Your to-do list is lying to you

About eight years ago, I started doing something that looked slightly ridiculous on my calendar.

I began cramming meetings together.

Instead of having two meetings on Monday, one on Tuesday, another on Wednesday and three on Thursday, I would try to squeeze as many as possible into the same one or two days. Those days could be exhausting. But suddenly, I had something much more valuable on the other side: an entire day with nowhere I had to be.

No Zoom call in 47 minutes. No meeting interrupting the afternoon. No need to repeatedly stop, switch context, and start again.

And I noticed something very quickly. I was actually more efficient in meetings when I did them one after another. But more importantly, I was dramatically better at writing, thinking and creating when I had long stretches of uninterrupted time.

I’ve been protecting at least one meeting-free day every week ever since.

It taught me something that now shapes how I organize almost all of my time: time management isn’t really about fitting or not more things into your calendar. It is about designing your calendar around the kind of attention different work requires.

Time management matters even more in the face of uncertainty

And I think this becomes even more important when you are going through a transition or dealing with uncertainty.

When things are changing, there is usually more to think about, more decisions to make, more people demanding your attention and less clarity about what actually matters. The easiest thing is to become reactive—to let your inbox, meetings and other people’s priorities decide where your time goes.

Organizing your time is one small way to reclaim some agency.

My tasks have dates

Of course I use a to-do list. I need one place where everything I have to do lives; otherwise, things get lost, and the mental load increases as you try to remember everything you need to do.

But one enormous list of 53 tasks doesn’t help me very much. It mostly reminds me of all the things I’m not doing. So my tasks have dates.

If I need to review a proposal, I don’t just put review proposal somewhere on a list. I assign it to Tuesday. Call someone? Thursday. Prepare something for class? Monday.

That means I am constantly making small decisions not only about what I need to do, but when I realistically intend to do it.

A task without a date can live on your list forever while still feeling strangely urgent every day. A date forces a choice.

I estimate how much time things will take

This is probably one of the simplest things I do, and one of the most useful. When I add an important task, I often estimate how long I think it will take: 20 minutes, 45 minutes, two hours. And I write it next to the task.

Then, when I plan the day, I can compare those estimates with the time I actually have available. And sometimes the math is brutal. You have three free hours and somehow you’ve assigned yourself six hours of work.

That is not a productivity problem. It is a planning problem.

Psychologists actually have a name for part of this: the planning fallacy. We systematically underestimate how long things will take, even when we have plenty of experience with similar tasks.

I still do it all the time. But estimating the time at least exposes the fantasy. It forces me to decide: What moves? What gets shortened? What doesn’t actually need to happen this week?

A to-do list shows your intentions. A calendar introduces reality.

Important tasks become meetings with myself

Once I know what I need to do and roughly how long it will take, the most important work goes onto my calendar.

Writing this newsletter might get 90 minutes. Preparing a workshop gets two hours. Thinking through a difficult decision might get an hour where nothing else is allowed in.

They become little meetings with myself.

There is a big difference between “I need to work on my newsletter this Thursday” and “Thursday, 9:00–10:30: work on my newsletter.” What occupies actual space on your calendar has a much better chance of happening.

And yes, plans change. Mine change constantly. The goal isn’t to obey your calendar like a robot. The goal is to start the day with an intention for where your time should go instead of discovering at 6pm where it went.

I design different kinds of time

Not all work requires the same kind of brain. Answering email is different from writing. Paying bills is different from developing a strategy. Scheduling something is different from solving a problem I don’t yet understand.

So I try not to scatter all of these across the day. Small tasks—email, admin, payments, quick responses—get grouped together into blocks. Meetings get grouped together too. Whenever possible, deep work gets larger uninterrupted spaces.

This is also why I try to solve things by email when a meeting isn’t really necessary. And when a meeting is necessary, my default is usually 30 minutes, not one hour. I’m still not sure how one hour became the default unit of human interaction. Some conversations need it. Many don’t.

I also try to cluster meetings onto the same days, which is what allows me to protect larger uninterrupted stretches for deep work - writing, thinking and creating. I know not everyone has enough control over their calendar to protect an entire meeting-free day. Start smaller. Protect one morning, one afternoon, or even a recurring two-hour block each week. The point isn’t the whole day; it’s creating enough uninterrupted space for the kind of work that needs it.

There is also a good reason why interruptions can be so costly. Researchers call it attention residue: when we switch from one task to another, especially before the first one feels finished, part of our attention tends to stay behind. We may be physically in the next meeting or document, but part of our brain is still somewhere else. That is another reason I try to group similar work together rather than slicing my day into little pieces.

Being human goes on the calendar too

When you start putting everything on your calendar, there is a danger that you create an incredibly efficient schedule for a person who apparently never needs to eat, walk, exercise or stop.

So those things get space too: lunch, a walk, exercise, a break.

I talked in the last two issues about energy and focus, so I won’t repeat why these things matter. But there is a practical lesson for time management: if something is important for you to function well, don’t rely on leftover time for it.

Leftover time has an unfortunate habit of disappearing.

Every hour, my watch brings me back

There is one tiny habit I particularly like. When I’m working, especially when I can easily disappear into something, I sometimes set my watch to vibrate every 30 minutes or every hour.

It doesn’t mean: Stop.

It means: Notice.

What am I doing? Is this still what I intended to be doing? Is this taking much longer than I expected? Do I consciously want to keep going?

I think of it almost like the gong in a Buddhist temple. It interrupts you for a second so you can notice where you are. Then you choose again.

That, to me, is ultimately what organizing time is about. Not optimization. Choice.

When things are predictable, you can sometimes get away with letting your calendar run on autopilot. During uncertainty and transition, that becomes much harder. More possibilities appear. More demands compete for your attention. You often have to continue doing the old work while figuring out what the new work should even be.

You will never have time for everything. So the question becomes: What deserves the time you actually have?

Your calendar is one of the places where you answer that question. And every time you answer it intentionally, you exercise a little more agency over where your life is going.

✨ Adventure of the week

Tonight, spend ten minutes planning tomorrow.

Look at every task you intend to do and put a rough time estimate next to it: 15 minutes, 30 minutes, one hour, two hours. Then look at your calendar and calculate how many hours you actually have available.

Compare the two numbers.

If you have six hours of tasks and three hours available, don’t try to become twice as productive. Choose what moves.

Do this for five days.

You may discover that your biggest time-management problem wasn’t how you used your time. It was how much you expected to fit into it.

Until next time, keep evolving ✊