The Planning Fallacy

A few years ago, my days were an utter mess.

Not in a dramatic way. On the surface, things were getting done and I was hitting all the deadlines I needed to hit.

But underneath the calm waters of seeming productive output, I knew the truth. Every single thing felt reactive, as though I was always slightly behind on every project, always catching up, always ending the week with a list of things that were supposed to happen but didn't.

To be honest, I put it down to not having enough time, or just not being efficient enough. Turns out I had plenty of time, I just had no clue where it was going.

The problem wasn't discipline; it was that I'd never actually looked at how long things take.

Daniel Kahneman, psychologist and Nobel laureate, called it the planning fallacy: our systematic tendency to underestimate how long tasks will take, how many things can go wrong, and how often the unexpected turns up uninvited.

The effect holds even when we've done the same task before and know from experience that it overruns. Kahneman says that when we plan, we imagine the best-case version where there are no interruptions or complications, and everything moves cleanly from one thing to the next.

As you probably know, this almost never happens.

The notebook changed everything

I don’t remember where I first heard of time blocking, but I do remember just how much smoother it made my days.

The system I landed on has two parts, and both of them are important.

Time Blocking

The first is time blocking in a calendar app. This is where I put every single task I need to complete into a specific hour slot before the day starts.

This forces the question I was never asking before: how long does this actually take? And because I now know my first estimate is always optimistic, I add a third on top before the task goes into the calendar.

Because it’s digital, nothing is hard-locked. If I finish something sooner, the whole day can adjust. This is where I struggled with having a physical calendar. Once something written down it’s locked, and if you want to juggle things around, the pages becomes a mess of scribbles as tasks, meetings, and so on are erased and rescheduled.

Physical To Do List

The second part is a physical to-do list running alongside it. The calendar holds the structure of the day, but then then notebook holds the detail. All the smaller tasks and the little things that come up mid-week.

Something about writing it by hand makes it real in a way that a digital checkbox doesn't quite replicate. Crossing something out with a pen still feels better than clicking a button.

With both of these together, the reactive feeling I described was gone in an instant. Suddenly I found that I had more time than I needed.

The weeks still don't always go to plan - I doubt that’s ever going to change. But they go to plan far more than they used to, because the plan finally accounts for the version of the day I actually live in, rather than the version I was hoping for.