I'm a Digital CEO, Help Me!

A series focused on navigating the creator economy, claiming the Digital CEO title, and answering your biggest business questions.
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Your Question: Why is my to-do list lying to me (and how to unf*ck it)?

Time Is Money, My Bébés

🗝️ Respecting Your Time and Energy
🗝️ Knowing Why You’re Doing What You’re Doing
🗝️ It All Comes Back to Scalability
🗝️ Embracing the Big Picture

‍Let’s have a little heart-to-heart, Digital CEO to Digital CEO.

If your to-do list is like mine, it can get longer than your toddler’s bedtime routine (and just as chaotic) if you don’t keep an eye on it. I long for the ease of the set-it-and-forget-it mentality in all aspects of my life—but bedtime routines and needle-movers for my business are two places that the dude cannot abide by that approach.

Unf*cking your to-do list is a tricky task because it’s so easy to misidentify the real root issue. But I’m here to let you know some things with certainty:

You’re not lazy. You’re not behind. You’re not bad at business.

My suspicion? You just haven’t been taught how to get your brain and your business systems collaborating. Yet.

That’s where we’re headed today.

If you feel like you’re constantly scribbling tasks, checking boxes, and still ending the day wondering what the heck you actually accomplished, your to-do list might be lying to you. It’s not telling you the whole story.

We can fix that! With structure, not shame.

‍This post is part of my “I’m a Digital CEO, Help Me!” series, where we strip the fluff out of online business advice and give you practical tools to run your business with more clarity, less burnout, and way more alignment.
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TO-DO LISTS DON’T RESPECT YOUR TIME OR ENERGY

Here’s the real problem with to-do lists: they’re a catch-all for every random task that pops into your brain. So if your brain is anything like mine, this means they’re often out of order, lack context, and don’t show how your work actually supports your goals.

And when that happens, you end up:

• Working on urgent tasks instead of important ones
• Dropping balls or duplicating effort
• Spending more time organizing the list than executing it

So how did I fix mine? By incorporating my oh-sh*t list to-do list into my greater task management system. Specifically, one that supports how my wild-west-brain works.

Most to-do lists treat your brain like a machine that can perform the same way every day. But you and I both know that our energy shifts by the hour.

One of the reasons I love systemizing my to-do list is because it allows me to organize tasks by priority, timeline, and context. I can:

• Batch low-energy tasks (like admin or commenting on posts)
• Block out time for deep work (like client strategy calls or writing copy)
• Plan buffer weeks for when life inevitably explodes

This means that on a high-energy day, I can see everything that needs to be done in my entire business and decide exactly what’s worth pouring into. What will move the needle the most and capitalize on that rare burst of energy?

And on a lower-energy day, I can still move something forward without burning out (hello low-hanging fruit!).
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TO-DO LISTS DON’T SHOW YOU WHY YOU’RE DOING WHAT YOU’RE DOING

Basic pen-and-paper to-do lists are often a reaction to the day. Emails you got, client feedback, a sticky note that fell out of your purse. We’ve all been there.

Yes, it feels good to check off tasks from that rat’s nest of word vomit on the page (if you actually get to check things off). But systems-first thinking is designed to flip that on its head while still letting you achieve that pile of in-the-moment brain dumpage.

My tool of choice is Asana because it organizes my business into repeatable rhythms and lets me prioritize with clarity. Instead of starting with tasks, I start with projects and outcomes.

Let’s walk through how I use it as the backbone of my digital business.

In Asana, every major part of my business has ONE home. Yes, you read that correctly. The five key operational categories that make up my business—which we cover in detail inside Scale-Ready Systems—all live inside that one home hub. And all of the tasks related to them live inside that hub, not on their own.

Do I still take notes the analog way? Of course, I’m from the 1900s. It’s a habit I have tried to break and simply cannot. So instead, I’ve taken that knowledge of myself and adapted it into my system.

When I have an A-ha! Moment that simply must be documented, I have two options:

• Open Asana immediately and document it there, whether I’m on my computer or my phone. Gosh, wouldn’t it be nice if I was disciplined enough to pick this option every time?
• Scribble the reminder in a notebook, on a sticky note, across the back of a piece of junk mail—whatever’s available at the time—and then add it into Asana when I have a second to breathe.
  

Option number two is extra steps, yes. But it also meets me where I’m at in my life. And that place is constantly buying new pens and notebooks and other miscellaneous stationery, thinking it will somehow cure me of my ADHD.

Just because it doesn’t cure me doesn’t mean I don’t use it 🤷

Whether I get that task into Asana in the moment, or later that same day, I know exactly where it’s meant to go because I already have a home for it.

FOR EXAMPLE
Instead of a sticky note that just says “write blog post” (inspired, I know!) that lives on the bottom of my computer monitor for six weeks, I will…

• Write it down wherever I’m making notes that day.
• Go to Asana when I get back to my computer.
• Go to the permanent Asana project I have called “Copy & Conjure”.
• Go to the permanent section I have in that project called “Marketing”
• Create a new task called “Blog Post: My To-Do List Sucks”
• Brain dump anything associated with that task in the description section
• Set a due date for the next business day, so that it doesn’t get lost in the nether. This is a flexible date that I can reassign as needed, but putting something in that section is so important.

Now I’m not just writing a blog—I’m moving my content strategy forward. If I feel like I need to write another blog post and I don’t have a specific topic in mind, I’ll just put a general category. Something. Anything. Like “Blog Post: Copywriting” to give myself at least an idea of where to get started.

TO-DO LISTS DON’T SCALE—BUT SYSTEMS DO

To-do lists are one-person tools. Which is great, because you’re a one-person business. Until you’re not.

Suddenly you have clients, collaborators, a team—and you’re behind the gun because you waited until you were already scaling to bring systems into the mix.

Oops.

If this sounds familiar, it’s because I lived this reality as well. So my advice comes from a place of please-dear-god-learn-from-my-mistakes.

Once I started treating my systems—specifically Asana, in this case—as my external business brain, it became the easiest way to hand off work, track progress, and make sure nothing fell through the cracks.

I don’t have to keep everything in my head, which is great news because that’s, like, the least reliable place I can think to put anything.

I have Asana integrated with the other core systems of my tech stack, and use them together to:

• Onboard and manage client projects
• Track deliverables by due date
• Assign recurring tasks (even if it’s to myself!)
• Share SOPs, templates, and timelines
• Prep my business for the next stage, so it’s ready whenever I am

The result? I don’t have to be the glue holding everything together. The system is. And when you’re trying to scale with your sanity intact, that’s priceless.

It gives me the peace of mind to know that I can take a vacation, or a mental health day, or maternity leave, and my business won’t collapse from the inside out just because I wasn’t there.

TO-DO LISTS DON’T SHOW YOU THE BIG PICTURE

Ever get to the end of the week and feel like you were busy but not productive? That’s a red flag that your work isn’t being filtered through strategy.

One of my favorite recurring tasks in Asana is my weekly CEO hour. This is an every-Monday check-in that I’ve set to review wins, financials, active projects, and next priorities. It’s this time in my business that makes me feel like a real business owner rather than a freelancing friend shrimp (fellow computer-hunchers, IYKYK).

This creates a natural feedback loop: I’m not just doing tasks, I’m evaluating and adjusting. And when you take advantage of systemizing your to-do list and incorporating it into the greater day-to-day operations of your business, then your system should readily show you:

• what’s working,
• what needs to change,
• where your energy is being wasted, and
• where your energy is best spent next.

Your to-do list doesn’t know how to do that. But a system built with intention? That’s where your next level lives.
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WHERE WE GO FROM HERE

Your to-do list isn’t the enemy. It’s just incomplete.

It’s a sketch, not the blueprint.

‍And when you build a system that honors how your brain works, aligns with your goals, and evolves with your business, that’s when everything starts clicking.

You stop running in circles and start moving with clarity.

And if you’re ready to build that system from the ground up? I’ve got something for you.
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TL;DR: WHY YOUR TO-DO LIST IS LYING TO YOU

• Traditional to-do lists are disorganized and disconnected from strategy
• Systems, like Asana, help turn your list into part of a structured, goal-oriented system
• Prioritizing by energy, context, and goals leads to better productivity and less burnout
• Systems scale—sticky notes don’t
• A real system helps you evaluate, not just execute

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READY TO SYSTEMIZE YOUR BUSINESS?

If this post lit a fire under you, but you're still not sure where to start—my MBA Foundations Checklist is the next best step.

It’s a free resource that walks you through the foundational systems, strategies, and storytelling your business needs to scale sustainably.

Whether you’re DIY-ing it for now or planning to hire support soon, this checklist will help you get your house in order.

👉🏻 Grab the MBA Foundations Checklist 👈🏻

You don’t need to hustle harder. You need systems that work for you.

‍Let’s build them together!