How to Knuckle Down and Do the Assignment You Dread

February 2021
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All of us have had to tackle “the thing we don’t want to write.” 

Whether it’s a recommendation for someone we don’t know too well, a financial report or analysis that bored even the number crunchers who compiled the data, the press release that you know will never turn into a story or the speech that the speaker and audience are both dreading, we have all had this albatross sitting on our metaphorical, or literal, desk at some point in our careers. 

It isn’t fun. But you can survive, and possibly even enjoy the process with a few simple steps.

Don’t procrastinate.

First of all, get on with it. The only thing worse than having to write something you don’t want to is sitting and thinking about how much you don’t want to write it for days, weeks or even months. 

Don’t let this report become the daemon hovering over you day and night. Get started as soon as you can. You don’t have to finish it in one shot (although bravo if you do), but putting a dent in it will help ease your mind. Maybe you work best by blocking out what you want to say. Maybe you prefer to just wade in at the top and figure it out later. Whatever works for you, just do it.

Of course, some more pressing matters may come up that should take precedence. Just don’t fall into the trap of thinking everything should be finished before you even start this dreaded project. As much as it hurts, let some more enjoyable projects wait.

Consider delegating the assignment.

What a great opportunity to find out if your intern, assistant AE or junior staffer can write. Present it as the opportunity it is — you can give feedback on how they do, and give them a chance to show their stuff. Also, they might find an interesting angle or approach that you didn’t.

Think: opportunity.

Instead of thinking negative thoughts, think “what can I get out of this?” Is there an angle or policy you want to highlight? Find ways to accomplish this in your writing. If there is something your company or client is doing that you think deserves more attention, then make it as much of the focus of the piece as you can. 

Break it up.

One of the worst parts of that assignment we don’t want to write is the dread of how long it is going to take. Breaking the project down into bits (or “beats” for theater folk) makes it easier to swallow. 

Give yourself assignments over a few days: day one — structure it and determine the open and close; day two — write the open and close; day three — finish the middle and edit the open and close. 

Again, if you work best by just putting your head down and plowing through, by all means do that. But for most people, dividing and conquering eases the burden.

Look for signs of life.

While you’ll never turn a quarterly earnings release into The Bluest Eye by Toni Morrison, you can find ways to liven up the prose. 

Intersperse questions into the text (“Why did we not expand into China? Well, our numbers show…”). Find appropriate metaphors to break up the flow (“Sales were not the rocket we expected, but they were a steady train heading where we want”). 

If you’re working with numbers, then don’t just list them, highlight them (“Our campaign reached 40,000 people in two hours, enough to fill Wrigley Field and the rooftop seats across the street”). Even if the “powers that be” remove all of these, you will at least have entertained yourself in the writing process. Just ensure you’re not going too far — don’t be goofy, offensive, and don’t make it more fun than work.

Reward yourself.

Whether it’s enjoying a favorite snack, allowing yourself to go down a YouTube rabbit hole or just enjoying 20 uninterrupted minutes with your eyes closed, come up with a treat for finishing each part of the assignment. 

But, be vigilant — don’t go easy on yourself. Don’t have half the donut because you wrote half of what you said you would. If you allotted 30 minutes to watch kitten videos, then set a timer and don’t hit snooze. Don’t tell yourself “I’ll eat the cheesecake now and use that sugar rush to finish.” 

You have to be your own drill sergeant. If that doesn’t work, then appoint someone else to dole out your rewards.

Walk away when you’re done.

However difficult it was to start, don’t belabor the process when you’ve finished. Re-read it a couple of times, but don’t torture yourself rewriting every phrase. Ensure that it’s professional, readable, comprehendible, spelled correctly, and the right length, and then ship it to whomever gets the pleasure of handling it next. It’s done, have your “I finished it” reward and then move on to the next assignment.

There isn’t a magic pill, elixir or spell that will make the most tedious writing assignment suddenly as exciting as skydiving (although hypnosis might). You are going to have to do some work that may not be as enjoyable as other projects — that’s why they’re paying you to do it. But these steps should make the process somewhat less onerous. 

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