Want to boost your productivity? Work from a calendar, not a to-do list

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Want to get shit done? In this article, freelance Cartoonist and Writer for The New Yorker Jason Chatfield shares his tried-and-true productivity technique that includes throwing out your notebook, and opening up your iCal.

One of the biggest productivity revelations I had in the last 15 years while working freelance, and trying to juggle a million different projects, was to work directly from a calendar.

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Row 1:
Tristan Kromopawiro,
Olga,
Frederique Matti.

On a given week, I do a daily comic strip, regular New Yorker and MAD Magazine cartoons, I do stand-up comedy shows all over the city, perform and voice act in TV commercials, and volunteer as the President of the National Cartoonists Society. If it sounds like a lot of work, it is. I do get a lot of questions as to how I fit it all in.

The short answer is: Good time management.

The longer answer is: I have a system that works around my brain, and subverts any tendencies to procrastinate—especially during periods of extreme willpower depletion.

One of the biggest productivity revelations I had in the last 15 years while working freelance, and trying to juggle a million different projects, was to work directly from a calendar, not a To-Do list.

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My old notepad of daily and weekly To-Do lists…

I worked from a To-Do list for a long time, using a page each day to cross items off. It felt good to run a line through things as I got them done, but sadly, I never really got as many done in a day as I should—or could have.

If you need to write down all of the things you need to do in a list to get them out of your head (especially before sleep on a Sunday night) then, by all means, do so. But, once they’re down on that list, start plugging them into your calendar to give you an actual idea of how much time you have to do them.

If you’re anything like me, you probably fall into the ‘dreamer’
 category of time psychology. The dreamers are the ones who have poor ability to predict how long something will actually take, and show up late to things, miss deadlines, and generally end up having all your work snowball into Friday afternoon.

Here’s how I use a calendar to boost my productivity, along with some tips and tricks to help set you up for success.

Trick #1: Copy & Paste

To remedy my old dreamer tendencies, I now make a habit of ensuring that on completion of a task, I adjust the calendar event to reflect the ‘actual’ time it took. For example, I may have allowed 30 minutes and it took an hour. I may have thought it would take an hour but it took 45 minutes.

I then copy and paste those similar or identical tasks that I’ve completed before when I’m scheduling for the week ahead. I usually do this on Sunday night. This gives me a realistic idea of how much time I actually have to get everything done, versus looking at a blank calendar. (Note: I’ve tried working from the freedom of a blank calendar… it’s not pretty.)

This gives me a realistic idea of how much time I actually have to get everything done, versus looking at a blank calendar.

If you have repeating tasks each week, as I do, you’ll be able to copy and paste entire series’ of repeating tasks that accurately reflect the time it takes to do them. For instance, I have to write comic strips, ink and color them, I have to sit and draw up my batch for the New Yorker each week, record an episode of the ITSIT
 podcast and, lastly, I know I always have to go in from 11 am — 12:30 pm every Tuesday to pitch my batch.

These things are repeating items on my calendar, and I’ve blocked out the exact time it takes each time (including travel time if needed).

Trick #2: Color code your calendar

To give you a clearer idea of the kind of work you’re going to be doing in a day, it can help to color code the kind of work that needs doing. You get a clear, concise 10,000ft zoom out view of exactly what kind of work you’ll be expecting to get done.

For instance, some work I do just needs me to be on my laptop, some needs me to be in my studio with my drawing equipment, and some things aren’t work-related at all, and need their own calendar—like going to the gym, stretching or making a medical appointment.

Tip #3: Know how long to block distractions

I use the Focusme app
 on my phone to block websites I know I habitually go to when I’m procrastinating, and SelfControl.app for the Mac to similarly block websites and social media on my laptop until the job at hand is completed. These are timer-based apps, and I know from the calendar how long to set each one.

Trick #4: Bundle similar jobs or ‘mindsets’

If you know you’ve got a bunch of admin tasks (emails, invoicing, Quickbooks, blog posts etc.) and you know you’ll basically use the same mindset and toolset for all of them, block those tasks together. If they won’t require the same amount of energy as, say, the really big project you have to start, leave them for later in the day when your energy is a bit lower.

If you need to move to a different desk for, say, drawing than you use for, say, writing emails, then bundle your drawing desk activities together, and bundle your emails desk activities together. I even have different color-coded calendars for the two kinds of tasks, to make it easier.

If they are high priority tasks, shift them to earlier in the day so you give them your full attention. Your energy and willpower wain throughout the day, so be sure to get your M.I.T.
 done first thing, before anything else.

If you’re more focused and creative in the morning, schedule your creative tasks for then. If you’re more productive in the afternoon, switch to then.

Also, be aware of your own individual habits and energy patterns. If you’re more focused and creative in the morning, schedule your creative tasks for then. If you’re more productive in the afternoon, switch to then. Obviously, deadlines sometimes rob you of the luxury of scheduling things for your optimum times, but do this when you have the opportunity to.

If there are certain days of the week that you know you’re going to be more available to get certain kinds of things done, schedule all your admin tasks for that day, or all your creative things for that day.

For example: I do all my admin work on Mondays when I’m most focused and I’ve just had a relaxing Sunday. I do my best creative work on Tuesdays, so I block that out for drawing and other creative work. Wednesdays, I go back to the desk and do invoicing, book-keeping, answering snoozed emails, etc.

Trick #5: Having an end time forces you to get it done

I remember John Cleese talking about creativity
 within confines. He and the Pythons used to write in 90-minute chunks so they knew they had a deadline. It kicked their brains into gear, knowing they didn’t have all day and night to get their work done. The same applies here—twofold:

  • You know you only have a certain amount of time to get the job done, be it from a self-imposed or externally-imposed deadline
  • You don’t sit around wondering what to do next because your calendar is telling you exactly what you should be doing and how long it should take. You don’t wonder “Should I be writing that blog post I’ve been meaning to write?” No. You put it in your calendar for Thursday. It’s scheduled. Do the thing you’re doing now.
  • Bonus upshot: Little to No procrastination.

Lastly, there is something known as Parkinson’s Law
, which states that “work expands so as to fill the time available for its completion”. Basically, if you give yourself two weeks to finish a project, you’ll finish it in two weeks. If you give yourself a deadline of half the time, you’ll figure out how to complete it in that given timeline.

Setting your own deadlines is an invaluable skill to cultivate as a freelancer, and I’d encourage you to make it a regular practice.

Jason Chatfield About Jason Chatfield: 🇦🇺 NYC Cartoonist/Writer for @NewYorker and stand-up comic. Syndicated daily in 34 countries. President of The National Cartoonists Society. #BlockedByTrump

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