Why Your Task List Is Killing Your Creative Projects

I've spent months feeling like absolute garbage about my creative projects.

I'd stare at my task list wondering why "figure out course structure" was still sitting there after three weeks. Am I just bad at this? Procrastinating? Neither is true but the guilt is real.

For years, I've felt disorganised & struggled to gain momentum on my creative projects. The problem isn't my work ethic — it's trying to force creative work into systems designed for something entirely different.

Conventional project management systems expect work to move in a straight line. They assume a top down approach where everything can be nicely defined and listed out step by step:

• Write report ✓
• Design logo ✓
• Send email ✓

But the problem is that creative knowledge work isn't like that. It's hard to list out in a neat little list of things to do. It spirals, it doubles back. It sits in my subconscious while I'm in the shower or out for a walk.

When I put a workshop or course together I often spend months collecting notes & ideas, exploring & experimenting with Tana systems. All of this activity creates a groundswell of ideas that eventually turn into a project I can define into a neat little list like outlines, slides, recording videos.

But I often get stuck in those early moments of a project when it's messy and chaotic and still forming in my brain. How do your organise choas like that so projects still get moved forward?

Think of work in modes rather than task lists

Rather than trying to stuff my work in to some project management system I've been thinking about it in modes.

1. Experimentation Mode 🧪

This is where I play, test, and explore. If I'm working on a YouTube video, I might spend time testing different ways to demonstrate a Tana feature. If I don't spend time in this mode eventually deliverables like course, workshops & videos stall. So it's absolutely critical for me.

2. Thinking Mode 💭

This is deep, intentional thought work. It might happen while staring out the window, on a walk, or sitting on my back deck — but make no mistake, this is REAL work. Traditional project management systems have no place for "think deeply about course structure" because it can't be measured in tidy checkboxes, but this thinking is often where the most valuable breakthroughs happen. Like number 1 I need to spend time in thinking mode otherwise projects will never seet the light of day.

3. Execution Mode ⚡️

This is the clear, defined work. Create presentation slides. Film video. Edit newsletter. This is the only mode that traditional project management systems handle well.

The way I see it we have two problems when it comes to these undefined more messy parts of creative knowledge work:

1. Allocating time for these important modes.
2. Being able to easily find the things we should work on when we are in these modes.

Setting Up Your Creative Container System

Here is how I'm tackling it - and it might help you too if you struggle to gain momentum on your creative projects:

1. Identify Your Modes

Take some time to observe how you naturally work. My three modes (experimentation, thinking, execution) might be different from yours. What are the distinct thinking and working patterns that drive your creative process forward?

2. Understand How Work Flows Between Modes

Notice the relationships between your modes. For me, I've discovered that when I neglect experimentation time, my deliverables get delayed. A YouTube video stalls or a new template doesn't get released. What dependencies exist in your creative pipeline?

3. Break Projects Into Knowledge Pieces

Rather than massive, undefined tasks like "outline course," break work into smaller knowledge building blocks that can be tackled individually. Instead of "write workshop," I bring together all the notes & pieces I want to explore and then work on them one by one. This is similar to Tiago Forte's Intermediate Packets idea – creating smaller, complete units of work that can be assembled later.

4. Build Containers In Your Knowledge System

Create dedicated spaces in whatever tool you use (Tana, Notion, Obsidian, etc.) for your modes so you can easily jump in. I've created an experiments container & a thinking container so I can find all these things easily. And I don't just dump random stuff in there - I connect each of them to a bigger projects so I know I'm moving things forward.

5. Schedule Mode Time

Now you have a system setup - block time on your calendar for each mode. I schedule experimentation time just as seriously as client calls now. Thinking time gets protected blocks where I can go for a walk or sit on my deck.

Organising like this has completely transformed how I feel about my creative projects. Instead of a mess of undefined tasks where I'm constantly questioning if I'm making progress, I have clear containers where I can direct my energy based on what mode the project requires.

If you feel a little chaotic or disorganised with creative work - I hope you give it a try.

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Whenever You're ready here are a couple of ways I can help:

1. Subscribe to Knowledge Work: Rebooted —Every Sunday, I share practical tools, workflows, and systems to help ambitious professionals build their own digital team - a stack of tools that works with you, not against you.
2. If you want to go beyond using AI as just a writing tool — the AI Creative Copilot Masterclass is for you. It’ll teach you how to build an AI Co-Pilot (an AI partner who thinks exactly like you do) that helps you get your best creative work out into the world.
3. Unlock your best ideas with ​The AI-Powered Note-Taking Playbook​. A curated list of powerful prompts to transform how you think, create & brainstorm with AI by your side. Because two minds are better than one (especially when one never gets tired)

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