My Best Writing Software and Workflow Yet
How I developed a systematic approach to efficient writing and the software I use every day

I was four years old when my world changed forever.
It was the summer of '75, as Bryan Adams didn't say. My grandfather (to be clear, Bryan Adams is not my grandfather) had taken the family to a local restaurant for a sunny Sunday lunch. And it was at that moment that I saw it.
The Desk.
The restaurant owner stood to greet us as we entered. Pushing his chair back from a desk, more functional than beautiful, he gently adjusted the position of a pencil box as he did so.
The Pencil Box.
In that moment, I knew.
Whatever job I ended up doing as an adult, I wanted my own desk and my own box of cool tools.
And I never forgot.
My favourite thing about school? My well-stocked pencil case. Beautifully laid out so I could quickly grab whatever stationery item the task required.
And in my first job, surveying on construction sites? My corner of the cabin, organised exactly how I wanted.
Fast forward to 2017, when I left employment and started writing. My passion for a systematic approach and the right tools for the job had never left.
Let me show you the tools I use.
And how I use them.
Hardware
A quick disclaimer before we unlock the toolbox.
There are no affiliate links in today's issue. I have no relationship with any of the companies and providers mentioned other than being a happy customer. Of course, alternatives exist for every product I'll mention.
(That said... Apple... You know where to find me...)
It was my younger brother who got me to buy into the Apple ecosystem. (He's not affiliated with them either... at least, he's never told me he is...)
Then, a graphic designer, now, head of the entire local government communications department. His faith in Apple products has never wavered.
And neither has mine.
Almost all my writing is done on my trusty MacBook Air, which replaced my old iMac in around 2020.
We'll get onto the software I use in a minute. But I'll take this opportunity to say that I support the laptop with a strong backup team of my iPhone (2nd Generation SE) and Apple Watch. (Again, the SE model is more than enough for my needs.)
How do I use the phone?
Several of the productivity and writing apps I use sync across the whole ecosystem. I can take notes and make small amendments wherever I go.
The watch?
One outstanding app beats all on this wonderful device.
Read on to find out more.
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Let’s get back to today’s topic...
Software
Other than the obvious operating systems, web browser and mail client, my writing software is made up of a simple trio of tools.
Voice Memos
For capturing thoughts quickly, nothing beats a voice recording app.
And that's where my Apple Watch stands out. Other than the few places and circumstances where I can't speak out loud, a quick tap of my watch face means I can make a note of my idea. Before the thought abandons me forever.
And the invaluable transcription service adds a critical second dimension:
Almost all my writing these days starts with me dictating into the app.
Why?
Because then what you read is my meaning, my tone, my voice.
Not the artificial strains of a regurgitating robot.
Trello
For project management and workflow... my goodness, it took me years to nail this one.
A few worthy mentions from trials gone by:
Apple Reminders
OmniFocus
Obsidian
Dynalist
None of them bad; not at all.
But the free version of Trello does everything I need it to. Across all aspects of my productivity and workflow, both professional and private.
I have six Workspaces, including one for each of my two newsletters, one for client work, and one for favourite recipes.
The labelling system removes all the friction from spotting what is where.
The template tool means I have many aspects of my work "prebaked" and ready to begin at a moment's notice.
And it's that ripple-free flow that gets results.
Bear App
Again, I've tried loads of writing apps. To name a few:
Apple Pages
Apple Notes
Obsidian
But Bear (Apple only, I believe—sorry!) gives me everything I need and nothing I don't. In one simple, elegant, beautiful package.
This is the one piece of software for which I decided to pay for the pro version.
Why?
The extra copy-and-paste options alone make it worth the coin.
And the syncing across my other Apple devices is the icing on the cake.
Websites and Workflow
I'll not go into every detail of my workflow here.
Those who need further details can take a look at my Newsletter Starter Pack for a step-by-step guide.
Or, for the exact workflow template, you could always take a look here.
But as an example taken from my newsletter writing workflow, here are the websites I use to get things outlined, written and published:
Capitalize My Title (I use this a little less often these days)
Monster Insights (Ditto)
Hemingway (Helps me stick to simple, audience-friendly phrasing)
Substack
Unsplash (When not using my own images)
My own website
Instagram (A recent addition)
And that's roughly the order in which I use them to get stuff out to you.
So, a whistle-stop tour of my tools and techniques.
I'd love to know how this compares to yours.
What do you use that's different?
Have my lists made you want to try something new?
Hit reply/comments and let me know.
You might inspire me to take a fresh look myself!
Thanks for reading.
Don't forget to check out my other newsletter, The Dancing Stepdad, for insights into the challenging and rewarding world of step-parenting.
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I am VERY interested in this newsletter/post. I think I’m likely doing things the hard way. Part of that is generational and has to do with technology. Part is that I am unschooled when it comes to writing (so I am unfamiliar with writer’s terminology, and methods.) And likely, the major part is I don’t even know what I don’t know.
But… my question for today, what is Hemingway?
I have heard folks refer to Hemingway before, but when I go to my App Store, there are 3 Hemingway products, each of which has only 1 review, and none of them look like an invaluable app.