To-Do Freshness

Hamilton Chan
3 min readApr 14, 2020

Are your To-Do’s stale?

Do you stare at items on your To-Do list as if they’re old vegetables in the fridge?

Then it’s time to inject some freshness into them! You need to mix up your To-Do list and give it some new life!

One hack I use to keep up my To-Do freshness is to use new ways to write them down.

Originally, I wrote my To-Do list in Word documents. But the documents started to propagate meaninglessly. I named them: to-do_1; to_do_2; to_do_today; to_do_6; to_do_all. What a mess!

I then switched to writing these lists on scraps of paper. Oftentimes, the same To-Do item would just migrate from list to list in a never-ending nomadic existence.

I tried giving my list a new name: “Today” instead of To-Do.

That was hugely beneficial, and is a system I’ve now maintained for around 3 years. “Today” was a list of only 4 important tasks that I wanted to accomplish each day. By design, the list only included action items that could be accomplished within a single day. That made my day feel purposeful, action-oriented and winnable.

Unfortunately, the immutable laws of To-Do physics crept in, and my Today lists would be documented only sporadically.

I then started journaling-while-I-work, wherein I type in a journal on a separate iPad, recording my extraneous thoughts and my tasks as I encounter them. It has been quite effective, though I would skip days eventually and To-Do staleness would set in.

And just a few days ago, I found a new feature that ties Superhuman’s email program to the Todoist app. What a revelation! I already use my Inbox as a To-Do list of sorts, starring email messages that need replying. But over time, starred emails would make their inexorable march down to the bottom of my screen and blip! Just like that, they’d be lost in the netherworld of forgotten tasks.

With Todoist (an app I hadn’t tried previously), I have a new shot in the arm. Software makes the problem fresh again! Yesterday, with the trepidation that only comes from knowing oneself too well, I dared to type in a single task in Todoist. I didn’t want to push myself too far. I certainly didn’t want to fail. I wanted to make a pact to myself that whatever I typed in to Todoist would get done. This first canary down the To-do coal mine was an old stale task that refused to get done.

Fortunately, I lived honorably and completed the lonesome task. I don’t even quite remember what it was; I only remember that I completed it.

And today, I took another cautious step forward. I recorded two tasks in Todoist. Lo and behold, the first one was completed, and by writing this blog post, I am now completing the second one.

Watching my motivation slip away this afternoon, I began to steel myself for the task. I will not sleep, I proclaimed, until I finish a blog post tonight. I was confident I would honor my self-promise.

It was because I couldn’t let down the new process. This process was my new talisman! I had to complete my two tasks in Todoist, because if I couldn’t, what would it say about me if I failed within just 2 days of coming up with a new system!

And so it was. I managed to move my To Do’s to Done.

Completing your To Do’s will always remain a battle (that is, if you are remotely like me). But you can do it. Keep your To Do’s fresh and your To-Do exterminating system fresher.

You may have failed on many past To-Do’s, but as Scarlet O’Hara reminds us in Gone with the Wind, “Tomorrow is another day!”

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