The Way We Work

Hi, my name is Jenna. I am a to-do list addict.

Or at least I was; I am now in the beginning stages of recovery. While I suspect I am not in the clear yet, I have seen the light — and it is calendars.

Regardless of whether you are a freelancer juggling multiple projects for different clients, or an entrepreneur trying to build your business and manage a growing team, your time is one of your biggest business assets and you need to manage it effectively. While to-do lists may seem like the best way to prioritize your time and attention, they are inherently flawed.

Why to-do lists do not work

This is the argument presented by Daniel Markovitz, president of TimeBack Management — a firm that “helps companies radically improve individual and team performance.” In his recent article for Harvard Business Review, titled “To-Do Lists Don’t Work,” Markovitz argues that to-do lists are “simply setting you up for failure and frustration.”

He focuses on five fundamental flaws in to-do lists:

  • the paradox of choice: being presented with too many options at once is overwhelming
  • heterogeneous complexity: some tasks are simple while others are complex and more time-consuming
  • heterogeneous priority: some tasks are urgent while others may seem relatively insignificant
  • lack of context: a list cannot capture the important pieces of information related to each task that help you decide how and when to work on it
  • lack of commitment devices: there is nothing forcing you to work on the most important tasks instead of picking off the most enjoyable ones

If you do not have time to read Markovitz’s article (even though it is short and quite compelling!), here is the synopsis: Lists do not capture important information such as the time it takes to do each item or how much time you have available. They also bring out less-than-productive aspects of human nature — we are overwhelmed by too much information, we consistently choose the easiest and quickest items over more onerous ones that may be more important, and we tend to only focus on the highest-priority items until the low-priority ones become critical and more difficult to handle.

Instead of to-do lists, he suggests an option called “living in your calendar.” This means estimating how much time each task on your list will take, as well as its priority, and scheduling the tasks onto your calendar like meetings.

The result? A structured day that takes into account a realistic estimate of how much time each task takes, in the context of how much time you actually have available. You will be forced to make some trade-offs, based on which items take priority.

“It’s an eye-opening exercise: you’ll probably find that it’s tough — if not impossible — to find a place for everything,” Markovitz writes. “But this is the reality of your life. You’ve simply used the calendar to paint a true picture of the time commitments you have on your plate. And whether or not you make these commitments visible, they’re there. After all, if you’re going to be run over by a truck, you might as well get its license plate.”

Living in my calendar


He speaks the truth. Giving this theory a test, I was astonished to see how few items I could realistically get done in a day, when I actually thought about how much time each one would take. While this is sobering, it also has the benefit of showing me – in black and white – whether I can take on any additional commitments.

Before, I had multiple to-do lists — including several long-term ones and a daily one. While I tried to be realistic about what I could get done each day, I always had items left over at the end of the day, which automatically made me feel like the day was not as successful or productive as it should have been.

This is what my day looks like now: I build in time in the morning to go through emails (as well as 15-minute chunks for email processing scattered throughout the day), and then schedule the rest of my tasks — according to priority — around my pre-existing meetings. I know when I am on schedule to accomplish everything I need to do for each day, and I have extra motivation to finish tasks and use my time effectively so I can stay on schedule.

In addition, I am able to adjust my calendar based on what I have control over that day; if I know I need to leave work at a certain time, running behind schedule means postponing a task until the next day. But if I know I need to get something done that day, I adjust the start and end times of my work day accordingly. At the end of the day, it feels like my work has been done and the day was a success, and I plan my schedule for the next day.

And let me tell you, the feeling of being ahead of schedule — essentially, being rewarded with free time I did not expect to have — is an even more satisfying feeling than crossing items off of a to-do list.

I used to think that to-do lists helped me stay in control of my day, but that was nothing compared to running smoothly along a pre-planned calendar of priorities. I urge you to try this method for a few days. If I can do it, you can too!

Have you found success with an alternative to the traditional to-do list? What are your favorite ways to stay productive and efficient? Let us know in the comments section below!

Jenna Weiner

Content Marketer

Jenna Weiner is the former content marketing manager at oDesk and was the editor-in-chief of the oDesk blog. With a background in business and technology writing, she specializes in content marketing and strategy, public relations, and branding. Before joining oDesk, Jenna was a writer and editor for Monitor Group’s marketing department (now Monitor Deloitte) and was the Business & Technology Section Editor for Brafton Inc.… read more