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Simon Theakston

@simontheakston.bsky.social
59 followers 30 following 193 posts

From tech co-founder to 4-hour workdays | Stroke survivor building differently | Sharing what limitations teach us about better systems Newsletter: fourhourfreedom.substack.com

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Simon Theakston @simontheakston.bsky.social · 08/06/2026
When I sit down at 8am, I already know what the day looks like. Emails summarised. Calendar checked. Tasks prioritised. And I haven't opened an app. It runs automatically as a skill I built once. This week's newsletter covers how the process works. fourhourfreedom.substack.com/p/i-rebuilt-...
fourhourfreedom.substack.com
I Rebuilt My AI Workflow From Scratch. Here's What Survived the Cut
A morning briefing, a 5pm wind-down, and a proposal that landed while I was resting on the sofa.
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Simon Theakston @simontheakston.bsky.social · 30/05/2026
My first mistake with Claude was saying please and thank you. That habit, and a handful of others like it, were costing me more of my allowance than the tasks themselves. This week I wrote about what I changed. And why I still haven't upgraded. open.substack.com/pub/fourhour...
open.substack.com
I’ve Been on Claude Pro for Six Months and Still Haven’t Needed to Upgrade. Here’s Why.
The habits that were burning my allowance - and the five changes that fixed them.
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Simon Theakston @simontheakston.bsky.social · 09/05/2026
I'm not a developer. I work four hours a day. Last week I built a live financial dashboard connected to QuickBooks and my bank account. No code. Plain English. One morning. Here's how (with a link to a live demo!): open.substack.com/pub/fourhour...
open.substack.com
I Built a Financial Dashboard Using Claude Code Without Writing a Single Line of Code
What it cost, how long it took, and a live demo so you can judge for yourself.
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Simon Theakston @simontheakston.bsky.social · 18/04/2026
After my stroke: 4 working hours a day, hard limit. Spending 20 minutes piecing together my day wasn't an option. So I built a briefing that runs at 7am without while I’m still in bed. By 8am I know what matters. This week's newsletter is the full story: open.substack.com/pub/fourhour...
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Simon Theakston @simontheakston.bsky.social · 15/04/2026
5 years ago I wrote content I couldn't back up. I knew the stat was out there. I knew there was a perfect quote somewhere. I couldn't find either. So I built a system where capturing something once is enough. It’s short, practical and you can read about it below. open.substack.com/pub/fourhour...
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Simon Theakston @simontheakston.bsky.social · 06/03/2026
A few days ago I gave a task to AI and went to do physio. When I came back, it was structured and exported to Notion. Ready to use. That moment changed how I work. Tomorrow’s newsletter is the full story. Subscribe and you’ll get it in your inbox tomorrow. open.substack.com/pub/fourhour...
open.substack.com
I changed one tool. Then I changed how I work.
I went to do my physio. My strategy organised itself.
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Simon Theakston @simontheakston.bsky.social · 25/02/2026
There’s a simple rule I follow: if losing it would cause stress, it gets scanned. I’ve scanned medical letters, contracts, tax docs, warranties to name a few. Paperless isn’t about minimalism. It’s about certainty and peace of mind. I’ve written about it here: open.substack.com/pub/fourhour...
open.substack.com
Why My Paperless System Needed an Upgrade
Clarity, control, and the hidden cost of paper.
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Simon Theakston @simontheakston.bsky.social · 23/01/2026
I’ve accidentally got into mechanical keyboards. I wasn’t chasing productivity or anything clever - just wanted typing to feel nicer. Ended up changing my keyboard and realised how much the little frictions were messing with my focus. I wrote about it here: open.substack.com/pub/fourhour...
open.substack.com
The Tools You Touch Every Day Matter More Than You Think
A New Keyboard, Chosen for How It Feels, Not What It Promises
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Simon Theakston @simontheakston.bsky.social · 20/01/2026
The goal isn’t working fewer hours. It’s designing work that fits the hours you actually have.
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Simon Theakston @simontheakston.bsky.social · 15/01/2026
I used to plan my days around ambition. Now I plan around energy. Ambition is loud and persuasive. Energy is quieter, but more honest. One ignores my reality. The other works with it.
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Simon Theakston @simontheakston.bsky.social · 02/01/2026
Three years ago today, my life changed. Not in a neat, story-friendly way, but in a way I’m still living with. If you’re building something quietly, or working within limits you didn’t choose, tomorrow’s piece may resonate. It goes out in the morning. open.substack.com/pub/fourhour...
open.substack.com
Three Years Later, I’m Still Rebuilding — Just Differently
Designing a way to work when the future stops looking familiar
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Simon Theakston @simontheakston.bsky.social · 24/12/2025
Working four hours a day doesn't leave much room for drift. Miss a week and you feel it. Miss a month and the business feels it. That's why reviews matter more to me than goals. I've written up the system I use every Sunday evening. open.substack.com/pub/fourhour...
open.substack.com
The Review System That Keeps My Business on Track — Even With a 4-Hour Workday
Planning from the sofa: a realistic review habit for limited energy days
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Simon Theakston @simontheakston.bsky.social · 17/12/2025
My best ideas don’t come from sitting at a desk. They arrive while walking, listening to podcasts, or half-thinking about something else. This is how I capture them in under five seconds - and why that matters more than the tools. open.substack.com/pub/fourhour...
open.substack.com
My Complete Capture System
How I Never Lose an Idea Again
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Simon Theakston @simontheakston.bsky.social · 13/12/2025
2025 taught me something uncomfortable: doing good work isn’t the same as building a sustainable business. I wrote an honest review of the year and how I’m changing things in 2026. It’s live now. open.substack.com/pub/fourhour...
open.substack.com
An honest review of 2025 - and why 2026 has to be different
Why good work wasn’t enough - and what I’m changing
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Simon Theakston @simontheakston.bsky.social · 10/12/2025
Since the stroke, I’m always on the lookout for things that reduce effort or improve output. This week’s newsletter breaks down the five best sub-$200 purchases I’ve made in 2025. If you’re building a smoother workday, this might help. open.substack.com/pub/fourhour...
open.substack.com
5 purchases under $200 that have made my life noticeably easier in 2025
The affordable gear that keeps my life lighter and my work flowing.
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Simon Theakston @simontheakston.bsky.social · 19/11/2025
The café on my rehab walk gives me jelly babies to get me home again. They probably think I work all day too! People think my 4-hour day is a productivity trick — it isn’t. It’s recovery, boundaries, and energy management. My 4-Hour Workday Explained: fourhourfreedom.substack.com/p/my-4-hour-...
fourhourfreedom.substack.com
My 4-Hour Workday, Explained
Tools, systems, and rituals that let me run a business without burning out
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Simon Theakston @simontheakston.bsky.social · 24/10/2025
No hustle. No hacks. Just a system I built from the sofa, with one working hand and zero energy to spare. It’s what let me grow after everything fell apart. Live tomorrow on Four Hour Freedom. fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 22/10/2025
I found focus through sound. Not music. Not noise. But adaptive soundscapes that shift as I do. After my stroke, I couldn’t handle Spotify. I needed something for recovery - not distraction. I found it. Now I use it daily to write, rest, and sleep. Info here: open.substack.com/pub/fourhour...
open.substack.com
Why Spotify Couldn’t Fix My Focus — But This App Did
How I went from sensory overload to deep focus — using sound, not silence.
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Simon Theakston @simontheakston.bsky.social · 01/10/2025
Just hit my all-time high of 242 newsletter subscribers. Slowly but surely, a little crew is forming. If you’re reading this and you’re one of them - thank you. If you’re not, come join us: fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 27/09/2025
This isn’t a hustle story. It’s a rebuild story. For anyone who’s had life punch them in the gut - and is now trying to build something that fits the new version of themselves. fourhourfreedom.substack.com/p/stroke-of-...
fourhourfreedom.substack.com
Stroke of Freedom: Turning Adversity Into Advantage
I planned to escape the 9–5 in three years. Life gave me three months.
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Simon Theakston @simontheakston.bsky.social · 18/08/2025
I don’t work 4 hours a day to be lazy. I do it so I’ve got energy left for walks, mates, music, and meaning. Work is part of life. Not the whole damn thing.
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Simon Theakston @simontheakston.bsky.social · 08/08/2025
- One night of 4-hour sleep = 70% drop in cancer-fighting cells. - 20 hours awake = legally drunk cognitive function. - Zero percent of humans can thrive on 5 hours without impairment. This Saturday: Why your productivity hack is actually sabotaging everything. fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 06/08/2025
Meetings without notes = decisions without follow-through. I use AI + transcripts to turn every call into clear next steps. It has saved projects - and improved my sales process more than I could imagine! Full process in today’s newsletter: fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 05/08/2025
My iPad weighs less than a hardback book, runs on the same M chip as desktop Macs, and lasts 10hrs on battery. For writing, editing photos, jumping on video calls, or managing client projects—it’s brilliant. I thought I’d miss my laptop. I don’t. fourhourfreedom.substack.com/p/the-day-i-...
fourhourfreedom.substack.com
The Day I Realised My Laptop Was Holding Me Back
The Surprising Truth About Working From an iPad in 2025
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Simon Theakston @simontheakston.bsky.social · 17/07/2025
One hour a day adds up faster than you think. I couldn’t work full-time, so I built a system that let me make real progress in short bursts. 12 months later, it’s working. Stop waiting for the perfect week. Start investing the 60 minutes you do have.
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Simon Theakston @simontheakston.bsky.social · 16/07/2025
DEVONthink changed how I collect. Obsidian changed how I think. After my stroke, my brain didn’t work the way it used to. These two tools became a kind of external hard drive. This afternoon, I’m sharing the real workflows I use to connect them - and the mindset shift that made it all work.
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Simon Theakston @simontheakston.bsky.social · 15/07/2025
There’s no perfect app. But there is a perfect combination. DEVONthink handles capture and search. Obsidian handles thinking and creation. Together, they’ve become my digital memory. Tomorrow’s issue is all about how I built the bridge between them. It’s free at FourHourFreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 14/07/2025
This one is for you if you’re juggling 5 ideas but making progress on none. I used to be the same - until a health scare forced me to cut the fluff. One idea. Four hours a day. Real traction. You don’t need more time. You need fewer distractions.
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Simon Theakston @simontheakston.bsky.social · 08/07/2025
I don’t want to remember everything. I just want to remember what matters. That’s why I built a system in Obsidian that catches insights and sends me the good stuff when I need it. Tomorrow, I’ll show you how it works - with real-world examples. 📨 Subscribe here: fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 04/07/2025
You want to be present. But your job needs 40 hours - and your kids need you. After I lost my health, I built a 4-hour workday that gives me both time and income. You don’t have to choose between family and freedom. There’s another way.
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Simon Theakston @simontheakston.bsky.social · 02/07/2025
It’s #Lego night. This is the end of Bag 2. Anyone want to hazard a guess as to what is?
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Simon Theakston @simontheakston.bsky.social · 02/07/2025
If your digital life feels like a mess of PDFs, receipts, and research notes… DEVONthink can fix that. This afternoon I’m sharing: ✅ My exact setup ✅ Screenshots ✅ Why it beats Google Drive Make sure you’re on the list: fourhourfreedom.substack.com
fourhourfreedom.substack
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Simon Theakston @simontheakston.bsky.social · 01/07/2025
DEVONthink isn’t my second brain. It’s my external brain. It’s where I store everything other people created: PDFs, research, invoices, letters, receipts. Want to see how I’ve set it up to work in 4 hours a day? Tomorrow’s newsletter breaks it down fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 01/07/2025
I don’t work 4 hours a day to be lazy. I do it so I’ve got energy left for walks, rehab, reading and family. Work is part of life. Not the whole damn thing.
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Simon Theakston @simontheakston.bsky.social · 30/06/2025
I used to treat AI like a search engine. Type prompt → get answer. But the real breakthroughs came when I let it ask me questions back. This week’s Four Hour Freedom is about two-way conversations with AI: fourhourfreedom.substack.com/p/the-power-...
fourhourfreedom.substack.com
Why You Should Talk With AI, Not To It
AI shouldn’t be treated as a tool. The real magic happens when you use it as a conversation partner
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Simon Theakston @simontheakston.bsky.social · 26/06/2025
New article on the power of my iPhone for work: medium.com/macoclock/wh...
medium.com
Why My iPhone Is More Powerful Than My Old Office Setup
I swapped my office setup for an iPhone — and now I work less, get more done, and carry my business in my pocket.
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Simon Theakston @simontheakston.bsky.social · 26/06/2025
I don’t work 4 hours a day to be lazy. I do it so I’ve got energy left for walks, mates, music, and meaning. Work is part of life. Not the whole damn thing.
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Simon Theakston @simontheakston.bsky.social · 25/06/2025
After my stroke, I had to relearn how to think clearly. One tool helped me more than anything else. It wasn’t AI. It wasn’t Notion. It was Readwise. This week, I’m sharing the exact setup that powers my business. First Four Hour Setup issue lands this afternoon: fourhourfreedom.substack.com
fourhourfreedom.substack
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Simon Theakston @simontheakston.bsky.social · 23/06/2025
I don’t want to scale endlessly. I don’t want a 10-person team. I want freedom. And I’ve found the tech stack that gives it to me. In this week’s Four Hour Freedom, I break it all down: fourhourfreedom.substack.com/p/the-apps-t...
fourhourfreedom.substack.com
The Apps That Run My Business (and My Life)
The exact tech stack that lets me run a business in 4 hours a day
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Simon Theakston @simontheakston.bsky.social · 21/06/2025
I don’t have a team. I have an app stack. This week’s Four Hour Freedom reveals it all: fourhourfreedom.substack.com/p/the-apps-t...
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 20/06/2025
Me, running a business: 🔴 CEO 🟡 Copywriter 🟢 Customer support 🔵 Tea-maker I’ve only got 4 hours a day to do it all. So apps do the heavy lifting. Tomorrow’s newsletter is my guide to the apps that keep me sane. Sign up to receive it tomorrow morning! fourhourfreedom.substack.com
fourhourfreedom.substack.com
Four Hour Freedom | Simon Theakston | Substack
From tech founder to stroke survivor to thriving creator - I share how to build profitable businesses around life, not despite it, in just four hours each day. Click to read Four Hour Freedom, by Simo...
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Simon Theakston @simontheakston.bsky.social · 20/06/2025
You don’t need a fancy website. Or a logo. Or a 5-year plan. You need one person to say: “That helped me.” That’s how it starts.
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Simon Theakston @simontheakston.bsky.social · 19/06/2025
Every time I wanted to quit, I reminded myself: I’ve been through worse. If you’ve survived the hard stuff, you can definitely survive starting a newsletter or posting online.
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Simon Theakston @simontheakston.bsky.social · 17/06/2025
The old me wouldn’t have dared post like this. I was too worried about what people think. Then I nearly died and realised: Most people aren’t even thinking about you. So you might as well do what you want.
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Simon Theakston @simontheakston.bsky.social · 16/06/2025
When I started, I didn’t have a niche. Just a story. Turns out that’s all you need. People don’t follow perfect plans. They follow you. Be human. Be helpful.
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Simon Theakston @simontheakston.bsky.social · 13/06/2025
Told someone I work 4 hours a day and they said “must be nice.” Nah mate, it was brutal. Stroke. Redundancy. Panic. Not ‘nice’—necessary. Comfort doesn’t build freedom. Rock bottom does.
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Simon Theakston @simontheakston.bsky.social · 12/06/2025
The stroke didn’t give me superpowers. It gave me perspective. I stopped wasting time on things that don’t matter. Now my to-do list fits on a Post-it. Freedom’s not found in doing more. It’s in doing less—but better.
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Simon Theakston @simontheakston.bsky.social · 11/06/2025
Just passed 80 new subscribers this week. That’s a first. Not bad for a newsletter started between rehab sessions. To say I’m grateful is an understatement. Welcome, everyone.
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Simon Theakston @simontheakston.bsky.social · 10/06/2025
I used to think success meant looking busy. Now it means logging off without guilt. Freedom isn’t about yachts or 6-figures. It’s about not needing permission to take the afternoon off.
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Simon Theakston @simontheakston.bsky.social · 09/06/2025
Something wild happened this week: The newsletter passed 80 new subscribers in 7 days. That’s never happened before. If you’re reading this and you’re one of them - thank you. I don’t take it lightly.
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