What's your favorite tool to "Write Every Day" and what's your take on dictation?

Hi Joan,

loved your recent posts on writing every day, and The Map is Not The Territory. The latter made me recognize myself in an almost painful way.

Keeping with my theme of over-analyzing – I’m curious if you have a favorite tool where your daily (free-form) writing is happening? Do you actually use a dedicated device like the Freewrite shown in the article?

I’m also curious what you think about voice transcription for Stream-of-consciousness-type journaling. I’ve had great joy in using Rosebud for this, and I also like the way it asks questions and finds patterns. But I can’t stop thinking I’m missing something when I’m not taking the time to slow down and actually write.

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Thank you!

Writing tools - I have always loved iA Writer:

I’d call this the single best / most beautiful writing software ever made.

I do own a FreeWrite, and most of my articles start life as a brain dump // “just write” session on my FreeWrite with headphones on playing rain and thunderstorm sounds. Been my process for a while now. FreeWrite is definitely a luxury item though, I’ll admit that. If you can get one, they’re brilliant.

Re: dictation and voice transcription….this is something a fair few writers I know have started using! They’ll even brain dump via voice to transcription, run it through ChatGPT to form their thoughts into an outline etc and go from there. Which sounds like a cool way to work, except - I genuinely don’t think that well out loud. I need my hands on a keyboard or I need a pen and a piece of paper to really think.

It likely stems from my childhood (not to over share) - I had quite a severe speech impediment and I struggled to be understood by folks, so I spent more time writing than talking, and even now I’d rather scribble notes than speak. Years of speech therapy enabled me to communicate via spoken word (obviously - YouTube etc) but it’s just not my preferred way of getting an idea out.

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I resonated to your comment about how you “really think.” Here’s a variant that is very true for me (from one of the people at Sean Blanc’s site ‘The Sweet Setup’):

Thinking happens on paper
Creating happens on the computer

— Mike Schmitz, 6/9/2020

My friendly amendment re: thinking… on paper, OR on a stick-on whiteboard on the wall behind where I’m sitting right now. :smiling_face_with_sunglasses:

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Oh wow, I haven’t heard about The Sweet Setup in a while - is that still going strong? That was one of my favourite places on the internet a few years back.

Keen to see what Sean’s been up to…

I’m a big fan of sticky notes and index cards. An interesting side effect of parenthood is that I’m pushed to think about positive // healthy ways to guide my kid (now 9) to do his school work, and form his thoughts, and it’s helping me get back to basics like just keeping a set of sticky notes with me.

A good reminder for me to never underestimate the value of just working with other folks…

Send Sean a link to ‘I deleted My Second Brain’; and I’ll bet he’ll send you a link to sign up for his course on ‘To Obsidian and Beyond’. More where that came from. I did the Ulysses course a while back, but not Obsidian.

I discovered the site many years ago when I was searching for reviews of some piece of software (don’t now recall what). He (mostly just Sean at the outset) had a top-25(?) list of his favorite pieces of software. Turns out I was already using many of them, so I immediately felt a “kinship” and have followed the site ever since. I don’t think I’m doing him an injustice to say It is now more PKM-focused, less on general Mac-umbrella software, but it’s still worth a visit occasionally.

Yes it’s really a special piece of software that I, too have always loved but rarely found a way to use consistently between many other tool. I might use that just for some free writing experimentation. Love the idea of a dedicated space for that. No AI, no publication, no end goals.

That’s super interesting because for me it kind of works the other way around. It feels freeing to think out loud and sort later. Then letting an LLM sort through my ramblings and sometimes even create drafts from it in my own voice it feels a bit like cheating. And it makes me constantly wonder whether I’ll lose important skills because I outsource them to the model, or if it’s just “smart” use of AI-as-a-tool.

Thank you for sharing your history for context why writing is so crucial in your life.

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I do think writing is actually far more individual and personal than many folks perceive it to be. It’s carving out your innermost thoughts, in your own voice, and putting them onto a page…that process is going to work differently for almost everyone.

I’d say it’s less about finding a system that works and more just picking and choosing bits and pieces and building a nest.

A bit late to the thread…

I have found that when transcribing, having a structure in mind can be beneficial. I find that dictating by myself requires me to speak complete sentences, which can be challenging. I have heard that Richard Feynman thought through ideas and problems in complete sentences and paragraphs. From my experience, taking this further by way of speech boosts verbal discipline.

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An update to this post…
I’ve actually stripped away most of the tools I’ve been using.
Even markdown as a tool. Gone back to plain text.
I can’t tell you how freeing it is but - just plain text edited with either vim or bbedit has been a gamechanger lately.

Much less room for excuses.

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have you tried any other dictation solutions aside from Rosebud? I’d prefer to just record audio with long pauses while driving or walking and have it converted to text immediately. I didn’t really enjoy the conversational style or the pressure to respond with the app. The feedback was also very basic and ELIZA-like.

Apple’s native voice recorder does a decent job of this, but the accuracy isn’t perfect especially with background noise, and having to transcribe and copy as a separate step adds a bit of friction.

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For the last month or so, I’ve been using Wispr Flow. I’ve barely written anything using my digit, skin bag thingamy bobs. I just speak and it transcribes with near perfection. Far far better than Apple’s native voice recorder does. And boy, it’s transformed my email inbox. I actually like replying to emails now. Now I can talk (riff) and I don’t have to get it all in the right sequence because Wispr Flow sorts all that out.

Then, like @klickreflex said, I chuck it into an LLM, get it to strip out the essence of what I’m saying, because I know what I’m trying to say, and I have a first draught that I usually handwrite and edit, with good old pen and paper, before pushing that back into an LLM to edit and clean up (Grammarly or whatever I happen to be using in the moment).

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I’m an early user of Monologue (wrote about it here, it looks different today) and on my Mac it quickly became one on my most used tools ever. As they don’t have an iOS app yet, I am also using WisprFlow, though I feel that is a bit buggy compared to Monologue (which is a shame given their multi-million funding and the fact that Monologue is created by a single dev).

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I’ve been forcing myself through the difficult process of learning Vim lately. Mostly because I want to, partly because I think breaking my muscle memory when it comes to text input / editing might be a good thing