Why Your To-Do List is Overwhelming

Whenever I discuss time management issues with my clients, sooner or later, we always get to their to-do list. They feel overwhelmed, they don’t know where to begin, and they never know how to prioritize when their to-do list has become “a mile long.”

Barn - A Project is not a to do list item

I’ll never forget the day I was working with Vic on his to-do list. Part of his career plan was moving from his farm back to the city. But as he thought about getting his farm ready to sell, his to-do list was so daunting that it had him almost paralyzed.

During one of our calls, I asked him to read his to-do list to me. He began: “I have to sell the tractors, fix the fence, paint the barn…”

“Whoa. Stop there.” I interrupted him. “Did you just say paint the barn?”

No wonder Vic’s list seemed overwhelming! “Paint the barn” is not an item for a to-do list, it’s actually a great big project all by itself.

And here’s where we tend to mess up our to-do lists: to-do lists should never contain projects, only detailed tasks.

A To-Do List Template

Each item on a proper to-do list should include three things:

  1. Priority Level (1, 2, or 3 is usually enough),
  2. The detailed task, and
  3. The amount of time it will take to complete it.

To Do List Template

The key word in all this is “Detailed.” A detailed task means it is a specific item that can be done in one block of time. Large, multi-step projects have no business on your to-do list; they first need to be broken down into detailed tasks.

So the detailed task list for our project might look something like this:

Paint the Barn:

  1. Rent a power washer
  2. Power wash the barn
  3. Measure the barn
  4. Assess barn for damaged wood
  5. Buy wood and nails
  6. Rent scaffolding
  7. Repair damaged wood
  8. Buy paint supplies and paint
  9. Prime the barn
  10. Put the paint on the barn!

Once Vic and I walked through his detailed task list, he was able to prioritize the order of completing each task. Then, he estimated how long he thought each task would take. Finally, he decided how many hours per week he planned to work on this project and was able to start deciding what days he was going to do which tasks.

Breaking big projects apart like this on paper (or on a computer/tablet/phone app) is critical to getting a handle on it, which in turn allows you to get started! If it’s Friday afternoon, you know you can’t paint the barn today. But maybe you can rent the power washer on the way home from work. Progress!

Relating this to Your Business

I love using this example, because “Paint the Barn” is such a great visual that anyone can instantly grasp (even though most of us have never painted a barn!), but it works the exact same way in your business. I often see projects on my clients’ to-do lists, when those projects should really be broken down into tasks first.

For example, when a salesperson reaches the point where they need some help, they might put “hire an assistant” on their to-do list. This is really a project that might be broken down to: determine duties, write a job description, create an on-line job posting, interview applicants, and so on.

Now that we’ve determined what goes on your to-do list, here’s how to tackle it:

Five tips for creating an effective to-do list

  1. Start your day by asking yourself, “In order for me to feel productive today, what do I need to complete?” Make sure those big-ticket items are at the top of your list.
  2. Create a NEW to-do list every day. Transfer any open items from your last list to your new list. If it’s important, you’ll complete it; if it’s not, you’ll stop transferring it to your next list. Note: Throw your old lists away! It drives me nuts to see stacks (or notebooks full) of old, un-organized lists. If you think you might need it someday, take a picture and then toss it (There. Rant over!).
  3. Every time you add an item to your to list, add the priority and the estimated time needed. This will help your decision making as you process your list.
  4. Whenever you can, take tasks off your to-do list and schedule them on your calendar instead. Larger tasks (more than a couple of hours) especially need to have dedicated time on your calendar.
  5. End your day by asking yourself, “What could I have done to be more productive?” Then work on changing that tomorrow.

Do you have a “Paint the Barn” item that’s been lingering on your to-do list for a long time? Break it down into manageable chunks and follow my guidelines above. You’ll get more done, your days will become easier, and your stress level will fall.

Guess what? Vic painted that barn, sold the farm and moved back to the city!

Until next time—go sell some stuff!


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