Showing Vs Telling Essay Contest

Ask any writer about their worst writing job — and they’ve got a story to tell.

If you’re a freelance writer for any length of time, some gig will go sideways on you. That’s just how it is.

The key is not to see that worst-case experience as an indicator of your skills, or a referendum on your future potential as a writer.

It’s just…business. Things go wrong. Misunderstandings happen. Everybody has a bad day.

Because so many writers seem to be devastated when they bomb at a gig, I thought it might be useful to collect worst-client stories and let writers compare notes. I thought we could collect them in the comments on this post.

So I’m having a contest! Details are below. But first, I thought I’d kick this off by sharing my own worst writing job stories.

I’ve been at this so long, it’s hard for me to pick an all-time worst writing job. I’ve got five nominees — maybe you can tell me.

  1. The brushoff. One of my first business writing clients agreed to $600 for a brochure — then decided to simply not pay me. “I feel really good about my decision,” she blithely told me. It was the ’80s. Feelings were big.
  2. The blowhard. Was it perhaps the guy who wanted to shout all his instructions to me on speakerphone, while he walked on his treadmill and listened to Rush Limbaugh at full volume? (This was a short relationship.)
  3. The tech-picky. Or maybe the woman who fired me from a Microsoft-contractor writing gig when I told her my home scanner was broken. (“You don’t understand how I need to work,” she told me.)
  4. The scope-creep kings. Then there’s the company that told me they wanted the same sort of blog posts I was doing for Entrepreneur — but turned out to really want posts that were twice as long, in which I ghostwrote for them in the voices of several different team members. When I suggested the fee should be quite a bit higher, they stopped returning my calls.
  5. The non-starter. Finally, and most recently, there was the company who wanted a quality-of-management research report for $3,000. These involve developing hundreds of leads you contact, and getting at least a half-dozen of these former employees of a publicly traded company CEO to tell you what they thought were the business leader’s management strengths and weaknesses. They approached me last summer. I’d done these before, and liked the work.I worked on this for over a month, and couldn’t get one single person to talk to me. None! Total loss. The company was understanding, and nice enough to let me keep my deposit because they knew I’d put in about 80 hours of work on it, and I offered to share my notes so the next writer wouldn’t waste time calling the same no-talkers I’d hit.I felt…awful. I never say die on an assignment — I always keep going and get the job done. And this one defeated me. Did I mention that they courted me for three months before we finally inked this deal? Yeah.

If you were thinking that seasoned writers never have writing jobs go bad, now you know. It happens to us all.

The contest: Tell us your worst writing job stories

Now that I’ve got you rolling, I want to hear your worst writing job stories. Here are the contest rules and prizes!

  • Post your worst client story here in the comments or on my Facebook page.
  • Only one entry per person.
  • Limit 200 words.
  • Contest ends: Monday (January 23, 2017) at midnight Eastern. I’ll come back and post the winner in the comments on Tuesday.

What can you win with your wretched tale of your most awful client ever? Here’s the lineup:

Grand prize: A 30-minute mentoring session with me and copies of ALL 9 of my currently available ebooks.

Runner up 1: A 30-minute coaching call with me plus all 4 Freelance Writers Den ebooks.

Runner up 2: A 30-minute coaching call.

Good luck, everyone! And here’s to great clients to come.

UPDATE: The Winners!

I’m back to announce the winners of this contest. Thanks to all for some amazing stories, and great lessons in what NOT to do. 😉

Grand prize: Esther Copeland, for her horrifying tale of working 1.5 YEARS without pay and being stiffed to the tune of nearly $80,000.

Runner up: Samita Sarkar, who entered on my Facebook page, for her story of the client who turned into a stalker.

2nd Runner up: Lana, for her tale of the client that freaked out over how fast her great post was indexed on Google…and ended up winning a refund through her payment processor, despite all work being done to the client’s satisfaction.

P.S. If you’d like a lot better clients, you might want to check out the free training video featured below:



Tagged with: contest, essay contest, writing clients, writing fails

You’ve heard the classic writing rule, “Show. Don’t Tell.” Every writing blog ever has talked about it, and for good reason. Showing, for some reason, is really difficult.

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Photo by Alan Cleaver

Telling is one of the hardest habits to eradicate from your style. I still struggle with it regularly. However, writing that shows is so much more interesting than writing that tells that it’s worth doing the work.

And the good news is that it’s pretty easy to show if you just learn this one trick.

Be More Specific

The simplest rule to remember if you’re trying to show is just to be specific. Specificity will fill in the gaps from your telling and bring life to your scenes. Let me give you an example of how being specific will help you show.

Here’s a very tell-y example:

They went to New York to see Cats. They both enjoyed it very much. When they tried to go home, their flight was delayed because of the snow so they stayed another night and decided to see the musical again.

That’s a fun story. A great trip to the city could be ruined by the weather, but they make the most of it. It’s all pretty vague, though, isn’t it?  Who is they? What theater did they see Cats at? Why did they enjoy it? How did they feel after their flight was delayed?

To show rather than tell, you have to interrogate your story. You have to be more specific.

Here’s that example with some of those questions answered:

Tanya and James flew to New York city in a 747. They got their bags, took a taxi to their hotel, and checked into their rooms. “I can’t wait to see the show,” Tanya said. “You’re going to love it.” James shook his head. “I don’t get it. It’s about Cats who sing and dance? Sounds sorta dumb.” Tanya smiled, “Just trust me.”

Their hotel was just a few blocks from the Foxwoods Theater so they walked. He had never seen buildings so tall or so many people walking on the street. When they got to the theater, Tanya noticed his eyes were a little wider, his mouth a little slacker. The foyer was covered in gold and white marble, with hundreds of people milling around in gowns and beautiful suits. He didn’t talk much. Finally, they took their seats, and the lights went down. He took her hand.


Let’s stop there. Once you get specific your story can get a lot longer.

But that’s a little better, right? Instead of “they,” we now see Tanya and James. We know a little more about them, that Tanya is a little more cultured, while James is more wary of it. We get a glimpse of the theater.

Interrogate Your Story

There’s still more room for specificity, though, which is why you always have to interrogate your story.

What was their flight like? Why is James so awed by New York? What’s the nature of their relationship?

Here’s another example with some of those questions filled in with specificity:

Tanya and James flew to New York in a 747. Tanya drank club sod and James had ginger ale. “Can I have the whole can?” he said. When they in LaGuardia, James turned to her and said, “Just so you know, that was the first time I’ve ever flown anywhere.”

“What?” said Tanya. “Why didn’t you tell me?”

“I didn’t want you to know I hadn’t left Oklahoma.”

She took his hand and kissed it and held it to her cheek.

“I’ll still love you, even if you are an Okie hillbilly.”

They both smiled and he kissed her.


That’s definitely more specific, but it’s also getting longer. We haven’t even gotten to the theater yet.

I hope you see by now that every story is like an accordion. You can get infinitely more specific, but the consequence of specificity is length. While you should want to be more specific, to show more than you tell, you’ll need to cut the detail that doesn’t add to your story.

Be more specific, but don’t bore us.


Rewrite the following story by being more specific.

They went to Los Angeles to see his parents.

Write for fifteen minutes. When you’re finished, post your practice in the comments.

And if you post, please give some feedback to a few other writers. I hope this is a community that helps each other improve.

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