Your to-do list is suffocating your business + the better solution

Do you have a to-do list?

Most of us do.

“And why wouldn’t I?” you might be thinking to yourself, “It keeps me on track and helps me get work done.”

But a to-do list managed the wrong way can suffocate your business and killing your productivity without you even knowing it. I’ve seen it.

Here’s what I mean:

Why to-do lists are killing your business: 4 BIG problems

In my experience, there are 4 enormous problems with using a to-do list to manage your daily business tasks.

If you have your to-do list handy (either in digital form or in that notebook sitting by the side of your keyboard), take it out and take a look at it.

If your list is anything like most, it might look something like this:

  • get more sticky notes
  • finalize and send proposal for Sammy’s Sandwich Hut
  • update my portfolio page online
  • print postcards for The Surf Depot

We’ll reference the list above in my comments below.

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1. To-do lists assume each item carries equal importance

Have a look at the sample to-do list above.

Each item on the list is an important task that needs to get done.

But let’s dig a little deeper and evaluate how each task might affect your business.

If you don’t send the proposal to Sammy’s Sandwich Hut (and fast) you’re likely going to lose a potential new client.

If you don’t print the postcards for The Surf Depot, you’ll have an angry customer on your hands soon.

But if you don’t get new sticky notes soon…nothing’s really going to happen (except that you might finally give up sticky notes and find a better way to organize yourself.)

One of the biggest problems with to-do lists is they assume each item carries equal importance.

This especially becomes a problem if you use a notebook or non-digital way of organizing your to-do list since priorities change and new, more important items will inevitably arise.

Soon, you have a jumbled list of to-dos and you can’t mentally sort which is most important. Which means you’ll miss important deadlines and projects.

Read more on prioritization and productivity here:

2. To-do lists assume each item takes the same amount of time to accomplish

Have you ever asked someone how their day went and they say something like: “it was okay, but I only got one thing done on my entire to-do list.”

I have.

It’s a huge mistake. And a common error.

Because the second thing wrong with to-do lists is they assume all checkboxes take the same amount of time to complete. Let’s take a look at that sample list again.

  • get more sticky notes
  • finalize and send proposal for Sammy’s Sandwich Hut
  • update my portfolio page online
  • print postcards for The Surf Depot

What if you worked an entire 8-hour day and, by the end of it, you only checked off the first item on the list: “get more sticky notes.”

Yes, you should be disappointed in yourself. 🙂

But what if you spent the entire day researching Sammy’s Sandwich Hut, writing a proposal, making it perfect, and sending it off?

Then your day was a huge win.

But, according to your list, each one of those items was just a checkbox.

Don’t get caught up in measuring yourself by how many checkmarks you’ve made at the end of every day. Because not all checkmarks are created equal.

3. To-do lists tend to go on forever, never ending, and never feeling “finished”

How long is your to-do list? And how long have some of the same items been on that list–perpetually living there until “someday” you’ll find a way to accomplish them?

My guess: your list is long and some items have lived there longer than you’ve lived in your apartment. 🙂

That’s the problem with having a to-do list where nothing is prioritized and all checkmarks are created equal: they go on forever!

Need more sticky notes? Put it on the list.

Need to revamp your contract templates? Put it on the list.

Need to fix a typo in a client project? Yep, the list.

And because you add everything and anything to your to-do list in the spirit of being organized and productive, soon you find your list is overwhelming and hard to manage. So you stop using it.

Once again, you forget to complete some items and you miss important deadlines.

4. To-do lists become so vague and unactionable

All of those to-do items that have been sitting on your list forever have been sitting there for a reason.

They’re likely way too vague and unactionable.

Take, for example, my list from earlier:

  • get more sticky notes
  • finalize and send proposal for Sammy’s Sandwich Hut
  • update my portfolio page online
  • print postcards for The Surf Depot

Three of the items on the list are actionable and easy to complete. The third item, “update my portfolio page online,” is such a vague to-do item, it’s likely to sit there forever.

Exactly what I need to update is not clear here.

A better way to write this to-do item would be: “add the Surf Depot postcards to my online portfolio.”

See how that’s much easier to act on? I know exactly what I need to do, how long it will take, and when it is completed.

For more on boosting your productivity through precise language, check out this post:

What to use instead of to-do lists

So if the traditional to-do list isn’t the right answer, what is?

There are as many different options as there are people reading this post.

The important thing is to find a system that works well for you. But one that actually works well.

It must offer a way to prioritize to-do items over others. It’s got to let you estimate how much time each to-do item will take. And it’s got to be measurably achievable and clear.

I personally like to use Trello (which I’ve mentioned on the blog here before). I’m not an affiliate or anything like that. I just really like the app.

Here are a few reasons I use Trello instead of a notebook. You’ll notice a lot of my reasons solve the issues I’ve described around to-do lists above:

  • I can reorder to-do items by simply dragging and dropping. (Prioritization.)
  • I can break larger tasks into smaller tasks. (Time management & expectation.)
  • I can move to-do items along a path from “started” to “finished.” (Managing to-do list size & feeling a sense of completion.)
  • I can add checklists. (Measurable.)

There are tons of options out there that do the same kinds of things.

I’m super-interested in hearing what you use for your to-do list and why. Take a second and comment on this post to let me know what you use.

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About Preston D Lee

Preston is an entrepreneur, writer, podcaster, and the founder of this blog. You can contact him via twitter at @prestondlee.


  1. I concur Preston. Trello is a life saver! I generally open a board and invite my client over with the start of any project. I find this is much easier than scanning through hundreds of emails making sure I’ve addressed everything. We can collaborate right there, in one easy-to-find place!

    • @jdsimpkins:disqus: That’s a really great idea. I’ve recently been on the client end of things with some developers who use Trello and for the most part it’s been a really great process. Allows me to check in without bugging them and keeps us all on pace. Thanks!

  2. Sharon Pettis McElwee says

    instead of to-do-lists I use a calendar with deadlines. Everything has a deadline, and I work on breaking large projects into smaller tasks so I don’t open my calendar to find I haven’t even started a large project that is due on that day.

    • @sharonpettismcelwee:disqus: great idea. Thanks for sharing!

    • I do something similar with calendars/deadlines, using them to break large projects into phases that I keep as a background on my computer. I combine that with Nozbe for smaller or recurring tasks that I can easily check off if I have a minute.

    • Hi Sharon,

      That’s a great productivity hack — I use a deadline-based calendar myself, although I don’t split up larger projects into smaller, more manageable ones. Thanks for the tip!

      Also — great post, Preston! I used Trello extensively when collaborating with a couple colleagues a while ago, and I think you’d be hard-put to find a better free project/priority management tool.


  3. This post couldn’t be more timely for me. I’m the most curious about getting into Trello, especially because of its time-tracking sync with my Harvest account (speaking of time-saving apps). I’m just still trying to wrap my head around the best practices for using Trello.

    • @noahhenscheid:disqus: I didn’t know they synced! That’s really fantastic. I’d love to hear what you learn about how they work together.

      • Oh boy. It simply, works. Period. You can track time inside individual cards in Trello and tag it directly to your project>task. I can track my time in Harvest without even leaving Trello. Then on the flip side, in Harvest, those times tracked are saved as separate line items. This is important for me, because that way I’m not tempted to sluff off on my tracking notes. I can’t tell you how often I’ve gotten lazy and describe four hours of work under Web Development as “edited home page” or something super vague. By connecting the time tracked to individual cards in Trello, it automatically pulls in that text, so I can see exactly what I spent time on.

        For anyone interested, check out Harvest’s page about integrating with Trello. It’s mad simple and worth it.

  4. We’ve been using Trello for a few years now as a complete project management system for our team, and we love it. Such a great and versatile tool.

    • Joe, I agree. Changed my life a few years when I first got into it. And I’m learning better ways to use it all the time. Glad it’s been good for you guys too.

  5. I do use a to-do list, but it’s color-coded. I like having a physical list in front of me, instead of in an app – it makes it easier for me to stay on track. I use different color gel pens. Every day I chose 1-3 things that MUST be done, which are written in red. Other important but not crucial tasks can be written in orange or pink. Quick tasks in green. And I cross things off in blue when they’re completed. Low tech, but it works for me 🙂

    I do like using Trello as an editorial calendar for blogs. It’s great for keeping everyone on the same page without inundating everyone in emails.

  6. I’m a pen and paper kinda gal myself when it comes to to-do lists – Can’t leave home without my notebook! I’ve been using a system that addresses the problem of “assuming each item takes the same amount of time” which has worked really well for me: I break my to-do list into 5 MIN, 30 MIN, 1 HOUR and +++ (which means I need to heads-down-focus for a while) so that depending on how much time I have or what I want to bite off, I can work smarter.

  7. I rewrite my list every single day. This way the most pressing things get done first. If something pops up that HAS to be done in preference to anything on my list, I write it down, highlight it, get it done, cross it off. I also have a white board of current projects and where they’re up to so I can keep track of longer term projects

    • @Inkandescent:disqus: thanks for sharing your process. I’m curious: how do you handle more long-term projects with multiple to-do items?

      • The main ‘to do’ points go on the white board under the main projects and get crossed off as they get done. The current ‘to do’ for each large project goes onto my daily list. I’ll usually break these down into acheivable goals for the day too, so at the end I’ve got 15 things checked off and celebrate the end of another successful day!

  8. Kylie Burgener says

    On the flip side, sometimes project management software creates more “busy work” than is really necessary and takes way too much time to manage. I’ve been in 3 different companies who used 3 different management software options, and every one of them was ultimately phased out because it was taking too much time to manage. As an individual though, I think a lot of those management solutions make sense.

    • Ky,
      I completely agree with you. I’ve had the same thing happen to me. For me (and Millo) the key is to not let the system become more important than the work. It’s not easy, for sure. Thanks for sharing. All the best to you and the fam. 🙂

    • Ky,
      I completely agree with you. I’ve had the same thing happen to me. For me (and Millo) the key is to not let the system become more important than the work. It’s not easy, for sure. Thanks for sharing. All the best to you and the fam. 🙂

  9. Debbie Campbell says

    I use Trello for managing projects and love it. I use Todoist for my to-do list and I chose it because it has (some) color coding and I can set up a list for each client, personal, learning, etc. But it never gets empty, I can’t see progress that I’m making and some days it’s overwhelming to look at it in the morning.

    I did move the long term goal-related tasks out of Todoist and into a board in Trello a few weeks ago to get rid of some things that had been hanging around on Todoist forever.

    I might try making a Trello board for more immediate things (Today, or This Week) and see if that works better than the never-ending lists on Todoist. Thanks for the ideas!

    • @disqus_3bHytDQZGI:disqus: If you’re really interested in using Trello for long-term AND short-term to-do lists, take a minute and look up the “Scrum method” of project management. It’s how I do things personally and a bit like we do them at Millo. Helps break down big projects into small tasks, but keeps them all in the same place. Good luck! Thanks for sharing!


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