Hello friends, and happy (belated) start to spring! I hope you’ve all been eagerly coming out of your winter cocoons and enjoying a little more sun and nicer weather (if that’s the case where you live, anyway).

Today we’re going to talk about how to proceed when your story just ... isn’t working. Stories fall apart for a million reasons, but that doesn’t always mean the story is dead. A lot of the time, they’re totally salvageable with a little extra effort!

Pretty early on after I became an editor, I was working with a freelancer on a story about disintegrating familial relationships. We had a general perspective and outline, a plan of action, and a pretty direct route forward. We were both pumped about it!

A few weeks later, the freelancer emailed me: sources were disappearing, the background reporting wasn’t aligning with what we thought the story was, and the writer felt that our plan was caving in. We talked about a few ways to dig ourselves out, but, eventually, the writer just stopped responding.

This, of course, is an example of what not to do when your story is falling apart. What could have eventually become a helpful, relatable story about family and relationships turned into ... nothing. This freelancer had called the game too early and ghosted.

Don’t do that! Believe me when I say that editors genuinely want to work with you through the entire process, even when it gets ugly, and it’s quite literally their job to do so. (In this editor’s opinion, it’s one of the most rewarding experiences for an editor.)

Stories fall apart. It happens to freelancers fresh to the industry and to veteran staff reporters who have been on a beat for 15 years. It’s not unique, it didn’t just happen to you, it doesn’t reflect on your skills or temperament as a journalist, and it most certainly doesn’t mean it’s automatically time to throw in the towel. Sources disappear, the reporting is completely counter to what you thought the story was (literally happened to me this week on a story I’m writing for next month), you get into the weeds and realize there just isn’t anything there, the moment passes ... these things happen, and a lot of the time it’s simply out of your hands. It sucks, it’s stressful, it can feel like failure, but this is the life we signed up for as journalists. Your editor understands this, and you won’t be the first freelancer whose story fell out from under them.

Upcoming Zoom workshop, please join me!

• April 23 @ 4:30 p.m. Eastern: How to write story pitches editors will actually read — and commission. Join me for an in-depth examination of what goes into a fantastic story pitch. How do you structure it? What must be in it, and what should you leave out? How much pre-reporting should you do? How can you head off the follow-up questions an editor will inevitably ask? How do you even find editors to pitch or know what publication to shoot for? We’ll cover all that and much, much more in this workshop. (All registrants will receive a playback of the full session, whether they attend live or not, and paid Substack subscribers get 50% off admission.)

Click here to register

P.S. — I know a few folks had trouble accessing a previous one of these; if that’s you, email me directly and I’ll comp you into this one.

But! With some redirection, refocusing, and reframing — sometimes a little, often a lot — even the most hopeless of stories can turn into something beautiful. *insert awful, tired cliché about how pressure makes diamonds*

So we know what not to do — give up, ghost, abandon the idea, generally just write off the story — but what can you do to pull a story back from the brink?

Here are a few simple Dos and Don’ts to pull the body out of the trainwreck.

Do: Communicate

This is by far the most important part. Again, editors have been to this rodeo before. To a certain degree, it’s expected! But the moment you realize things aren’t shaping up as you thought they would, just reach out. A super simple email laying out exactly what’s going on is the best move here, and it doesn’t have to be complicated:

“Hey, can we hop on the phone when you have a minute? It’s starting to look like our story isn’t panning out how we thought it might. [X source pulled out, Y research showed something totally opposite, Z time peg has passed unexpectedly soon], so I’d love to chat through some ideas with you.”

That’s it! When things look shaky, communication is your ladder out of the hole. It might seem like an insurmountably uncomfortable conversation, but truly, honestly, it’s not.

Don’t: Keep the problems to yourself

The worst thing you can do here is never mention the problems and then file a story completely different from the version you talked about with your editor. No editor in the world will be upset when a writer tells them things aren’t looking great at the moment, but editors will be miffed if you file a 900-word explainer when the agreed-upon idea was a 2,000-word narrative feature. It’s perfectly fine that every single thing isn’t working out! They rarely do. But resist the impulse to try to fix everything on your own. You’re not on your own here.

Do: Bring ideas

I know, I know, we’ve all heard it before: Don’t bring problems without bringing solutions. That worn-out axiom certainly applies here. Even if you don’t have a fully formed idea, at least try to have a few rough thoughts about potential paths forward. It’s the editor’s job to work with you and help shape those thoughts into ways forward.

Similarly, it’s important to have some specifics about what’s not working with the story. The editor won’t have any clues on how to fix it if you don’t tell them what’s wrong, so be forthright (however awkward that might feel in the moment) about exactly what is falling apart.

Don’t: Expect your editor to completely fix everything

This is still your story, and as much as your editor can help you with it, they can do only so much; you still have to report and write it. A good editor will be there every step of the way, but at the end of the day, they can’t report your story for you. I know this seems self-evident and obvious, but you would be astounded how many times a writer will file what is essentially an outline and expect the editor to do the rest. (Like, for real, it happens way more than you think.) Your editor can, and should, help devise solutions, but the writer is still the one who has to execute.

Do: Establish a realistic revised timeline

If you bring up the issues early enough, an extended timeline will almost literally never be a problem. (But, of course, nothing is ever guaranteed in life, sigh.) If you think you’ll need an extra two weeks to iron things out, just ask for the full two weeks. If you realize — and communicate — the problems as soon as you encounter them, reworking a pub sked is generally not a major problem. (Bringing these up a week before your pub date, on the other hand ...)

Don’t: Force it if it’s not there

We’ve all had to deal with it, probably many times: The story just isn’t meant to be. It happens. Take the loss — and if you’re lucky, the kill fee! — and start on your next story. A few years ago I was unbelievably excited about a story idea I loved and successfully sold to GQ, but for a multitude of reasons it utterly unraveled and there just wasn’t a way to bring it back to life. This sucks in the moment, so give yourself a beat to be bummed, but don’t linger. It comes with the territory.

Do: Forget it and move on

Fail, recover, retry. That’s all we can do. (And if you’re doing things right, you should be failing a whoooole lot.)

Good luck out there!

Oh, a few other things …

• How much were you paid for your last assignment? Feel free to contribute to our ongoing freelance rate database here. And if you’d just like to see the regularly updated database, check it out here.

• Sell a pitch recently? I want to see it! If you had a story picked up not long ago, I’d love to feature you and your story in our ongoing series highlighting pitches that sold. Email me at tim@freelancingwithtim.com and put “Pitches that sold” in the subject line. Can’t wait to see ’em!

  Email me

• I offer one-on-one coaching! Is your story falling apart and you need a second pair of eyes on it? Want a seasoned perspective 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 below to book a one-on-one coaching session to talk about pitches, story ideas and development, editing, careers, or anything else you might need help with!

  Click here to book a session

Hello friends, happy holidays! The year is almost over! It’s officially winter now! It’s all happening!

In the time-honored tradition of publications rounding up their best work of the year, this week I’m pleased to present 2025’s most popular FWT posts. Below are the newsletters and stories that have most resonated with the FWT community, not only in terms of traffic, but also in the robust conversations that surrounded these topics. Some are super practical — like the nuts and bolts of getting started in freelance journalism — while others are more abstract, like how to get editors to come to you.

But more broadly speaking, what did we learn this year?

Not to get too ~down~ during the holiday season, but one of the overarching themes of many conversations I’ve had this year with freelancers is that ... well, it’s rough out here. Between budgets being slashed, opportunities disappearing, and competition being tougher than ever, so many of us have had a rough year in the industry.

Personally, I have found a weird sort of comfort in that. Despite all of us facing pretty rough headwinds, the freelance community has rallied around each other and supported one another in ways I haven’t seen since the worst days of the pandemic. The generosity of freelancers has been on display in a wonderfully heartening way this year, and though the bad times aren’t going to end any time soon (or ever?), the succor I’ve seen freelancers offer has been a beautiful example of lifting others up. No freelancer makes it without the support of fellow freelancers, and it’s a pleasure to be a part of it. (Sorry to get all sappy, but I really mean it!)

With that, below are the 10 best posts from FWT this year. I hope you’ve gotten as much out of them as I did researching them and putting them together, and I’m so excited for a ton of really great stuff coming in 2026. (And a quick programming note: I’ll be off this Thursday, but back in the saddle after that.)

Happy holidays!

Click here to register

Hello friends! 2025 is rapidly coming to a close (literally how, wasn’t it March last month?), so now is as good a time as any to reevaluate your client list. Let’s call it the Great EOY Purge.

Dropping clients?! In this economy?!?!

Just hear me out.

As freelancers, we put so much time and effort — both emotionally and practically — into finding new clients. After all, that is our livelihood, and it’s a sometimes grueling task that never gets easier. And, before we get too far, yes, I fully concede this does sound kind of insane: Why would we dump a paying client after spending hours, weeks, or even months landing them? But the calculus gets a little more complicated when we take a step back to think about what we’re sacrificing to get that paycheck. Sometimes it’s really just not worth it.

It can even be freeing to let go.

I was inspired to write this newsletter after I saw someone on LinkedIn a while back say, more or less, that a paycheck is a paycheck, and everything is so precarious that sometimes you just have to eat the shit sandwich and put up with whatever it takes to get paid. I understand the intention behind the idea — again, it can seem ludicrous to drop a paying client — but I fundamentally disagree with it. No paycheck is worth sacrificing your mental well-being.

To wit: One of my first gigs after I went independent was a copywriting position. It paid exceptionally well: about $5 per word. Wild, I remember thinking. I had discovered the key to the freelance kingdom! Nothing but fat paychecks for easy work from here on out! I’ve made it!

But I hated the work. It wasn’t rewarding, it was dull, I wasn’t proud of it, and it just wasn’t what I wanted to be doing. The people I was working with were wonderful, which made the decision that much more complicated, but I needed to make a decision nonetheless. It took some deep introspection — Come on snowflake, are you really gonna give up a $5/word gig because it’s not ~rewarding~ enough for you? — and ultimately I concluded that the psychic toll it was taking on me wasn’t worth those lovely paychecks.

How do I know when it’s time to cut ties?

Read more

Hi! I’m sure you usually skip past this, but please take a sec to read! I started FWT years ago to provide resources to help journalists thrive in our industry and to demystify the world of freelancing. I want to continue that mission and offer more and more resources, so if you like what you’re reading want to help this grow, please consider upgrading to a paid subscription. A paid sub includes an extra newsletter every week, 50% off all Zoom events, access to all past and future paid-only posts, and much more. Subscriptions start at just $7/month or $70 /year. Either way, so thrilled you’re here!

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Hello friends, and happy holidays! First, I just want to apologize for not having been around much lately. The past few months have been extremely ... complicated ... for a few very significant reasons. But everything is evening out now, and I’m back in business.

So! Today we’re talking about a more subtle approach to landing more freelance work. We all know the obvious stuff: pitch more, network more, build a stronger brand presence, be shameless about self-promotion, etc. Of course, that stuff is necessary. But there’s something a little more subtle and nuanced that is just as important.

Let me explain.

Lots of freelancers I work with ask some version of the same question: How do I impress editors? How do I stand out? How do I sound smarter in my pitches? How do I make my work impossible to ignore?

It’s perfectly natural to fall down this rabbit hole! Freelancing can feel competitive, and when work is uneven, even a slight edge can make the difference between paying rent with a paycheck or dipping into savings (should we be lucky enough to even have savings). It’s normal to assume the solution is to be more impressive, more original, more insightful, more undeniable.

And to be clear, those things do help. It goes without saying that the best way to get more freelance work is to create truly impressive, original, and standout work. Be so good they can’t ignore you, and so on. But after years of editing freelancers, talking with other commissioning editors, and freelancing myself, I’ve come to believe that this line of thinking is slightly off. Or, at least, incomplete.

A better question is: How do I make myself an obvious, low-risk choice?

A great idea sells once. A great partner sells as much they want.

I’ve said it before, and I’ll say it again: Editors absolutely would prefer to work with a dependable, reliable, consistent freelancer than a superstar. No question about it. The writers we come back to most are the writers with whom our last collaboration was smooth, calm, and predictable. When an editor is scanning their mental list of possible writers on a tight deadline, they’re not asking who impressed them the most. They’re asking who will make this assignment go the least sideways.

That’s the quiet truth most freelancers don’t hear early enough.

Generally speaking, most working freelancers are good writers and have good story ideas. And even if they’re not at that superstar status just yet, it’s our job as editors to get them there. It’s one of the great joys of being an editor! And the freelancers we love working with most are those who actively want edits and want to grow and learn.

So the differences that determine who editors go to in a pinch — or even just who we want to work with more regularly — tend to show up in much subtler places, like how easy (or not) it was to work together, or, again, how eager and receptive the writer is to take edits and improve. Were things manageable even if they got way off track? Or stressful and full of unnecessary surprises? Stability makes just as strong an impression as chaos.

Being impressive is memorable. Being low-risk is assignable.

Another bell I ring often is that clear, early communication is one of the simplest ways to become that low-risk choice. We editors notice when expectations are aligned early, when details are clarified instead of assumed, and when questions are asked before they become problems. A short email that says, “Just confirming scope and deadline so I’m aligned,” does more for your reputation than an extra clever turn of phrase in your copy. Clarity is crucial.

All the same can be said for reliability. You can file perfect, clever, insightful copy all day, but if an editor doesn’t know when they can actually expect you to file, you’re probably not the type of freelancer they’re going to actively assign to. Editors don’t need perfection; they need consistency. It’s literally our job to make your story the best possible version of itself that it can be! So a writer who hits deadlines most of the time and communicates early when issues arise is far more valuable than a writer who occasionally delivers something brilliant but unpredictably.

And, to be clear, predictable doesn’t mean boring. It just means an editor knows roughly what will happen when they work with you. They know how you communicate, how clean your drafts will be, how you handle edits, and how you respond under pressure. That predictability makes you an easy, and obvious, choice for assignments.

Is this the most glamorous way of working? Of course not; there’s no Pulitzer for “Most Dependable Freelancer.” But it is a surefire path to getting more consistent work, and to building a reputation as someone editors actively want to work with.

I’d say you can’t put a price on that, but the price is right there in your bank account.

Oh, a few other things …

• If you like what you’re reading, please consider subscribing to the paid version of this newsletter. Paid subs get an extra newsletter every week, access to all past and future paid-only posts, 50% off all Zoom workshops, a guide to avoiding the 7 most common mistakes in freelancing, a must-have checklist for getting your assignments right, the exact text of a pitch I sold to The Atlantic, practical tips for diversifying your freelance income, and much more.

  Subscribe now

• How much were you paid for last assignment? Feel free to contribute to our ongoing freelance rate database here.

• Sell a pitch recently? I want to see it! If you had a story picked up not long ago, I’d love to feature you and your story in our ongoing series highlighting pitches that sold. Email me at tim@freelancingwithtim.com and let’s talk!

• I offer one-on-one coaching! Is your story falling apart and you need a second eye on it? Want a seasoned perspective 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 below to book a one-on-one coaching session to talk about pitches, story ideas and development, editing, careers, or anything else you might need help with!

  Click here to book a session

There was a time, many internets ago, when Twitter was the end-all, be-all network for journalists. In some (decreasing) ways, it still kind of is, but I think we’ve all come to the conclusion that ... it just kind of sucks now. What used to be a fun place to meet other journalists, find work, network, and just goof around has become something very different. 

But what you probably don’t know — or have written off — is that LinkedIn has become the new hot spot. It has everything: jobs, gigs, networking, weird personal life posts that feel oddly intimate, life and career updates from people you actually know, and a place to make genuine connections with others in the industry. This is a tune I’ve been singing for years, but I really mean it. (Also hi let’s connect, here’s mine!)

This sounds weird! I realize that. LinkedIn still hasn’t fully shed its 2013-era reputation of being a lame place where middle-aged guys post motivational quotes and self-righteous soliloquies. But I promise it’s not that. On top of being an absolute gold mine of full-time positions and freelance work, it’s a place to find news in real time, make connections that actually pay off in ways that Twitter never did, promote your work, and, practically speaking, drive real traffic to a story. I worked in audience dev for years, and my secret weapon was always LinkedIn.

So how can you use it to your advantage? Here are four things I always advise:

Update your profile

If you’re like most journalists, you probably set up a profile years ago and haven’t changed it much since. It’s time to fix that! A current, engaging profile is one of the most important things you can do to get yourself out there and find work.

A few things: Your profile pic and header. Friend of FWT Kaitlyn Arford has a fantastic pic/header combo — check it out here. Her profile has a specific visual identity that aligns with her personality, and it fits well into her other online profiles, including her website. On top of that, her header image says right away what she does and that she’s open for work. Having a consistent visual identity screams professionalism, and it’s worth the effort. (If it’s in your budget to hire an illustrator for a few images, go for it.) I do the same on mine.

Aside from visuals, update your profile with your skills, recent experience, clips you want to show off, and services you offer. This not only helps anyone who finds your profile, but it will also help you surface in more searches that people conduct around your areas of expertise. Updating all of this is super easy: Just click View Profile from the top-right dropdown menu, and explore everything you can. Be sure to drop in a bunch of keywords that align with your business anywhere you can. (Also, make sure you update your Basic Info section with some keywords, too.)

Don’t be shy about advertising what you can do

A few times a year, I’ll use this exact text in a standalone post: “Hello friends! Reminder than I am available for copywriting, editing, consulting, and any other media needs. DM me! :)” It’s literally one sentence, and from that post I get at least seven or eight DMs from people interested in hiring me for those services. It really is that simple. It can feel weird, but the only way people will know that you’re available is if you tell them. No one is paying attention to your career as much as you are, so let them in on your skills.

Network network network!

Something I always say: Networking is only weird if you make it weird. Just think of it as making friends with other folks in your industry. It’s perfectly fine to request someone you admire, want to work with, or just want to be industry friends with. Those connections may end up leading to more and more work. Include a little note with your request if you want, too, but no more than a sentence, otherwise it feels like an email.

Engage with your peers

Conversations on LinkedIn are, while often corny, exponentially kinder and more civilized than anything you can find on Twitter these days. People are actually sincere! Imagine that! Those in your network want to hear from you, and they can be a great resource of feedback or just general discussion for you, so take advantage of that. It’ll never be as silly as Golden Age Twitter, but it can be just as fulfilling.

See you on LinkedIn!

Oh, a few other things …

• Sell a pitch recently? I want to see it! If you had a story picked up not long ago, I’d love to feature you and your story in our ongoing series highlighting pitches that sold. Email me at tim@freelancingwithtim.com and let’s talk!

• I offer one-on-one coaching! Is your story falling apart and you need a second eye on it? Want a seasoned perspective 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 below to book a one-on-one coaching session to talk about pitches, story ideas and development, editing, careers, or anything else you might need help with!

  Click here to book a session

Hello friends! Today we’re going to talk about what is probably the second most common question I’ve gotten over the years from freelancers when it comes to pitching: “When should I send my pitches?”

Here’s the simplest answer: Don’t worry about it!

Being a freelancer is stressful enough, and worrying about timing your pitches is a lot like trying to time the stock market: You might get lucky every once in a while, but on the whole, it’s not worth the stress of worrying about it and it will rarely pay off. It’s true that some editors do have a specific day of the week they tackle the pitches in their inbox, but trying to nail down that little window won’t be the difference between your pitch getting accepted or rejected. Editors will read your email when they read it, and, frankly, it’s not your job to make sure editors do theirs.

The timing question speaks to a much larger issue that essentially boils down to: What are the tiny things I can do to improve my chances of selling a story?

Here’s a truth I hope you will take some relief in: You should stop worrying about most of that stuff. It’s causing you far more anxiety than it’s worth. And, as I always say: If you get the big stuff right, the little stuff — like timing your pitch — doesn’t really matter.

Still, I know these things can weigh on freelancers. So with the hope of easing your stress a little, here are a few things that most editors generally don’t think about when it comes to pitches.

Read more

Hello friends! Welcome to another edition in our series of Q&A posts, in which I’ll pick a few reader-submitted questions and offer my take. Got something you need advice on? Email me at tim@freelancingwithtim.com or leave a comment at the bottom of this post.

Now, onto the Q’s!

The place I used to write for disappeared, along with all my clips. How can I explain this to a new editor?

I'm about to send out my first pitches, and I have a question about clips. The only place I've been published in was a retailer's blog that has since been taken down. How do I handle this? Add links to my drafts and briefly explain the situation? Contact the editor to see if he'd be a reference? Leave them off altogether? —Anonymous

Ohhhh boy, yep. This tragedy is near and dear to my heart, and one that is sadly all too common among journalists, myself included. There’s basically no evidence of the first three years of my career because the publication I worked at redesigned its website and wiped out the entire archive. Cool, super fun.

First, the solution to this problem — and how to avoid being caught in it in the first place — is to always save PDFs of your clips once they’re published. You never know when an outlet is going to fold, or a site redesign will wipe out its archives, so saving those PDFs is critical. Your browser likely has a screenshot function built in, so you can capture the entire page super quick. If you’re not already in the habit of doing this, make it a top priority. Once your clips are gone from the internet, odds are they’re gone for good. (You might get lucky if Wayback Machine happened to snap it, but certainly don’t rely on that.)

Alas, we don’t always have the foresight to do that. In this reader’s particular case, I would be upfront with the new editor and explain the situation. This probably wouldn’t be the first time the editor has heard this tale, and it won’t be the last, so they’ll understand. If you don’t have any other clips whatsoever, it probably wouldn’t hurt to see if that old editor wouldn’t mind serving as a reference, but that will get you only so far (if the editor is even willing to go with it). I typically wouldn’t advise a freelancer to send along drafts of a story, but if you have the final, published version of your best clips, it probably wouldn’t hurt to include them with your explanation. Editors understand this happens, and there’s really nothing anyone can do about it, so just being honest and open about it is kind of the only option.

Still, this is a good learning experience (if quite a difficult one). Save those PDFs, y’all!!

What does a rejection *really* mean?

I got a cordial rejection from NYT, and it got me thinking — what’s in a no? What does a non-response mean, what does a thoughtful response mean, and can you pitch another editor at the same publication? How long before you can pitch the same editor another idea? And do you respond to the rejection or spare their inbox? — Anonymous

Sigh, yes, rejections are unfortunately just a part of the freelance life. Some are pleasant (as much as they can be, at least), some less so. But they all kind of sting on some level. (Here’s some advice on how to deal with them.)

But as this reader is getting at, rejections are most certainly not the end of the conversation, and are very much not the end of your idea or pitch. A no from one editor is not a no to the entire story idea. Always keep that in mind.

In order, let’s tackle the individual questions at hand:

What does a non-response mean? Tbh, nothing really. Don’t read into it! Editors get dozens of pitches per week, and editors at big publications may get hundreds. To wit: When I commissioned stories at NYT, it wasn’t uncommon to receive hundreds of pitches per day. If editors responded to every single pitch they got, that would be their entire job. In a perfect world, they’d have the time to, but they just don’t. If you’ve sent a few follow-ups (no more than two!) and you still haven’t heard anything back, assume it’s a pass. Things do slip through the cracks, but if the editor really wants it they’ll get in touch. But again, a no from one editor isn’t a no to the idea.

What does a thoughtful response mean? Generally, if the editor takes the time to individually respond with a rejection, it probably means you’ve got the go-ahead to continue pitching them (doubly so if they give you specific feedback or give you a reason they turned it down that had nothing to do with the idea). If you’re lucky enough to get more than a generic, “Thanks, but it’s not the right fit” type of response, keep sending along ideas.

Can you pitch another editor at the same publication? This one is tricky. I generally advise against pitching the rejected idea to an editor in the same section — it may be likely that your idea was discussed at an editorial pitch meeting or something like that — so it’s best to avoid. That said, if there’s a completely unrelated section of the outlet that it might fit in, that may be worth considering. If you go that route, try to modify the pitch to best fit the new section you’re pitching. As for whether you should mention that you pitched it elsewhere in the newsroom ... I dunno. I know editors who would be offended by the very idea of repurposing a pitch for a different section, but I also know editors who would just be happy you might be able to land it elsewhere in the organization. So feel it out and use your best judgment. (Sorry, I know that’s squishy, but this one really depends on the situation and the personalities involved.)

How long before you can pitch the same editor another idea? This all depends on your relationship with the editor, but also the editor’s preferences. If this is an editor you work with somewhat regularly, give it a week or two then have at it. On the other hand, if this is an editor you constantly work with — say, at least one or two commissions or more per month — you’re probably safe to send more pitches whenever. And really, that’s the goal place you want to be at with an editor. My regular freelancers at NYT would pitch me multiple times per week (sometimes even just over text for my super-regulars), so the stronger your working relationship with an editor is, the more free you should feel in pitching them. But also remember the golden rule: Don’t be an asshole. That’s it!

Do you respond to the rejection or spare their inbox? If they offer thoughtful and specific feedback, a little acknowledgement doesn’t hurt at all (and may help foster an ongoing working relationship). But if it’s a boilerplate “not the right fit” type of rejection, you can probably skip the reply.

Good luck out there y’all!
-Tim

P.S. — Thanks to everyone who has contributed to the FWT database of freelance rates for 300+ publications. I’ll update the database about twice a month, so please feel free to share some of your own recent rates here.

If you like what you’re reading, please consider subscribing to the free or paid version of this newsletter. Paid subs get access to all past and future paid-only posts, including the archive of recorded Zoom panels, an expert panel on launching and growing a newsletter, a post about the 10 best things I did for my freelance career, the exact text of a pitch I sold to The Atlantic, practical tips for diversifying your freelance income, 50% off all Zoom workshops, and much more.

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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.

• Got a question about freelancing or the wider world of journalism? Let’s hear it, and I may feature it in a future Q&A post! Drop any of your questions, comments, and thoughts about freelancing and journalism in general in a comment below, or email me at tim@freelancingwithtim.com.

Leave a comment

***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.)

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.)

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.

• If you like what you’re reading, please consider subscribing to the paid version of this newsletter. Paid subs get access to all past and future paid-only posts, including the archive of recorded Zoom panels, an expert panel on launching and growing a newsletter, a post about the 10 best things I did for my freelance career, the exact text of a pitch I sold to The Atlantic, practical tips for diversifying your freelance income, 50% off all Zoom workshops, and much more.

Subscribe now

• 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.

Please join me on Nov. 19 for a workshop on the art of structuring longform narrative features. See below for more details, then register here, and don’t forget to use the promo code “subscriber” to get 50% off!

It’s the night of the living dread!

Whoa, sorry there, didn’t mean to frighten you! But what …

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In my recent workshop on pitching, an attendee asked a question that struck me. It was something along the lines of, 

Why bother pitching [x publication] if I already know they’re going to say no?

First, setting aside the fact that there’s no way to actually know if a publication is going to reject your pitch, it kind of misses the point. Sure, rejection is a fact of life, but for us freelancers, if we’re being rejected, it means we’re aiming high, but it also means we’re not settling. Anchor clients are wonderful and we should all have them, but the goal of any profession is to continually work to improve your craft. Freelancing is no different. 

If you’re not failing often, you’re not aiming high enough.

This is all a long way of saying: Go pitch The New Yorker or The Washington Post. The worst that can happen is they say no, which is simply an impetus to move on to the next publication on your pitch list.

I was inspired to write this newsletter after coming across an excellent post on Study Hall headlined “How to bring a killed story back to life” (which, coincidentally, is an idea I’ve been kicking around forever and was expertly written by Hannah Docter-Loeb). It basically boiled down to an idea I both sincerely believe in and talk about on pretty much every workshop: A “no” from one editor is not a “no” to the idea.

There are a million reasons editors decline ideas, and shockingly few of those reasons are about the idea itself. 

If you like what you’re reading, please consider subscribing to the paid version of this newsletter. Paid subs get access to all past and future paid-only posts, the freshly updated archive of recorded Zoom panels, an expert panel on launching and growing a newsletter, a post about the 10 best things I did for my freelance career, the exact text of a pitch I sold to The Atlantic, practical tips for diversifying your freelance income, 50% off all Zoom workshops, and much more.

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Ignore imposter syndrome. As freelancers, it’s easy to take rejection as a personal failing, as if we’re not good enough to make it. This is a common thought! I have gone through that emotion countless times, as I’m sure every person reading this newsletter has as well, whether it’s pitching a top publication or tackling a project my stupid brain “knows” I can’t do. But whenever I find myself spiraling down that (misguided) rabbit hole, I think back to my years as a commissioning editor at NYT. 

I can tell you firsthand: Don’t assume your pitch, story idea, or concept was shot down because it’s bad. Of course, sometimes those things just don’t work, but many, many times, the reason I would turn down an idea, story form, project, or something else wasn’t because I didn’t like it. It was very often for reasons completely unrelated to it, and, if I’m being honest, sometimes the decision was simply out of my hands.

We need to take the high shots and reach. I hate myself for referencing this awful, embarrassing cliché, but it really does ring true: Shoot for the moon. Even if you miss, you'll land among the stars. Cringe as that saying is, it’s something we all should keep in mind. 

So write the longform feature you’ve obsessed over time and again, dive into that investigation you’ve been avoiding because it feels intimidating, or start that other line of income you don’t feel fully qualified for. As we’ve all learned, it’s nonsense to apply to only jobs you’re 100% qualified for, because that just means is you’re not stretching and growing. The same philosophy applies to freelancing at every step of the process.

Now go forth, and write stories beyond your abilities, pitch places where you never thought you’d be published, and revel in rejection. If you’re stretching and failing, it means you’re on the right track.

Okay bye ily!

-Tim ❤️

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Oh, a few other things …

• I offer one-on-one coaching! Need help developing an idea or sharpening one you already have? Or want to talk about careers and building your freelance business? I gotchu! Book a one-on-one coaching session to talk about pitch reviews, story development, editing, and anything else you might need help with.

• Get a pitch commissioned recently? I want to see it! I’d love to feature you and your #pitchesthatsold in an upcoming series examining great pitches that resulted in stories. Let’s see ’em!

Email me

• I’m now 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. Let’s hear it!

Greetings from Covid quarantine! It’s my third time on this ride, feels second nature at this point. Sigh.

Anyway! Today we’re talking about working with editors.

I’ve said it before, and I’ll say it again: Editors need freelancers as much as freelancers need editors. It’s easy to conflate the job title with actual author…

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Hello friends! Today we’re talking about something that, for many freelancers, is often top-of-mind: moving from a career as a freelancer to a full-time staff position.

Now, certainly, taking on a staff job isn’t the only path for a freelancer, and it is far from being the “right” path. Some people want to stay freelance for their careers becau…

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There are a thousand things to worry about as a freelancer. Some are big, some are small, but no single thing should occupy an overwhelming amount of space in your brain as you build out your freelance business.

That said: There absolutely are some things that most freelancers worry about that they just shouldn’t. But it’s understandable! We’re…

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Hello friends! This week I’ve invited friend of FWT Paulette Perhach to share some advice about treating your freelance business like … a taco truck. Yes, a taco truck! It can sound a little odd at first, but there are more parallels between being a freelancer and running a taco truck than you might think. Paulette is a freelancer and a writing coach, so I wanted to get her take on how we all can reframe our thinking a little to build a stronger and more sustainable business. Take it away, Paulette!

My coaching students stare up at the brick wall that I, too, used to believe blocked me from launching into freelance writing. The wall is scrawled with graffiti: 

“Who cares what you have to say?”

“You’ve never done this before!”

“Why would anyone hire you?”

I don’t want to waste our time even talking about it. I want to reach through it and pull my writing students to the other side, show them it’s just a mirage. Which is how I found myself begging a newbie freelance writer to treat her writing like a taco and her writing business as she would a taco truck.

The time had come to put the word out that she was starting to freelance, and to make the smallest ask possible of people in one of the best places to find work — her weak ties. These are the people whose social circles do not overlap yours, but merely bump. It’s the old co-worker, the fellow committee member, the person from whom you buy your morning shame scone or what have you. 

The ask: If they hear of someone who needs a writer, they keep her in mind. 

Total panic.

If you like what you’re reading, please consider subscribing to the free or paid version of this newsletter. Paid subs get access to all past and future paid-only posts, the archive of recorded Zoom panels, a guide on how and when to follow up with editors, an exclusive workshop on selling and writing a book, tips for diversifying your freelance income, 50% off all Zoom workshops, and more.

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I love this student, she’s a regular at A Very Important Meeting, my daily freewriting group, so I know her and that she is a joy, which is half of being great to work with. She worked as an editorial assistant in New York, and then in education for two decades. And I know that she needed to become a writer once she got diagnosed with cancer, then sat in her car and screamed because she’d never become the writer she wanted to be. She could no longer stomach spending her time on earth doing a job she didn’t really love, which is why she’d signed up for my Powerhouse Writers freelancing program. 

But when I asked her to tell 50 people she’s opening up a writing shop, this woman who’d braved cancer made a face like I’d ordered her to cha-cha naked through her high school reunion. 

“You’re opening a business, just like any other,” I said. “If you had a taco truck, would you be embarrassed to put out a sign that said, ‘Tacos this way?’”

She admitted she would not. 

And yet, we have such a hard time conceiving of the fact that our writing could bring as much joy and satisfaction to the world as carne, salsa, and cilantro wrapped in a tortilla. Writing! The very thing we love so much that we dedicate our lives to it.

Bleh, nope, impossible. 

If you’re a writer, you’re a craftsperson, as much as a chef. People out there are hungry. Sure, they could go to the store and buy tortillas and pork and look up the recipe, but they’re so busy and they’ve never been good at cooking and it’s just not their thing. But behold, an A-frame sign! “Tacos, this way.” Blinker. 

Never: Who the hell do these people think they are to make tacos, when so many other people are making tacos, when so many tacos have been made before!

What a relief, that sales is not just getting, getting, getting. It’s about finding the person who needs you, who’s happy you’re there, who’s so relieved there are people in the world who love to do what they don’t really like to do so much that they’ve studied it, practiced it, become people of value in the field. 

You don’t have to be special. You don’t have to be the first. You just have to be a writer and a professional, work on the craft of writing and the craft of business, and let people know what’s cooking.

Oh, a few other things …

• Our dear friend Rax King — aka your favorite personal essayist — has granted our wishes and is teaching a six-week online course on writing personal essays! She is a frequent guest on FWT panels and offers some of the best advice for writing essays around. Apply for her course here!

• I am now offering one-on-one coaching and personal pitch reviews! Coaching sessions can include anything you need help with: writing and/or editing coaching, story development, story editing, social strategy, and anything else. And pitch reviews are exactly what you’d think: Let’s review a pitch of yours together! Book a timeslot for either session here.

• For paid subscribers: There are very few concrete, unbreakable rules in pitching. However … I wrote about the only four mandatory components that need to be in every pitch, regardless of the story. Read them all here.

If you’re not yet a paid subscriber, click here to see options for subscribing to get access to past paid-only posts, including the full archive of recorded Zoom panels; a round up of what a bunch of publications pay freelance writers; the dos and don’ts of writing the perfect pitch; and much more. (Subscribers also get a discount to every paid workshop, plus free access to any paid panel.)

• Don’t forget to follow us on Instagram!

Okay bye ily!

-Tim ❤️

Our holiday sale is live! From now until Dec. 15, I’m offering 25% off a yearly subscription to this newsletter. With a paid subscription, you’ll get a second, subscriber-only newsletter every week; invites to subscriber-only panels; access to the full archive of Zoom panels; free access to every paid panel; and discount…

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One of the most common things we talk about on FWT panels is: Where do I even look for a job?

Mandy Hofmockel has the answer: Her newsletter Journalism Jobs and a Photo of My Dog. 

Every Monday she emails subscribers with dozens of fresh job listings she has painstakingly collected by hand, along with — you guessed it — adorable pup photos. 

You …

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Hello friends! Before we get to it, don’t forget to snag a spot in this Sunday’s free Zoom panels! We have two amazing sessions lined up:

• 3 p.m.: So you want to write a book, feat. literary agent Kate McKean and Matt Ortile, author of the essay collection "The Groom Will Keep His Name.”

• 4:30 p.m.: How to launch and host …

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