Succeeding as a Freelance Item Writer: Baa, Baa, Black Sheep

As discussed previously in the Quality Manifesto, the questions on tests are written by freelance item writers. Their name is legion. How can you stand out from the herd?

One or two or six are like me. This odd niche of educational publishing is our bread and butter, our career, our all in all. As to the rest–many work only part-time, some are teachers who write items during breaks or in the cool of the evening. Some are retired teachers. Many are woefully inexperienced and untrained. Some—judging by the errors in their work—adhere to the Sloth Philosophy and dedicate themselves to getting by in life with exerting as little effort as possible. It appears to be a religion with them, and I commend them for their devotion and consistency. Some view item writing as a hustle because they get paid to do something they know nothing about. Says this anonymous (read on, you’ll see why this dime store hustler prefers to remain anonymous) freelance item writer:

That’s right: my side hustle is writing questions for a couple of major standardized tests. … The way that I got hired to write standardized test questions is pretty straightforward: one of my family members works full time for the organization that hires question writers (in the business, we’re referred to as “item” writers) and they circulated an internal email indicating that they were in need of item writers in a few different subjects. My family member forwarded it to me, I sent in my resume, and the rest was history! I was hired and had my first assignment within the week.

Doesn’t it seem strange to you that an item writer is hired knowing absolutely nothing about how to write items when the stakes for tests are so high? Especially when the item writer is tipsy?

I can come home from school, eat dinner, open up a bottle of wine, and crank out a few questions before bed.

What Drunken Dipstick Dimestore Hustler hasn’t considered before clickitty-clacking at the keyboard:

But Drunken Dipstick Dimestore Hustler doesn’t care, because “Whoa! Is This the Perfect Side Hustle or What?!

We can all agree that those stakes are high for children, teachers, and schools. And yet, the test publishing industry at large hires drunken, untrained, unqualified item writers to create the items for the tests. (The client for which I’m doing most of my work these days, a client that has earned Most Favored Client status, cannot be lumped into this category. They don’t hire drunks. That I know of. They don’t hire just any drunk off the street loser inexperienced writer. But–which is so pleasant for me–this client radically departs from the industry at large in many respects. For example. They consistently treat content developers with courtesy and respect and even, on occasion, affection. God bless them, and I mean that sincerely, not in the Southern way.) What these drunken, inexperienced, and unqualified item writers know about professionalism in the workplace would fit in a shot glass thimble. Unfortunately. But without someone to hold the standard, to light the way, to point at the signpost, how are these writers to learn? I don’t think they set out to do bad work. Who rises up in the morning and plans to do a rotten job at work today? They probably all think they are doing pretty good. Truly, we need more mentors in this line of work. More on that another time. What all this means for you, the freelance item writer: I guarantee that if you follow these guidelines, you’ll distinguish yourself from the competition, which can only lead to positive referrals and repeat business. As you read, try not to think of me as the cranky old lady that I am. Instead, remember that this advice is coming from someone who doesn’t carry business cards or, indeed, market myself at all as a content developer. Because I don’t need to. I haven’t had to look for content development work in five years because it comes to me. For now. Listen, if I have to start making cold calls again, I’ll do it. With no shame. It’s just that I haven’t had to.

Seven Steps to Distinguishing Yourself as an Awesome Freelance Item Writer

1. Hold yourself to a higher standard. Don’t be like everyone else. In the immortal words of Samuel Johnson, “What we hope ever to do with ease, we must first learn to do with diligence.” Practice conscientiousness even when no one’s looking. Proofread one last time. Triple-check that the correct answers are correctly indicated. Be sure the title of your Word document is correctly spelled. Check that your fonts are consistent in type and size. Put your items in a logical sequence. Don’t skip steps. Do everything decently and in order. Don’t let yourself slide even when you’re sure no one else will notice. You’ll notice, and it will be bad for your soul and your business that you noticed and you let it go. You’ll lose respect for yourself. When you hold yourself to a higher standard, you develop your character. You inhabit a new identity: that of someone who does things the right way. There’s always a right way. Learn it and do it. In the immortal words of Helen Keller, “When we do the best we can, we never know what miracle is wrought in our life, or in the life of another.”

2. Always go the extra mile. Undertake that next step that you know your editor would have to do if you didn’t. Always provide source documentation just in case, even when no one asks for it. Look up and note the use of above-grade-level vocabulary. Provide another option for a distractor if you suspect there’s even a slight possibility that it’s too attractive. Offer alternative wording if you have any doubt about the stem you provided. Even if the project doesn’t require you to write rationales (justifications) for your distractors, be sure that you have rationales in mind. Your editor may not consciously notice or express gratitude for all the little things you do, but your editor will feel relief or pleasure, rather than dread, when your deliverables show up in the inbox, which means that the editor will be much more likely to call you for the next project.

3. Be part of the solution. In the immortal words of Eldridge Cleaver, “You’re either part of the problem or you’re part of the solution.” Don’t be a problem. Don’t make work for your editor. Your job is to make your editor’s job easier. Toward that end, never introduce a problem to an editor unless you’ve already considered at least one solution, preferably more. Identify the problem and offer the solutions. You may take the extra step and give the pros and cons of the solutions, too.

4. Be self-sufficient. A person who is self-sufficient is one who doesn’t expect to be rescued by others. If you are upset about how an assignment is going, figure out how to make it better or find a substitute developer to take your place and bow out of the project. There are times when you should bail off the wave. Sometimes there will be scope drift in a project without a compensatory increase in pay or an adjustment in the schedule. Sometimes the project is not a good fit with your knowledge and skills. Sometimes you can catch up, but sometimes you can’t. Sometimes there is no way you could have seen the tidal wave coming at you. Part of being a grown-up is learning how to say no and what to say no to. If you’re complaining all the time, stop. What needs to happen for you to have equanimity about your work? Figure that out and make it happen. That’s your responsibility. Don’t expect sympathy from your editor. That’s what friends and family are for. The assignment may be difficult, the templates may be unwieldy, the item authoring system may have eleventy million levels of clickage, and the timelines may be too short. You can always find something to complain about, but don’t. Be a soldier. (At work. Go ahead and seek sympathy from loved ones. That’s part of their job description.) If that’s too much to ask and you’re still going to complain–come on, we’ve all met ourselves before–at least be funny.

5. Accept responsibility. Everyone makes mistakes. We’re all human. Let’s do our best and then accept that we’ll go sideways sometimes. Be graceful when mistakes are pointed out to you. Do this by saying something along the lines of Dang, I didn’t notice that. Yes, that’s a mistake. I will fix it and get this right back to you. Then learn from your mistakes (#6). Making a mistake isn’t so bad, but making the same mistake over and over is both stupid and preventable. You don’t want to be known as the item writer who never fills out templates correctly, or the one who never abides by the style guide, or the one who always writes items with outliers, or the one who always makes a mistake on her invoice (that would be me–I must have some kind of subconscious aversion to getting paid, because try as I might, I’m as likely as not to make some dumb mistake on my invoice). If the mistake is incorrectly blamed on someone else, speak up and take ownership. Don’t let someone else take the fall for your error. You don’t have to explain why you made the mistake. You don’t justify your mistake. Don’t waste time feeling bad, either. Really—and I don’t intend to be mean—no one cares. We all just want to get the work done and move on with our lives, go make dinner or walk the dog or take a bike ride or help the kids with their homework or read Anna Karenina or watch 5 episodes in a row of House of Cards and then take a hot shower and scrub off all our skin in an attempt to purify ourselves from the filth. Life is short, people. Are we really going to consume five minutes of someone else’s precious life by rationalizing what we did wrong? And believe me, I’m preaching to myself here.

6. Be teachable. The possession of a flexible mind is a treasure beyond value. When we’re able to embrace the possibility that we might be able to learn from someone else, we are so far ahead of the pack. The item writers that land on the DNU list share the trait of being unable or unwilling to submit themselves to instruction, suggestion, advice, or, indeed, any form of corrective or constructive feedback. This step applies to all areas of the work. Instead of crossing one’s arms and setting oneself resolutely against a method, strategy, or tool of the trade, how much better it makes one’s life to consider giving new things a go. This step is not always easy for me. I do think I know everything, but I know I don’t know everything. I have vast Grand Canyons of ignorance. Especially in matters of technology, I know very little. And so I consistently find that there is much I can learn from others when I choose, and such learning consistently adds to my skills or otherwise enriches my life. Teaching is a joy, but it takes a lot of energy. It’s exhausting and annoying to teach someone who’s unwilling to learn. Editors are already pressed for time; it’s kind of a miracle if you find one who feels inspired to teach you something you don’t know. Don’t disdain miracles.

7. Become an expert. I don’t know any content developers who don’t consider themselves experts. This is the Lake Woebegone of professions. We all of us like to call ourselves “assessment nerds” or “testing geeks.” Doesn’t it kind of sound like a humble brag that we are so smart, that we love this work, and that we know everything there is to know about assessment? I do it, too, lest you think I’m being judgmental, and Anyone can say anything is what we all need to remember. A high number of years of experience does not an expert make. One can have twenty years’ experience, or one can have a single year of experience twenty times. Without training and without the consistent, dedicated application of the principles and best practices in item writing, a content developer will never become an expert, regardless of the number of years of experience notched on the desk top. I frequently work with and review the items of self-identified highly experienced experts. If I went by their About Mes and their resumes, I’d be impressed and sometimes even intimidated by the breadth and depth of experience they claim to have. But then in comes the pudding. I am shocked by the low-quality work of some item writers who have been writing crap for lo, this many years and they aren’t getting better at the work. An expert has a thorough and unshakeable understanding of the principles and best practices of item writing, and uses this understanding to inform and guide content development. When I review an item written by an expert, I can clearly see the intention underlying the item. The item has a solid premise, a strong focus that aligns tightly to the designated standard, a correct answer that is clearly correct, and three distractors that are plausible but not possible to the student who has mastered the skill. The answer choices are rooted in the text, and there is overwhelming text support for the correct answer, even if the item calls for inference. Moreover, the distractors are based in reasonable mistakes students might make. The item is written at or slightly below grade level, but the sophistication of the item and the cognitive demand are grade-level appropriate. It takes time and hard work to develop this expertise.

We must do it, or we must find another line of work where there is less opportunity to do harm. The stakes for the end user are too great to allow for mediocre item writers. An item writer who is not dedicated to gaining mastery of this domain is doing a bad and—yes, I’ll say it—immoral thing. There are plenty of professions in which one may settle like a warty toad in the mud puddle of mediocrity without actually causing any harm.

As for you, you aspiring freelance item writer who swears to me a sacred oath that you will devote yourself to gaining proficiency and then mastery, the field is clear. If you gain the skills and the knowledge, and if you adhere to the Seven Steps, you will find that you have no competition. At all. Say it with me: in the immortal words of Seth Godin:

I pledge to know more about my field than anyone else. I will read and learn and teach. My greatest asset is the value I can add to my clients through my efforts. I realize that treating people well on the way up will make it nicer for me on the way  back down. I will be scrupulously honest and overt in my dealings, and won’t use my position as a fearless bootstrapper to gain unfair advantage. My reputation will follow me wherever I go, and I will invest in it daily and protect it fiercely.


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  1. Stephanie Quinn Westphal says:

    Your blog is BEAUTIFUL! It’s smart, savvy, and compelling–
    an excellent and needed addition to the blogosphere for
    writers. Thanks for sharing your knowledge and insight with all of us.
    I’m excited to have this new and informative resource.

    • Leslie Hall says:

      I’m beaming AND blushing. Thank you, Stephanie! That means a lot to me coming from you. You know how much I value your opinion.

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