Why I Threw Out My To-Do List & Started Making Appointments with Myself

I love making lists. I love making lists almost as much as I love crossing completed items off my list. But after I’d been working from home for about a month, I made a drastic decision. I threw away my to-do list.

And haven’t looked back.

Why I Ditched the List

Perhaps it was the shake-up of my routine or my climbing stress levels. Whatever the reason, each morning I stared at my list feeling immobilized. The ambitious list writer hadn’t accounted for future burnout and listlessness (no pun intended). Why was it so hard to tackle the things I needed to get done?

  • The list was always growing. Because new priorities were always popping up, my list was longer at the day’s end than at the start. This left me feeling discouraged and overwhelmed. Instead of feeling accomplished at the end of the day, I felt anxious about what I’d left unfinished.
  • The list rewarded procrastination. It’s tempting to pick off the easy tasks. The instant gratification of completing something prevented me from starting more meaningful projects.
  • The list didn’t reflect effort. A small, quick task looked exactly the same size as a special project I hadn’t yet thought about how to tackle. I had little sense of whether I could say yes to new commitments since the list always loomed large.

Goodbye List; Hello Agenda

The pandemic made me re-examine both my personal and work priorities. With all these new worries holding space in my brain, I needed to commit to only what was essential to stay afloat.

First, I examined each item on my to-do list and whittled away special projects and rainy-day tasks. Most of the items languishing at the bottom of my list were out of date or no longer valuable.

Next, I assigned each of the remaining tasks a slot in my calendar. Yes, my agenda suddenly looked very scary. But it also looked more realistic. I was looking at a concrete plan to get things done — no more “choosing my own adventure” every morning while staring down my list.

At the end of the week, I looked at my calendar and saw all the things I’d accomplished. And I was no longer worried about everything left to finish. Those were next week’s problems (each with a spot carved out in my calendar). Instead of spending so much time thinking about what work to do and in what order to do it, I was, well, actually working.

A New Way Forward

I decided to stick with my experiment and set a few guidelines for myself.

1. If it takes less than five minutes, do it now.

The small, insignificant items that once earned a spot on my to-do list seemed silly to add to my calendar. It was easier to handle emergent tasks as they popped up than leave them for another time.

2. Make time to really focus.

Tasks requiring focus or “getting into flow” received their own events on my calendar. Adding a task to my calendar felt like a commitment. With dedicated, un-interruptible time set aside, I became more self-aware of procrastination. And instead of using focus blocks to visit my triage list, I could start on the task at hand immediately.

3. Leave room for flexibility.

A lot of the tasks I had to complete were flexible and not time-sensitive. These items I either added as Gcal reminders or using the “free” status. This left room on my calendar for meetings. I wasn’t too sacred about moving tasks around on my calendar, as long as I still completed them within the week. If I didn’t complete a task in the time allotted, I scheduled a new time commitment.

4. Re-consider tasks you keep putting off.

Some low-priority tasks I scheduled and rescheduled into the future. Doing so prompted me to consider why. Was it really worth doing? Should I delegate? Am I unsure where to start? I had to ask the important questions instead of skipping over the task in favor of the next one.

5. Optimize.

Soon, I was able to identify new routines to help me batch my work for the week. I grouped like time blocks together by project or the amount of energy needed to complete.

In the same way that I wouldn’t schedule back-to-back meetings without a break, I try to space out more intensive tasks throughout the week. I feel less overwhelmed knowing I’ve set aside time for everything and won’t be scrambling to wrap things up on Friday afternoon.

My to-do list had become a neverending story of good intentions. Adding the constraint of time boosted my productivity and granted me peace of mind. Whereas a list can grow forever, my calendar has finite space.

Maybe when we all return to the office and settle back into our normal routines, I’ll fire up my beloved Things App once again. But for now, I’m enjoying the structure provided by working directly from my calendar. This new approach has enabled me to think critically about how much I can actually do in a day and to spend my time on what really matters.

  • Roman says:

    Been in a similar situation. Another solution is to do the planning the day before. Cherry pick items from your long list onto a shorter list. That way it’s not dauntingly long and all of the decisions about what to do are done.

    • Kaitlin Diemer Kaitlin Diemer says:

      Hi Roman,

      Yes, I’ve also had success with the method you mention (as long as I’m not overly ambitious when writing up my short list!) Thanks for sharing!

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