What To Do When a Writing Assignment Seems Overwhelming

Big, hairy, long-form writing tasks can seem daunting, but they can be controlled with some planning

I stepped out of an insurance adjuster’s job into an organizational communications role on the basis of having sold one article and having won a national essay contest. I was the only “professional” writer to apply for the job. After I moved into my new office, the excitement turned to abject terror. I had no idea what I was doing.

Big, hairy writing tasks are scary even for experienced authors. It’s daunting when we are faced with researching and writing a book-length manuscript, tackling a major marketing campaign, or juggling a multi-deliverable communication project. Suddenly, that blinking cursor on a blank word document looks like an enemy sighting us in their crosshairs.

Long-form writing is challenging, especially if we’re used to writing work that is less than a few thousand words. A novel or non-fiction book often is well in excess of 50,000 words. Even a 10,000-word investigative piece for a major publication can be daunting. Unlike high school when we could pad our writing to reach the mandated word length, professional writing means that every word must serve a purpose.

I spent more than 20 years writing nonfiction books and writing and consulting with organizations to manage large communication or marketing projects with multiple moving pieces, legally-enforced language requirements and distribution deadlines, and, sometimes, the need to have some materials translated into more than a dozen languages.

The keys to surviving any big, hairy writing job are organization, self-confidence, and an Excel spreadsheet or project management software. The following steps are based on using an Excel spreadsheet and have been my go-to process throughout my career for writing and managing long-form content and projects.

8 Steps for Managing Large-Scale Writing Jobs

You can’t cross a football field in one step, but you can when you take one step at a time. This also is how you tackle large writing challenges whether you’re writing a book, a manual, a multi-part communication campaign, or a major article. Success relies on your ability to maintain control of all the moving pieces at all times.

Break up large writing tasks into small, actionable steps.

1. Brainstorm

Brainstorm every major task that must be accomplished for you to produce the final product. This can include planning the contents, researching, organizing, writing, subject matter reviewing, revising, proofreading, designing, distribution, and more.

2. Create a spreadsheet

Set up an Excel spreadsheet by creating a major category for every task you listed above. This is the X-axis. The Y-axis is a timeline, starting with the deadline for the final product and working backward to today’s date.

3. Break down tasks into individual steps

Break down each major category of a task into the steps you need to take and estimate how much time each step will need for completion. Generally, if you’re new to writing major projects, you will underestimate the amount of time you need, so I always recommend upping the estimates by 25%.

4. Schedule reviewers

Keep in mind that most organizational communications require reviews by subject experts, legal departments, and compliance. This can take a toll on the schedule. It’s always best to line up reviewers ahead of time and let them know when to expect the draft for review. In organizations, this process can involve several rounds and may require you to negotiate conflicting comments from reviewers.

5. Enter every step from start to deadline

Enter each step on the spreadsheet under its corresponding major category in sequential order starting from the deadline for completion of the step to today’s date.

For example, under “Research”, the following steps will be listed starting with the step closest to the deadline and ending with the task that must be started first: verifying sources and references, choosing information to be included, transcribing interviews, preparing questions, setting up interviews, tracking down subject experts, and identifying credible sources, which is the first step to take now. You will work your way up the list, crossing out each step as you complete it.

6. Show start and end dates

Using the Y-axis, show start and end dates for each step. You will begin to see where certain steps overlap and must be worked on simultaneously and which steps must be performed sequentially.

7. Establish critical dates

Establish critical dates, which are necessary when you are writing to a deadline. Critical dates are dates when you must have a task or major category completed before you can move on to another task or category. They are full stops for the entire project. For example, a critical date may be the day that you must finish research and interviews for a section in order to start organizing it. Missing a critical date can jeopardize meeting the deadline.

8. Set milestone dates

A milestone date is a date you finish a major portion of a category or an entire category. For example, it could be the day you finish the first draft. Milestones also serve as motivators, so set more than one —for example, set milestones for the days that you finish 25%, 50%, and 75% of the first draft.

Unlike critical dates, missing a milestone may not affect the deadline date. Reward yourself when you hit milestones. The key is to celebrate and recognize each achievement as you move through the writing task.

After your spreadsheet is completed, use color-coding for each major category, so you can easily see at a glance where you are in the project.

“Overwhelm is, most often, a mindset. If you think about all the things you have to do, you’ll be face down on the floor. It really helps to break it down into smaller pieces.” — Jen Sincero

Big Hairy Writing Jobs Lead to Big Hairy Income

If you are able to manage and deliver major projects, you open the door to higher-income assignments, especially for organizations that don’t have sufficient internal staff to handle them. If you can present strong writing and professional project management skills, you have a foot in the door to this type of writing.

When I left my corporate communications job, I consulted with financial institutions and insurance companies — my career industries— and managed communication projects for them, just as I had for the bank, but with a much bigger payout.

If you aspire to write for major publications, you may have to work your way up the food chain by tackling longer pieces for lesser publications. This lets you practice managing large assignments and grow your influence with readers before you approach the larger publications.

My system may not become your system. Your system for writing and organizing may be different from mine, but there may be tips and tools that you can adapt for your own use. Check out this system from Jeff Goins.