Scheduling for Life’s Surprises: When Timeboxing is Toast

You have more control than you think

Some days, the world seems intent on sabotaging your timeboxed calendar.

A meeting goes longer than expected. The daycare center calls to say that your child is ill and has to be picked up ASAP. A project you thought would take an hour to complete instead took three.

Before you know it, the end of the day arrives, and you’ve barely given time to the tasks you had wanted to do.

But what can you do? Some events are just outside your control… right? When it comes to the unpredictable, a timeboxed calendar just can’t hold up.

Well, no. If you regularly fail to follow your timeboxed calendar, you might be doing it wrong.

The mission of a timeboxed calendar is to protect your time. We can bolster it using five methods to avoid a derailed calendar and to recover when it does happen.

1. Be Honest About What’s Really Unpredictable

Be proactive about preventing distractions from your timeboxed calendar.

This means getting real with yourself over which events are truly unpredictable.

A family member put in the hospital after an accident is unpredictable. This kind of event is rare, and you couldn’t have done anything to prevent it.

But if you experience the same distractions repeatedly, they are not unpredictable. You know there’s a good chance they could happen, even if you don’t know exactly when. Meetings that go over time and client calls out of the blue are actually very predictable. And considering that more than 100,000 Americans had to skip out on work because of “childcare problems” in October 2022, calls from the daycare to take home your kid are predictable too.

Identify the most common “unexpected” events that tempt you away from your timeboxed calendar. What can you do ahead of time to thwart those distractions?

2. Have a Contingency Plan

The best way to combat recurring “unexpected” events is to plan for the worst-case scenario.

If a certain meeting often runs late, timebox an additional half hour for it so you have some leeway.

Handle random client calls by implementing availability hours for clients to call you, or split availability hours among your team so one person is always on duty. Or you might pad your daily agenda with 30 minutes in case clients call.

Parents and guardians can build a reliable network of people who can pick up and watch their kid for a few hours when the daycare center calls for an early pickup. Search for three or four parents or guardians in your neighborhood or at your child’s school, or use Facebook or another app to find them. (See—social media can be a good thing.) Everyone from single parents to those with a partner or family members nearby will be interested in a free network like this.

3. Over-Allocate

Overestimate how much time you need for every timeboxed task in your day.

Our instinct is to pack as much as we can into the time we have. But that greatly increases the risk that one small disruption—say, chatting with a coworker for 10 minutes—will throw our entire day off-kilter.

Try allocating 20% or even 50% more time for a task than you think it needs. If you have extra time left over, then you can either take a break or address the next task early.

Over time, you should gain a better understanding of how much time you need for each task, and tweak your timeboxed calendar accordingly.

4. Don’t Over-Timebox

Avoid shoving every little task into a timeboxed calendar. They’ll just pile up and bleed into other tasks. Or, having too many things to do may overwhelm you and make you not want to do any of it.

A timeboxed calendar is not a to-do list with scheduled tasks. The goal of timeboxing is not to get everything—or even anything—done. The goal is to work without distraction when you said you would, on what you said you would.

So, instead of scheduling every little task, do what I do: Schedule time for “admin.”

Three times a week, I schedule an hour and a half for admin, during which I choose whichever tasks I want from a list of to-dos that aren’t time-sensitive. If I feel overwhelmed, I start with an easy task.

5. When You Miss One Task, Adhere to the Next

Despite all your efforts, something might still manage to derail your timeboxed calendar.

If so, don’t let the domino effect occur. Call it quits on the missed timeboxed event, and recommit to tackling the next without distraction. Reserve extra time in your calendar every few weeks to handle the overflow.

Having a hectic life is no excuse for constantly breaking a timeboxed calendar. “People make time for what they want,” as the saying goes. You should too.

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