Do Not As I Do….My Top 10 Most Embarrassing Freelance Writing Moments


We talk a lot about the importance of being professional, but I’d be lying if I said I didn’t make some gaffes once in a while. I don’t think I’m alone, either. Plenty of freelance writers have unprofessional and even embarrassing moments. I’ll bet even some highly paid best sellers did a few things that don’t make them very proud. While they’re usually inadvertent errors, it doesn’t make them any less embarrassing.

Can you relate to any of these?

My Top 10 Most Embarrassing Freelance Writing Moments

10. Pretending I knew how to do something I couldn’t

Several years ago, I was offered a very lucrative deal – to create a couple of ebooks. My client asked me if this was something I could handle and I said, “of course.” The truth is, I didn’t know a thing about writing or formatting ebooks. After sending in the first few chapters my client asked me if I really had ebook experience. When I confessed that I didn’t he said he still would have offered me the ghost writing part of the project, but he would have hired out the formatting part. I admitted I didn’t want to lose the gig and we laughed. I ghostwrote several ebooks for this client but never had to format a single one.

Lesson learned: Honesty is always the best policy, especially with established clients.

9. Not proofreading the blog

Not a day goes by that someone doesn’t send me a letter complaining about my lack of proofreading on this blog. I tend to write in a hurry and post without going over my work. I know blogs are supposed to be less formal and we’re supposed to write the way we talk and all, but freelance writers want their freelance writing bloggers to take care with their blog posts. Eventually, I’ll hire an editor to handle that sort of thing, but until then I’ll try my best not to post and run.

Lesson learned: Proofread the damn blog already.

8. Didn’t change the info on a form letter

When I first began freelancing, I naively had a one size fits all, cookie cutter cover letter. I sent the same pitch to the different editors and potential clients. You can imagine how well that went over.

Wait for it, it gets better.

A couple of times I also forgot to change some of the info on the form letter. For example, I used the wrong editor’s name or didn’t name the correct publication or website. One editor called me on it and I was mortified.

Lesson learned: The obvious lesson is to proofread the cover letter. However, during my conversation with the above-referenced editor, she hinted at the importance of creating a pitch tailored to each individual market. It was an important lesson for sure.

7. Got sick before a speaking engagement

A few years ago I was invited to speak at a conference and some members of the FWJ community were in attendance. It was my first ever speaking engagement and I was overtaken by a case of nerves. I spent the hour before my talk in the stall of the rest room losing what little food I managed to eat that day. People came and went and commented about the woman in the stall. Some hinted at a night of drinking the night before. I felt awful, not only because of my nervous stomach but because I was embarrassed. Some of the people who saw me in the ladies room even attended my session, and one nicely offered me a breath mint. The talk went fine, but knowing people knew I was upchucking right before, or that I could lose what was left in my stomach at any minute, didn’t make it any better.

Lesson learned: No lesson here, sorry. I still get attacked with nerves before speaking but fortunately it’s not as bad. I have to no hard and fast lesson for potential speakers and that picturing people in their underwear thing never worked for me.

6. Didn’t take the time to read the guidelines before querying

You know how I talk about how important it is to read all the instructions and guidelines before querying or applying for a gig? I learned that lesson the hard way. I remember once applying for a job I felt was perfect for me. It was on a personal finance topic at a time when I was the go to person for these types of topics. When I received a thanks but no thanks letter, I swallowed my pride and asked the editor for feedback. She said she enjoyed my writing samples and thought I showed promised but I didn’t give her what she asked for. There were specific instructions and I didn’t follow them.

Lesson learned: Follow instructions. Also? Don’t be afraid to request feedback. Editorial feedback is valuable and every writer needs it to succeed.

5. Posted the wrong post on the wrong blog

Several years ago I blogged for about a dozen different clients. This meant twelve different dashboards and log ins and every now and then I got a little confused. Once or twice I even posted the wrong blog post to the wrong blog. While I usually figured it out pretty quick, I wasn’t quick enough for the feeds.

Lesson learned: Kind of obvious, but I’ll put it out there anyway. Pay attention to what you’re doing, proofread, don’t mix up clients, etc., etc., and etc., again.

4. Sent the wrong email to the wrong person

I hate that gmail thing that suggests addresses as you type. For example, once I was contacting someone with a very common name and sent the email to someone else with the same first name. The email was detailing a possible collaboration and the recipient was so excited I contacted her.  Telling her the note was sent in error was one of the hardest things I ever had to do.

Lesson learned: Don’t let gmail suggest email addresses… OK… and that proofreading thing too.

3. Didn’t proofread a query or cover letter

There was a time I felt freelancing was a race – a race to get to clients first before the competition. Remember the cookie cutter cover letters? In addition to those, I sent out some hastily put together cover letters. Once or twice after not hearing back about a particular gig, I reread my cover letters and found a typo or two.I don’t think I need to tell you I’m the worst proofreader possible. That doesn’t fly without potential clients, however. They want to know I’m going to take care with their projects and turn in clean work each time.

Lesson learned: Proofread, proofread, proofread.

2. Queried the wrong editor

I remember the first time I queried a wedding publication. I went to the library and looked up several wedding markets in the Writer’s Market. I didn’t have a laptop at the time and jotted the details down on paper. When I came home I sent out what I thought was a killer query. The problem? I sent the query to the right magazine but addressed it to the editor of a rival publication. The good-natured editor sent me a note back asking if I meant to query her publication. I apologized. (I do that a lot apparently.)

Incidentally that editor rejected my query because they were about to publish something similar, but I did land a successful assignment with their online edition a month later.

Lesson learned: Stuff happens. Own up to it, apologize and do your best to salvage the relationship.

1.  Sent in the wrong draft

I always keep two drafts of my projects – one on an external hard drive or flash and one on my laptop’s hard drive. This way if something happens, I’m covered. My most embarrassing freelance writing moment happened when I landed an assignment I really wanted. I worked hard on this one. It was my highest paying gig yet at the time and I wanted to continue working with this client. So what happens? You guessed it, I sent the wrong draft – an unfinished work in progress. The good news is that I caught it before my client and sent the right draft before he could wonder what I was smoking.

Lesson learned: Read before sending, and, also, if saving two drafts always save the most current copy to both places at the same time.


6 responses
  1. P.S. Jones Avatar

    As someone who is in direct competition with you for the worst proofreader, I thoroughly enjoyed this post. I smiled a lot and made a note to be a little more diligent myself.

  2. Anne Wayman Avatar

    Sorry, I’m the worst proofreader… of my own stuff or anyone else’s — I hire editors, but not for my blog.

    Frankly, the folks who have time to pick apart my blog or yours, Deb, should probably be doing something else.

    I love this post… I’ve made every single one of these mistakes – every one. And like you I’ve not only survived but thrived.

    Good thing we’re human is what I really think.
    .-= Anne Wayman´s last blog ..Some Authors On Valentines Day – Videos About Writing =-.

  3. allena Avatar

    You could hire a proofreader. I have one. I mean, I can’t afford to pay her for 24/7 vigilance, and sometimes my readers get to it before she does, but overall it’s been a great experience.
    .-= allena´s last blog ..The Freelance Writers Money Conundrum =-.

  4. Christopher Avatar

    I’m the same way when it comes to proofreading. I haven’t had the pleasure of experiencing some of these but I can definitely relate to the proofreading thing. Most definitely.
    .-= Christopher´s last blog ..Happy Valentine’s: Make a Difference =-.

  5. Sharon Avatar

    Why be embarrassed? These are nuggets of wisdom from which others can learn. Remember the old saying ” ’tis an ill wind that does no one any good.”

  6. Christina G. Avatar
    Christina G.

    Great Posting Deb! I can relate to the cookie cutter cover letters. I thought all you had to do was write one awesome cover letter and the clients would flock to you. I can hear some of you snickering already, but a lot of us were taught that way! When the clients weren’t flocking I had to research what I was doing wrong. I started reading all the writing blogs and going to various forums and found out. When I did, I seriously wanted my money back from my writing instructors who only taught me only half the story about becoming a writer. Thank God for people in the business who tell it like it is.

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