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Freelance Writing Coach

Author: Kaleigh Moore and Emma Siemasko

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Kaleigh Moore and Emma Siemasko have long shared a dream: to build the world’s most fulfilling freelance writing businesses. Over the past 8 years, the two friends have become successful freelance writers, finding new clients (hello Salesforce + Vogue Business); refining their service offerings; building six-figure businesses; and ultimately, creating their dream careers.

Now, they’re sharing everything they know and discussing what they’ve yet to find out. Why? Because they know you can build a great freelance writing business, too. But first, you gotta get real.

On Freelance Writing Coach, Kaleigh and Emma discuss all things related to building a successful freelance writing business. Topics include things like client boundaries, digital products, rates, proposals, loneliness, and much more.

Their promise? To tell it like it is.
88 Episodes
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For our final episode of this podcast, we look back at our past 10 years of freelance writing and look forward to what we hope is next for us.This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
In this episode, we're diving into the details around the templates we use, tweak, and sell as freelance writers. If you've ever wondered how we boost efficiency in our workdays and cut out the repetitive pieces of day-to-day work, this is a must-listen. This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
In this episode, we'll share a look under the hood at what it takes to plan, market, and host your own in-person gatherings (meetups, retreats, etc.) as a freelance writer, sharing our own experiences doing just that!This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
If you're looking for ways to increase your income as a freelance writer, you should consider opportunities for upselling. In this episode, we look at a few options for additional services and add-ons you can offer clients to earn more money and become even more valuable to your clients.This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
In this episode, we get into the career path of journalism, the education/types of training available for those wanting to get a secondary degree for it (with costs!), and some hard truths from firsthand experience doing this work. This is a great episode for anyone wanting to pursue this path!This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
Today we're talking about freelance writers who are launching courses, templates, digital products, and more + the promotion it entails to be successful. To do this well, does a freelance writer need to think of themselves as a full-time Creator or Influencer? We discuss our different stances and experiences doing this work.This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
Today, we want to talk about social media in an age of complicated social media. This is more about how we focus our efforts on social media when there is a lot of tumult in the space, whether it's due to political concerns or their own mental health concerns.This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
Maybe you're at a stage in your career where you're looking to pivot away from freelancing and into something new. Emma and I are considering this ourselves! In this episode, we get into how to think about what's next for you post-freelancing, get out of your own way when it comes to limited beliefs, and take real, incremental steps toward something new.This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
Catch up with your hosts Kaleigh and Emma and hear about what's changed for them since the last season (spoiler alert: a LOT) as well as how we're feeling about the freelance writing landscape in 2025.This season is brought to you by Collective, and they’re giving you your first month free! Just use code FWCP at checkout.Tax season is stressful—no doubt about it. Are you overpaying? Are you even doing it right? It’s a headache, but here’s the good news: you don’t have to figure it all out alone. Collective is built exclusively for solopreneurs and is here to help. If you’re a freelance writer, you could be leaving major savings on the table by not having an S Corp. Collective helped me make the switch last year, and they handled everything—S Corp election, bookkeeping, payroll, taxes—you name it. Now, I get to focus on what I love, without stressing over receipt tracking and tax forms.
Most of us believe that we can build better businesses if we niche down to become a go-to writer for a particular type of asset in a specific space. Once we do this, however, it can feel hard to expand and grow. What if we want to work in another industry? What if we want to write web copy instead of longform content? In this episode, we offer advice on how to expand, broaden, and pivot your offerings.
Finding a freelance writing mentor is no easy task: They need to fit in with how you work and take instruction best. In this episode, we share our most impactful mentor experiences and the editors/mentors we learned from the most, plus tips on how to find one for yourself.
An email newsletter is a great way to stay in touch with your audience and build your personal brand. But wait…is an email newsletter necessary? Will it actually help you market and sell your freelance services? In this episode, we share how we think about email newsletters and what we’ve seen from our freelance friends: the successes, downfalls, and our personal experiences
What do you say to people when they ask what you do? Does your professional identity as a freelance writer affect how you show up in the world? In this episode, we talk about how to explain what you do when you’re off the clock, surrounded by people who don’t “get it.” We’re also covering what we’re doing outside of work in 2024, what we’re thinking about as freelancers and as people.
You see a post on LinkedIn calling for freelance writers with 750 comments. Is it just you… or does the market seem super saturated? What can you do when it feels harder than ever to differentiate? In this episode, we explore what we’ve been seeing lately and how it’s affected us mentally. We offer advice on how to work around this saturation to continue to build a solid business.
The writing process consists of three steps: (1) researching and outline, (2) productive writing, and (3) editing. But are the tools we use designed for this process? Are we as efficient as we think we are? Is there room to save time and increase our creative output? We sat down with Rob Carpenter, content strategist and Head of Marketing at Butter, to talk about ways to work smarter, not harder.
Companies sometimes hire writers for short-term contract roles to help with specific projects. They might hire a writer to work with them for 30-40 hours per week for a set period, such as three months. What are the pros and cons of taking on these roles? In this episode, we share our own experiences taking on contract work and offer some things to think about if you’re considering such a role.
Some freelancers suggest clients “book their day” if they want to work with them. Clients reserve a day… and work gets done. What does this look like in practice? How do freelancers successfully structure it? Are “book my day” offerings a good idea for your business? In this episode, we dig into the benefits and pitfalls of clients paying for a day.
Did you know we are really good friends? HA. We enjoy each other’s company, love chatting about WHATEVER, and are catching up and giving you a picture of our holistic selves beyond the world of freelance work. We talk about Kaleigh’s history as a dancer, Emma’s weird modern house, and get into what’s happening outside of work. For anyone who wants to get to know us better, listen in on this episode to learn what’s happening outside of work.This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
Freelance writing is really weird right now. Layoffs, the rise of generative AI, and internal chaos at a lot of companies have made many of us feel super insecure about the field. Our friends and colleagues are kinda freaked out… and maybe we are too? In this episode, we talk about what we’re seeing in the world of freelance writing and what we’re doing about it. This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
We both work in B2B SaaS. So do A LOT of writers. But what even is B2B SaaS? Why does it seem like so many writers are working in this area? In this episode, we talk about how we got into B2B SaaS, explain why it’s so popular, and offer some guidance on how to figure out whether it’s the right niche for you. This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
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