Navigating the Contract Maze: Expert Strategies for Freelance Success
“The Devil is in the details!” That describes the importance that successful negotiations play in getting contracts that are comprehensible, unambiguous, and mutually beneficial.
That’s the ideal. Reality is often far off the mark.
In March 2025, the Canadian Freelance Guild hosted a webinar on Contracts and Negotiations for Freelancers featuring expert panelists Don Genova, donalee Moulton and Paul McLaughlin. They have been negotiating and focusing on the fine print for decades. A summary of this discussion is below. To view the webinar, you can access it here.
Three veteran freelancers share battle-tested advice on negotiating better deals, spotting red flags, and maintaining professional relationships while still getting paid what you’re worth
When it comes to freelancing, your creative skills might get you in the door—but it’s your contract savvy that determines whether you’ll thrive or merely survive. In a recent Canadian Freelance Guild panel on contracts and negotiations, three seasoned experts shared insights from their decades in the trenches, revealing both practical tactics and psychological strategies for navigating what many freelancers find to be the most intimidating aspect of their careers.
The panel, moderated by CFG President George Butters, featured Donna Lee Moulton, an award-winning journalist and corporate communications specialist from Halifax; Paul McLaughlin, a Toronto-based writer, broadcaster and author with more than four decades of experience; and Don Genova, a longtime food and travel journalist from Victoria who has helped freelancers interpret and negotiate contracts for many years.
Their message was clear: understanding contracts isn’t just important—it’s essential to your freelance survival.
The Freelancer’s Mindset: Business Owner First, Creative Second
An audience poll at the start of the session revealed what many might expect—most freelancers feel uncertain about their contract and negotiation skills, with many specifically identifying “fear of talking about money” as a major obstacle.
“I can appreciate the trepidation that we often have when it comes to talking about money,” acknowledged Moulton. “As freelancers and as business people, we want to establish a relationship with our clients, with our editors. And somehow when money gets involved in that process, we worry that it will in some way affect that relationship.”
McLaughlin cut to the heart of the issue: “If you’re going to be a freelancer, you’re a business owner, a small business owner. And you have to understand your business, and you have to learn how to price, and you have to learn how to make a profit.”
He illustrated this with a simple example: “The same way that if you start a painting company, you go door to door and say, ‘I’d like to offer my services.’ And they say, ‘Well, how much?’ You don’t say, ‘Well, I don’t know. What do you want to pay?'”
This mental shift—from thinking of yourself primarily as a creative person to recognizing yourself as the owner of a business—forms the foundation for successful negotiation. As Moulton noted, it requires “wearing the two hats, wearing the hat as writer and what I want to do as a writer and how I want to tell the story as a writer. But then the business hat has to come out.”
The Rate Paradox: Why Today’s Writers Are Making 1970s Money
One of the most eye-opening moments came when the panel discussed the stagnation—or even decline—in freelance writing rates over the decades.
“I started writing for magazines in the late 1970s and I was making a dollar a word,” McLaughlin revealed. “I was also being assigned four and five thousand word articles. That was 45 years ago.”
Genova added: “At one point, you could start at a dollar a word, and now, if you get a dollar a word, that’s still considered to be a good rate if you’re writing for a magazine.”
Butters shared an even more stark example: “My experience with the dollar a word, early, very early 80s to 2010. Same magazine. The father to the son, literally a father was the editor, then the son in the ladder. Same rates. The same rate, exactly the same. And I don’t think it’s changed today.”
The panel attributed this partly to the flood of aspiring writers willing to work for exposure rather than fair compensation. As Genova recounted from a conversation with a magazine editor who was asked why they pay writers so little: “His answer is very simple, because we can. Everybody wants to be in print. They want to see their name on an article, and they’re willing to do almost anything for almost nothing to do it.”
This reality led to unanimous advice: freelancers should look beyond traditional publishing toward corporate clients who often offer more respectful compensation. “The magazine world isn’t [respectful of what you need to earn]. And the newspaper world doesn’t even think about it,” McLaughlin noted. “I really think they’re doing, they think they’re doing you a favor by publishing you.”
The Three Numbers Strategy: Know Your Worth Before You Talk
One of the most practical takeaways came from Genova’s “three numbers” approach to negotiation:
“The first number is the one that’s something you’d really like to make for this. That’s kind of like, you know, almost ridiculous, right? The second number is what you can say is considered to be, well, it’s a fair price. I would make a reasonable profit on it. And the third number is your bottom line. You won’t, you don’t want to go under that, because then you’re in a losing proposition.”
This strategy provides both psychological preparation and practical boundaries. McLaughlin emphasized that knowing your bottom line helps project confidence—a critical element in successful negotiation.
“People kind of smell each other, you know, and sense each other. So if you’re there and you have no idea what you’re going to do, you’re just desperate for the work or desperate for the money… Desperation is one of the least attractive qualities a human being can ever have,” he explained.
“If you can appear at least to be confident, to be self-assured, even if you have to kind of put it on at first, you’ll eventually, I think, take it on.”
Value-Add Strategies: Getting Paid More Without Working More
Rather than simply asking for higher rates, the panel suggested looking for creative ways to add value that costs you little but justifies higher compensation.
Genova shared a personal example: “When I was doing items for CBC… I wanted to negotiate above the minimum, and they didn’t want to do that. And I said, ‘Well, listen, how about if I provide you every Monday night a promo that you can use on Tuesday morning before I come in?’ And then maybe pay me two extra minutes.”
This arrangement meant he earned about $100 more per column for work that only took him 10-15 minutes to complete—a win-win situation.
Similarly, if you have a substantial social media following that could help promote published work, that’s a negotiating point worth mentioning. While this might seem like giving away more of your labor, the panel emphasized that strategic value-adds can lead to better long-term relationships and compensation.
Corporate vs. Media: A Tale of Two Worlds
A recurring theme throughout the discussion was the stark contrast between negotiating with traditional media outlets versus corporate clients.
McLaughlin didn’t mince words: “With corporate people, I find it’s a very professional, healthy experience… they expect you to charge them professional rates and then produce, of course, professional product.” By contrast, he described dealing with magazine editors “who try to make you feel that every penny they’re giving you is coming out of their children’s educational fund.”
Moulton noted that in the corporate and government world, the negotiation process itself is often more structured: “A lot of corporate work you have to bid on or government work you have to bid on… Well, then you set your own rate. You say this is what I would do the work for. Here’s the work that I would do and you either win the contract or you don’t.”
This approach eliminates some of the uncomfortable back-and-forth that many freelancers dread. However, she cautioned that corporate and government contracts often have inflexible elements beyond just pricing: “You might be able to negotiate your rate… But there are things like hotels. You don’t get to upgrade your hotel, right? Because there’s a list of hotels and you have to pick from the list of hotels.”
Red Flags That Should Send You Running
All three panelists had encountered problematic contract clauses that freelancers should watch for—with several unanimous “deal-breakers” identified:
Payment on publication topped the list. “You just don’t sign that because if they don’t publish it, you don’t get paid or if they wait two or three years, or if the editors change,” McLaughlin warned. Genova agreed, noting that if a magazine goes under before publishing your piece, writers are “very low on the list of payees that deserve to get paid in a bankruptcy.”
Moral rights clauses were another universal concern. As McLaughlin explained: “If you sign away your moral rights, they can do anything they want with what you wrote. If you are like anti-Trump in your writing, you could become pro-Trump if they change it. They can change, they can put someone else’s name on it. They can do anything they want.”
Genova shared a powerful example: “Anne Douglas, who is a longtime PWAC and CFG member, she actually quit the Toronto Star rather than give up her moral rights because she wrote parenting columns. And she was concerned that suddenly her parenting columns could have been reworded to put her in favor of some sort of parenting style that she was not in favor of.”
Indemnity clauses were flagged by Genova as particularly dangerous: “Basically you’re saying, if I do anything wrong, it’s all on me. And I will pay all the damages that you may negotiate.” He warned these clauses often ask writers to guarantee things they can’t possibly verify, especially regarding third-party rights like photos.
Inadequate kill fees also made the list. “They’re saying that, well, at some point we may kill the story. We don’t want to publish it anymore. And we’ll give you 25%,” Genova explained. “Excuse me, I did all the work.” His rule of thumb: if all the work has been done, you should get 100%; if you’re halfway through, you should get 50%.
Book Contracts: A Special Case
When audience member Sharon Bird asked about book publisher agreements, the panel offered specific insights for authors navigating this distinct territory.
McLaughlin described his “protracted negotiations” with Dundurn Press: “First of all, they didn’t want to give me an advance. And I just refused. I said, I’m not doing it if you don’t give me an advance…Then they said, well, we’re going to dole it out in three payments. The third one after the book is published. No, not doing it. It’s not fair.”
He encouraged authors to review contracts line by line: “I think I got 10, 15% of the clauses removed.” However, he advised strategic flexibility: “If you’re in a protracted negotiation, you’ve got to give them something. I think maybe if you want to win eight, you’ve got to lose two.”
Moulton pointed out the different approaches required for fiction versus nonfiction: “If you’re writing fiction, you write the manuscript before you get the publisher… You’re just waiting now for Steven Spielberg to come along and turn it into a movie.” By contrast, “nonfiction is a little different because you tend to sell the idea, you submit a proposal and then you write the book.”
She also highlighted a valuable resource for Canadian authors: “There’s an organization in Halifax and it may exist in other provinces as well called ALICE. And it’s a legal clinic…that will actually take your contract and read it and come back to you and say, ‘Donalee, I think these clauses are just fine. You’re giving a little here, you’re getting a little there. These are the three we think you can’t live with.'”
The Impact of AI: The New Frontier
When Butters raised the topic of artificial intelligence in contracts, the panel acknowledged this emerging area.
Genova noted that while he hadn’t yet seen specific AI clauses in contracts he’s reviewed, “most contracts traditionally say that this must be your work, your creation.” He predicted: “I suspect that it will be coming… to say, it will mention AI, that your content should not be generated by artificial intelligence in any way, shape, or form.”
Moulton had already encountered these clauses in her fiction work: “The AI clause is in all of it… And it’s like the floodgates open. So it wasn’t there on Monday. And on Tuesday, everybody and their dog was including it.” However, she noted these clauses often lack clarity: “There’s no attempt to explain what AI generated means, or why it can’t be AI generated, or if my grammar check is a form of AI.”
McLaughlin approached the issue from an educator’s perspective: “My university writing students, I have a clause in the syllabus, where they have to tell me if they’ve used AI, and for what a part of their work, because there’s no way around the fact that people are going to use it, including freelance writers.”
Butters, who serves on an AI committee with the News Guild-CWA in the U.S., observed that major publishers are “being particularly vague about their use of AI” while creators are pushing for “protectionist clauses” to safeguard their work from being replicated or repurposed through AI.
The Power of “No” and When to Use It
Perhaps the most empowering message throughout the session was the importance of being willing to walk away when terms aren’t acceptable.
As Butters noted in his closing remarks: “You said the magic word for freelancers. No. It’s the most powerful word you have—use it carefully. But sometimes you’ve just got to say no.”
This sentiment was echoed by McLaughlin’s experience: “We went through every single clause. And I think I got 10, 15% of the clauses removed. And the person I dealt with was very professional, very polite, very difficult. But I won most.”
Genova referenced a Canadian Media Guild freelance branch brochure titled “Draw Your Line in the Sand,” emphasizing: “At a certain point, you have to, you say, I can’t sign this. It’s not going to work for me the way it is.”
While this may seem intimidating, especially for freelancers worried about losing opportunities, McLaughlin offered an encouraging counterpoint: “Over the many, many decades, when I’ve asked for more money, I’ve almost always got it. Not every time, but almost always.”
The key, according to Moulton, is understanding that professional negotiations are “not going to affect your relationship with 99% of the people you work with, they are going to see this as routine and ordinary and to be expected. And so don’t feel like you’re jeopardizing your livelihood. In fact, you’re doing just the reverse.”
Practical Steps You Can Take Today
Throughout the discussion, several actionable tips emerged for freelancers looking to strengthen their negotiation skills:
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- Know your three numbers before any negotiation: dream rate, fair rate, and absolute minimum
- Create your own simple contract when none is offered. As Moulton suggested: “The onus is on us almost to create the contract, to say, you know, ‘My rate is 50 cents a word, and I sell only these rights.'”
- Use the phrase “what is your proposed rate?” McLaughlin recommended this specific wording because “that word ‘proposed’ opens the door to negotiation.”
- Look for creative value-adds that cost you little time but justify higher compensation
- Read contracts thoroughly, especially before final signing. As Butters cautioned: “Look for the stuff that’s changed. Because there are people that will do that to you. And the thicker the contract, the more likely that is to happen”
- Remember that informal agreements are still contracts. Emails and text messages where you agree to terms constitute legally binding agreements
- Consider the book angle. As McLaughlin noted, “My first [book] that I wrote—it was published in 1986—has made me a huge amount of money from everything but the royalties.” Being published enhances your credibility and can lead to speaking engagements, training opportunities, and higher-paying client work
For freelancers navigating the often-murky waters of contracts and negotiations, the panel offered both tactical advice and psychological reassurance. Perhaps most importantly, they emphasized that advocating for fair compensation and terms isn’t just about the immediate transaction—it’s about building a sustainable career that allows you to continue doing the creative work you love.
As McLaughlin pointed out from his teaching experience, when editors visited his class, they consistently said they valued the freelancer who “delivers what they said they were going to deliver and delivers it on time. And if they do that, they’re gold.” The quality of writing, while important, often came secondary to reliability and professionalism—exactly the qualities that successful contract negotiation demonstrates.
