time management

5 Reasons Why Your To-Do List Isn’t Working

May 4, 2020

Reading Time: 6 minutes

5 Reasons Why Your To-Do List Isn’t Working

Ah, the to-do list. An inescapable part of managing work, life and finding some sort of balance. In this episode, I’m sharing 5 reasons why your trusty to-do list might now be serving you so well after all, but don’t worry – I’ve got some tips for exactly what you can do to get it working for you so you can start ending your day feeling accomplished.






Ah, the to-do list. An inescapable part of managing work, living life and finding some sort of balance.

In this episode, I’m sharing 5 reasons why your trusty to-do list might not be serving you so well after all, but don’t worry – you know I’ve got some tips ready with exactly what you can do to get it working, so you can start ending your day feeling accomplished.

You know that feeling when you cross the last item off your list. You smile and fist pump in the air and music plays – everyone starts cheering for you – the crowd goes wild! and then someone hands you a glass of champagne, a trophy and a gift certificate to a spa!

Ok – so maybe that doesn’t actually happen, but GOSH DARNIT IT SHOULD!

If you’re reading these shownotes, I’m going to go out on a limb and guess that you’ve written a to-do list before.

But how often have you found yourself  totally frustrated at the end of the day – whether the end of your workday, or the day in general – with a whole bunch of unchecked stuff just staring at you. Taunting you. Weighing down your tomorrow that hasn’t even started yet.

It’s not uncommon to feel like a total failure, like you’ll never finish and get to rest. It feels a nonstop hamster wheel of never ending stuff, all of it begging for your precious time and attention.

If you’re a to-do list junkie but you’re not getting that satisfaction at the end of the day that comes with crossing all of your items of the list – you’re in for a treat.

Let’s dive right in!

MISTAKE #1: You have TOO MANY lists.

When you write down whatever you think of on the scrap of paper that just happens to be closest to you in that moment – you’re not actually making a to-do list, you’re making a to-do…. Mess. Scattered, fragmented, and all over the place.

SOLUTION: Give your brain a break by simplifying. Try to narrow it down to two, and only two places where your to-do’s live. One high tech, and one low-tech. My high tech spot is Trello. My low tech tool is my Simplified Planner. Whatever you decide to use, BE CONSISTENT.

MISTAKE #2: You don’t have a list AT ALL.

David Allen, author and creator of the Getting Things Done system, famously said “Your mind is for having ideas, not holding them.”

And he’s right, the more we try to hang onto things in our heads, the less free space we have available for making good decisions, for thinking creatively and other important brain functions.

SOLUTION: if your to-do list is living in your head, give your brain a break. Choose your high tech spot and your low tech spot, and see if you feel a difference in your mental clarity.

 MISTAKE #3: Your list is TOO LONG.

A too-long to-do list is not serving you for two reasons

  1. It makes you feel like crap at the end of the day when there’s still a ton of stuff left on it. You end the day defeated, and you start the next day already feeling overwhelmed. Well, THAT’S NO FUN.

  2. There’s a huge possibility that you’re filling it with things that you don’t actually need to do today, or things that could be automated – like with a routine or technology, delegated, or eliminated all together. But I’ll save that can of worms for another episode. 

SOLUTION: Keep a master list of ALLLLLLL the things. This could live digitally, like in Trello, or in a notebook, or even “notes” pages in your planner.. That way, instead of keeping ALLLLLLL the things in your head, they have a place to live. Then – instead of looking at everything on the whole list at once – which can get overwhelming, you scan the list and pull JUST the things for today.

BUT! How do you know what to pull from the Master List onto the smaller, more manageable “today” list?

  1. Scan your calendar: Take a look at how much available time you actually have. What meetings are scheduled? What windows are available to do the things on your list?

  2. Take a guess: Estimate how much time something on your list is going to take. And then consider adding 30 minutes, because we almost always underestimate how long something is going to take. You can even go the extra mile and decide when on your calendar you’ll do each thing, and create appointments in your digital calendar, or draw time blocks in your planner.

A shorter, but intentionally planned to-do list that’s based in reality, not a dream world where time is endless and everything only takes 5 minutes – is key to ending your day feeling accomplished.

MISTAKE #4: Your list is TOO SHORT.

Chances are, a too-short list is a list full of projects instead of tasks or action items. Let’s talk about the difference real quick.

A project is something that has more than one step.

  • Planning a birthday party.

  • Pitching podcast appearances.

  • Prepping for a board meeting.

You get the idea. All of those things are projects because it takes more than one step to accomplish, or finish them.

A task or an action item is one and done. It’s just one step.

  • Cancel dentist appointment.

  • Write podcast pitch

  • Print board meeting agendas

So when your list is short, but full of projects, you’re not seeing the whole picture – and once again, you’re letting those action items that make up each project live in your head instead of on paper.

SOLUTION: Write out every step or action item required to complete the project. Let all the steps live in a notebook, or in a digital tool like Trello. Then, pull JUST the action item that you can complete today and put it on today’s list.

MISTAKE #5: Your list not ACTIONABLE. There are no verbs.

For example. Imagine a to-do list that says this:

  • Dentist appointment

  • Car

  • Babysitter

Do your to-do lists look like that? A collection of nouns?

A to-do list that’s just a collection of nouns is almost as bad as no list at all, because once again, you’re keeping the details in your head. And like our friend David Allen says, Your mind is a place to have ideas, not hold them.

Here’s what I mean. Instead of this, try this:

  • Dentist appointment >>> Cancel dentist appointment

  • Car >>> Schedule car maintenance

  • Babysitter >>> Call Marie and ask her to babysit on Thursday night


If you’re just starting with whatever is at the top of the list and you’re working your way from top to bottom, you could be sabotaging your productivity.




SOLUTION: Always take a moment to scan your list, identify which items are most important to your goals – whether those are personal or professional goals.

You don’t have to make a list, and then rewrite it in your new prioritized order. Just pop a little number next to each item.

If i’m handwriting a to-do list, I like to write a little box next to each one (for something to check off) and when I run through to prioritize, I’ll write a number in the little box. Easy peasy.


Where does your to-do list live? Are you a notepad kinda list maker? Or are you high-tech all the way with something like Trello, Asana or something else altogether.

I’ve love to hear all about what works for you – or if there’s something I missed in this episode. Keep me in line!

Come join us in the It’s About Time Podcast community and tell me!


If you’re enjoying It’s About Time so far, I hope you’ll take a moment to subscribe if you haven’t yet – I don’t want you to miss an episode! I’ve got a few bonus episodes in the works, and you might miss them if you’re not subscribed. Click here to subscribe on iTunes.

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with anna dearmon kornick

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