Image by Peter Olexa from Pixabay

I’ve only been freelancing full-time a little over a year, but I’m already making a decent living. If current trends continue, in 2021 I should match or even overtake my salary from my last full-time job.

So I’m successful, even if it doesn’t always feel like it while I’m continually marketing myself, juggling existing clients and projects with new ones, and trying to identify the right digital tools. I get asked for advice regularly, so here are my top tips.

  1. Have a financial plan for the first year. I got a severance package from my job when I was laid…


Image by Jill Wellington from Pixabay

Among the Christmas ornaments I unbox every year are a few handmade gingerbread men, a hole punched through their foreheads with a loop of colorful ribbon threaded through it. My mother made them from balsa wood painted a glossy brown accented with white “frosting,” modeling them after the cookies we made together every year, and sent them out as holiday cards. There’s a cheery holiday greeting penned in silver marker in my mother’s distinctive capital letter print on the back.

My mother adored Christmas, and baking gingerbread men was just one of the cozy rituals she carried out around the…


On Saturday, August 9, Chicago mayor Lori Lightfoot visited the concrete-lined lakeshore just south of Montrose Beach after hearing of a large gathering there. “This reckless behavior on Montrose Beach is what will cause us to shut down the parks and lakefront,” she tweeted along with a photo of the group in question. “It’s being addressed,” she followed up soon after. It sounded ominous. …


The other morning I woke up with the word “plinth” in my head. I couldn’t remember the dream, but the word hung at the front of my consciousness for several minutes. “What a great word,” I thought. The plosivness of the first letter followed quickly by the satisfying conclusion of the fricative. Curious, I looked up its origins — Latin and Greek from a word meaning “tile, brick, or squared stone.” The similarity to the “lith” sound, so common in English today — monolith, Neolithic, etc. — was a clue as to its flinty history.

I like words — I…


While the most severe lockdowns to contain the Covid-19 virus have been easing around the world, for many of us, our usual spheres of activity are still severely limited. It can be hard to find inspiration when you’re walking the same blocks, looking at the same four walls, and talking to the same people (or no one at all) day after day. For people in creative roles especially, it can be challenging to be creative when all of our usual tactics for inspiration are cut off and we feel trapped.

But there are ways to jump-start your creativity that don’t…


black and white silhouette of man at typewriter
black and white silhouette of man at typewriter
waldryano (pixabay.com)

Your company has something it needs to communicate. “We need a writer!” you cry. No problem — there are plenty of writers. Almost too many. How and where do you find the writer with the skills you need for your project?

If you don’t have someone on staff who has hired and worked with writers before, it can be difficult. As a full-time writer at a company where I was also responsible for hiring and managing freelance writers, I knew where to look for and how to recognize writers with the experience and style that aligned with ours. …


CC) Gavin Llewellyn. www.onetoomanymornings.co.uk. Original image at https://www.flickr.com/photos/53682558@N06/6826303487

Recently a LinkedIn connection shared a photo she’d taken of an ad at the airport. I don’t want to ID the company, so let’s just say it read something like this: “We think digital business solutions empower employees and improve collaborative teamwork.” Not being quite sure what the message was supposed to mean, I looked up the business and found that it is a provider of fiber-based digital communication technologies. In other words, its product and services help employees connect with each other and work together using phones, email, the Internet, etc. …


The New York Times Book Review, 12/22/19

Last month the Apostrophe Protection Society called it quits, saying that “ignorance and laziness” have won the battle for the proper use of the apostrophe. I can’t say I blame them, especially when I regularly see the wrong “it’s/its” in such respected publications as The New York Times. While such errors could (and should) be blamed on a lack of copyediting staff (a sad state of affairs across all types of publications as media owners seek to cut editorial costs), it’s actually not that hard to discern between the two. …


Most small businesses and startups don’t have an editorial style guide. By a “style guide” I mean a document that not only outlines style issues such as whether to use the serial comma and how to write numerals in text but also identifies and describes the brand tone and voice. Most organizations will put off creating one, usually because it’s perceived as non-essential.

In fact, a style guide is a vital element of your marketing efforts that should be put in place as soon as you start creating content. It’s not just a boring document that editors and writers like…


One of the challenges content and copywriters face is a misunderstanding of the effort and craft that goes into writing. This is because the best content writing tends to be invisible.

When you’re reading to gain information (as opposed to for pleasure), you’re typically not paying attention to the word choice, cadence, or narrative structure. You’re not thinking to yourself, “My, this blog post on cybersecurity is extremely well-written! Kudos to this illustrious author! I wonder if she has other work I can read.” No, you’re noticing whether you can understand what is being described and whether you receive the…

Heather Kenny

Writer with deep thoughts on writing. Content creation, strategy, and crack editorial skills, all in one package. http://www.heatherkenny.com.

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