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James Chartrand made headlines in 2009 when she outed herself as a woman writing under a pen name. News about the thirty-something copywriter from Canada appeared in Newsweek, Huffingpost Post, and numerous other media outlets. Of course, she’s also known as the owner of Men with Pens, a wildly successful web design and copy agency that publishes a blog by the same name.

Chartrand shared her insights on starting a successful blog, teaching entrepreneurs to write, and earning a living as a creative freelance writer.

Men with Pens was successful even before the big reveal. What do you think is the secret sauce that’s made the blog and the Men with Pens brand so darn popular?

Luck and timing was a good part of it, to be honest. (Yes, I realize I’m supposed to say something smart about how it was all excellent content people were looking for at the time, but hey – like I said, let’s be honest.) The blog began before everyone and their uncle started blogging, so it built up a very strong following in a short period of time.

And also, being named a Top Ten Blog for Writers several years in a row certainly helped!

But all that said, popularity comes from having something special, something different that others don’t have, and I think Men with Pens fits the bill well. I write posts that are bold and strong, that tell it like it is… even when the subject I’m discussing flies in the face of current beliefs.

I think people like that honesty and truth. It’s refreshing to hear someone take a stand or put forth a new opinion. Zig when everyone else zags, as Brian Clark would say.

Certainly, the advice, expertise, counsel and general good stuff on Men with Pens is… well, good! Everything I write and discuss is geared to help others get ahead and do well in business. You can’t go wrong with that.

Your class, Damn Fine Words, teaches entrepreneurs how to get results from their own copy. Are you afraid you might be teaching yourself out of a job?

Nope. I’m confident of my skills, abilities and expertise. And quite frankly, if someone does apply everything I teach and ends up a successful writer because of it, fantastic! Competition is a good thing, because it continually keeps you on your toes, working towards improving what you offer.

Plus, it’s a pretty awesome situation when a successful person can say, “I owe it all to Damn Fine Words.”

Keep in mind too that while my job is writing, it’s also now teaching – I can’t teach myself out of that job, because I’ll always continue to gain experience and skills that I can transfer to others through Damn Fine Words.

And should I ever find myself with less writing work? Fantastic! That just gives me more time to teach and make Damn Fine Words a powerful language university… which is a good thing. People need this.

When should someone use DIY copy and when should they hire a professional writer like you?

When someone knows the skills and techniques that go into creating professional-level web copy. And sadly… most don’t have the skills or knowledge to write their own copy.

I find this a serious problem. Business owners have a huge need for great copy and content, whether in an online context or an offline one. And when they try to skimp and write their own without having the necessary skills… well. Their businesses struggle. Or even fail.

And these are good businesses! Businesses with dedicated owners and brilliant products and services! But if they can’t communicate properly, in a way that gets their message out there, then it’s game over.

That’s why I feel Damn Fine Words is so important – it gives business owners the tools and skills they need to reach better success. And what it teaches them stays with them for life.

Aside from dealing with gender bias (which, as we know, you overcame by using a male pseudonym), what other freelance or self-employment challenges have you faced and how did you overcome them?

Here’s a huge challenge for almost all freelancers and small business owners: the famous feast or famine cash flow cycle. I’ve been very fortunate (and made sure I never got caught on that roller coaster ride!) but I hear people complain about it all the time: When things are good, they’re very, very good.

When things are bad, they’re horrid.

I avoided the feast/famine cycle by learning how to properly manage my business cash flow into a smooth, steady stream of income. I marketed when times were slow – and when business was booming. I learned relevant skills and branched out my services. I put together a solid team and increased productivity and efficiency.

And I learned about money – how to manage it, save it, and use it effectively to grow my business.

What mistakes or faux pas do you notice most often in online content?

Where should I begin?

Look, anyone can write. We’re all taught the basics in school. But writing for your business in an online environment means you need to know more than the basics. You need to be more than a good writer.

You need to know about sales. And marketing. And consumer psychology. And behavioral psychology (for those times when you just can’t write). And all sorts of other fields of expertise that people constantly think have nothing at all to do with writing.

They do. They have a lot to do with writing.

So most of the writing I see online just… isn’t very good. It’s nice to read or tells a good story, but it doesn’t drive business or encourage readers or create action or build success. It’s just… there. A nice read.

That’s just not effective for business results. Which is why I created Damn Fine Words.