Why Your To-Do List is Failing You (And What to Do Instead)

How to stop spinning your wheels, get everything in one place, and finally build a system that works for your brain.

Photo by Kari Shea on Unsplash

Back in the nineties, my first mentor and boss, Kai Romanchak, promoted me to director of technology and training for a large travel agency in Dallas. Along with the title, she handed me what I can only describe as the most beautiful planner I had ever seen—thick, crisp pages, perfectly structured layouts, the kind of tool that practically oozed efficiency. Kai swore by it, and she expected all her director-level hires to use it.

Fun fact: I found that same planner last week while cleaning out a closet. And let me tell you—Baby Chelle was a baddie.

Kai was the kind of person who just had her life together, and I was determined to follow in her footsteps. She also wrote exclusively with blue felt-tip pens, so naturally, I did too—trying my best to be her mini-me. And honestly? I still write with blue felt pens. Some habits just stick.

For a while, that planner was everything. It organized my days, kept my deadlines straight, and made me feel like a Real Adult™. But, as with most planners, it eventually failed me. Or, more accurately—I failed it. I had kids.

Suddenly, the planner didn’t fit into a diaper bag, which meant I stopped carrying it everywhere. And the minute I stopped using it for everything, it became good for nothing. Appointments were scattered between sticky notes, mental lists, and frantic texts to myself. Half my tasks lived in my head, the other half on scraps of paper that may or may not have ended up in the wash.

Two big lessons hit me fast:

Your processes have to adapt over time. The system that worked for me in one phase of my life was useless when my entire schedule changed. For me, that shift happened when I had kids—but you don’t have to be a parent to have that experience. Maybe you started a new job, took on a big project, moved, had a health change, or just found yourself juggling more than you used to. Whatever the reason, life throws curveballs, and when your system doesn’t adapt, it stops working.

And here’s the second hard truth: you need to have everything in one place. The minute your tasks get spread across too many places, things will get missed. And that defeats the entire purpose of having a system in the first place.

So that’s where we’re starting: getting everything in one place.

Why Most To-Do Lists Don’t Actually Work

We’ve all been there—staring at a to-do list that somehow manages to be both overwhelming and completely unhelpful. Instead of feeling prepared, you feel paralyzed. And if you’re like most people, that’s when the classic cycle begins:

• Step 1: Make a fresh to-do list. This time, it’s definitely going to work.

• Step 2: Get a quick dopamine hit from crossing off something easy, like “drink coffee.”

• Step 3: Realize half the tasks on the list are too vague, too big, or already outdated.

• Step 4: Ditch the list, wing it, and promise yourself you’ll start fresh tomorrow.

Sound familiar? That’s because most to-do lists aren’t built for the way our brains actually work.

The problem isn’t that you’re lazy, unmotivated, or bad at productivity. The problem is that traditional to-do lists rely on discipline when they should be built on systems.

Where To-Do Lists Go Wrong

1. They’re too long.
   A mile-long list isn’t motivating—it’s exhausting. Instead of getting things done, you waste energy deciding where to start.

2. They don’t prioritize.
   Checking off “buy cat litter” feels productive, but it doesn’t move your big goals forward. Your most important work gets lost between grocery lists and admin tasks.

3. They assume all tasks require the same energy.
   Writing a chapter and sending an email are not the same. To-do lists don’t account for energy levels, focus windows, or how long things actually take.

4. They don’t adapt when life changes.
   What worked for you last month might be useless today. A rigid list doesn’t adjust—it just leaves you feeling behind.

What Actually Works: Task & Time Management Systems That Don’t Set You Up to Fail

If traditional to-do lists don’t work, what does? Instead of relying on a never-ending checklist that doesn’t adapt, the key is to use systems that fit how you naturally work.

The goal here isn’t just to get things done—it’s to create a workflow that makes doing the work easier. That means focusing on habit-building, time structuring, and prioritization techniques that keep you moving forward without feeling overwhelmed.

You might find that one system works perfectly for you, or you might be like me—pulling pieces from different frameworks to build something that actually sticks. Personally, I use all four of these:

1. Atomic Habits & Habit Stacking (James Clear’s approach)

Most people set goals like, “I’m going to write 2,000 words a day!” and then get frustrated when life inevitably gets in the way. The problem? Goals are outcomes—but what you actually need is a system.

• Instead of saying, “I’m going to write every day,” build a habit trigger: “Every morning after I make coffee, I open my manuscript.”

• Start so small you can’t fail. If you don’t feel like writing, just open the document. That’s it.

• Habits compound. Small wins turn into consistent action.

📌 Think of this as training your brain to do the thing automatically, without relying on motivation.

2. The 5-Second Rule (Mel Robbins' method for instant motivation)

Ever sat there, knowing exactly what you need to do, but feeling zero motivation to do it? That’s where The 5-Second Rule comes in.

• The moment you feel resistance, count down from 5: 5-4-3-2-1, GO.

• Your brain won’t have time to argue. The second you hit “GO,” move—open the laptop, stand up, start typing.

• Motivation follows action, not the other way around.

📌 This works for everything—writing, working out, making difficult calls. Don’t wait to “feel ready.” Just start moving.

3. Maker vs. Manager Time Blocking

Indie authors aren’t just writers—we’re publishers, marketers, and business owners. That means our time has to be split between two completely different kinds of work. As my friend Tony Lee put it, indies are publishers who write, not writers who publish—which means we have to think like business owners when it comes to structuring our time.

• Maker Time → Deep, creative work (writing, editing, outlining). This requires focus and should be scheduled in long, uninterrupted blocks.

• Manager Time → Admin tasks (emails, social media, marketing, bookkeeping). These don’t require deep focus and should be done in smaller, structured time slots.

The mistake most authors make? Mixing these two types of work. You start the morning planning a social media post, check your email, and suddenly, your writing time is gone.

📌 Pro tip: Schedule Maker Time when your brain is naturally primed for deep work. Instead of assuming it has to be first thing in the morning, use Ultradian Rhythms to figure out when you’re most focused. Energy naturally cycles in 90-minute waves—some people hit their peak early, others in the afternoon. The key is knowing when your brain is at its best and protecting that time for writing. (More on that here if you're curious.)

4. The 2-Minute Rule (David Allen’s Getting Things Done Method)

One of the biggest reasons tasks pile up is because we let tiny things linger on our to-do list. The 2-minute rule solves that:

• If a task takes less than 2 minutes, do it immediately.

• If it takes more than 2 minutes, schedule it or automate it.

This keeps your task list from filling up with tiny things that could have been handled in seconds.

📌 Want to dive deeper into these productivity frameworks? If you’ve never heard of these, or if you want a simple breakdown of how they actually work, we created book club summaries on IndieAuthorTraining.com. They’re free, and I walk through how I pulled from each of these methods in plain, no-fluff language—so you can start using them without reading a 300-page book first.

The Starting Guide to Braindumps: We Can’t Plan for What We Don’t Know

Before you can create a system that actually works, you need to see the full picture. That means getting everything—literally everything—out of your head and onto paper (or a screen). Enter: the braindump.

A braindump is exactly what it sounds like:

• Every task, idea, deadline, commitment, worry—all of it—goes into one place.

• No structure. No overthinking. Just dump it all out so you can see what you’re actually dealing with.

Most people skip this step and jump straight to organizing—but you can’t organize what you don’t fully see. If you’ve ever had that nagging feeling that you’re forgetting something, this is why. Your brain is holding onto too much at once.

And if you’ve ever wondered where to start automating, this is it. If you’ve heard me speak, you’ve probably heard me talk about the "suck list"—aka, automate all the things that suck. Well, this is how you get there. This is the pre-suck list. Before you can delegate, streamline, or automate anything, you need to see what’s actually taking up your time.

How to Do a Braindump

1. Pick a capture tool – This can be as simple as a Google Doc, a notebook, or a Google Sheet. (Personally, I love using a digital doc because I can copy/paste later.)

2. Write down EVERYTHING – No categories, no structure—just dump it all out. Work tasks, life tasks, half-finished projects, random ideas that pop into your head.

3. Set a timer (optional) – If your brain resists, give yourself 10–15 minutes and see what spills out.

4. Come back to it – More will pop into your head over the next day or two. Keep adding.

Once it’s all out, then we can start organizing and then automating.

Laying the Foundation: Capturing Everything Before Choosing a System

Right now, the best workflow system for me is Notion and Notion Calendar, and I use Thomas Frank’s Ultimate Brain (affiliate link). It works for my neurospicy brain because it’s everywhere—I can access it on my Apple Watch, iPhone, MacBook Pro, iMac, and Mac Mini. (Yes, I have a lot of devices, but when you travel as much as I do and have a satellite office in Austin and a home office in the Hill Country, you need seamless access to everything.)

But I *also* work with companies and projects that use Basecamp, FluentBoards, and Todoist. And they assign me tasks.

Since I’m constantly bouncing between companies and locations, Notion keeps everything in sync, no matter where I am. But here’s the thing—the tool itself isn’t the point. What matters is having one place where everything lives.

Next week, we’ll start to decide what system will work best for you. I know you want to dive right in, but before we start choosing the right system for you, we need to make sure you know what you’re managing in the first place. That’s why we’re starting with the braindump.

Your Action Step This Week

This week, your only job is to braindump:

✅ Get everything out of your head and into one place (Google Doc, Notion, paper, whatever works).
✅ No organizing. No color-coding. Just dump it all out—work tasks, life stuff, random ideas.
✅ Set a 10-minute timer if it helps. Then come back later and add more.

Next week, we’ll take that messy list and start making sense of it—choosing a task management system, considering calendars, if and where where paper fits in, and figuring out how to actually make this work for you.

For now? Just start capturing. I always start with a Google Sheet.

🔥 What’s the weirdest or most random thing that popped into your braindump? Hit reply and tell me—I love knowing what’s rattling around in people’s brains.