Is Your To-Do List Mocking You?

by Joan Garry

Every time you look at the to-do list they are there. Right where you want them. At the bottom of the list. How can you ever get them done?

Cindy Pereira basically runs my business.

She also produces my podcast and entertains me all day long. And I’m really lucky. I know it.

To know Cindy is to know that she is ambitious, and she gets more done in a day than any human I know.

But there are still things she just doesn’t get to.

One day I’m at her desk and a reminder pops up on her screen. Just two words:

Write novel.

I was weak with laughter. She returns to the office and I can’t even talk, I’m laughing so hard. I point to the reminder. She says, “Oh yeah, I have had that daily reminder for like years.”

Today I am not going to talk about your big hairy audacious aspiration and how to get it done.

I want to talk about those things on your to-do list that just keep showing up. They have been there for what feels like years. They never make it to the top of the list. You’re not putting them off because they are super hard, like “Call angry donor”.

These are regular things you are supposed to do. Every time you look at the to-do list they are there. Right where you want them.

At the bottom of the list.

For me, it’s “Update Database Contacts”. I see it on the list and I swear it’s staring back at me, judging me. I try to ignore it.

You know what I’m talking about, don’t you?

If I asked you if they were important, you’d say “Yes, BUT”. Yes, BUT I first need to focus on the IMPORTANT stuff higher up on the to-do list. And it happens again tomorrow. And the day after. The week after. The YEAR after.

Is there a way out? You can’t just take it off the list. You can’t really delegate it either. The task matters and you’re the one who has to do it.

Can you imagine how amazing it will feel to be able to cross one of these off?

I have some advice. I have conquered one of these beasts recently – cleaning up my contact database – and I believe my recipe could really help you.



It comes down to two big reasons:

  • The tasks don’t feel urgent
  • They feel really big

Am I right or am I right? Figuring out WHY you don’t get to them might offer you some insights on how to tackle them.

It did for me.

And so here are the two strategies I employed to tackle that demon on my to-do list.


For the purpose of this blog, I’m going to focus on my CRM and the 2,000 contacts contained therein. Please look at your own to do list and select the one staring back at you, mocking you.

I am the only person who can reasonably go through those 2,000 contacts, update them, tag them, create a new tag, change the tags. Are they a client? Were they a podcast guest? A vendor? A key influencer?

I’m having trouble keeping my eyes open as I write this. Feels about as exciting as flossing.

But that is not true. I have just made it true. I have to make it untrue.

And so why might it matter that your database is clean and up to date? I needed a why.

It didn’t take long to figure out. I thought about the time early on in my tenure as a nonprofit executive director when we sent out a direct mail fundraising appeal. My phone rings and on the other end is a sobbing person. The partner of the person the appeal was addressed to. He had died exactly one year ago. It arrived on the 1st anniversary of his passing.

I can still feel to this day how mortified I was. I never ever want to get a call like that again.

I had my why.


Take a lesson from BJ Fogg. Go grab a copy of Fogg’s book, Tiny Habits or check out his TED Talk (he actually gets the audience to floss – it’s pretty hilarious) OR be on the lookout for my upcoming podcast with him, coming to ears near you.

BJ wanted to get in good shape and focused on push-ups. His goal was 70 push-ups a day. Wasn’t happening. So, his tiny habit theory has two components to it.

First, cut the task into bite size pieces (like toddler meals). He starts with two every morning.

Second, he layered the two push-ups on top of a habit he already had. Fogg wakes up every morning and hits the can. That’s a habit he already has. Then he does 2 push-ups. He kept doing that and until he wanted to add more. He did and over some reasonable period of time, he worked up to 70 push-ups.

This works btw. I want to drink 8 glasses of water a day. Every morning I drink 2 cups of coffee. I added a big glass of water (2 glasses’ worth) to every cup of coffee. So, before breakfast, I’ve got ½ my 8 glasses in the books. Also, I enjoy my coffee so it’s layered on something I want to do.


You met Cindy at the start of this post. Now meet Joi. She handles all things admin at my firm. She is the calm amidst our storm – wheels always turning about how to get things done efficiently. She is managing the database project. I am in her way, thwarting her success.

She could say that, but she never would. So, she went a different route. She has not, to the best of my knowledge, read Tiny Habits but I think she could have written it.

At our weekly check-in, she doesn’t shame me by asking if I’ve done any clean up. She knows I have not. Instead, she came with a plan.

“Joan, I have created an excel spreadsheet with columns. Put an X in the column that says CHANGE, so I know you made one. Otherwise, if the info is AOK, continue on.“

But here’s where it gets good. “Do you think you can do like 25 or 50 at a time?” Many of the contacts are fine, so I thought that felt very manageable. Yes, I can do that Joi.

Then the icing on the cake. “When might you do that? Is there something you like doing where you can kind of multitask?”

I had two answers immediately. Yankee baseball and (true confessions) American Idol.

So, we agreed that I would open the spreadsheet and keep it on my desktop. And that while chilling and watching a Yankee game or my guilty pleasure American Idol, I would tackle 25-50 contacts.

And so that’s what I’m doing, and my to-do list is no longer judging me in the same way. At least about that. I’m going to look at the other items and see if I apply the formula.

Many folks reading this are not lucky enough to have Joi in their lives. But maybe you have someone who can help in this way? Or if not, I believe there is a DIY component to this advice that can really help.


I showed an earlier draft of this post to Joi – wanted her to know that she was getting a shout out in this week’s post.

She had a different reaction.

“Oh good, does that mean you’ll actually finish the clean up?”

I sputtered that American Idol wasn’t on this past week because of the Oscars but she wasn’t buying it and frankly neither was I.

2 Yankee games + 1 two-hour episode of young folks singing for stardom and my work was done.

I guess I was also motivated to finish because otherwise, the credibility of this post and this advice would be totally shot.

I’d love to hear about the item(s) that have been on your to-do list for way too long and how you might apply the advice.

Meanwhile I better check if there is a Yankee game tonight. I have to clean out my email inbox.

Leave a Comment