It Actually Works

Testing dialogue dictation took me from zero confidence to absolute certainty

My apologies for the avalanche of posts recently. I’m slowly catching up by republishing everything I posted on Substack over the last few months. As I’m posting twice daily, the weekly newsletter, I should be all caught up soon. Then back to weekly posts. Previously published November 2 2025, on Writer on the Edge.

This has been an interesting morning. It’s Tuesday, October 28th, as I dictate this, just a few days until the start of Novel November, and I thought it would be a good idea to experiment with my process. Specifically, I wanted to see how it handles dialogue.

There were two parts to this experiment. At first, I didn’t feel confident at all. I felt like a complete fraud, with no clue how to handle conversations. But it turns out that it wasn’t anywhere near as difficult as I thought.

Rice Fields in Northern Thailand

Another non-related image. This was taken in the area of Chang Rai in Northern Thailand. We’re going to Thailand next year, images like this help me get into vacation mode.

The First Test Run

The process was quite simple, really. My first dictation session was for a video call dialogue between two people, which came to about 650 words. As a first attempt, it wasn’t too bad, but it needed quite a bit of editing. Those 650 words took about six and a half minutes to dictate, roughly 100 words a minute. Not much, but it’s a start.

The editing process was quite extensive before I was ready to put it into the project. I then followed up with a conversation between two other people, also via video call, which resulted in approximately 400 words.

This is where it started to get really interesting. That second round, from starting the dictation, getting the transcription, feeding it into Claude, asking Claude to reformat it with all the dialogue tags and punctuation, and getting it ready for the project, took less than 20 minutes total.

Comparing that with the hour and 20 minutes for the first session, that’s an enormous improvement. The only difference was that my level of confidence was effectively close to zero before the first attempt. Clearing that mental block allowed me to relax and fully immerse myself in the characters for the second session.

Think about it. On my working days, I should be able to get one or two dictation sessions done in the morning, very quickly. That would be around 1,000 words already. Then, in the evening, when I get home, another 20 to 25 minutes, and they’ll be edited and ready to go into the project. Maybe a little bit of extra work, possibly another scene or two, and then the target is met.

The Game-Changer

So we’re looking at 10 to 15 minutes every morning. On the days I’m off, that could easily be extended to 30 minutes, and the entire target done in one sitting. And for the weekends? Even more.

The great thing about it is that I don’t have to worry about family commitments, household chores, or going to the gym. Because I’ll have more than enough time for all of that. Even walking the dogs fits in nicely (the doggies are waiting for me right now to go for their walk.) It all seems to be fitting in perfectly.

The Muddy Middle Problem

My problem, if you can call it that, is the infamous muddy middle. I’ve had a good look through the nearly 30,000 words I’ve already written. There are some huge holes and quite a bit of research work to do, but that can be done on days off and weekends. Not too much research, though. The whole point of this challenge is to write 50,000 words.

The second pass, once the first draft is completed, will be where the work really starts. Depending on the genre, if it’s a thriller, for example, you might find it a bit flat and in need of excitement and pace. That can all be injected later in the second draft. No problem.

A Shift in Mindset

So now, I’m actually looking forward to it. It’s going to be an interesting time. Assuming that this will be successful, to be honest, even if I don’t make the 50,000 words, it will still be successful. It already is successful. I can feel it. The process works.

So why not Book 2 and Book 3? Yes, I’m envisioning a trilogy for this particular series. Once that’s all done, then it’s a matter of getting it out there.

A professional editor to go through it after ProWritingAid has had its turn. Professional covers, all combined with a consistent theme. All that stuff comes later. Right now, the most important thing is to get the damn thing (things?) written.

I’m absolutely 100% sure now that it’s going to happen.

Why This Matters

This morning’s experiment proved something important: dialogue isn’t the monster I thought it would be. In fact, it might be one of the easier parts to dictate. When you put yourself in a character’s mind and speak as them, the words flow naturally. It’s almost like method acting, but for writers.

The efficiency gains are massive. If I can maintain this pace, I don’t see any reason I can’t. For example, three quick sessions during work weeks get me 4,500 words. Add morning sessions on days off for another 6,000-plus. And weekends? The sky’s the limit.

Novel November Week Calendar

That’s more than enough to hit 50,000 words in a month, even accounting for the messy first-draft nature of dictated content. It might just be a little bit over-optimistic, but it is what it is, I suppose.

Novel November Scoreboard

I made a promise to share my Novel November progress each week, so here we are — accountability in action.

Since this newsletter lands in your inbox on Sunday, November 2nd, we’re basically at the starting line. But I wanted to establish the scoreboard early and give you a glimpse of how this challenge is already unfolding.

The Ground Rules

The Novel November target is 50,000 words in 30 days, which breaks down to 1,667 words daily. That’s the number I’m chasing. Some days I’ll crush it, other days I’ll barely scrape by — that’s the nature of this beast.

I’ve decided to track progress in weekly chunks, Monday through Sunday. It keeps things simple and aligns with when you’ll hear from me. That means yesterday (Saturday) and today (Sunday) are my unofficial “Week 0” — a warm-up lap, if you will.

Week 0 Status: 5,127 Words

Not bad for two days, right? I’m already ahead of the pace, sitting at roughly 308% of where I “should” be at this point. But let’s be real — it’s way too early for celebration or panic. We’re two days into a 30-day marathon. Anything can happen.

The real test begins tomorrow when Week 1 officially kicks off.

The Running Tally

Here’s how I’ll present the scoreboard each week:

• Week 0 (Nov 1–2): 5,127 words ✓
• Week 1 (Nov 3–9): 0 words
• Week 2 (Nov 10–16): 0 words
• Week 3 (Nov 17–23): 0 words
• Week 4 (Nov 24–30): 0 words

Check back next Sunday to see if I’m still riding high or desperately caffeinated and questioning all my life choices. Either way, you’ll get the honest truth.

Final Thoughts

This experiment changed everything for me. I went from feeling like a fraud who couldn’t handle dialogue to being completely confident in my ability to finish this book. The process works. The tools work. The time is there.

Yes, there will be holes to fill. Yes, the muddy middle is still muddy. But that’s what second drafts are for. That’s what editing is for. Right now, the goal is simple: get the words down. Get the story told. Make it exist. And you know what? For the first time, I genuinely believe it will.

If you’re thinking about trying dictation for your own writing, I can’t recommend it enough. Start small, try a conversation between two characters. See how it feels. You might surprise yourself, just like I did last Tuesday morning.

In case you missed it

Just a quick note, if you missed the short post last Friday, to let you know I’ve rebranded the newsletter from “The Everyday Solopreneur” to Writer on the Edge. Read more here.