disciplines of Execution Transcript

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. Write While True Episode 40: Let’s Write a Pamphlet Write While True Episode 4: Make a Schedule Transcript

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. 4DX: Applying the First Discipline Write While True Episode 13: New Ideas In Praise of Pamphlets Generating Podcast Episode Ideas Transcript

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. A Modest Proposal by Jonathan Swift Prompted Morning Pages Journals Transcript

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. How to Write a Sentence [amazon affiliate link] by Stanley Fish The Tools and Materials of Writing Write While True Episode 28: Complex Sentences Jabberwocky by Lewis Carroll Sponsor: Prompted Morning Page Journals Transcript

Today I want to talk about one of the rules that’s in Strunk and White. It’s actually in almost every book about writing, which is to use the active voice and to prefer it over the passive voice. Larry McEnerney analyzes the Gettysburg Address [YouTube] The Gettysburg Address by Abraham Lincoln The Sense of Style [amazon affiliate link] by Steven Pinker The Elements of Style [amazon affiliate link] by Strunk and White Politics and the English Language by George Orwell Transcript

The advice applies to any kind of writing. It resonated with me because I feel like I might be having that problem in my written work. That sometimes my writing feels like a stack of paragraphs. I am feeling the lack of propulsion that John and Aline described. Scriptnotes Episode 60 (transcript only) Scriptnotes Episode 61 (transcript only) Write While True Episode 1: Training to Unblock Yourself Write While True Episode 19: Prompt Your Morning Pages Write While True Journals Transcript

I recently came across the phrase zombie nouns, which was coined by Helen Sword. She’s an author and currently runs a private consultancy to help writers. Back in 2012, she was teaching at the University of Auckland in New Zealand, and she wrote an article for the New York Times called Zombie Nouns. Write While True Episode 30: Finding Nouns and Verbs Zombie Nouns by Helen Sword in the New York Times Writers Diet tool for finding zombie nouns Transcript

What we’re trying to do is we’re trying to learn how to recall fit words when we need them in our writing. To get better at that, we need to be exposed to more interesting words and to practice using them. Imagine situations where they would be perfect. Making it memorable and ridiculous might help you remember the word when you need it. Write While True Episode 1: Training to Unblock Yourself Write While True Episode 19: Prompt Your Morning Pages The Sense of Style [amazon affiliate link] by Steven Pinker Transcript

The idea of collecting quotes is not something new. I think that’s the way most people think of note taking in general. There’s even a style of journal some people keep called a Commonplace book, which builds on this idea. In a Commonplace book, you are mostly collecting the thoughts of others. You might also put in your own reaction to those—your thoughts on those thoughts—but the focus is on the collecting. I want to recommend a spin on this idea. How to Take Smart Notes [amazon affiliate link] by Sönke Ahrens Transcript

I think one sentence from David Lambuth really sums up what I want to say about paragraphs. Here it is. There is no absolute rule for paragraphing. Your own feeling must be your guide. The Golden Book on Writing [amazon affiliate link] by David Lambuth The Elements of Style [amazon affiliate link] by Strunk & White Transcript

I’m going to use these three books again for today’s topic, which is the order of words in a sentence. I love that these books tackle mundane topics, things that seem innate, but aren’t. I mean, we can order words into something grammatical without much thought. Even though a ten-sentence word has ten factorial possible orderings, we can easily find the handful that are legal English. The Golden Book on Writing [amazon affiliate link] by David Lambuth The Elements of Style [amazon affiliate link] by Strunk & White Writing Down the Bones [amazon affiliate link] by Natalie Goldberg Transcript

Every book on writing tells you to avoid adverbs (and even adjectives). I find that hard to do in first drafts, but I do try to remove them in edits. You can tell that I haven’t done enough editing if you see that I “really like” something or that a new programming language is “pretty good”. Season 3 Write While True Episode 28: Complex Sentences Write While True Episode 29: Loose Sentences Books The Golden Book on Writing [amazon affiliate link] by David Lambuth The Elements of Style [amazon affiliate link] by Strunk & White Writing Down the Bones [amazon affiliate link] by Natalie Goldberg Sweep Editing Write While True Episode 6: Editing First Drafts Write While True Episode 7: Find Your Voice Edit in Sweeps Transcript

Last week, I spoke about something very fundamental—how to write complex sentences, and I’m going to continue along in that theme for what I’m now calling season three, drawing lessons from some of what I consider the greatest books about writing, and picking out ideas related to using words, sentences, and paragraphs. These are things that I’ve found that I need to work on, and I hope that that can help you too. The Golden Book on Writing [amazon affiliate link] by David Lambuth The Elements of Style [amazon affiliate link] by Strunk and White Write While True Episode 5: Audience and Message Oz: Review of wizard projection technology Transcript

I like to sketch, mostly with pencil and charcoal on paper. One of the first things I needed to learn was how my drawing tools and the paper interacted. What kind of mark did each level of pencil hardness make, and how was that different from charcoal? What kind of paper worked best? I did various exercises that helped me understand my own tools.  I’ve been thinking a lot about this and trying to figure out what is the equivalent for this in writing. Here’s what I’ve come up with. Write While True Episode 20: Extemporaneous Writing The Golden Book on Writing [amazon affiliate link] by David Lambuth Transcript

This is the fourth and final episode in a series I’m doing about the book Art & Fear [amazon affiliate link] by David Bayles and Ted Orland. In this, the final episode of the series, I’m going to tell you what they think you need to be in order to be an artist. Art & Fear [amazon affiliate link] by Bayles and Orland Write While True Episode 24: Thousands of Variations (part 1) Write While True Episode 25: Stopping vs. Quitting (part 2) Write While True Episode 26: Making Makes a Maker (part 3) Write While True Episode 5: Audience and Message Transcript

I decided to do a four-part series on the lessons I learned from Art & Fear by David Bayles and Ted Orland. This week, in part three, I want to talk about a quote about what art means to the maker. Art & Fear [amazon affiliate link] Write While True Episode 24: Thousands of Variations (part 1) Write While True Episode 25: Stopping vs. Quitting (part 2) Transcript

I reread the book Art and Fear by Bayles and Orland and they had so many ideas for how to get people to make art, that it worked for me to start my blog going again, and then ultimately restarting this podcast. For part two of this four part series on Art and Fear, I’m going to share the what they said that inspired me to not quit. Here’s the quote. Quitting is fundamentally different from stopping, the latter happens all the time. Quitting happens once. Quitting means not starting again, and art is all about starting again. That quote is really the inspiration behind season two, and the episodes I’ve made since I restarted. Art and Fear [amazon affiliate link] by Bayles and Orland Write While True Episode 24: Thousands of Variations (Part 1 of the series) Transcript

One of the things that got me back to podcasting after a two year break was rereading Art & Fear by David Bayles and Ted Orland. This time, while I was reading it, I kept a lot of notes and found four themes that resonated with me and helped me get going again. The first theme is very practical. It’s what they think is the secret to being prolific. For the past two months I have been applying it a lot. Write While True Episode 11: Quantity and Quality (discussed Art & Fear) Write While True Episode 3: First Drafts Write While True Episode 6: Editing First Drafts Art & Fear [amazon affiliate link] by Bayles and Orland Bird by Bird [amazon affiliate link] by Anne Lamott Transcript

We just passed the second anniversary of the break that I didn’t come back from right away. I know exactly what was going on. I had a lot of travel to visit family and for work and it was just hard to find the time to plan and record podcasts. Well, since it’s exactly two years later. It’s summer again, and I want to take another break. But this time I have a plan to take a break, but still publish on schedule and hopefully, not lose my momentum. Write While True Episode 8: Lower the Bar Write While True Episode 5: Audience and Message Write While True Episode 11: Quantity and Quality Write While True Episode 20: Extemporaneous Writing Transcript

When I was done with a journal, I’d put it on the shelf with others. I do a good job of making sure to transfer anything important to a real tracking system at the end of the day, so there wasn’t much in the journal that I thought would be useful. At some point, though, I picked up an old journal, it was probably a few years old at that point, and just flipped through it. As expected, it was mostly boring. Just a mundane list of what was going on that day. Meetings, task lists, chores. But every once in a while … Write While True Episode 21: Dedicated Journals Write While True Episode 2: Small Bits of Writing Write While True Episode 12: Keep a Topic List Write While True Episode 13: New Ideas A Technique for Producing Ideas [amazon affiliate link] by James Webb Young Write While True Episode 19: Prompt Your Morning Pages Transcript

I’ve been using a paper journal for years. Even when I worked on big teams, I still kept a separate journal with my personal daily tasks and schedule. For years, I just used a single journal for everything. I’d just go through it and then start another one when I hit the last page. Any kind of paper capture that I needed to do was in that one journal. A couple of years ago I started splitting out separate journals based on the purpose. Write While True Episode 2: Small Bits of Writing Write While True Episode 14: Spaced Repetition Write While True Episode 1: Training to Unblock Yourself Write While True Episode 19: Prompt Your Morning Pages Recurring Journals Introducing Page-o-Mat Transcript

When I was 13, my mom got me an electric typewriter for Christmas. She was a secretary, and she taught me how to touch type, and she wanted me to have something to practice on. But unfortunately, when I opened it up, it didn’t work. Write While True Episode 1: Training to Unblock Yourself Write While True Episode 3: First Drafts Write While True Episode 19: Prompt Your Morning Pages I Didn’t Have a Disk Drive My New Podcast Generating Workflow Whisper (for transcribing) Audacity Audio Hijack Transcript

If you are just coming to this podcast on this episode, I have to tell you that I talk about Morning Pages a lot. It was the subject of Episode 1. Listen to that for the full description of what they are or read the book The Artist’s Way by Julia Cameron [amazon affiliate link], which is where I was introduced to the idea. The main thing to know is that I start each morning by writing three pages of long hand writing in an automatic stream of consciousness style. I never show them to anyone and they aren’t meant to be published. The point is to train my brain to generate text on demand. If you read the entire thing, I would have a couple of sentences in a row here and there that make some sense, but overall, it’s not well-structured in any way. My pages tend to stray from topic to topic because I’m not considering the entire text. This is the breakthrough I had today. Write While True Episode 12: Keep a Topic List Write While True Episode 1: Training to Unblock Yourself Write While True Episode 18: Taking My Own Advice The Artist’s Way by Julia Cameron [amazon affiliate link] Transcript

I thought it would be a good idea to re-listen to all of my podcasts from season one. Each of them is only about 10 minutes and there are only 15 episodes, so it doesn’t take too long. This had two effects. First I realized they weren’t as bad as I thought, which made me feel better about restarting. The second thing is that I started to hear the advice almost as if it was coming from a third party because I had recorded these so long ago. I had dropped many of these practices during my break, so it was almost like hearing from a different person. But that person was making podcasts and I wasn’t, so I decided to listen to him. The Artist’s Way [amazon affiliate link] by Julia Cameron A Technique for Producing Ideas [amazon affiliate link] by James Webb Young Skin in the Game [amazon affiliate link] by Nassim Taleb Transcript

I thought about things that were going well, where I had a lot of output, like my programming projects. One thing I realized that helps a lot is that I am proud of that work. Doing it is a self-esteem builder, and I have a lot of confidence that I can meet my own standards. I’ve been programming for a long time, so this isn’t much of a surprise. All during that time I challenged myself by doing bigger projects and learning new things. While learning new things and working on bigger and bigger projects helped me improve, it wasn’t the most important factor. What helped me the most was the people I worked with. Transcript

I did season one of this podcast a couple of years ago. I did 15 episodes. They were about some of the basics of building up a writing habit, and then I stopped. In this season, I am going to explore how to restart projects in the context of restarting this one. I want to talk about one of the lessons I’ve learned. Transcript

I made this podcast, but I wanted to self-host, so I learned how to do that with s3 and wrote my own way to get analytics. So, Podcasting leads to programming. And then I wrote up a blog about that program (so it led back to writing) and now I am telling you about it on this podcast. Round and round it goes. The more times I go around the circle, the easier it becomes to write or podcast or program about one of the other things I’m doing. The content for this podcast is mostly taken from a blog post I made in February. Back then I just said that I should come up with some way to combine programming and writing more. This podcast was the result of that thinking. Sprint-o-Mat WatchKit articles on App-o-Mat Personal Finance script Transcript

Last week I encouraged you to collect general knowledge. Viking trade routes, anime, Rothko paintings, architecture, typography, bluegrass standards -- where ever your interests lead you. For these kinds of things, it may be hard to write a note though. You could certainly write down something, but it's unlikely that you'll develop a few paragraphs of a coherent thought about lots of random things. James Webb Young said to use index cards for that. That would certainly work, but I recommend using spaced-repetition card software instead.

New ideas are combinations of old ones.

In the past, when I set goals to write more frequently, I was always stopped by not having ideas ready for what to write about. Or when I got one, I didn't have a systematic way of collecting them. I would sit down to write, but getting started on a new piece was too difficult. My ONE thing is make it so that when I sit down to write I have a checklist to work from.

I know that a lot of my episodes are variations on the theme of quantity. In episode one, I asked you to write morning pages every day. In episode 4, I asked you to make a schedule where you write multiple days a week. I've talked about the importance of producing many first drafts. In episode 8, I said you should lower your bar and just last week I shared my personal “why”, which is all about playing the infinite game because it’s fun. The title of this podcast is a play on the idea of the infinite game.

The exercise this week is to think about your "why"? I don't think it's wrong to write for money or fame, but if you're an amateur like me, I'd find something easier to attain.

I don't use a lot of social media, but if I don't plan my time intentionally, I'll find myself watching a lot of YouTube. It's not that I think that my life should be 100% dedicated to making new things or in solitary contemplation. But, there are times when I notice that level of output isn't where I want it to be, and so I take a good look at how I am spending my time.

This episode is about lowering the bar, and I'm tempted to just say go do it and sign off. That would be the ultimate lowering the bar for this podcast. I won't do that, but I am going to keep the bar on this episode pretty low. And, you're probably thinking -- Lou, I thought the bar for Write While True episodes was pretty low already.

Lately, I'm thinking a lot about what this podcast sounds like. I'm new to podcasting and I'm very aware that I have a lot to do to sound more natural, but that's not exactly what I'm talking about.