Conquering the tyranny of the to-do list

Conquering the tyranny of the to-do list

When I decided to leave my job, I began to make a list of how I would spend the ample free time ahead of me. It was fun to think about the possibilities – from fixing the little things that have been bugging me forever to investing in friends and family. It seems like everything I’d ever wanted to do was on the list.

  • Train the dog
  • Learn to make donuts, knit, code, play the guitar, etc.  
  • Plant a garden
  • Get chickens
  • Finish painting the house
  • Reconnect with old friends
  • Clean out kitchen gadget drawers
  • Figure out Google Photos  

Lack of ambition was not my problem. But there was one valuable item I’d forgot to put at the top the list that would change everything.

No, the answer’s not “me.”  Not really … well, sort of … oh, keep reading.

Whether organizing projects or mapping out a midlife reinvention, lists can be useful methods to plan and monitor progress, but they can also be tyrants – relentless reminders that we have so much we should or could be doing.

Maybe your to-do list lurks in the back of your mind keeping you awake at night. Mine is always front and center. I set my expectations high, adding more things to my to-do list than could ever realistically be completed and setting myself up for failure.

An example of this happened when I took a six-week sabbatical in 2012. I had just purchased a second home, a 200-year-old farmhouse in northern Vermont badly in need of renovation. I was looking forward to the time off, and my to-do list was lengthy.

  1. Clean everything
  2. Order appliances
  3. Paint walls
  4. Install new furnace
  5. Hire contractors
    … the list began.

Since I would be at the house alone during the week, I figured I could also learn to knit, write the first few chapters of a book, and explore all that Vermont had to offer in food, arts, and nature.

What I did was clean – vacuuming up piles of mouse droppings, scrubbing floors with a toothbrush, washing years of grime off windows, and filling dumpster after dumpster with rotting wood and other debris. At the end of each day, sore and discouraged, all I could do was binge-watch West Wing episode with my to-do list hanging over my head.

About two weeks into my time off, I had a melt-down. I was sitting at a café in town when an overwhelming sense of stress and misery swept over me. The sun was warm, the leaves turning crimson and gold, a plate of locally sourced food and craft brew sat in front of me, but I felt no sense of ease or gratitude. My undone to-do list had become a symbol of failure.

“I’m not getting enough done on the house, there is just so much to do; I am too tired to write or do any of the fun things I had planned,” I cried to my partner on the phone that night.

As usual, he cut right to the chase. “You know the only one who thinks you have to do everything on your list is you. There is no pressure for you to do anything; just relax and try to enjoy Vermont.”

I’d like to say that the lightbulb went off for me right then, but there have been many versions of to-do lists since. However, that early to-do list fail did plant the seeds for a different approach.

Begin with a goal.

In a business context, lists are synonymous for project plans, tactics, or work breakdown structures. And in business, these lists are always based on an ambitious but achievable goal and a set of objectives that are realistic and measurable.

Imagine back then if I had declared “Enjoy Vermont” to be my goal. My sabbatical to-do list would have been different, and I would have felt differently about my accomplishments or lack there-of.

But I did not establish a goal then, and I was about to make the same mistake now. As I started to plan the next phase of my career, I did what came naturally. I started a new list.

As I looked at the growing number of both practical and stimulating activities on my to-do list, I got anxious. I would not be bored, that was certain. But what was I going to DO?

The first item was “update LinkedIn profile,” and I was immediately stuck. What would I list under current employer?  I did not want to say retired; consultant seemed presumptive; writer felt premature. How should I describe my experience? What skills should I highlight? What do I say about my ambitions?

That one to-do item stymied me for months as my last official working day drew closer. I felt I was failing at reinvention before I had begun.

And then I remembered, “there is no pressure for you to do anything.”

How could I possibly update my professional profile when I hadn’t defined a new goal for myself. I need time to detox from a high-pressure job and time to recover my confidence and purpose.

I tore up the to-do lists. I realized my list-driven plans would only distract me from the real work of forming, articulating and committing to a goal. I might have a well-trained puppy, tidy gadget drawers, and organized photos, but those outcomes are not the point of this midlife reinvention.

So, I scrapped the to-do lists and when asked “what are you going to do,” practiced saying “I am purposefully not committing to anything,” or “I am purposefully taking time just to be while I think about what’s next.”

My only goal is to set a goal.

Pivotal Points

  • It’s not possible to know what to DO if you don’t do the work to discover who you want to BE.

4 responses to “Conquering the tyranny of the to-do list”

  1. Cathy, A most enjoyable read! I am very familiar with that feeling of failure of not having completed all on my list. My go to is writing lists. Your goal-setting approach will prove to be a tough change for me, but one worth working towards. Thank you for making me continue to think.


    • I have to admit, sometimes the first item I add to my to-do list is a task I’ve already completed just so I can have the satisfaction of checking something off right away! 🙂


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