How To Make Your To-Do List Doable

There’s no better feeling than checking something off your to-do list. Done! Finished! Mission accomplished! Yet it’s so easy to let a whole day or week go by without knocking one task off your list. How does that happen? Well, your to-do list can be a tool that guides you through your work, or it can be a big fat pillar of undone time bombs taunting you and your unproductive inadequacy. It all depends on how you write it.

The following is an excerpt from Lifehacker: The Guide to Working Smarter, Faster and Better, available at Amazon and bookshops.

Think of your to-do list as an instruction set your Boss self gives your Assistant self. Like a good computer program, if the instructions are clear, specific and easily carried out, you’re golden. If not, you’ll get undesirable results, such as fear, procrastination and self-loathing. Read on for a closer look at how to write a to-do list that makes getting your stuff done dead-simple.

You Are the Boss of You

At any point during the workday, you are in one of two modes: thinking mode (that’s you with the Boss hat on) and action mode (that’s you with the Personal Assistant hat on). When a project or task comes up, the steps you need to take start to form in your mind. Now you’re in thinking/Boss mode — the guy/gal who gives the orders. Your to-do list is a collection of those orders, which your Assistant personality will later pick up and do.

When you’re wearing your Boss hat, it’s up to you to write down the instructions in such a way that your Assistant self can just do them without having to think — or stress. Taking the thinking out of the acting is one of the best ways to make your to-do list a cinch to finish off.

How to Order Yourself Around

When it’s time to add something to your to-do list, think it through using the following guidelines.

Only Put Items on the List That You’re Definitely Doing
Sometimes you think of tasks you’re just not ready to do yet. Maybe learning a new language — while it’s an eventual goal — just doesn’t fit into your life right now. Maybe upgrading the website is low priority because your business is shifting gears in a major way, and any site overhaul will look very different — or maybe won’t be needed — in six months.

Instead of letting tasks you’re not quite committed to loiter on your to-do list until you’re sick of looking at them (and sick of the reminder that you’re not quite there yet), move them off to a separate list, a holding area for Someday/Maybe items. You’d tell your assistant to do something only if you absolutely, positively want it done, so only concrete actions you’re committed to completing should live on your to-do list.

Break It Down
The quickest route to a task you’ll actively avoid working on: Make it a vague monstrosity. Put a nonspecific item such as “Clean out the office” on your to-do list, and I guarantee that’s the last thing you’ll ever start working on. Actually, “Clean out the office” isn’t a to-do at all; it’s a project. Author of Getting Things Done David Allen says projects are not tasks; projects are collections of tasks. That’s an important distinction. Internalise it, because your to-do list is not your project list. Don’t add multi-action tasks to it, such as “Clean out the office.” Break projects down to smaller, easier-to-tackle subtasks, such as “Purge filing cabinet”, “Shred old paperwork”, and “Box up unneeded books for library drive”. Your Assistant self will ask, “What do you want done?” and when Boss you says, “Clean out the office,” that won’t get you anywhere.

The smaller and more atomic these subtasks are, the more doable they are. Inspirational writer SARK breaks down her tasks into five-minute increments, and calls them “micromovements”. She writes, “Micromovements are tiny, tiny little steps you can take toward completions in your life. I’m a recovering procrastinator and I have a short attention span, so I invented micromovements as a method of completing projects in time spans of 5 minutes or less. I always feel like I can handle almost anything for five minutes!”

Coming up with those tiny tasks requires thinking up front, when you’re putting the task on your list. The following examples contrast vague to-do’s (the kind that can throw up roadblocks) next to their doable counterparts.

Roadblock To-Dos Doable To-Dos
Find a new dentist. Email Jayne and ask what dentist she goes to.
Replace the broken glass table top. Measure the table dimensions. Call San Diego Glass at 555-6789 with dimensions.
Learn Italian. Check U of Whatever’s website ( for fall Italian class offerings.
Upgrade website. Draft a list of five website upgrades.

As you can see, breaking down your tasks into next actions creates more than one task for items that look like regular to-dos but turn out to be small projects. For example, replacing the broken glass table top involves measuring the table, calling and ordering a replacement, and possibly going to pick it up, which brings us to the next guideline.

Focus Only on the Next Action
When you have a multi-action task — such as replacing the glass table top — keep only its next sequential action on your to-do list. When the task is complete, refer to your project list (again, separate from to-dos) and add its next action to your to-do list. At any given moment, your to-do list should contain only the next logical action for all your working projects. That’s it — just one bite-sized step in each undertaking.

Imagine that you’re at your desk, you have a spare 10 minutes before a meeting, and you pull out the preceding roadblock to-do list. Can you find a dentist or learn Italian? No. But you could get an item done from the doable list. You could email a friend about a dentist referral, or check the university website for class offerings.

Use Specific, Active Verbs
When you tell yourself to do something, make it an order. An item such as “Acme account checkup” doesn’t tell you what has to be done. Make your to-do’s specific actions, such as “Phone Rob at Acme re: Q2 sales”. Notice I didn’t use the word Contact; I used Phone. Contact could mean phone, email or IM, but when you take out all the thinking and leave in only action, your verbs will be as specific as possible. Literally imagine instructing a personal assistant on her first day on the job as to what you need done.

Include as Much Information as Possible
When formulating a to-do, the onus is on your Boss self to make it as easy as possible for your Assistant self to get the job done. For example, if you have to make a phone call, include the name or number. Instead of “Donate old furniture”, assign yourself “Call Goodwill to schedule pickup, 9876-5432.” When you’re stuck in the doctor’s waiting room for 20 minutes with only your cell phone, you can’t donate your old furniture, but you sure can make a phone call — if you have the number. Be a good Boss. Arm your Assistant self with all the details she needs to get your work done.

Keep Your List Short
Just as no one wants to look at an email inbox with 2386 messages in it, no one wants to have an endless to-do list. It’s overwhelming and depressing, as though there’s no light at the end of the tunnel. Instead, keep your to-do list under 20 items. (This morning, mine’s only 17 tasks long, and I call myself a busy person.) Does that sound like too short a list? Remember, your to-do list isn’t a dumping ground for project details, or “Someday I’d like to” items. These are tasks you’ve committed to completing in the near future, such as the next two weeks. Keep your projects and someday/maybe items elsewhere. Your to-do list should be short, to-the-point commitments that involve no more deciding as to whether you’re actually serious about doing them.

Prioritise Your Tasks
Although your to-do list might have 20 items on it, the reality is that you’re going to get only a couple done per day (assuming that you’re not writing down things like “get up, shower, make coffee, go to work…” — and you shouldn’t be). So make sure the most important tasks are at the very top of your list. How you do this depends on what tool or software you use to track your to-do’s, but do make sure you can see at a glance what you need to get done next.

Keep Your List Moving
Although my to-do list is only 20 items or so, it’s 20 items that change every day. Every day, two to five tasks get checked off, and two to five tasks get added. Remember, your to-do list is a working document, not some showy testament to organisation that quietly gathers dust because you’re off doing real work that’s not written down anywhere.

Purge and Update Your List Weekly
In addition to sorting by priority, you should sort your list by age. What items have been on your list the longest? Chances are you have mental blockage around the tasks that have been sitting around forever, and they need to be reworded or broken down further. Or perhaps they don’t need to get done after all. (Remember! Deleting an item from your to-do list is even better than checking it off, because you’ve saved the time and effort of actually doing it.)

Just as a manager would meet with her staff members once a week, schedule a 20-minute meeting with yourself every Friday or Monday to review your to-do list, project list and someday/maybe list. Use that time to rewrite any items that aren’t broken down as much as they should be, purge irrelevant items, and move next actions from your project list to your to-do list.

This short, weekly ritual can make you feel more on top of your game than ever. It focuses your energy and weeds out any detritus that accumulated over the past week.

Log Your Completed Tasks
As any good assistant does, you want to show the boss exactly how much you accomplished. Make sure you stow your done items somewhere so that you can revel in your own productivity and even refer to past work activities. Your “done” list is a great indicator of whether your to-do list is working. If more than two days go by without a new done item, it’s time to revamp your to-do list and get back to best practices.

Practice Makes Perfect
This may seem like a long set of guidelines for something as simple as adding to your to-do list. But 90 per cent of the work involved when you’re tackling tasks that matter is the planning, and that’s true for what may seem to be the most trivial tasks. As with any good habit, practice makes perfect. The more you practice the art of creating effective to-dos, the faster and easier it will come to you, and the more you cross items off your list and leave the office with that delicious sense of completion.

Note: Many of the concepts listed above (especially those of Next Actions and Projects) come from David Allen’s productivity bible, Getting Things Done. Also, Merlin Mann’s two-part feature on building a smarter to-do list (part 1 and part 2) and his follow-up article for Macworld magazine in July of 2006 (especially the second page) inspired and informed this post.

Lifehacker: The Guide to Working Smarter, Faster and Better

Availability: Lifehacker is available in paperback from Amazon, on Kindle, as an epub, and in bookshops.

What’s It All About? For a better understanding of what Lifehacker is about, read the book’s introduction.

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