Apostrophes sort of resemble elusive, wriggly creatures, and in a sense, that’s what they are. Apostrophes often worm their way into plural nouns where they don’t belong, and the English language will always have writers who mix up your and you’re and its and it’s. But in the past two decades or so, apostrophes have a new trick. They’ve learned to flip themselves upside-down.

For example, take a look at the apostrophes in this movie poster…

…on this greeting card…

…and on this ironic T-shirt.

These three phrases indeed need apostrophes to signify that letters or numbers are omitted. Yet, the punctuation marks in these examples are not apostrophes. They are opening single quotation marks.

Microsoft Word is at fault for this state of affairs. The program has a feature called “smart quotes” which automatically creates curly quotation marks when it senses the user is writing a quotation. The problem is that the program cannot identify a word beginning with an apostrophe. When the user has smart quotes turned on, Word will instead render a curly single quotation mark, and only attentive, tech-savvy writers know to correct the program’s correction.

The problem has become so entrenched that many people aren’t sure how an apostrophe is supposed to look. Flipped apostrophes now show up in handwritten signs and on embroidered caps where Word’s autocorrect feature holds no dominion. Case in point: in 2005, the Baltimore Orioles came out with a logo marred by a flipped apostrophe.

As a Baltimore Sun writer notes, the Orioles haven’t had a winning season since 1997. She interviewed the ESPN blogger who publicized the Orioles’ mistake and asked him if he thought there was a connection. He said, “I do think the same management approach that results in lousy baseball can also lead to lousy grammar and lousy typography.”

An article on Slate yesterday adds valid new points about the problems with Word:

Like the fax machine, Word was designed to put things on paper…That’s great if you’re making a lot of church bulletins or lost-dog fliers. Keep on using Word.

…For most people now, though, publishing means putting things on the Web. Desktop publishing has given way to laptop or smartphone publishing. And Microsoft Word is an atrocious tool for Web writing. Its document-formatting mission means that every piece of text it creates is thickly wrapped in metadata, layer on layer of invisible, unnecessary instructions about how the words should look on paper.

I must agree. I’m writing these words in Word, then I’m pasting them into an online tool to scrub all the junk that the program adds on.

It’s an extra step and a waste of time. The problem is most other word processors (like the one built into this WordPress site) are too bare bones, but Word is overkill. Maybe one day, something will come out, by Microsoft or another company, that hits the sweet spot somewhere in between.

Proponents of plain language assert that the jargon, legalese and general unintelligibility of government documents are part and parcel of the bureaucratic red tape that everyone finds frustrating. A group called the Center for Plain Language encapsulates the movement’s populist mission with its motto, “Plain language is a civil right.”

At a time when revving up the economy is a top political priority, businesses large and small suffer when they can’t figure out how to comply with regulations. Confusion frequently forces them to purchase “translation” services from lawyers and accountants. On the other side of the fence, government agencies waste resources trying to explain policies to citizens and businesses that online and print documents could do on their behalf if the writing were comprehensible.

Why is government writing so poor? One reason is because government workers in specific areas naturally develop jargon for professional use (as do specialists in many fields). This jargon is not decoded for the public. Also, when the civil servants who draft documents add in special-interest exceptions, CYA-digressions, and voluminous reams of legalese, concision is obliterated.

Fundamentally, writing clearly and concisely takes effort; it isn’t easy. The federal government is trying to deal with the problem. It recently published a set of plain language guidelines, which were created to support the Plain Writing Act, passed in 2010. The act requires federal agencies to write all new publications intended for the public in a “clear, concise, well-organized” manner. Now working its way through Congress, another bill called the Plain Regulations Act of 2012 will strengthen plain language requirements. Nevertheless, any citizen without legal training trying to read either of these acts (PDFs here and here) will find them quite difficult to understand.

Many freelancers are reluctant to reach out directly to prospects and prefer to rely on more passive marketing methods such as word of mouth and social networking.

Sure, it’s great when unexpected clients come my way, but I find there’s no substitute for making direct overtures to the people and companies I want to work with. That means sending e-mails to strangers and, yes, often picking up the phone and calling them.

On one of my calls, something serendipitous happened. I didn’t find work. Instead, I found a mentor.

It began when I was writing a report for a market research firm. When doing my background work, I happened upon a website that invites consultant-panelists to contribute their comments on issues that were relevant to my topic. I phoned one of these consultants—I’ll call him John—to give me some insight into what I was writing. As a source, he was smart, insightful and helpful. I quoted him in the report.

The core of my business is marketing copywriting, but one market I’ve been exploring is doing writing for consultants. I’m looking to help them with projects such as white papers, case studies, and thought leadership articles, which I already do for clients in other industries. After that market research report project had ended, I called John to present my services to him.

Nothing came of it at first. I keep track of every time I call or e-mail a prospect, and my early notes on John indicate that he didn’t have much of a need for my services but still showed some mild interest. That reaction happens often, and in these situations I simply move on to the next prospect but try to make a point of following up every few months or so.

One day, John was on my list of follow-up calls. Like most times, I was expecting to leave a voice mail or to have a quick conversation if my contact picked up. But after John answered, he began to ask me questions. We didn’t talk about what writing projects he might want to hire me for but instead about what characterizes good writing and communication in general. Our conversation ended up lasting a full hour. Later, John e-mailed me some websites to critique, and we discussed my opinions on a call some days later.

At the end of that call, we scheduled another one, and then another. For over a year now, John and I have developed a pattern in which we talk around every five or six weeks. We start each session with a few minutes of friendly banter and then get down to business on our topics of the day.

What are these topics? As already mentioned, we’ve discussed the characteristics of good communication. He’s also given me business advice. We’ve talked about ways I can present myself as someone who solves client problems, not just as someone who handles writing projects. We’ve discussed how I can sell my services through conversations instead pitches. He’s illuminated these points by describing his own client-acquisition process, which takes a long view instead of going for the quick sale. Our conversations can also be rather philosophical and free-ranging, touching on topics like human relations, empathy, and the nature of wisdom.

Considering that he seems at least a little older than I am and that he is one of a handful of partners in a firm of 200 people, he seems well positioned to give me advice. I’ve said I think of John as somewhat of a mentor, but I’m not sure if he’d describe himself in that way. We often delve into subjects that are important to him or relate to projects he’s working on. He seems to value my insight and opinions. In some ways, he might consider me a peer.

One thing John is not (at least not yet) is my client. John is more of a friend now than a prospect, so I feel it would be out of place for me to press him for work.

I continue to follow up with the quality prospects on my list and reach out to new ones. In these efforts, I often send quick e-mails for efficiency’s sake, but every so often I make a point to pick up the phone and call. If I keep an open mind and look for opportunities to engage with the other person, I know that I might have a conversation that leads somewhere unexpected.

Has anything like this ever happened to you?

Even if you’re never been on a diet, you’ve most likely noticed 100-calorie snack packs on store shelves. In this selling tactic, a food manufacturer will take a brand of chips, cookies or crackers and package 100 calories worth of them into a small bag. Although this food trend is probably past its peak by now, these snack packs still sell very well. Their success is rooted in dieters’ struggle with self-control, and considering that many of us self-employed creatives have difficulty staying focused in our home offices, snack packs can teach us a lesson about willpower and productivity.

Hundred-calorie snack packs are not a good deal in objective terms. According to Consumer Reports, consumers are paying 16% to 279% more per ounce than if they purchased the same product in standard bags or boxes. “If you can buy snacks in their regular packages and use an ounce of willpower, your wallet will stay fatter,” says the magazine.

But apparently that “ounce of willpower” is hard for some people to come by. Shoppers who pick up the snack packs undoubtedly know they are paying more than they need to, but what that extra cost ultimately buys them is portion control.

External controls can help people stick to their goals, whether that means eating less or focusing on work. As a self-employed writer, I understand that the more I work, the more I get paid. At the same time, I can find myself tempted by distractions. So over the years, I’ve developed a number of tricks to help me shore up my willpower and stay focused on what I need to do:

• Track time – I track all the time I spend on my business using an online service, whether or not the time is billable. Whenever I take a break, I clock out. I’ve set goals for a certain number of hours to work each week and run a report every Monday to see how I did.
• Write detailed task lists – When I have big project or just find myself struggling to get started, I take the time to write up a list of small tasks and then gain a sense of accomplishment each time I check off a completed item.
• Use the Pomodoro technique – I’ve been experimenting with this productivity strategy and have never been able to do it all day long (and am not sure I’d want to), but sometimes it does help me get into a productive groove. Basically, thePomodoro technique has you work in 25-minute increments broken up by five-minute breaks.
• Keep a “distraction dump” – When I’m working and I feel a sudden urge to check Facebook or look up something pointless on Google, I note that urge in a little book I keep on my desk. Simply writing it down can make the urge go away, and if it doesn’t, I’ll take care of my curiosities during a break.

The list of my little tricks goes on. They won’t work for everyone, and truthfully they don’t always work for me. My processes are always changing. But generally speaking I find that if I want to remain productive, willpower alone won’t cut it. I need to develop an external structure for my workday.

To an outside observer watching me work, my productivity habits might seem overly complex and even counterproductive. For example, someone might argue the process of writing down lots of little tasks simply to check them off is waste of time. Sure, maybe it is a waste of time. Then again, 100-calorie snack packs are a poor value. Whatever works.

Since 2006, more than 800 new products have included the word on their packages, according to Datamonitor, a market research company that tracks such things. Granted, food companies routinely latch onto trendy words. “Organic” has been a major one in modern times, but at least organic products must meet certain standards to make that claim. Not so with artisan. Marketers simply stick the term on a package when they wish to signify that the product is higher quality than its mainstream counterpart and (it goes without saying) more expensive.

Starbucks stocks so-called artisan breakfast sandwiches, Tostitos hawks an artisan line of chips, and Fanny May offers artisan chocolates. Even Domino’s Pizza sells artisan pizzas, notwithstanding that Domino’s is basically a form of fast food and fast food is the opposite of artisanal.

Domino’s at least seems a little embarrassed about its claim. The box for this pizza announces, “We’re not artisans,” in an old-timey font, and the copy begins, “We don’t wear black berets, cook with wood-fired ovens or apprentice with the masters in Italy.” Even so, the writing goes on to assert that the pizza in the box still deserves the artisan label. Domino’s basically wants to have its pizza and eat it too. Admitting that it’s incongruous to call assembly-line food the work of artisans doesn’t excuse the claim from being absurd.