AI wrote part of this post. It's, um, not great.

Will ChatGPT replace me? 😳

via ChatGPT

***Hi, real Tim here. I’ll denote where the AI portion starts***

There are three things we journalists love to talk about more than anything else: how important journalism is; how hard it is to be a journalist; and the looming threat of AI taking all of our jobs. Facts is facts, y’all.

So this week, let’s dig a little bit into that last one, which so many of us have come to view as a potentially existential threat to our industry. I know we’re all sick of hearing about it, but the use of AI is only going to get increasingly more impactful and widespread — and devastating to publications. As WSJ put it last month in a headline, “News Sites Are Getting Crushed by Google’s New AI Tools.” Reporters Isabella Simonetti and Katherine Blunt wrote,

The AI armageddon is here for online news publishers.

Chatbots are replacing Google searches, eliminating the need to click on blue links and tanking referrals to news sites. As a result, traffic that publishers relied on for years is plummeting.

[...]

Google’s introduction last year of AI Overviews, which summarize search results at the top of the page, dented traffic to features like vacation guides and health tips, as well as to product review sites. Its U.S. rollout last month of AI Mode, an effort to compete directly with the likes of ChatGPT, is expected to deliver a stronger blow. AI Mode responds to user queries in a chatbot-style conversation, with far fewer links.

Not only is AI demolishing once-reliable search traffic for some outlets, but more and more newsrooms are integrating it directly into their editorial workflow. For example, Nieman Lab reported earlier this month that Law360 is now mandating reporters to use an AI-powered “bias indicator,” which is supposed to ferret out what it deems to be non-neutral viewpoints. The outlet’s union, which represents some 200 editorial staffers out of a 350-person newsroom, wasn’t thrilled. From Nieman Lab,

On June 17, unit chair Hailey Konnath sent a petition to management calling for the tool to be made “completely voluntary.”

“As journalists, we should be trusted to select our own tools of the trade to do our information-gathering, reporting and editing — not pressured to use unproven technology against our will,” reads the petition, which was signed by over 90% of the union.

Legal blog Above The Law summed it up pretty succinctly: Law360 “has an AI tool to scold reporters and it's bad at its job.” And Jason Koebler of 404 Media wrote a fantastically interesting post this week: The Media's Pivot to AI Is Not Real and Not Going to Work. “AI is not going to save media companies, and forcing journalists to use AI is not a business model,” reads the post’s subhed.

On the other hand, I’m kind of loving The Washington Post’s new-ish AI-powered feature, Ask The Post, which draws on WaPo stories to answer questions readers may have about news events. Kinda cool! The Post is also set to test out using AI to coach outside writers to contribute Opinion pieces, The Times reported last month. (The jury seems to be out on that one for now.)

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Want to learn the nuts and bolts of writing the perfect pitch? Join me July 22 for a pitching workshop that will cover everything from structure, what to include in a pitch, to how much pre-reporting you should do, how to find editors to pitch, and so much more. Click here to register. (All registrants will receive a playback of the full session, and paid subscribers get 50% off all events.)

Ever wanted to learn how to write a longform narrative feature? Join me July 24 for an in-depth workshop on the art of structuring a longform piece. This will be a deconstruction exercise of a published longform narrative feature, and I’ll give you tips on how to use those tools in your writing. Click here to register. (All registrants will receive a playback of the full session, and paid subscribers get 50% off all events.)

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Now, whether it’s ethical — or, indeed, moral — to use AI in one’s work is a question for another time. But as an experiment, I thought I’d hand part of today’s newsletter over to ChatGPT to give us its best advice for freelancers who want to increase their commission rate for pitches. Spoiler: It’s not very good advice! But I’ve never used AI to write before — and if I ever do in this newsletter, I’ll of course make a note of it — so I wanted to test it out to see if it can add any value to what we talk about here, mainly thriving as a freelance journalist.

First, though, I want to know: Are you using AI in your freelance work? If so, how? (E.g., help writing/editing stories, automating certain tasks, fact-checking or general research, etc.) Leave a comment below and let me know, or email me at tim@freelancingwithtim.com and I may include your response in a follow-up to this post.

Without further ado, here is ChatGPT’s okay-ish advice on how to get more pitches commissioned, in response to the following prompt: “Act like you’re a veteran editor at a national news outlet. You assign and edit stories primarily from freelance journalists. A freelance journalist asks you for advice on how to write better pitches to editors, increase the overall percentage of those pitches being commissioned, and how to break into bigger news outlets across the industry. This freelancer also wants to know what they can do to develop stronger working relationships with editors so they get more assignments. What advice would you give? Give practical, concrete, actionable advice, and limit your response to around 400 words.”

***ChatGPT starts here, without any editing***

Subject: The Editor’s Inbox: How to Actually Land More Assignments

Hey there,

Let’s talk about the thing every freelancer wants to know: How do I get more editors to say yes?

I’ve been assigning stories for years at national outlets, and most of what lands in my inbox falls short — not because the ideas are bad, but because the pitches are weak, vague, or misaligned. So here’s my no-fluff, straight-from-the-editor advice:

🧠 Your pitch is a story, not a topic.

Bad: “I want to write about student debt.”

Good: “Inside the secret Reddit groups helping student borrowers fake loan forgiveness letters — and what it means for the future of debt relief.”

Lead with a proposed headline. Then give me:

• A sharp one-sentence summary
• 2 short paragraphs explaining the angle, why it matters now, and how you’ll report it
• Why you are the right person to write it
• 2–3 relevant clips

🎯 Tailor every pitch.

Reference a section or recent piece to show you understand the outlet’s voice and coverage. “This feels like a fit for your [X] column…” is music to my ears.

📊 Track everything.

Keep a spreadsheet of who you pitched, what you pitched, when you followed up, and how they responded. Over time, you’ll spot patterns — and improve your hit rate.

🔑 Breaking into big outlets? Start where they say yes.

Major outlets are more open in service journalism, opinion, essays, and trend coverage. Nail a piece there, and you’re on the radar. Strong clips from respected mid-size outlets also help — I need to know you can deliver.

🤝 Want a stronger relationship with an editor? Be a pro.

File clean copy. Meet deadlines. Take edits with grace. Ask: “Do you need help with anything coming up?” That simple question has led to countless assignments.

Pitching isn’t just about good ideas — it’s about trust. Show me that I can count on you, and I’ll keep coming back.

Until next time,

Your friendly assigning editor

***Tim back, no more from ChatGPT***

Hmm. I mean, it’s fine, if a little cold and generic. Nothing in there is necessarily wrong, but it’s certainly far from the advice a human editor would give if they really wanted a freelancer to succeed. (For more specific and practical advice on pitching, join my pitching workshop on just that on July 22.)

Of course, this is just one example of using AI to write. As of now, I don’t think it’ll be replacing Freelancing With Tim anytime soon, but hey, we’re still veeeeery early days here, so who knows when AI will come for me.

Until next time,

Your friendly (human) assigning editor

P.S. — Thanks to everyone for contributing to the FWT database of freelance rates for 300+ publications. I’ll be updating the database about weekly, so please feel free to share some of your own recent rates here.

Oh, a few other things …

• I offer one-on-one coaching! Need help developing an idea or sharpening one you already have? Want a seasoned eye on a pitch you’re kicking around? Interested in talking about careers and building your freelance business? Maybe just want an edit on a story draft? I’ve got you covered! Click here to book a one-on-one coaching session to talk about pitch reviews, story development, editing, careers, and anything else you might need help with.

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• Got a question about freelancing or the wider world of journalism? Let’s hear it! Once or twice a month I’ll be doing Q&A posts in the newsletter to answer all of your questions, comments, and thoughts about freelancing and journalism in general. Drop any and all questions in the comments section below this post or email me at tim@freelancingwithtim.com, and I may feature it in a future newsletter.