Freelance Writing Coach Podcast Season 5 Recap

My friend and fellow freelance writer Emma Siemasko and I have been talking about all things freelance writing on our podcast, and season five just wrapped up.

If you’re a freelance writer (or thinking about becoming one), this podcast is for you. This season, we talked about things like client boundaries, how much to charge for different services, managing overwhelm, and lots more.

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I Changed My Mind About Public Speaking

For many years, I’ve resisted speaking gigs. In fact, I’ve even taken a stance against conferences in the past.

I haven’t raised my hand for opportunities to be on stage and always preferred to stay in the background, working behind the scenes.

I recently read this in Glennon Doyle’s book Untamed, and it rang true for me in a big way:

“I am a sensitive, introverted woman, which means that I love humanity but actual human beings are tricky for me. I love people but not in person. For example, I would die for you but not, like...meet you for coffee. I became a writer so I could stay at home alone in my pajamas, reading and writing about the importance of human connection and community.”

Aside from introversion, the other reason I haven’t thrown my name in the hat for these opportunities is because public speaking made me NERVOUS.

Like: Can’t eat, can’t sleep for days before the thing nervous. I once was so nervous before a speaking gig that my shaky hands spilled steaming hot coffee all over my pants (thank God they were black.) Now my family refers to the nervous version of me as “ol’ coffee pants.” Sigh.

BUT! Last November, I was hired to present a 60-minute session (in person) to a marketing agency in New York. The topic was based around an article I’d written for Vogue Business, and they brought me in to dive deeper into the topic and facilitate a brainstorming session for a small group of their employees and clients.

Needless to say, it felt *very* grown-up and serious. So I went into my default mode and planned everything I could to eliminate stress-inducing anxiety.

  • I built out my slides and made notecards of my talking points.

  • I picked out the perfect outfit. And coat. And shoes. And accessories.

  • I booked at a hotel across the street and arrived the night before the event to eliminate travel friction.

All of this seemed to help, except for the part when I got to the airport and realized I didn’t have my driver’s license on me. I’d left it in a pants pocket back at home, 90+ minutes from the airport.

I was able to fly after waiting for an extra-thorough security check and an overnighted passport (thanks, Dad.) So…yeah. Close to covering all my bases to make things go smoothly, but not quite close enough.

Anyway: I made it there. I was the first speaker the next day, so I walked over early that morning (as in: I was there before the organizer was) and got my slides set up before hiding in the bathroom for a few minutes to collect myself.

A pic from that morning

Ready to go!

When I came back to the meeting room, people were filing in, and I grabbed a cup of hot tea (that I didn’t spill!) and waited up by the front of the room where my slides were.

And guess what?

  • I didn’t feel nervous.

  • I felt calm.

  • My hands didn’t shake.

  • My breathing was normal.

  • I wasn’t sweating through my clothes.

  • I didn’t have a splotchy red rash creeping up my neck.

It was the strangest thing.

I gave my presentation, pausing along the way to answer questions and pursue tangents based on the conversation the topic sparked. People nodded while I was speaking. I felt myself getting more comfortable as I went on, speaking with my hands and my face getting more animated.

I felt…confident. Sparkly. Like I really knew what I was talking about (I did) and that people in attendance were interested in what I had to share (they were.)

was the expert in the room, and it felt really good. No more Imposter Syndrome. At 33, I finally felt self-assured enough to realize: I can do this. Not only that, but I’m good at it.

So guess what?

I’m changing my stance on public speaking and attending/speaking at conferences.

This is the year I’ve decided to lean into getting on stages and adding my voice to teach what I know. It’s time for me to get over this mental block that speaking is something that’s “just not for me.”

The reality is: It’s not that I don’t like public speaking. I was just scared. I was very much in my head about it. And that limiting belief has held me back for years.

I’ve already got a handful of events lined up for the coming months so far, including the Creator Economy Expo in Phoenix, an eCommerce event for women in LA, and the Retail Innovation Conference in Chicago. (Please let me know if you’ll be at any of these…I’d love to say hello!)

I also want to put it out there: If you hear of a conference looking to add female voices to its speaker lineup (so…most conferences!) where you think I’d be a good fit, please send it my way or pass my name along. I’m doing my booking in a very DIY fashion right now with no formal speaking agent, so it really takes a community effort to spread the word I’m doing this now, you know? I’d super appreciate that.

I Hired an Editor. Here's Why.

spend a lot of time editing these days. I mean…a LOT.

Whether it’s a draft or an outline from a subcontractor, a podcast write-up for our side business Content Remix, or just a final read-through on a super long-form post, the reality is: I’ve been spending hours each day staring at words on a screen.

After experiencing some burnout and feeling overwhelmed, I decided it was time to outsource some of the heavy lifting when it comes to editing.

The reality is: When you’ve stared at a piece for a long time, your eyes kind of glaze over. You’re too “in it” to see the content with fresh eyes and a sharp mind.

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How to Break the Fourth Wall in Writing

Today, I'm going to teach you an easy way to help your writing connect with readers.

You know how sometimes you’ll read something and it comes across as stiff, overly formal, or stuffy?

It happens a lot (especially in the business world.) The cure for this situation is to break down the walls between the writer and the reader so there’s a deeper feeling of connection, emotional resonance, and an overall more conversational tone.

This type of writing is far easier to read (and it’s much more memorable.)

I was recently reminded of a brilliant way to accomplish this: It’s called breaking the fourth wall.

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The fourth wall is a term that comes from the acting world, referring to the fourth “wall” that actors pretend separates them from the audience. When an actor directly addresses the audience, it’s called “breaking the fourth wall.”

But this isn’t limited to visual formats.

In writing, you can also break the fourth wall by speaking directly to your readers. Sometimes these are called “asides” or “authorial interjections." It often means the writer pauses one thought to hop in with his or her internal monologue, directed at the reader.

Here’s an example: “I love living in New York. (Well...only the East Village. I wouldn't be caught dead signing a lease in Midtown). The culture and excitement here can’t be beat.”

See how the original thought is broken up by a peek at the writer’s thoughts and feelings? It’s essentially a cheat coat for more conversational, natural-sounding writing.

Of course, you can’t use this tactic just anywhere. There are pros and cons to deploying it (as there are with most things!)

Pros of Asides in Writing

  • They help stress important ideas/provide a deeper understanding around the complexities of events or concepts

  • They help illuminate the writer’s thoughts, feelings, or opinions

  • They allow the writer to reveal something they want the readers to know

  • They make the reader feel personally addressed

  • They allow the writer to advise and act as a guide for readers

Cons of Asides in Writing

  • If done too subtly, they can go unnoticed or be interpreted as sloppy, unfocused writing

  • They can sometimes disrupt the pacing of your writing, thus hurting overall readability

  • They can seem clumsy or awkward if correct punctuation isn’t used

So...how do you do it right? There are a few easy ways:

First person

In the first person format, the writer is already relaying the story to the reader. This means addressing the reader in a slightly more direct way can happen naturally.

Example: I'm always running late for work. In reality, it's because I oversleep, but I tell my boss it's because of terrible traffic. Added downside: I'm always left with the final grainy dregs in the break room coffee pot.

Using asides while writing in first person helps the writer create a feeling like putting a hand on the reader’s arm to say: “Here’s what I really think about this”, or, “Here’s what this really means.”

Em dashes, parenthesis, and footnotes

Interjecting a sentence with a thought inside em dashes or parentheses makes it easy for you to briefly re-direct the reader’s attention to a point you want to make or a piece of information you think he/she should know.

Example: Micheal roamed down the street, his shoes tripping along the rough stones. His ambling, slow pace was unusual to the people watching from balconies in his neighborhood—they were used to seeing him zip along at a fast clip, head down, arms swinging—but tonight, limbs heavy with wine, he moved without any sense of hurry, as if underwater.

This approach works well in highly conversational writing, but keep in mind that it can break up the flow of your writing. Try to keep the interjections short and then get back to what you were saying.

Or, if you’d rather keep things moving and use a less invasive approach, you could instead use footnotes to relay these comments to the reader at the bottom of a page. Writer's call.


No matter which approach you choose, remember: Writing this way helps you quickly and easily connect with your readers.

It's also a shortcut to more stylized writing, giving your writing voice a more signature sound and flow.

The bottom line here: The fourth wall can be broken.

The question is: Are you willing to give it a try?

Want more insight on how to write conversationally? I've got a whole chapter on it in my eBook!

Write Better Right Now: Digital Book + Exercises
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10 actionable writing how-tos that will help you write better, faster plus 6 bonus lessons with writing exercises and workbook.

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Pricing How-to for Freelance Writers

Everyone loves to tell freelance writers to charge more.

But "charge more” is a little...vague.

What does more mean? What are other freelance writers charging? What can you expect to earn when you go full-time? How can you make sure you don't get stuck under-charging and working with the most stressful clients?

Today, I want to share a bit about how I answered these questions (and how you can, too.)

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