I Hate To-Do Lists

here's how I prefer to approach weekly tasks instead 📆

It didn’t always used to be this way. Once upon a time, I loved to-do lists.

I also loved pretty notebooks (still do) and particular kinds of biro (that too) and running a thick line through a finished task. Well, that one—that last point—I don’t really love doing that anymore because now I know the truth.

It took me a while to get there, though. Years, in fact. Years to realise that to-do lists are not, in fact, the productivity-enhancing tools I once thought they were.

What they are is guilt-tripping, self-sabotaging, analog little monsters 👿

Here’s why.

To-do lists never end

Show me a person with a completed to-do list and I’ll…

well, I’ll be very very surprised.

These things are impossible to complete because it’s 2024 and because (here in the UK at least) the retirement age is soon to be 101* and because we’re constantly distracted and because we’ve got to post on Instagram and then Substack and then read our emails and quickly empty our phone’s overloaded storage and then respond to the group Whatsapp message and remember to send an invoice and we haven’t even got to the actual work yet.

*they’re talking about 71, but still. It’s a lot.

Suffice to say the to-do list will truly never end. It cannot.

You always feel guilty

As a result, to-do lists only ever get longer. Just as soon as you’ve crossed off two items from the top, you’ve added another three to the bottom.

Then somehow it’s 4 p.m. and you’re meant to be finishing work in a couple of hours and there’s no way you’ll get through everything by then.

So, the to-do list you made on Monday rolls over onto Tuesday, then Wednesday, and on and on it goes until one day in a fit of rage you grab hold of the weeks-old worn-out scrap of paper that governs your life and tear it into tiny little pieces and start afresh.

You will not be made to feel guilty by a bulleted list that’s long overstayed its welcome.

You will begin again with a new to-do list. A new set of priorities.

And so the cycle continues.

Cathryn Lavery via Unsplash

Here’s what I do instead

I’m not sure exactly when or where I heard the term ‘Parkinson’s Law’ or ‘timeboxing’ (probably around the time I read Cal Newport’s ‘Deep Work’), but these two concepts changed the way I think about time.

Parkinson’s Law is the idea that work expands to fill the time given to complete it. For me (in the old days), that meant working on task #1 on the to-do list until I was finished. And because there was no defined cut-off point by which to finish, that task could last anywhere between 15 minutes and two hours… or three days.

So, at last, I had a name (a Law, in fact) for my issue with to-do lists.

But what was the solution to this problem?

Guardrails.

Or—in productivity speak—timeboxing.

What the eff is timeboxing?

Really, it’s just a w*nky way of saying ‘allocate specific chunks of time to specific tasks.’

Depending on the kind of work you do, these boxes of time might be item-specific (e.g. 30 minutes to write a proposal to X) or they might be a little broader (e.g. 2 hours for ‘Substack’).

Rather than working through a paper to-do list in chronological order, you figure out what you need to accomplish that day/week and from there, add tasks (‘events’) to your calendar. The duration of these tasks is up to you to decide.

But remember—it’s important to set limits on how long you’ll work on any one activity because your focus will naturally diminish over time**.

If you know that writing your weekly newsletter takes you about 4 hours, break this up into 2x 2-hour or 4x 1-hour chunks of time (or whatever chunk of time suits your ability to concentrate best). You’ll be able to accomplish a lot more, a lot faster that way. Especially if you get rid of all distractions (phone, open inbox tab, etc).

**The range for most people to be able to stay focused is between 10 and 52 minutes, studies have found.

A snapshot of my timeboxed calendar from last month

So, I never ever touch pen + paper?

While to-do lists and I will never be the best of friends we once were, I haven’t sworn off them completely.

I usually start with pen and paper to list out my priorities for the week. Then I allocate them to my calendar (see above) and then, as I go through my day, I’ll jot down anything ‘unplanned’ that comes up. New emails I need to reply to. Invoices I have to chase. Ideas for clients I’d like to suggest.

If they’re small tasks, they might stay written down in the physical diary I keep beside me as I work to complete later/tomorrow. If they require more time or mental energy, I allocate them a slot in my Google calendar.

So yes, I do still use to-do lists ish. But they no longer run my days.

What do you do?

This way of planning time isn’t for everyone. Some people prefer more fluidity, others need an impending deadline to do their best work.

What approach do you take?

And what do you think of to-do lists?

Love/hate/couldn’t care less either way?

I’d love to know.

If you enjoyed this article and know someone else who would, please consider sharing it with them. I really appreciate it!