How To Change a To-Do List to a Could-Do List

Going from a To-Do List to a Could-Do List

Icome from a long line of list makers. I’m a list maker, my mother is a list maker, my grandmother and great grandmother were list makers. (We’re also a bunch of do-gooders, get-’er-done-ers, and eyebrow-cocking know-it-alls, but that’s another book entirely.)

The nice thing about making a list is that I get the to-do chatter out of my head and onto a piece of paper. But there’s no way to prioritize. There’s no indication of how important anything is relative to anything else, how much time each task might take, and the order in which I ought to attack the list.

Of course, some people number their lists, but the order in which things occur to you does not necessarily reflect their order of importance. And while some people naturally prioritize, others have every item swimming around their brain in a hazy, interrelated cloud, so the list comes out all willy-nilly.

As an artist and entrepreneur, I usually have a bunch of pretty big projects going on at once, and so looking at that long, undifferentiated list of urgent actions makes me feel tired. Also overwhelmed and overworked — even before I’ve actually done anything.

There’s some conventional wisdom out there that says You Should Focus on Just One Thing. To which I say: Hooey. People who like to focus on one thing should focus on one thing, and those of us who like to have lots of things going on should have lots of things going on.

Running Your Career from Your Heart

As opposed to the usual to-do list, a good could-do list factors in time, budget, potential return on investment, and, most important, the truth about you. Running your life and your career from your heart is the only way out of the brambles of “should-do” and into the clear sunshine of “love-to-do.”

In short: a good could-do list can mean the difference between life as a frustrated, struggling artist and life as a happy, smiling, thriving artist.

Here is a story about a practical and heart-centered way to make lists, and the positive effect this system has had on my life and, subsequently, on the lives of my clients.

Vanity and Christmas Cards

One year just before Christmas, I found myself with an extremely long to-do list (you know how the holidays are), and I was having that exhausted-before-I-even-began feeling.

The first item on my list was “Make and send Christmas cards,” which was something I had proudly done for years. Everybody I knew received a Christmas card with a handwritten note — always. I loved the tradition of it, I loved letting people know that I was thinking of them, and I loved the little feeling of superiority I got when I thought about how much time and care I always took at this busy time of year. I’ll note that this superiority thing is not my favorite character trait, but it’s important to realize how big a motivator one’s vanity can be. And I was quite vain about my Christmas cards.

Adding to the pressure was the fact that I had gotten divorced that year. So not only had I moved and changed address, but also there were a number of people I felt I might “lose” in the divorce if I didn’t reach out to them. Finally, I felt it was important to reassure people that even though I was no longer married to the man I had been with for nearly fifteen years, I was still me and I could still be counted on to do all the “good-girl” things I had always done. Even though I wasn’t entirely sure that was true.

And Christmas cards were just one of the complicated things on my long, long, loooooong list of things that had to be done before December 25. Clearly, I needed to prioritize.

How I Prioritized the List

I took a sheet of paper, and with a big blue marker I made four columns with grid lines going across. The first column I labeled “Item/Task,” and under that heading I listed all the bits and pieces of things I felt I needed to do. Every last little one I could think of. The first one was “Christmas cards,” and the rest of the list filled two pages.

The next column I labeled “Time,” and next to each item I estimated how much time each task might take. “Call my sister” was 10 minutes. “Finish baby gift” was about an hour. “Pay bills” got 45 minutes. If I didn’t know how long something might take, I just made a wild guess or put a question mark next to it and moved on. After all, this is just a worksheet, not a government form.

“Christmas cards” got 12.5 hours. Which seems like a lot, I know, but I figured out that if I sent 150 cards and each card took five minutes to write, address, stamp, and send, then that was 750 minutes, or 12.5 hours. And that was assuming that I sent only 150 cards.

The third column I labeled “Expense,” and there I listed how much money, if any, was required to complete the item. “Call my sister” got zero, since we’re on the same cell phone plan. “Finish baby gift” was also a zero, because I’d already bought the supplies. “Pay bills” got $1,200, because that was about what was due. “Christmas cards” got...well, honestly, I can’t remember what it got, and it wasn’t a fortune, but at the time I was pretty broke and I remember it represented a significant investment for me.

Going from a To-Do List to a Could-Do ListThe final column I labeled “Inclination.” That column wasn’t for facts like time or money: it was for feeling. On a scale of 1 to 10, how much did I really feel like doing the project? It was for the intuition-belly-check I often forgot to do. And when I neglected that intuition-belly-check, I ended up with my plate piled high with obligations to other people that left me tired and stressed out and with very little time for the things that were important to me.

“Call my sister” got a 10 — I love talking to her. “Finish baby gift” got a 7 — the little cashmere sock monkey I was making was really darling and I was excited to finish it. “Pay bills” got an 8 — I’ve actually never minded paying bills because I’d much rather get it taken care of than have them floating around, possibly gathering late fees and causing trouble. (I told you I was a get-’er-done-er.)

“Christmas cards.” I took a deep breath. How much did I really want to send cards? Setting aside my guilt, my fear that I would lose friends, my concern that I would lose my standing as a “good girl,” my sense of tradition, and my ever-lovin’ vanity, how much did I want to do it?

I entered a 0 in the column.

That’s right — I had absolutely no inclination to send even one card.

And then, in what was possibly the single most radical act of my adult life, I crossed “Christmas cards” off the list.

My little worksheet helped me to determine not only that sending cards was time-consuming and pricey but also that I just plain didn’t want to. I felt strange and liberated and free, and it made me laugh. After all, any friends that I might lose because of a silly Christmas card probably weren’t friends worth keeping, anyway. I had gotten the mandate from my deep inner wisdom and it said, “NO CARDS, BABY.”

But, Wait...

One final word about that Christmas season. Eventually, I started to feel some twinges about a few of the people that I really did want to send cards to: my aunts and uncles, a girlhood friend, an old neighbor of mine. But I was so enraptured by my no-Christmas-cards policy that I dared not break it. See, I know me — I’d go to the store to buy just those few cards, and my resolve would crumble and I’d end up doing the whole durn thing after all.

So six weeks later, I made some lovely Valentine’s Day cards and sent them off. Why? Because it wasn’t expensive, it was only a little time-consuming, and I really, really wanted to do it.

Good Prioritization Can Earn You a Thousand Dollars

In time, I added one more column to my worksheet: “ROI,” which stands for “Return on Investment.” That’s a way of determining (I just guess on a scale of 1 to 10) what, or how much, I might get back from completing an item.

For example, I had a could-do item that had been hanging around my desk for a few weeks — it was silly, really. I had found a product in a catalog that I thought a client of mine might like. I had wanted to just slip the clipping in an envelope with a quick note, but the weeks had passed and I just hadn’t gotten around to it.

When I worked the list, it came up like this:






Send Clipping to D.G.

2 minutes

44 cents



Wait a sec.

This was something I really wanted to do, that I thought would really pay off in the future, and that cost almost no time and no money. Duh. I got it right in the mail, and she called me three days later to book me for another ten sessions.

That little could-do item netted me more than a thousand dollars, but more than that, it helped me be the kind of person I want to be — the kind who sends thoughtful little notes to clients that I like. Again — marketing straight from the heart.

I don’t use this worksheet every day, but I do use it when my list of things to do feels long, unwieldy, and confusing. Whenever I use it I discover something new, and it helps me remember why some things are important and some things, darling, just aren’t.

©2014 by Samantha Bennett. All Rights Reserved.
Reprinted with permission of New World Library, Novato, CA. or 800-972-6657 ext. 52.

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Get It Done: From Procrastination to Creative Genius in 15 Minutes a Day
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About the Author

Sam Bennett, author of: Get It DoneSam Bennett is the creator of the Organized Artist Company. In addition to her multifaceted writing and performance work, she specializes in personal branding, career strategies, and small-business marketing. She grew up in Chicago and now lives in a tiny beach town outside Los Angeles. Sam offers her revolutionary Get It Done Workshops, teleclasses, public speaking engagements and private consulting to overwhelmed procrastinators, frustrated overachievers and recovering perfectionists everywhere.

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