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Forget Your Endless To-Do List: Try Time Blocking Instead

by | May 11, 2017

Are you the kind of writer who’s always worried about meeting deadlines?

Do you begin every day with a to-do list and end it with only half of the items done? Do you get stuck working late, staying up all night with a draft or sending apology notes to editors?

At least half of being a successful freelance writer is time management.

When you work in a career that pays by the project instead of by the hour, it’s to your advantage to maximize those hours and complete as much work as you can. It’s also good to get in the habit of meeting your deadlines, avoiding all-nighters and maintaining a work-life balance — especially if you plan on freelancing for the long haul.

I’ve definitely done my share of working late, worrying about deadlines and writing overly ambitious to-do lists.

But as I became a more experienced freelancer, I started learning how to time-block my freelance work: that is, to know not only what I’m going to do, but when I’m going to do it and how long it will take me.

Time blocking is a strategy often attributed to professor and author Cal Newport, although similar elements show up in productivity systems like Bullet Journaling or Getting Things Done. I started time blocking without really knowing what it was called, but it changed the way I scheduled and completed my freelance work — and it definitely helped me earn more money.

How long does it take to write 1,000 words?

I have 90 minutes in which to write this piece. I think it will take me closer to 60 minutes, but I added a 30-minute buffer just in case.

I can’t go longer than 90 minutes, because I have an interview scheduled with a source that will take between 45 and 60 minutes, and after that I need to prep and send some invoices and do one more email pass, and then it’s the end of my workday.

That’s how time blocking works.

I’ve known since the beginning of April that I would write this piece on either Monday, April 24 or Tuesday, April 25, so I could make sure to have it done before its deadline of Wednesday, April 26.

I’ve known since last week that I would write it on the afternoon of Tuesday, April 25. Today, I looked at my to-do list and decided that I would give myself between 1:30 and 3:00 p.m. to get it done.

How do I know that it’ll take me between 60 and 90 minutes to write this 1,000-word post?

Because I’ve been writing these kinds of posts for years now. I know that, once my research and outlines are assembled, I can write roughly 500–600 words in 30 minutes. Writing twice as many words should take about an hour, but longer pieces also require a bit more structure, which means I might need a little more than an hour to get everything done.

If you’re new to freelancing, you might not yet know how long it takes you to write 500 words. You might not know how much prep work is required before you can sit down and write a piece like this, or interview a source, or draft a pitch, or send an invoice.

I have the advantage of experience here — but no matter where you are in your freelance career, you can start figuring out how much time your work actually takes to complete.

The three elements of time-blocking

My to-do list is currently scheduled through the end of May — which means I have a spreadsheet that lists every item I need to complete in May, on the day I plan to complete it. (As a reminder: I’m writing this post on April 25.) As the work gets closer, I’ll start planning the time at which each task will get completed as well.

Some people time block by literally setting appointments on their calendar. I used to write time and duration notes next to every item on my to-do list (“The Write Life: 1:30 p.m. to 3 p.m.”) but by this point I can do a lot of my time blocking in my head because I know my typical daily routine. I check email from 9 a.m. to 9:20 a.m., I write two short pieces for The Billfold between 9:20 a.m. and 11 a.m., and so on.

I know that I need to schedule easy-to-complete administrative tasks, like sending invoices, between labor-intensive tasks like writing, researching and interviewing. This gives my brain a much-needed break and still allows me to get things done.

Time-blocking also helps me know how much work I can take on, which helps me maximize my income. Work expands to fill the time allowed, as the saying goes — and if you’re a freelancer it’s really easy to let that work expand to the point that it prevents you from taking on more income-producing gigs.

Right now I’m working on a large, heavily researched project that will come due on May 15. If I didn’t time-block that project into daily segments lasting between one and two hours, I could easily tell myself that my schedule was full; that I didn’t have time to write this article for The Write Life or to pitch a new client.

That’s a money-losing move on my part.

But back to that big project for a minute. When I divide the project into individual time-blocked segments, I don’t label those segments “work on big project.” I write “research and draft questions to ask sources” or “write introduction and methodology section.”

Time-blocking only works when you combine three key elements: what you need to do, when you’re going to do it, and how long you have to get it done.

Rescheduling and time-swapping

Time blocking is not a perfect system.

Maybe a source asks to reschedule the interview, maybe an editor asks for some extra revisions or maybe you start coming down with a cold. Maybe you sit in front of your laptop and realize you don’t know what you want to write yet, or maybe you write an entire piece based on your carefully-planned outline and then decide to throw it out and start over.

So yeah, life happens. Just because I plan to write a specific piece between 1:30 and 3 on Tuesday afternoon doesn’t mean that something won’t happen on Tuesday morning to throw everything else off schedule.

But the great thing about time-blocking is that you can look at your to-do list and your calendar and say “Okay, I didn’t get this done. Where else will it fit?”

Let’s say something came up and I wasn’t able to write this piece today. My deadline is actually tomorrow, which means I have a full day in which to solve this problem. If I need 60–90 minutes to get this done, I could either work late this evening, reschedule some of the administrative work I had planned to complete tomorrow or push back the piece I had scheduled to write tomorrow afternoon.

I could also do a time swap: if my 90 minutes got cut down to 30 minutes, for example, I could look ahead on my to-do list, find a 30-minute task that I had planned to complete tomorrow, and get it done right now.

Then I’d have 30 minutes free for tomorrow, and if I also planned to work 30 minutes late tomorrow, I’d get my 60 minutes back and complete my piece by the deadline.

So that’s how time-blocking works.

Yes, it takes time to time block, so you’ll want to schedule that work into your calendar. (I set aside 60–90 minutes at the end of each month to plan the next one.) But if you can master the art of knowing how long it takes to complete something, you can start planning your freelance day to hit your deadlines, clear your to-do lists, and maximize both your time and your income.

Are you going to try time-blocking? If you’ve tried it before — or if you’re a veteran time-blocker — what tips and advice do you have?