A New Way to Schedule Your Workweek

The key to an effective weekly calendar is pessimism

Illustration: Simoul Alva

As a time-management consultant, I see a lot of schedules — so I know what I’m talking about when I say that Catherine Gillespie’s schedule was a work of art.

Gillespie, a strategy consultant, tracked her time for me last year as part of a time-makeover project I recently led. She was freelancing 30–40 hours a week while homeschooling her five kids — before the pandemic. She exercised in the mornings; she got together with friends. She made it all work.

So why was she seeking advice from me? She told me that she wanted to protect time for creative writing in her full life. Her husband was happy to take the kids for a few hours on Saturdays so she could write. But when work took longer than expected, or a client asked for a new project, she’d log the extra hours during those Saturday windows. And just like that, her writing time would be gone.

Her schedule worked when everything went according to plan. But it had to go according to plan.

It’s a common dilemma. People make time for things that matter to them. Then life happens, and the time gets taken away. It’s easy to get discouraged, but that’s not the only option. You can be more optimistic about life if you become more pessimistic about time. When you plan for what you’ll do when plans go awry, you increase the chances of making progress toward your goals.

Everything in life needs a back-up slot

In Gillespie’s case, I suggested the option of scheduling in a back-up slot for additional work, such as one to two designated weekday evenings, so that she wouldn’t need to use her Saturday time for any lingering tasks.

Other people find success by scheduling a back-up slot for an activity they’re trying to do. Elizabeth Morphis, a professor, needed to submit a journal article by a June 1 deadline. She planned to work from 6–9 a.m. each day during the week of May 18th to fit the writing in around her teaching commitments. “But I decided to carve out additional hours each day of the weekend to work on the manuscript, just in case,” she says.

By the time the weekend rolled around, she was glad she did. “I needed it,” she says. “My two-year-old was not sleeping well that week and I was up with her more than once during the night.” Morphis could only use the 6–9 a.m. slot once, but instead of panicking over her four lost mornings, she used her designated extra time and submitted the article ahead of schedule. “Scheduling back-up slots has been how I have been able to stay productive this summer,” she says.

The back-up approach isn’t just a tactic. It’s a mindset.

To be sure, designating a back-up slot is not easy in a full schedule. If finding one chunk of time for research or creative projects or exercise feels challenging, finding time for two or more — that you hope you won’t need! — might feel impossible. Consciously leaving extra time open involves trade-offs, often difficult ones.

But good time management means planning a resilient schedule, not a perfect one. When you schedule one slot a week for something, you only get to it if nothing else goes wrong. If you schedule an extra slot, then the priority still happens even when all doesn’t go perfectly. There is a big difference between spending zero time on something and spending some time. The narrative changes from “I never go to yoga” to “Hey, in a crazy week I still got to go to a yoga class!”

To achieve that victory, it’s worth a little pessimism on time — assuming something might go wrong and planning accordingly. It’s a smart calendar strategy, but it’s also a smart mindset about life. We hope for the best, but design our lives to still work in other circumstances. Even if a client looks like she’ll confirm a project — meaning your business makes its numbers for the month — you put out a few other inquiries, and have another project that could start earlier, just in case. You hope for sun at an outdoor wedding, but you scout out an indoor plan B as well.

The back-up option doesn’t just keep you from scrambling — it lets you relax about life in general. When the client says she’ll need more time, you don’t think “How can you do this to me?” Instead, you can just smile and say “we’re ready when you are!”

Laura Vanderkam is the author of several time management books including Off the Clock and 168 Hours. She blogs at LauraVanderkam.com.