23 Unstick your To-Do List

Who doesn’t have a challenge or two squatting on their to-do list?

Stuck ‘to-dos’ tend to be important, which is why they keep making the list.

So why the lack of progress? Perhaps you’ve been putting it off so long, JUST THINKING ABOUT IT makes you feel sick. For me, it’s writing the book I’ve been meaning to start for 15 years…

We’ve noticed ‘stuck challenges’ usually fall into two camps:

Too Big: The task is so huge, it’s overwhelming. Where to start?!
Too Focused: The task is so process-driven (or dull!) JUST THINKING ABOUT IT makes you want to stab the back of your hand with a fork.

To break free, try this experiment.

THE EXPERIMENT: Break It Down…or Build It Out

Step 1: Identify Your Stuck Challenge

It could be a big one (like “write the book”) or a small, tedious one (like “do the expenses for the TCX Christmas party”).

Step 2: Break Down the Big Challenge

If your challenge feels overwhelming, use the power of HOW.

Ask “how?”, then ask ‘how?’ again…and again! Break the big challenge into smaller, actionable (doable!) tasks.

So, I’m stuck writing a book? Here’s ‘how’ I can break it down:

How can I best decide which topics the book should cover?
How to frame it as a practical guide to bringing joy and productivity to working life?
How can I draft an outline of key themes (eg mindset shifts, daily habits, and team dynamics?)
How can I create a first chapter summary?

Yay, I’m feeling the sweet jiggle of a man coming unstuck! Forget ‘WRITE THE BOOK’, I’ve got a niffy to-do list of manageable steps – • Brainstorm book ideas.

Write a one-page outline.
Set a timer and draft the first chapter.

Step 3: Build Out the Boring Challenges

If your challenge feels tedious and uninspiring, use the power of WHY.

Ask yourself “Why?’ repeatedly to uncover broader, more meaningful expressions of the task.

So, “Do the expenses for the TCX Christmas party” can evolve into –

Why? Because I need to reconcile the budget.
Why? To understand if we can plan another event.
Why? To create opportunities for the team to bond & have fun.
Why? Because a connected team is more productive and happier!

By zooming out, you’re no longer just doing the expenses. You’re building a foundation for team connection and morale. Suddenly, your task has energy and purpose!

Why This Experiment Works

When we’re stuck, it’s often because we’ve framed our challenge at the wrong level.

By using “How” to narrow down – or “Why” to broaden out – you reframe the problem into something actionable and inspiring. This simple shift:

Turns vague overwhelm into clear steps.
Infuses boring tasks with purpose and meaning.
Helps you build momentum where you’ve been stuck.

Your Turn: Try It Out

Take a challenge from your to-do list and run it through this experiment. Break it down or build it out? Discover a new perspective, and (crucially) the motivation to tackle it!

Anything beats having a chore chart…