First, here's a method that's worked for me at times and when I've been advising and teaching others--when it's tough to get started and keep going:
Think of lists--to-do lists, shopping lists, top 10 lists, how-to-do-it lists, vacation/travel suitcase lists, Christmas present lists, thank-you card lists, party invitation lists, and so on. Each item on those lists might have a lot of meaning, but just writing down the key words helps the list-writer figure out what he or she needs, likes, wants to do, and so on.
Apply that type of list-making to whatever you need to write about. Start with the simple: What's important to you about the topic? What's important to your boss? What's important to the project? What's important in the research? What's important to the audience? And so on. But don't rank or explain anything; just start listing short answers to those types of questions.
Do NOT worry about writing complete sentences at this point. Think of topic headings or book titles or just prompt words, words with symbolic or deeper meaning to the writer.
And don't think of writing the list items in some dreaded outline, as we may have been taught to do in school. In other words, don't worry about the structure of the list--and all those numbers and letters and Roman numerals. Instead, think of it as a bulleted list (the bullets can help separate items from one another).
And once you're exhausted doing that (for now), think about lists that could go below some or all of those original list topics--other bullets that provide more info about each original bullet ... or your brief thoughts or feelings about those original bullets ... or reference sources to get more information about those bullets ... and so on.
Perhaps you'll find that some of those sub-bullets need to stand alone. Pull them out and add them to the original list.
THEN start ranking the list items: What's the highest priority? What's most meaningful? What's most interesting? What's most useful? And so on? Also think about what could be scratched off the list as nonessential (or, at least, set aside for future consideration). If you're writing this list on a piece of paper, simply circle the most important list items--or start numbering them (in pencil--or be willing to cross out numbers). If you're using a computer, save the original list--unchanged--and start moving things around on a copy of that list.
NOW, you can start filling in the blanks--with words that make complete sentences of the list items. And then think about how to organize the sentences into paragraphs or sections or chapters. The original bullets might be sections of a report or paper--the heading or first paragraph--and the sub-bullets could be additional paragraphs. Heck, the bulleted items could actually become bullets in the paper. But don't overdo that--it can start looking tedious and uninteresting to the reader.
Also, if you've ranked list items by number, think of using those numbers in the sentences: First, here's some important information. Second, here's some other information to explain that. Third, here's additional evidence. And so on. Or use transitional words between the list items like "Next," "Then," "Later," "Also" "For example," "Likewise" and so on. That helps you as the writer keep things in order. But more importantly, it helps the reader follow your thought process.
In my original message to my former colleague, I concluded my writing advice with this statement: I'm going to blunder and do something I've told myself NOT to do in other places--I'm not going to proofread or edit my words above; I need to do something else. But there's a lesson in this, too: Tell your colleague not to start judging and revising what he's listed--or even written--until he's done with the list or a section of the document. Just get it out on paper or on the computer. THEN he can go back and start editing or revising it.)
Second, here's a Web page of mine that includes links to other Web pages that provide advice on the writing process and overcoming writer's block: Garbl’s Writing Process Links. It's been a while since I reviewed the links and can't endorse any particular website. [Please note: I learned recently that this Web page is not working properly in Internet Explorer or Opera; it’s working fine in Firefox. I’m trying to fix it and some other pages.]
Third, check out the King County Plain Language Writing Guide. The first two sections--on Reader/Purpose and Organization--can aid getting started. (If you’re interested, I can provide many other excellent online resources about plain language.)
And finally, here are three books on writing that could be helpful, even inspirational. All three are good, but I've listed them in order of complexity, from the simplest and least overwhelming:
- The Little Red Writing Book: 20 Powerful Principles of Structure, Style and Readability, Brandon Royal.
- Writing Tools: 50 Essential Strategies for Every Writer, Roy Peter Clark. Part IV, called Useful Habits, has 11 short sections that can help a writer get started and overcome writer's block.
- A Writer's Coach: An Editor's Guide to Words that Work, Jack Hart. The first chapter, in particular, is about Process and covers getting started and writer's block. But it's all good.