I have a love-hate relationship with to-do lists.

One one hand, they’re magical. You know how sometimes, when your purse gets too full, you end up just dumping everything out on the bed? As you wade through gum wrappers, crumbled receipts, and broken tubes of lipstick, you can clearly see what you can throw away and what you can take with you. To-do list have the same effect on my brain – I can dump everything out and organize it neatly on paper!

On the other hand…to-do list are evil. Well not really, but they can feel that way! Don’t you hate having a ton of “unchecked” items left on your to-do list at the end of the day? If you let it, to-do lists can make you feel like a failure, which can kill your motivation as you try to get things done everyday.

While I’ll never give up list making because — well duh, I’m completely a Type-A personality — I have given up on all the mistakes I used to make that made keeping a to-do list such a pain.

Are you suffering from “unfinished-to-do-list-itis”? I present to you…

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

Reason #1: You Put Too Much On Your List! I hate to break it to you, but there are only 24 hours in a day. You’ll be sleeping for 6-8 of them, eating for 3 of them, and if you have a standard 9-5 job, working for 8 of them. That means, on an average weekday, you truly only have 5-7 hours to play with. If you have kids and a family to manage after work, then that number is even less.

Don’t despair though! I point this out not to depress you but to show you that you aren’t a failure, you’ve just been putting more on your plate than is humanly possible for you to do. So how’s a girl supposed to get it all done? Firstly, get realistic and stop putting so much on your to-do list and secondly…

Reason #2: You Don’t Know Your Priorities. You must determine your priorities. Why? Because everything is not a priority. I know it feels like everything is a priority but truth be told, the majority of things on the average person’s to-do list don’t have to be done right away. Many times, we confuse a brainstorming list with our to-do list; we end up writing down everything in the world we’d like to do, then we label it our “to-do list” and expect to get it all done in one day.

Uh uh.

Talk about a recipe for failure! The question I ask myself every morning that has literally changed my life is “What are the top three things I can do to make the most progress toward what I want in life? Of those three, which ONE is the most important?” Notice the criteria for this question: the tasks have to be (1) things I CAN do (not “should” do, or “could” do, or “waiting to” do), (2) they have to help me make the MOST progress, and (3) they have to help me make the most progress toward WHAT I WANT in life!

This is how you set priorities!

1. Decide what you want
2. Determine what will get you the closest to what you want
3. Do it first thing in the day before anything else has a chance to distract you.

People will put all kind of stuff on you if you let them but only you are in control of your day. Work on your own priorities first and let everything (and everyone) else “get in where they fit in”.

Reason #3: You Underestimate How Long It Will Take. This is the underlying reason why we overload our to-do lists (see #1) — we don’t know how long things take. We typically only have 5 or so usable hours in a day, remember? Every time you go to write something on your to-do list, ask yourself how long the task you’re committing to is going to take. Better yet, write it in your calendar to gauge whether or not you really have the time. If it’s important, move other things around on your schedule to make room for it. And if it’s not that important…come back to it when you have time.

Side note: Lately I’ve talked a lot on the blog about how the key to self-discipline is training yourself to do what you say you will do. When you consistently don’t follow through on the commitments you make to yourself, you build the habit of being a promise breaker, which undermines your confidence and makes it difficult to be a self-disciplined person down the road. Treat everything you put on your to-do list as a promise to yourself, meaning, don’t put it on there unless you are reasonably confident you can complete it. This will force you to prioritize (see #2) and be more selective about the tasks you undertake, which is the whole point. Okay, carry-on…

Reason #4: You’re Trying to be Perfect. Ah, that good ol’ enemy of progress: perfectionism. I know this productivity villain quite well. How many times have you put off doing something because either (1) you weren’t sure you could do it perfectly or (2) you weren’t in the perfect mood or environment? I’m going to tell you what a wise woman (hey Auntie!) told me: “You and your conditions will never be perfect. If you want to do something, the perfect time to do it is now.”

Ouch, right? Yeah, it stung when I first heard it too. But it’s the truth! Let go of perfection because, this side of Heaven, perfection doesn’t exist. So you might as well do what other mortal yet insanely productive humans have done and train yourself to “do it now”. Your future self will thank you.

Reason #5: You’ve Forgotten Your “Why”. This is the biggest reason why we experience to-do list failure. If we can’t see what life goal each item on our to-do list is connected to, then we lose motivation. Before you write down anything on your to-do list, ask yourself “What do I want?” and ‘How is this task going to get me closer to it?” Then, as you start to work on each item on your to-do list, take a second to reconnect with WHY you need to do this and how this is going to positively impact your life.

Yesterday, I was emailing back and forth with a client I’m coaching to help improve her time management and she asked how I was able to stay on task and remain focused. I shared a story about how, back when I was still learning how to be productive, I committed to working out for 30 days to a Jillian Michaels DVD because, at the time, that’s the most intense workout I could do because I wasn’t exercising regularly. I also wanted to become a fit person because I believed if I could train myself to workout everyday, it would build my “self-discipline muscles” and spill into other areas of my life. I wrote:

I found one thing I could do – workout for 20 minutes to a Jillian Michaels DVD – and I invested ALL my energy into doing that for 30 days straight. It sounds kind of ridiculous, but at the time, committing to that DVD for 30 days was not just about exercise. It was about me taking back control of my life and as such, I treated that commitment very seriously. I knew it was the gateway to the self-discipline I desired. So I worked out to that Jillian Michaels DVD like my life depended on it because, really, it did.

If you really want to your to-do list to be authentic and powerful, you need to be able to connect each task on your list to a higher outcome for yourself. As I stated above, my daily to-do of working out was not really about the exercise — it was about planting the seeds of self-discipline so that I could change my life!

Are the tasks on your to-do list connected to something with greater meaning for you? If not, that’s probably why you lack motivation to get through your to-do list everyday. Everything you do should be connected your big “why”.

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Hopefully the above 5 lessons will help you make the most out of your to-do list today! Here’s some other great resources to help you stay productive:

Book: Eat That Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time

Book: The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results

Blog Post + Free Worksheet: How to Motivate Yourself Out of a Rut

Talk to Me:

Do you struggle with to-do lists? What’s your process for getting things done? Leave me a comment and let me know!

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