Welcome to the ultimate guide to moving through your to-do list with ease—without pressure, shame, or perpetually rolling tasks into next week.

If you’re anything like most of us, you know that making lists can feel both energizing and anxiety-inducing at the same time. If you experience both of those conflicting feelings when you write out a list, you’re not alone.

The reality is that lists can feel genuinely overwhelming—especially when they contain tasks that feel too big to tackle.

Maybe you have a task on your list that feels enormous—not literally an elephant (we hope), but something so big, unclear, or daunting that you don’t know where to start. So you leave it. You work around it. You hope it will resolve itself. And week after week, it sits in your planner, staring back at you.

Here’s the reality: there’s no magic wand to make big tasks disappear. But you also don’t have to force yourself through them with sheer willpower. There’s a gentler, more sustainable way forward. And when you do finally complete that daunting task? It feels genuinely freeing.

So how do we gently work through those lingering tasks—the ones that sit in the planner for weeks without being touched? How do you approach something that feels overwhelming without the pressure?

As the saying goes: one bite at a time.

Here are five practices to help you move forward with clarity instead of force:

1. Start with what matters most (when you’re fresh)

It might feel easier to build momentum by tackling the smallest, quickest tasks first. But those lingering tasks—the ones that sit on your list for weeks—often require the most mental energy.

Even if they’re not technically difficult, they tend to pull you out of your normal rhythm. These are the tasks that create mental resistance, the ones that make you want to do literally anything else.

Start with the most challenging task when your mind is clear and your energy is high. Tackling it early lifts the mental weight it’s been carrying, leaving you lighter and more focused for the rest of your day.

2. Set yourself up for success

Life already has enough moving parts. We often amplify overwhelm by piling too many difficult tasks into a single day without providing ourselves with the necessary support to complete them.

Instead, make hard tasks easier by preparing:

• Gather what you need
• Clear your workspace
• Create a comfortable, focused environment (warm drink, favorite music, cozy spot)

Preparation doesn’t make the task disappear—it makes it approachable.

3. Break it down into smaller steps

Just as the only way to eat an elephant is one bite at a time, the same is true for your to-do list. Big tasks can feel paralyzing, but breaking them down into bite-sized steps makes them feel more achievable.

Whatever task has you feeling stuck, break it down into manageable pieces. Keep breaking it down into smaller, more manageable pieces until you reach a point where they feel achievable.

Don’t worry if your list becomes longer in the process. Smaller, clearer tasks are always easier to approach than a few vague, daunting ones. And here’s the truth: the more you check off, the more momentum you’ll build—not from force, but from clarity.

4. Group similar tasks together

Constant task-switching drains your mental energy. If you want to move through your to-do list with more ease, reduce distractions. Put your phone in another room (or at least on silent), turn off email notifications, close unnecessary tabs, and give yourself permission to focus on one thing at a time.

Once you’ve created that mental space, group similar tasks together. When you’re already in the rhythm of a particular type of work, stay with it. You’ll accomplish more with less effort than if you keep jumping between unrelated tasks.

Batching similar tasks keeps you in the flow and helps you accomplish more with less effort.

5. Acknowledge your progress

Some tasks are genuinely unpleasant. We all have things we dread doing. The tasks that feel paralyzing or exhausting. But here’s what helps: celebrating the small wins.

Cross something off your list. Enjoy a few minutes in the sun. Treat yourself to a break, a coffee, or a quiet moment. Acknowledge your effort. Celebrate the progress.

These moments reinforce momentum. Not through pressure, but through encouragement.

Your gentle path forward

You don’t have to conquer your list with force or guilt. You don’t have to “own” it or push through with sheer willpower. What you can do is approach it with intention, break it into manageable pieces, and move forward one gentle step at a time.

You’re not behind, and you’re not failing. You’re simply finding your way through, and that’s enough.

The Nourished Planner: Designed for Gentle Progress, Not Pressure

The Nourished Planner gives you the space to tackle overwhelming tasks without a rigid structure. With generous white space for brain dumping, flexible layouts, and a focus on progress over perfection, it supports clarity without pressure.

This isn’t about grinding through endless lists or shaming yourself for what didn’t get done. It’s about a planning system that reduces overwhelm and lets you approach your days with ease.

Whether you’re escaping planner anxiety, seeking a gentler approach to productivity, or simply want a tool that supports how you actually work, the Nourished Planner meets you where you are.

Ready to move through your tasks with less pressure and more clarity? Explore the Nourished Planner and discover a more compassionate approach to planning your life.