Run a to-do list like a Boss

It’s a thorny issue: interruptions can massively disrupt a person’s capacity for creative thinking and productive output, and yet the modern workplace is frequently a culture of interruption.

Jason Fried put it nicely a while ago: “Interruptions are the enemy of work. They are the enemy of productivity, they are the enemy of creativity, they are the enemy of everything. But that’s what the modern workplace is all about, it’s interruptions.”

Adjusting the culture of the modern workplace is a massive task — and it’s become the mission of the smart people at workplace consultancies, as well as sociologists and guys like Jason. But unfortunately it’s not an issue that is going to be resolved overnight.

In the meantime, many digital producers (arguably some of the most consistent deliverers of product out there) have optimized the humble to-do list as a killer way to cut through the chaos, prioritize the day and keep them delivering day after day.

Running a killer to-do list does not involve a special app, it involves a disciplined syntax and a daily regime. It’s an approach so simple that one thinks less about what to do and more time doing the things that matter.

A killer to-do list with all the elements and syntax

Part 1: The Elements and Syntax

There are only 4 elements to a killer to-do list:

1. Verbs
2. People
3. A Time Estimation
4. Icons
5. Syntax (all of the above)

Used properly, and with consistency, these elements help conquer the fragmented workday. Let’s break it down.

Verbs:

These are the action words: stuff like Call, Buy, Design, Write, Think. Always use a verb at the beginning of a to-do list item. It’s actually a tough thing to do sometimes, but it forces you to think about what actually needs to happen: The Action. By defining the action you have already imagined yourself actually doing the task. This helps with recall as well as activity performance when the time comes time to actually do the task.

Side benefit: When you scan through a list of to-do’s the verbs pop and you can select task based on Action.

Without Action words, to-do’s languish: ☐the lawyer’s issue

People

Following your verb, try to use a person’s name. This creates strong associations between what and who. Again, when you do this, recall and performance improves.

Side benefit: Including a person’s name allows you to mentally “sort by” person, because you can now find them simply by scanning down the second word in each to-do item.

A Time Estimation

Estimate how long it will take to do the task, and write it down. This is a simple but powerful addition. Doing a time estimate takes some thinking, and it prods one to imagine doing the task in further detail. Don’t know how long? Guess. You probably won’t be off by much, and if you are, you’ve identified a problem to solve.

Side benefit: One gets an overview of what’s actually doable in a day and the ability to thoughtlessly “sort by” tasks that fit the time available.

Icons:

There are generally 2 types of to-dos:

1. Things you need to do

2. Things other people are doing for you, that you need to keep track of.

Place an asterisk in front of tasks you are waiting on other people to complete, followed by the person’s name first. The asterisk is the short form for “waiting to hear back from” (which is one long-ass verb statement — way too long for a concise list).

☐Request Pablo’s design notes (5min)

Becomes:

☐* Pablo’s design notes (you can drop the time estimation)

Pro tip 1: Group asterisked tasks by person. This way when you finally corner Pablo in the kitchen, you can ask him in person about those goddamn design notes.

Pro tip 2: Get specific, and include relevant information in your notes that’ll help you complete the task. Eg: ☐Call Kevin, 415–555–5555 (future you will thank present day you for that little extra detail)

Syntax:

What have we done here? We’ve created a syntax, that makes it easy to think less. We’re consistent, making it easy to do a visual search. We got specific, so we know exactly what we need to do.

Each of the elements of our syntax allow one to parse a to-do list in different ways. Why? People tackle to-do lists based on urgency, difficulty, attractiveness, availability, and time available.

• Urgency/Difficulty: I have some tough things I need to tackle; Write SOW (2h)
• Attractiveness: I want to connect with Fred, my buddy: Scan by name
• Availability: There’s Jimmy, that slacker, I’ll talk to him about those asterisked things on my list
• Time Available: If I’ve got 15 minutes until my next meeting, I can easily pick something off, because I can now scan by 15 minute tasks

Part 2: Running your List

In the last part you got the syntax:

☐Verb(or *)_Person_Description_Detail_TimeEstimation

Now let’s activate the power of the syntax by learning the three habits that will form your daily regime and keep everything running tight.

1.

Do big tasks in the AM; short tasks in the PM. In other words, hardest first. What’s the hardest thing? The thing that needs the most sustained and arduous effort, eg a 2 hour task.

Why?

• Fragmentation: The day becomes more fragmented as it progresses, leaving us with progressively shorter windows of time. Fatigue, and coffee’s diminishing returns, means one is typically dumber later in the day.
• Consistency: One always knows where to start the day: hit that hard thing that’s already top of mind.
• Immediacy. You don’t waste a second, so you have more time for self directed awesome stuff.

2.

Separate out the to-do list so it can’t be ignored. I print mine, and draw all over it by day’s end. Many tasks live and die without ever entering an app. Other people might throw it on an iPad, or keep it as a sticky that floats on top. Just don’t let it get buried under a jumble of windows.

3.

Revamp the to-do list before the end of the day. Here’s how:

• Place the most urgent tasks at the top
• Group asterisked items
• Check off or redact finished tasks (the fun bit!)
• Rewrite any that need it

In Conclusion

I’ve seen a kajillion articles written on productivity and to-do lists — and I bet you have, too. My goal here was to distill what’s worked for me in the hopes that it may also work for you. I look forward to hearing your thoughts — and maybe even some new ideas — in the comments.

Thanks go to Greg Bolton for encouraging me to publish this piece and helping with the edit, as well as the larger team at Jam3 for providing feedback on a very rough draft.