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.

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/).

If you’re creating original content, you’ll likely find yourself conducting interviews. You might interview subject matter experts, customers, or your client’s customers! Emma does it all the time when she writes case studies. Kaleigh does it for more journalistic assignments. In this episode, we offer advice on how to conduct a gosh darn good interview that guarantees you’ll get the info you need to do your best writing.

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/).

Working with an intense editor can be, well, intense. It has the potential to elevate your writing, poke helpful holes in your sentences, and take you to the next level. But it can also be really annoying. In this episode, we’re discussing our experiences working with editors who’ve got high high high standards.

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/).

What does it mean to be a REALLY GOOD writer? In this episode, we’re exploring what content managers, thought leaders, and others look for when they’re hiring writers. In particular, we discuss writing abilities and editorial chops.

WOOOOOOO boy. Where do we start with this one? Unless you’re living on the moon, you have *feelings* about what generative AI tools mean for your business, livelihood, and craft. In this episode, we explore our thoughts and feelings on AI and offer some ideas on how we can rise to the occasion in the new world of robot writers.

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/).

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.

We’ve all had clients that were...awful. But what if we told you avoiding nit-picky, cheap, or boundary-crossing clients was well within your control? We believe a screening process makes the difference! Don’t worry– we’ve made our fair share of mistakes, too. In this episode, we’re explaining how we screen prospective clients to avoid bad eggs and maximize good experiences.

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/).

Outsourcing frees up your time so you can focus on tasks that generate revenue and ultimately build your business. But how can you get started with outsourcing and why might hiring editors be a good place to start? In this special episode, we sat down with John Doherty, founder of EditorNinja and sponsor of this season of the Freelance Writing Coach Podcast, to discuss editing, outsourcing, and his path to offering services to freelancers.

Freelance writers benefit from great editing! After all, having a second (or third) set of eyes on a piece of writing can help you better understand its strengths and weaknesses, ultimately helping you deliver higher quality assets. But what IS editing and how do you make sure everything you turn in is sufficiently polished? In this episode, we talk about the importance of great editing, how to become a better editor, and the tools you can use to help.

A new lead comes in, you sell them on your services, and you both agree it’s a great fit. YES, this is the dream! But rolling out the red carpet for a new client doesn’t end after they sign your contract or proposal. What can you do with a brand new client to get the relationship off on the right foot? In this episode, we talk about how to make sure clients are well taken care of from the second they say yes. After all, this is the beginning of a client relationship that hopefully leads to more business and more referrals.

What happens when a prospective client asks you to write a trial post for free? What about an unpaid test? Are there circumstances where doing work that’s unpaid makes sense or is this always a big NO? In this episode, we talk about writing tests, trial posts, and when it might make sense to write for free (or not!).

There’s lots of talk about niching down by industry, but what about becoming the go-to person for a specific offering? Freelance writers see success when they’re THE person for a particular thing. In this episode, we talk about our experience niching down and how you can get people to remember you as the “go-to person for writing podcast summaries,” for example.

Making efficient use of your time is essential to running a successful freelance business, but lots of freelancers waste time on tasks that have little impact on revenue or lifestyle. In this episode, we discuss how we create efficient work days. We get into how many hours we typically work, tools to help ensure efficiency and focus, and what we recommend to freelance writers on how to divide their time.

Whether it’s getting paid on time, avoiding scope creep, or dealing with micromanagement, a contract is every freelance writer’s best friend—as long as it’s done right. 

These documents are a point of reference and a tool to help keep both parties on the same page around timing and deliverables (and other important stuff, like payments.)

As you read, keep in mind that this is not legal advice. We strongly recommend hiring a lawyer to draft a contract template for you. It’s a one-time investment that’s well worth the small fee.

What should you include in your contract?

You want to ensure you’re not leaving any loose ends in your contract, which is why being detailed works in your favor. The specifics may vary depending on your work, but some of the essentials to include in your contract are.

• Ownership of work: In most cases, you’ll transfer the ownership of the work to the client. Once the client clears your invoice, the rights automatically transfer to them.

• Payment terms: You want to be paid in full and on time. You can also require the client to pay a deposit in advance. If the client fails to pay on time, you can include a late fee in your payment terms. 

• Contract duration: Define the time period you’ve agreed to do business with the client. If it’s an ongoing engagement, you can enter a termination clause instead of contract duration defining the process and notice period required for terminating the contract.

Cancelations

Projects can get canceled. So what about the work you’ve already done? Do you still get paid for your work? What about your contract’s dissolution? Layout a cancellation clause in your contract that answers these questions. 

“The last thing you want is never to get paid for your work. Having this cancellation clause laid out in a legally-binding document that would hold up in court gives you a leg to stand on.”

You’ve probably been in a situation where a client suddenly stops responding. If the client signs a contract, you can sue them to recover the due amount. That said, suing might not always be feasible. For example, if the amount due is only $500, it’s best to move on (even though it sucks.)

Non-compete clause

Freelancers often work with clients in a specific industry or niche. If a client’s contract has a non-compete that prohibits you from working with their competitors, that’s a problem.

You might consider negotiating with the client and explaining why that wouldn’t be practically possible. You can offer to add a clause that requires you to keep their information confidential instead.

If you’d like to accept the non-compete, set a reminder for the day it ends.

“Within my project planning software, I’d get a ping once the one-year mark is up, reminding me that it’s okay to pitch a specific client.”

Subcontractor Agreements

Let’s talk about contracts for freelancers working for you. Having freelancers sign a subcontractor agreement helps eliminate gray areas, establish rules, and set expectations.

There is an overlap among the essentials, but some things differ in client and subcontractor agreements. 

Here are examples of things to include in your subcontractor agreement:

• Ownership: Can subcontractors use the work in their portfolio? In most cases, you’ll want to show the work in your own portfolio and disallow the subcontractor from doing so. In instances where the client disallows you from using work in your portfolio—such as ghostwriting, the subcontractor can’t use the work in their portfolio either.

• Workflow: Freelancers have their own processes. Yours might differ, which can lead to friction and disrupt the workflow. Adding your workflow to the contract sets the right expectations and provides freelancers with an overview of your processes. For example, you might require freelance writers to get an outline approved before moving forward with the first draft. Or you might want the option to request two rounds of edits.

• Payment terms: Like with clients, you should include the payment terms in your subcontractor agreement. Specify the price, invoicing date, and payment date in the contract. You might also mention penalties in cases where the work is plagiarized or subpar.

• Non-compete: In the case of subcontractor agreements, the non-compete clause differs a bit. You’re not binding them from taking more work. Instead, you’re safeguarding your relationship with a client. Suppose you’ve subcontracted work from one of your clients to a subcontractor. Once the subcontractor’s agreement with you ends, they reach out to your client and offer a lower price. See the problem? A non-compete clause prohibits the subcontractor from working with the client for a fixed period. One year is a reasonable time frame, but the duration may vary based on your industry and type of work.

Should you use contract templates?

Yes, using contract templates is fine. There are many options from The Contract Shop or one of the other websites that offer freelance contractor templates. You can always customize the contract, but remember to have a lawyer review it and make sure that you’ve read the entire contract yourself and understood every clause. That’s the only way to ensure your contract is foolproof.

Final note: Remember that you can have an airtight contract and not get paid. However, a contract ensures you have a legally-accepted document to show in court when you need to recover a large amount or protect yourself in a lawsuit.

This season of the podcast is brought to you by EditorNinja. Stop looking for an editor or editing content yourself. Use EditorNinja's flat rate content editing services to save yourself time and money by having all of your marketing content professionally edited. Book a free editorial assessment today to learn more.

Freelancing (AKA being your own boss) means being the master of your time. Effective project management is a big part of doing this well. 

So, how do you keep track of your freelance writing projects without working beyond capacity? We’re breaking it down for you, sharing the tools and processes we use along the way.

Tools for freelance project management

There are more project management tools for freelance writers today than ever before. But…what’s the right one for YOU?

Simple to-do lists

A simple combination of to-do lists and calendars can be effective. Let's say the assignment is to write five blogs. You can create a task for each on your to-do list tool and set a deadline on your desktop calendar to manage them. This setup is no-frills, easy to use, and simple.

Basic tools

For more ongoing projects, creating a plan via a Google sheet template helps. To spare your inbox, it’s also wise to get into the client’s Slack channel for day-to-day project management if that’s on the table.

For freelance writers who frequently miss calls or get into deep work minutes before an important call, setting up alarms that go off five minutes before a meeting can solve this. The same goes for email: Email reminders are a great way to automate the process of following up. It flags emails you haven't responded to so you don't forget about them.

What are freelancers using for project management? 

Many freelancers use software like monday.com, Trello, or Asana to monitor project progress. However, they are most useful for monitoring blog content rather than complex multi-stage projects like websites and case studies. 

Trello is excellent for tracking assignments. If you're subcontracting, you can use this tool to assign a project manager to oversee projects to completion. 

Even with the tools available, having a good old-fashioned steno pad in front of you is super handy to track what you need to do for the day—pay a bill, send an invoice, or follow up on a proposal. Note: You might want to maintain your to-do list and calendar for personal deadlines separately while using email, Slack, sheets, and docs for external collaborations with clients.

“It doesn't matter which software or tool you use. Simple or complicated, it's meant to help you manage your projects internally and appear professional externally.” 

The case for workflow management

Consider using a workflow manager to identify when you're working to capacity. Using this, you can let clients book you for the future (so you have a steady workflow) while also ensuring you're not overworking to the point of burnout. 

A workflow manager also helps you identify high-paying or repeat clients. Repeat clients signal an opportunity to move to a retainer package or price your offerings better. If you lock in a three-month deal, for instance, you can offer your client a small discount for the work guarantee. 

“Freelancers are not great at looking at data and making informed decisions regarding their workload - that’s where a workflow manager can help.” 

How to find a project management system that works for you

If you're looking to invest in project management software, choose a free or low-cost option first and scale up depending on how much you can afford. 

When investing in a tool, your key considerations should be:

1. Does this tool best suit your workflow?
2. Does this tool help you stay on top of things?
3. Does this tool make you look professional?

Remember, project management is about doing the minimum you need to do to get things done. Monitor your workload, and don't just say yes to everything that comes your way.

This season of the podcast is brought to you by EditorNinja. Stop looking for an editor or editing content yourself. Use EditorNinja's flat rate content editing services to save yourself time and money by having all of your marketing content professionally edited. Book a free editorial assessment today to learn more.

Events, conferences, and retreats offer freelance writers a break from the average day-to-day grind in front of the computer. They claim to help you learn from experienced speakers and grow your network, but…do they? 

Emma and I chat about our experiences with events and conferences and how we look at them moving forward. Fun Fact: We met at a conference for the first time after knowing each other online for a long time.

Our experiences with conferences as freelance writers

Kaleigh’s stance has been negative on conferences and events most of the time. Primarily because she finds it stressful to travel, and going to an event requires her to break from her normal routine. Post-pandemic, she’s been trying to challenge herself and try speaking at events and conferences to see if her views change. 

Earlier in 2022, Emma attended a conference or an event every month, sometimes even two. Even though giving keynotes and moderating panels were great experiences, her stance on events as a freelance writer has mostly stayed the same. Travel is still exhausting. She still doesn’t think conferences and events bring enough value to go to all that trouble.

At the beginning of Emma’s freelance writing career, she found conferences to be much more helpful in gaining insights and connecting with people she could work with. But as she has grown her freelance writing business, her reason for going to conferences shifted from learning to meeting friends in the trade.

Shortcomings of events

There are two broad categories of events: one is the hustle-centric category with “go for it” events. The sessions have titles such as “how to 10x your revenue” and often boast a male-dominated speaker panel. 

The other category is “follow your dream” events—usually branded as hyper-feminine and very “woo-woo.” Sessions can be helpful if there’s a middle ground between these two extremes, but often, there isn’t.

“When it comes to conferences, I don’t care about the branding of the event. I think: Just teach me something without the special packaging.”

Then there’s the matter of the content. Some conferences are great for beginner writers, but not many cater to experienced freelance writers. The ones that do can be extremely expensive: At a couple of thousand dollars for the tickets, then a couple more for your travel and stays, it can be a substantial investment. 

Other issues

What does a typical conference look like? You wear a badge, listen to people speak—the learning part—and try to meet other attendees. But is “sit in a 30-minute session and listen” the best format for learning in today’s world? Eh, maybe not. We both would prefer to go to dinner with the people who were at the conference, skip the actual sessions in the conference, and just hop in during a happy hour.

“I’m so bad at sitting in a chair and listening to somebody talk for any extended period.”

What about virtual events, you say? Virtual events seem nice for the sessions initially, but it’s hard to stare at a screen and fully pay attention when you’ve already been doing that in your job. Moreover, they also lack the in-person connection between attendees.

When we met at a conference, we realized that the best part of the conference was meeting each other IN PERSON. Several years ago, Emma and I hosted a retreat for female freelancers. It stemmed from our dissatisfaction with big marketing conferences and wanting to deliver something different. And guess what? It was great. The in-person aspect is huge.

Conferences: Your call as a freelance writer

We’re not saying don't go to conferences. We just want to highlight that it’s more of an investment than just the money it costs. If you decide to make that investment, our advice is to be mentally prepared to introduce yourself and put yourself out there. The connections you make are often more valuable than the session content.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

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.

Website content, social media posts, marketing emails, press releases—freelance writing is an umbrella term for many types of writing. But most freelance writers specialize in either content writing or copywriting (not both.)

Writing in any form produces content, which is why copywriting is often lumped together with content writing. Confusing, right?!

The good news: We’ve done both types, and there are plenty of differences between the two. Today, we’re breaking down how they’re unique entities (to clear things up.)

Content writing vs. copywriting: What’s the difference?

Content writing often refers to the writing found in articles, long-form blog posts, and ebooks. Copywriting is usually found in advertisements, landing pages, and sales letters. 

The primary difference in both writing forms is how they relate to the reader's response. Copywriting corresponds to a direct response, whereas content writing does not. 

Copywriting works to get people to take action and make a conversion (AKA to get them to purchase something, sign up for a newsletter, etc.) On the other hand, content writing often focuses on educating the reader—for example, a how-to article or a blog post on upcoming trends in your industry niche.

The style of writing also differs between content writing and copywriting. Content writing has a narrative style that relies on storytelling. Copywriting is persuasive, backed by the psychology of human behavior.

Variety in pricing approaches

Aside from the writing differences, copy and content projects are priced differently. (Lots more on pricing in this episode!)

Due to their direct response nature, copywriting projects can have result-oriented pricing. For example, copywriters can experiment with getting paid a percentage of the sales generated by the copy they’ve written in addition to a flat fee. 

Content writing projects are more often priced per word or per project and don’t have a scope for royalties. 

You can make good money in both content writing and copywriting, but copywriting has the potential to make large amounts of money in a short amount of time. This makes it more financially lucrative for freelance writers (especially if you’re writing for a company with a huge sales volume and you can tie the results to your work.)

Client expectations and experiences

Copywriters help generate more sales, and content writers help build brand authority and thought leadership. The outcome of copywriting is easy to visualize and measure. It’s much harder for content writing. 

Thought leadership and brand authority are tricky to measure, and thus ranking higher in search results is sometimes treated as the measure of the quality of content writing. This difference in the measurability of results means that content writers often have to work a bit harder to sell their services and raise rates over time.

What about case studies?

The skills of content writing and copywriting tend to overlap in offerings like case studies where you're telling the story of a customer's success while also working to convince a reader to buy.

“One of my case study clients told me: “Whatever you’re thinking of charging, double it.”

Case studies are valuable to every business. Their sales teams use them as tools on sales calls, during walkthroughs, and as testimonials, especially on the enterprise level. Since case studies bring your clients more money, you can also price them at a higher price point.

What should freelance writers do: Content or copywriting?

You can be good at copywriting and content writing and take on both types of projects. However, most freelance writers prefer to specialize in one as their core marketed service. This is primarily because clients remember freelance writers based on the type of content they specialize in. The good news is that you can occasionally take on different projects but not actively market them.

The best way to figure out what’s best for you is to try various freelance writing services. From there, you can figure out which one suits you best

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

AI-powered writing tools have gained a lot of attention recently. These tools are impressive in their ability to understand natural language and create content in seconds. But are these machine-powered tools advanced enough to replace (human) freelance writers?

Social media is filled with screenshots of AI-generated emails, blogs, poems, and much more. Across the spectrum of fear and excitement, most freelance writers are wondering how these tools will impact them. Today, we’re sharing our two cents on the topic.

Can AI tools replace freelance writers?

Short answer: We don’t think so. There’s a long way to go for these tools to be able to put writers out of jobs.

In fact, most of these tools are marketed toward writers to help them in their process of writing. These tools claim to help writers generate content quickly, which they can edit and clean up later. 

Despite this, much of the feedback we’ve heard from fellow writers is not positive (at least thus far.) The content generated by these tools is mediocre at best. Artificial intelligence is good enough to get you past the blank page. However, the content still needs to be heavily edited and is not a replacement for a human’s ability to add context, add original insight, address key pain points, etc.

“I don’t have any real concerns about these tools replacing the work we do. Especially because we have industry-specific expertise which these tools don’t bring to the table.”

Yes, we are worried that robots will become sentient (Kaleigh mostly.) AI taking over humanity in the future would be a much bigger problem than just getting our work as freelance writers taken away (um…have you SEEN the movie Ex Machina!?)

But big picture: thinking about how these tools can help you in your freelance writing journey is a much more worthwhile use of time than worrying about if AI will replace freelance writers completely.

How can AI-assisted writing tools help freelance writers?

Some AI tools have more of a content processing application, such as checking for consistency with a style guide—which, in our opinion, is an extension of features like spellcheck and punctuation. Most freelance writers we know use Grammarly today. Grammarly also uses AI to predict the tone of your writing and provide suggestions or check for plagiarism. We expect these tools to integrate into our work processes similarly.

The other category of these tools, the ones that generate content on their own with the help of a prompt or an outline, have an unprecedented set of applications. These “write for you” tools have various features targeted toward different target users and their needs. Writer is more geared toward enterprise teams, whereas Jasper and Copy.ai are toward freelance writers.

How these applications can help you as a freelance writer depends on the type of services you provide. For example, in the case of blog posts, generative tools can help freelance writers by:

• Speeding up the process: These tools can generate a full-length blog post, but they require heavy editing. Using these tools, you can put in your outline and get that first draft going within minutes.

• Helping with specific sections: Some of these tools are good at a specific task, let’s say, generating SEO headlines for an article you wrote. If you are struggling with an intro or creating headlines, these tools can help.

We can also imagine a future where these tools can evolve and help with context switching. Imagine a tool that provides recommendations according to specific brand requirements by referencing a version of their style guide. That’d be nice, right?

What should freelance writers do?

AI tools are not replacing expert freelance writers anytime soon, but can discourage new writers and stop them from even giving freelance writing a try. If you’re in this boat, the key is approaching these tools with curiosity, not fear.

“There are always going to be threats. The freelance writing market is more competitive than ever—even among humans, not just tools.”

Think of how you can use them to improve your self-editing skills when you get the first draft written by an AI. Can the use of these tools help you scale your services? Focusing on specialization, be it developing subject matter expertise, having a unique voice, or leaning into a niche, can help you stand out among these tools and the increasing competition.

Freelance writers are not going anywhere

The takeaway is that none of these tools are self-sufficient, and we don’t see one being soon (yes, not even with ChatGPT). These tools can help writers more or less depending on how advanced they are, but the job of a freelance writer is not going anywhere.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

Running a freelance writing business can be extremely rewarding, but sometimes, you feel stuck and unsure of the next step. When this happens, there are several things you can do to “unstick”' yourself. One of these is getting help from a freelance writing coach. 

Several coaches specialize in freelance writing. However, it's important to figure out when coaching is right for you, when it isn't, and whether it is a justifiable investment. 

Both of us worked as freelance writing coaches, and our insights from this discussion can help you figure out the whys and hows of investing in coaching. 

What kind of freelance writing coach do you need?

There are different coaching styles, so it's important to figure out the kind of freelance writing coach you're likely to work best with. Do you want a crash course with information, answers to all your questions, and plenty of resources to explore? Or do you need someone who is more of a listener and can help you troubleshoot?

“Coaching is best served when people know their ideal learning style.”

Also: Talking to a coach’s past coaching clients is invaluable. It can help you get honest feedback (testimonials or other marketing materials don't count.) The last thing you want is to sign up for an expensive freelance writing coaching program and find that you don't relate with the coach or don't like his or her format or communication style.

Some people prefer self-directed online courses, which they can do at their own pace without being on a specific timetable. Others need accountability, having to check in with somebody once a week, homework to do, and assignments to complete. Identify a coach that offers what you need. 

How much can you afford to spend on coaching? 

A $350 coaching session that helped you revamp your proposal process and win three new clients in the same year is money well spent. It paid for itself in leaps and bounds. 

On the other hand, if you're considering a freelance writing coaching program asking for a one-year investment of say, $12,000, you'll need to vet it carefully. It's a huge commitment, and you'll want to ensure you're at the right point in your business to earn back that money and gain maximum value from it.  

“Ask yourself if the amount you invest in coaching is a sum you can earn back.”

If you're a beginner freelance writer looking for clarity and direction and hoping to find answers to basic questions like: 'Where do I start?' or 'How do I position myself?', be judicious with your first investment in freelance writing coaching.  

How do you get the most value from a freelance writing coach?

The freelancers who fare best with a coach are those who have a clear idea of their goals and pain points. This helps the coach offer better, more relevant recommendations to help their clients get where they want to be. 

“Before investing in coaching, have a clear idea of the outcomes you can expect.”

Freelancing can be lonely, and coaches often find people paying for coaching just because they want some human contact. While it's up to each person to decide if that’s a good use of their time, it's may not the best use of their money. Instead, finding freelance communities, making friends where you live, or going to therapy could be better alternatives. 

Similarly, be wary of freelance writing coaches advertising things they can't deliver. No one can guarantee you'll become a six-figure freelancer; that's not the purpose of coaching. The outcome is to help you navigate roadblocks and guide you along your freelancing journey.  

Invest in a freelance writing coach for the right reasons 
If you're struggling with your freelance writing business, you're not alone. Coaching can help you learn how to navigate tricky situations and apply the right principles. But don't be unreasonable or expect to leverage your coach's network - that's not within the scope of coaching or what you're paying for. 

Coaching is not a perfect science. It's a way to offer advice, insight, and perspective. When you are stuck, don't know what to do next, and feel you can afford coaching, it may be a step in the right direction. There may be other unexpected benefits just from connecting with someone further ahead in their freelancing journey.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

We think freelance writing is a pretty sweet gig—but it’s not for everyone. Some lead successful careers as self-employed people, while others miss the structure of a full-time role. One isn’t inherently better than the other, and deciding which one is right for you can take some trial and error.

Some leave freelance life behind and return to a traditional, full-time job. But why?

Why it’s tempting to consider going back full-time

The demand for quality writers is higher than ever, and some freelancers see a bump in requests from recruiters related to a full-time gig. Other freelancers get great offers with their existing clients because they work closely together and are already embedded within the business. Some of these offers can be enticing.

One thing is indisputable: freelancing is hard work. All of the business admin and sales elements of the job aren’t for everyone, and the financial burdens of freelancing can be too much for some people to handle. 

If you don’t have a partner or spouse to support you, or you’re struggling to make ends meet with your freelance career—even though you’re taking all the right steps and making all the right connections—the pull to return to a source of consistent income and healthcare makes a lot of sense. And sometimes, you’re just ready for the next chapter in your career.

If you’ve freelanced for a bit and you’re thinking about going full-time, your background as a freelancer and the body of work you’ve produced can help you ask for a lot more money than you would otherwise. If you’re interested in becoming a full-time employee again, consider the pros and cons first.

The pros of going full-time

There can be a lot of benefits to going back in-house after working as a freelancer for a while. One of the biggest ones is the ability to work with a team again. Freelancing can sometimes create a sense of loneliness because so much of what we do daily is solo work. There are no team retreats, no conferences, and no spontaneous lunches with coworkers. Going full-time would bring a lot of that back into your workday.

If you want to focus only on writing instead of the other elements of running a freelance business, a full-time role will help you do that. It eliminates the constant context-switching between creative work, admin tasks, and different clients.

There’s no shame in saying freelancing isn’t working for you for whatever reason.
Another significant pro of going full-time is healthcare coverage and taxes. Businesses will handle healthcare for you and manage tax payments with each paycheck. Freelancing puts all of that responsibility on your shoulders—and there’s a bigger tax percentage due, too.

The cons of going full-time

One of the biggest reasons people become freelancers is because of the flexibility it provides. You can determine your working hours, what work you choose to take on, and when you need to take a break. If you want a raise, you can raise your rates and find clients that will match them. If you want a raise at a full-time gig, many more steps are involved—and you still might not get it.

By going full-time, you lose some of that authority. You’re working for more than yourself now—you have a team, a manager, and a set of expected responsibilities that come with the job. The flexibility isn’t near what you would have as a freelancer, and your desired work-life balance may be harder to maintain.

If you enjoy the context-switching that comes with freelancing—and you’re pretty good at it—that’s not something you’ll find with full-time work, either.

As a final con to consider: the economy has made it so that working full-time can be just as uncertain and unstable. With layoffs across most industries, relying on a single source of income could be risky. If you lose a freelancing client, on the other hand, it can be easier to bounce back and supplement with new projects or different offerings.

The answer? It depends.
If you’re trying to find out whether or not a full-time role is a potential fit, ask yourself (and the hiring manager) these questions:

What would working full-time look like for me?
What would I need to make financially for it to make sense?
What kind of flexibility would I need?
What kind of projects would I be doing?
Will I get the work-life balance I crave?
What are my non-negotiables and priorities?
What would the expectations be for me and my work?

Remember: Going full-time in-house is not a failure in the realm of freelancing. Deciding to stay freelance is great if that’s what’s best for you; choosing to become an employee is great, too. Make sure it’s your decision, not any external idea of what you “should” be doing.

You must be clear about what you’re trying to accomplish and what’s best for your personality type. It’s worth doing the work to get clarity around what you want out of your career and your life.
What do you want out of your 40-hour work week? What are your goals? What do you want to be able to accomplish outside of work? Let those details guide you.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

Is writer’s block even real?

Any writer knows this is a contentious issue. Some believe writer’s block isn’t a legitimate thing—an excuse for not getting words on the page—and it’s entirely made up. Others swear by the concept and can distinctly mark times when they have writer’s block and when they don’t.

No matter how you feel about it, the concept of writer’s block is real. Sometimes, we all struggle to focus or put words on a page. So how can you get yourself to write and break through these struggles, especially when you have deadlines.

What do we mean when we talk about writer’s block?

If you’ve ever sat down to write and couldn’t focus, found you had a significant lack of energy, or repeatedly avoided starting a project or task, you’ve dealt with what we consider to be writer’s block.

Maybe you had too much on your plate, felt overwhelmed, or lacked the mental bandwidth to write. These are valid, and it’s happened to all of us (whether we admit it or not.)

Despite being career writers, there are some days when we just don’t want to write. We stare at the blank page and think: This is awful.

The good news is: Writer’s block is a surmountable problem. And quite frankly, as a freelance writer, you have to be able to get through it. Here are some of the strategies we’ve used in the past.

Get through writer’s block with these methods

A lack of inspiration, joy, or focus doesn’t mean you can’t physically write great words. Writer’s block is often a symptom of something larger—maybe you haven’t given yourself a proper break in the last couple of hours or even days.

We feel out of our depths when we can’t get words on the page. There are moments in freelancing when you’re just not as inspired by the writing process as other times.

Take a step back, see why you might be hitting writer’s block, and see if any of the below methods might work for you.

Work from a detailed brief or outline.

When an assignment is incredibly open-ended, it’s easy to get overwhelmed. At some point in your freelance writing career, a client may give you a simple outline or brief with no guardrails, sources, or suggested ideas. When that happens, it’s harder for you to get started—and it’s more likely that what you give the client isn’t what they wanted, at no fault of yours.

As a freelance writer, it’s your job to try and get as much information as possible about what your client wants. More context for the assignment is always better, so ask your client for more clarity or direction if you need it. This could be in the form of bulleted ideas, a conversation with a subject matter expert, or even an asynchronous Loom recording or video that gives you some insight into their thought process and goals with the piece.

Break the job into manageable chunks.

Writing isn’t only about having your research and outline in front of you—it’s about creating the right milestones to break up the work.

Freelancing gives you a lot of freedom, but you have to be the one to create your delivery schedule and subtasks. Build a timeline where you deliver something smaller more often, with more components to help you along—like interviews, outlining, drafting, etc.

Just write something, even if it’s messy.

We know the idea of writing something you don’t like isn’t a comfortable one. But sometimes, throwing thoughts, links, or blurbs into a messy document is an excellent way to get started, especially if your brain is too scrambled to write a coherent sentence.

You just need to get the words out. It doesn’t matter if they’re good. Once you dump things on your page, the process is so much easier.

Instead of writing a polished draft in that blank document, go freeform and sort your ideas out. Place relevant links or quotes under headings. Add placeholders or reminders to expand on an idea later. The writing process doesn’t always have to be so scientific and structured. 

Get out of your head and away from your desk.

Sometimes, just walking away is the best cure for writer’s block. Doing something else and letting your brain relax can do wonders.
We’ve even heard reading poetry is a unique way to get the creative juices flowing. Reading unusual formats, especially ones you don’t encounter often, can help you get a fresh perspective on your work and break through if you’re feeling stuck or uninspired.

When in doubt, get help from another freelance writer you trust.

If you feel totally directionless or lost—even after some of the other methods above—consider bringing in another freelance writer to your process. For example, if research is difficult for you, freelancers specialize in that step of the writing process. When all else fails, bring in outside support so you can focus on what you do best instead.

The freelance writing community is incredibly supportive, and many of us are happy to lend an ear. Like we said earlier, we’ve all been through this at one time or another—likely more than once.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

Why did you become a freelance writer? For freedom? Flexibility? The ability to work on your own terms? Whatever your reason, sometimes life can get in the way and throw your plans off course. 

Learning to navigate the issues that crop up when you’re trying to run a business can help you weather the storms and deal with them. More importantly, it enables you to manage the impact these setbacks have on your work (and makes them feel less disastrous.) 

Emma and I have been navigating our own personal disasters lately, so hopefully, this discussion is a cold comfort to you.  

Go back to the essentials

Whether you need to go on a maternity break, care for an aging parent, or deal with a sudden health scare, some life situations force you to question everything. One of the questions you’ll find yourself asking is: “Can I sustain this workload and keep my business afloat through this period?”

In these situations, it's important to pare things down to their most essential.

Ask yourself some tough questions:

• How much money do I need to make?
• Do I really need to keep on all of my clients?
• Can I afford to cut my working hours down?

In a crisis, you need to figure out the minimum you need to do to deliver for your clients that will keep your bills paid.

"The perk of being a freelancer when disaster strikes is that you're very flexible. You have choice and control over your work hours, clients, and more." 

Give yourself permission to shift gears; acknowledge that there are ebbs and flows in life, and take the time to adjust to changes in business and your personal life. Be honest with yourself and your needs at that life stage, and know that it's okay to take a step back and refocus. 

Learn to delegate

Another tip: Get used to outsourcing work. When things get crazy in your personal life, getting help on the work front is okay. When personal disaster strikes, your mental bandwidth shrinks, and it's at these times that you risk letting the quality of your work slip. Remember that your clients trust you to do a good job, and delegating some of your work can help maintain that trust. 

Consider what your strengths are and which tasks are tedious or you may not be the best at doing. Then find the right people who can help you with different projects: bookkeeping, accounting, admin work, or anything else that drains you of time and mind space. 

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Make space for the things you love 

We often forget why we became freelancers: to have the flexibility to do the things we enjoy. We lock ourselves into an incredible workload, and before we know it, there's no time or space to do the things we love. Instead, we're constantly scrambling and falling into the hustle-culture trap. It's a culture that reinforces the need to rise and grind constantly. 

Putting your targets on paper is a great way to stay focused on what you need to do and when you can give yourself a break.

“Create a template for success and when you hit your goals, know it's time to stop working.”

Ask yourself: “How much money do I want to make, and how much bandwidth do I have?” Don’t keep adding projects or telling yourself you can fit in just one more project once you’re done. Keeping track of the work you're putting in and the actual capacity you have is a great way to start setting boundaries.  

Recognize burnout

We've all heard about the new trend of 'quiet quitting,' where people are so burned out that they're doing the bare minimum at their jobs to get by. Sometimes the personal emergency you're dealing with is just complete burnout. It may sound extreme, but if that's the case, don't shy away from putting a hard stop on work. You can always come back to it the next month or whenever you feel rejuvenated and able to. 

In other cases, while you may not be experiencing burnout, you may have an unexpected chronic health issue you want to deal with. Or, you now have a growing family and can't continue doing what you used to do without childcare. These are all valid reasons to take a complete break. Be kind to yourself; we’re all only human.

“Sometimes you need to fire clients. Get out of a guilt mindset about being productive all the time.”

Take a hard look at reality

You can't be an A+ mom, worker, house manager, and wife all of the time. The bottom line is that protecting your mental peace and navigating a personal crisis comes down to accepting the situation you’re in. It requires a willingness to change course in your personal and professional life. Often, this requires temporary sacrifices, but in some cases, you may need a complete mind-shift and a change in the direction of your business. 

Give yourself room to evaluate and make changes. From delegating work to making space for the things you love, identify the strategies you need to adopt to navigate the small and big crises that life throws your way.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

Existing on the internet these days is a bit of a double-edged sword—and if you’re running or growing your business online, it can be even worse.

Many of us have met amazing people online that become our friends, colleagues, and clients. Still, for each excellent interaction and connection, there are bullies, devil’s advocates, and naysayers. Everything you say in public forums and social media is subject to online “haters.”

How do you deal with this negative feedback without letting it affect your work and self-worth?

Remember: It’s not personal

There’s a lot of bravery associated with the anonymity that comes with operating online, so you have to take everything people say with a grain of salt. Some naysayers are combative and aggressive by default when they can hide behind a screen and keyboard. We’re not dismissing the fact that what people say is hurtful. It’s scary. And it can throw you off your rhythm for days, weeks, (or months!) especially if you’re a particularly sensitive person.

If you’re very sensitive, bullies and naysayers can be difficult to handle. It’s not something you think about or prepare for when starting a freelance writing business.

We find comfort in the fact that what people say online to us and about us often has very little, if anything, to do with us. Either the haters are commenting purely to spark outrage, engagement, and controversy for fun or to support the algorithm, or they’re dealing with stuff in their lives that makes them angry and prone to lashing out. 

So when someone comments on your casual post about an evening walk with some manufactured outrage, remember that it’s not about you and your actions. It’s about them.

Control your inputs and outputs

When you receive comments or direct messages on social media that are triggering or hurtful, you don’t have to deal with them if you don’t want to. It’s your content and page people are commenting on, so don’t be afraid to take control. Moderate your profiles and content like it’s your job:

• Block the trolls
• Mute and unfollow people who post content you don’t care for
• Ask to see certain ad types less often or never
• Report comments, posts, or ads that are inappropriate or hateful

If you want to deal with comments and add nuance to the conversation that was missing before, you can—just be prepared for the possibility that it won’t make any difference. That’s often a losing battle, especially on social media.

Most of us are just trying to do our best: grow our businesses, put out our best work, and do a good job. Sometimes, we either misstep or misinterpret things. There’s not a lot of room for nuance on the internet, especially on social media platforms.

You don’t only find bullies and haters online—sometimes, clients and potential partnerships end up this way, too. Sometimes, clients can come back to you with feedback that isn’t constructive or with anger that doesn’t seem to be related to you.

As you get more experience as a freelance writer, you’ll get better at screening potential clients and projects and seeing these red flags up front…but you can always get surprised. You might get feedback from a potential client that the way you do business makes no sense or some feedback on your blog draft that you “completely misunderstood the assignment.” 

It’s up to you how you handle these interactions; make it clear who you’re willing to work with and who you aren’t…and stick to that.

Create a supportive community 

Sensitive people struggle with hatred and negativity on social media and in the real world; women are confronted with much of it. Instead of dealing with it alone, find friends or coworkers you can talk to when something happens.

Even if it’s just one person, talking to someone who understands the field you’re in can be helpful—it’s someone to commiserate with and a way to get the support you need.

Whether through a group text, Slack community, Facebook group, or something else, you have to have people to check in with, commiserate with, and get a sanity check. Sometimes, just hearing someone say, “You’re not crazy,” or, “They’re overreacting,” can mean all the difference.

Say goodbye to bullies

It’s hard to avoid haters online and in the real world, both for your business and life in general. That doesn’t mean you have to retreat and let them scare you away from the world, especially through online communities. Control your inputs, build a supportive community, and stick to your morals and boundaries. With this support, you can get through any negative feedback or harsh words thrown your way.'

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

Things may be a bit quieter right now, and it’s easy to slip into a mindset that makes you think it will be that way for a while (or there’s just not enough work out there.)

“Don’t let the headlines be a self-fulfilling prophecy. Don’t see something that says, ‘No one’s hiring freelancers,’ and think, ‘No one’s hiring freelancers, so I guess that’s it for me.’ Look at your business and see how things are going.”

You may see social posts or news articles that report a slowdown in the freelance writing market, but that doesn’t mean you won’t find any work. Depending on your business and the industries you work in, you may even have the opposite experience.

There’s value in leaning into the scarcity, though. If it makes financial sense for you to take a break right now, you should do it. Taking time to appreciate the pause can benefit your mental and emotional health.

When business gets slow, experiment
There are so many paths to explore as a freelance writer—and the freedom to explore those is one of the reasons many of us decided to freelance in the first place.

If business is going slower than you’d like, this might be the perfect opportunity to try that thing you’ve had your eye on. Consider trying out social media posts and email newsletters if you usually write blog posts and ebooks. If you’ve worked in one industry for a while, consider adding strategy or coaching packages to your offerings.

For us, we’ve each experimented with something slightly different than our everyday work—but still within our wheelhouses. Emma’s grown the coaching arm of her business, taken on some larger projects, and scheduled things out further in the future than before. Kaleigh offered one-page website audits with a flat rate to change things up.

Especially with the rise of the creator economy, you can create a financial buffer by diversifying your income streams. If you have a newsletter, you could consider a newsletter sponsorship; if you have a significant social media following, sponsored posts or whitelisting ads might be something to try.

Diversifying your income stream is a good insurance policy for recessions; it allows you to pivot your business as needed to match the industry’s needs. You never know—you might find something you really enjoy and decide to keep doing, even when the economy recovers.

New season, brand new episodes

Be proactive and reach out to potential clients

Right now, getting new projects and clients is an “early bird gets the worm” situation. To get that competitive edge over others, you need to be proactive and get your foot in the door for year-end projects or projects currently slotted for the start of the new year.

This is always good advice, but it’s especially true right now. As budgets become more conservative and approvals for hiring freelance writers comes under scrutiny, reaching out proactively can help keep your workload full.

“One of the benefits of freelancing is that it’s easy to pivot if things come up and you’re not getting as much work as you were in the past. When companies cut back, they rely more on freelancers because they may not have the option of hiring internally.”

As you’re preparing to find new work, ask yourself these questions:

• What things can I do to make myself more appealing as a freelance writer for this particular job?
• Are there solutions I can bring or simplifications I can add to a process to make myself stand out?
• What else can I do to make potential clients more likely to hire me?
• Is there a way I can ask current or previous clients to refer me to others?
• Is what I’m doing attracting the right kind of clients? If not, how can I get more of the right kind?
• Does it make sense to adjust my rates? How much should I increase them by?

Don’t panic

The upcoming recession doesn’t mean you have to panic or your business will suffer. Consider different ways to grow your business—through various industries, offerings, different-sized projects, and so on—and expect to try things out. Recession-proofing your business is possible.

This season of the podcast is brought to you by Catch, the personal payroll and benefits app. If you buy your own health insurance, Catch has you covered. You can renew your plan, enroll in a new one, and enjoy extra savings with Catch’s ability to find government tax credits that can save you hundreds of dollars on your monthly premiums. Open Enrollment is here. Check out catch.co/health to shop for coverage or cut your current bill today.

This episode needs a disclaimer which is that we are not lawyers. However, someone told us to get business insurance so we looked into it. In this episode, we discuss business insurance. One of us has it and one of us doesn’t. The person who doesn’t was unlikely convinced by this episode. Basically, talk to an insurance agent. But if you’re looking for a brief overview of what two experienced freelancers know about business insurance, listen in.

Both of us have done our fair share of speaking gigs throughout our freelance careers. Speaking is a great way to share your authority and meet new people. At some point in your business, you may want to start booking speaking gigs so you can share your knowledge with the world. In this episode, we discuss how to start small and what to keep in mind as you embrace speaking. Emma also shares a comedic and bizarre tip for getting people into your talks.

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.

Kaleigh got a new L-shaped desk. Emma’s is vintage. Kaleigh works in an office. Emma works in the corner of her bedroom (thanks California real estate + COVID). In this episode, we’re sharing our freelance desk and office setups. You’re going to hear about a zen-like place and a corner of chaos. By the end of this episode, you’ll want one of our desks and not the other’s… ;-)

WE ARE GETTING REAL ABOUT WHAT WE CHARGE FOR CERTAIN ASSETS. In this episode we share what we think are reasonable rates for blog articles, case studies, websites, and more. We thought we’d be able to share numbers WITHOUT explaining the nuance but couldn’t really do that. There is always nuance when it comes to pricing. If you’re wondering if you’re totally off base with your rates, give this a listen.

Neither of us are LinkedIn masters, but we’ve seen freelancers get massive amounts of value from the platform. In this episode, we discuss how we approach LinkedIn and how we’ve seen others leverage it. We call out Michal Eisikowitz and Leah Neaderthal who are both doing awesome things with the platform. If you’re interested in how freelance writers are using LinkedIn, give this one a listen.

Some freelancers work with one or two longterm clients while others do a series of one-offs. It can depend on the type of work you do, but it can also depend on what you like and what matters to you. In this episode, we discuss the pros and cons of longterm clients, retainers, and one-off projects. There’s no perfect mix, but there’s probably a right(ish) mix for you.

Are your clients texting you in the middle of the night? Do they expect instant responses on Slack? Do they want you to deliver a draft within 24 hours or hop on a call right now? AHHHH. You became a freelancer so you wouldn’t be beholden to a boss, but it feels like your clients are owning you. We know the feeling, and it’s one that can be solved with good boundaries. In this episode, we cover everything client boundaries. We discuss how to create them and uphold them so you can take back control of your business (and your life!).

A listener asked us how we juggle the daily demands of our lives and careers: how do we eat nutritious meals? How do we make sure we get outside every day? How do we make the most of the flexibility that freelancing has to offer? Well, it’s a work in progress for both of us. We’re far from perfect, but we have been freelancing for a long time and have some ideas. In this episode, Emma confesses to just how long she went without renewing her car’s registration. This episode references the “Wheel of Life” exercise which can be found at this link: https://storiesby.us/wp-content/uploads/2022/04/Wheel-of-Life-Reflection-Exercise-1.pdf

There’s nothing wrong with starting your freelance career on Upwork, Fiverr, or another platform. In fact, we know many successful freelance who did (and still do!) gain a lot from these marketplaces. But what do you lose when you continue to rely on these platforms to get work? Freelancers often tell us they want to get “off platform” but aren’t sure where to start. In this episode, we discuss the pros and cons of these platforms, why it might make sense to get off, and some strategies on how to move away from them.

Both of us write about fairly technical topics we once knew nothing about. But now, we’re experts. In this episode, we talk about our strategies for understanding a topic when we’re out of our league. This will be particularly helpful for those who write about topics they haven’t encountered before. 

Some freelancers have a staunch “no negotiation” rule, while others are willing to wiggle on their prices depending on the client and project. In this episode, we discuss our own approaches to negotiation. Warning: neither of us is a good negotiator– we would not get a good deal on a car. 

A proposal is a summary of a project plan, something that you and your client can agree upon. Seems simple, right? Proposals can be super helpful for making a sale, but they can also waste a lot of time. In this episode, we go over how to use proposals, available software options, and clever strategies for closing more deals. 

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.

Kaleigh has been Tweeting for more than a decade. She’s winning on Twitter with 44,000+ followers. In this episode, she shares how she thinks about Twitter, how she grew her following, and what she thinks other freelance writers can do to get value out of the platform.

Can you really freelance and parent at the same time? With childcare, sure. But what if you don’t have it? In this episode, Emma discusses how parenting has affected her freelance writing career. She goes over maternity leave, the necessity of childcare, and how the COVID-19 pandemic brought more of these issues to light. SPOILER: If Emma has another kid, she’s doing it differently next time.

It’s every freelance writer’s nightmare: a client who doesn’t pay! In this episode, we discuss our experiences with non-paying clients. Should you hire a lawyer, use a collections agency, send a strongly worded email, or just walk away? If you’re trying to track down payment, give this episode a listen.

There are lots of reasons people might want to pick your brain– perhaps they want to get started as a freelance writer themselves or think you’ll have perspective on a particular industry. But if you say “yes” to every request that comes your way, you might waste a looooooot of time. In this episode, we go over how to respond to “pick your brain” requests. When should you say yes, when should you charge, and when should you walk away?