Welcome, ProWriter!

Today is October 3rd, the day the internet (including our company Slack) is filled with this GIF:

It also means we only have 89 days left in the calendar year 😲🤯. So let’s not waste any time and get right into this thing.

In today’s edition:

• Should you ask for more money? (Spoiler alert: Yes).

• More media companies are poking AI right in the A-👁️.

• Learn content marketing easily through this pro writer.

• Feeling insecure lately? This essay will feel like a nice hug.

• Make up to $70/h writing about tech (and 8 other writing ops).

Let’s get into it…

- Dave and Dusten

#ProWriterTips 💡

Am I charging enough?

This clip from the movie Road to Perdition lives rent-free in my head:

Just in case you’re currently in a movie theater watching a completely different movie and can’t turn your sound up (shame on you, put us away), the little guy (played by future TV Superman Tyler Hoechlin) asks his dad (played by famous dad Tom Hanks) if he can have a share of the money they just robbed from a bank.

Hanks asks how much, and Hoechlin responds “$200.”

“Okay. Deal.”

Hoechlin is happy until he realizes that Hanks agreed pretty fast.

Too fast.

“Could I have had more?” he asks.

“You’ll never know.”

We’re all grownups here. We know employers want to get the best possible deal on content. Heck, even the good clients often try to lowball you early on.

And there might be good reasons to accept a lower rate than you want. Maybe the work is easy and consistent enough that it’s worth squeezing in. Maybe you get a byline, or it’s in a niche you’re trying to get into and you could use the experience.

But a lot of writers, especially early on, agree to low rates for one reason only.

They’re afraid of missing out on a job.

Again, there are a lot of reasons you might be willing to settle for less money. Some of them are bad, some of them are good, some of them are purely strategic.

But we’ve all felt that pit in our stomach when we’re about to agree to a gig that we know is all wrong.

Maybe we really, really want to work for the brand, but…

…we just know that it’ll be more work than it’s worth.

In those moments, we want you to remember one thing:

It’s always okay to ask for more money.

The employer might say no!

But that fear you have, that merely asking will somehow offend the employer? That you’ll ruin the relationship?

That is never going to happen with a serious client.

If it happens, there is something seriously wrong with that client. Not with you.

In fact, and this is a big “employers don’t want you to know” kind of secret, asking for a higher rate can create more opportunities for you down the line.

Which brings me to this tweet (or X-eet… zeet?):

Let me assure you from an employer’s perspective: this happens more than you might think.

It’s pretty easy to nudge most employers a little higher on payouts. But even if they say "no” at that time, you might just leave an impression on them.

A “they must be worth the money!” kind of impression.

It’s something we talked about for a full 20 minutes at yesterday’s editorial meeting (don’t forget, we also run a content agency).

Everyone on the content management team had pretty much the same take: that when a qualified writer turns them down, it creates a “one that got away” impression.

Here’s a direct quote from one of our account leads:

“If the portfolio is strong, I definitely remember the writer. I’ve actually nudged clients to give us more budget so I could go back and hire them. We do often end up working together eventually, or I’ll try to keep in touch if/when the right thing comes along.”

So, what did we learn today?

Always ask for more.

There’s honestly no downside. And if you don’t ask, like your dad Tom Hanks said, “you’ll never know.”

Eye on AI 🤖

In this section, we bring you the top stories about AI that actually affect you. Mostly so you can stay informed, but also, worry less.

The longest writer’s strike in history appears to be over

Sure, we’re talking about scribes of film and television, not content marketers and tech writers.

But it’s still relevant to us, considering that AI was a pretty big secondary theme of the strike.

While the WGA was mainly concerned with bread-and-butter topics like streaming residuals and shorter seasons (ELI5: fewer scripts = less money), some of the studios were holding out because they seemed to think they could just get ChatGPT to binge The Office and Friends and have it churn out scripts that a near-minimum wage writer would merely “touch up” for human consumption.

That appears to have not panned out, since the WGA got a pretty big chunk of what they wanted.

The deal ain’t done until the ink is dry, but considering this was one of the first high-profile “artists vs. robots” battles of the AI era, the outcome here is noteworthy.

Other headlines:

• Major orgs like the New York Times, CNN, and companies like Medium are blocking AI tools from crawling their sites, depriving them of sweet, sweet content for their data sets.

• You, too, can tell Google’s Bard to leave your website’s sweet, sweet content alone.

And, while you may not trust AI to write the next great American sitcom, maybe you’ll trust it with far more menial and soul-crushing tasks, like helping you find the love of your life.

Bumble’s CEO Whitney Wolfe Herd says to think of AI as your digital wingman, jumping on “grenades” and helping you improve your swipe game.

“I really think about AI as a supercharger to love and relationships,” she said at Code Conference 2023 last week.

If they can figure out how to swipe left on bad clients before they hit our inbox, sign me up. 

100 content people you should be following 🤝

We made a big list of the most successful and influential voices in marketing.

The main thing they have in common? They post free content advice that will make you a better writer.

This week, here’s who we think you should follow + connect with on LinkedIn: 

#99 Derek Flint

Derek is a Marketing Manager at Ten Speed, an SEO and content marketing agency that partners with SaaS startups to help them compete with the bigger fish in tech.

We’re pointing you in his direction for two big reasons:

1. He posts a ton of valuable content

Derek looks at content from a strategic perspective. If you understand how strategy connects to the stuff you create, then you automatically become a more competitive freelance writer:

2. He’s a good ‘explainer guy’

When it comes to major updates in SEO, AI, or marketing, Derek offers a grounded, practical take while everyone else is running around saying sh** is in the fan.

In short, 10/10, would recommend you connect (and if you see Dave or Dusten in his comments, say hello).

👉 Connect with Derek on LinkedIn

Makes you think 🤔

One of the subtle, silent killers of our freelance mojo is insecurity.

The vast majority of freelance writers work remotely. Most of the time, this is a good arrangement.

Freelancers are masters of self-directed productivity. We were making stuff happen in our PJs long before COVID made it cool.

But one of the drawbacks is that we can get into slumps where we’re pretty starved of professional human interaction.

We don’t always get a ton of feedback from our clients (if any) and it can leave us wondering if we’re doing the right things.

• Are we growing in our careers?

• Are we missing out on opportunities?

• Are we too comfortable (i.e. stagnant)?

Then we go into a headspace where we’re feeling insecure, and that productivity we’re so well-known for?

What the heck happened?

Don’t worry. This happens to all of us now and again.

Even the highest-earning freelance writers who have been at this for a long time go through periods like this. It’s totally natural.

How do you get out?

If you’re stuck in this kind of rut, I’m going to send you over to Nick Hammond’s excellent newsletter The Calculated Creative.

Nick is a career coach for creatives, and he recently wrote a post that offers 9 tips for pulling yourself out of those mojo-killing insecurity spells.

Click the image below to read it on LinkedIn. Give us a shout while you’re there!

Top Freelance Writing Jobs 💼 

1. Creative Circle is back on our list with a B2B Copywriter role paying $45-$50/h. Apply here, and if I was you, I’d keep an eye on this company. They appear to be hiring a lot.

2. Campfire Labs is hiring freelance writers with B2B/SaaS experience. It’s PT work for 3-6 months, and the pay is in the range of $25-$50/h. Apply on-site.

3. Staffing agency Nmble is looking for a freelance copywriter in tech (science, energy) for $50-$70/h. Apply on LinkedIn.

4. If you’re into climate stuff, Distilled is looking for a freelance journo/researcher type for $50/h. Apply here.

5. If you want to help other freelancers get jobs in the tech sector, Free Agency is looking for an hourly copywriter for $20-$40/h. If you’re a bit earlier in your career, this gig might come with the added bonus of helping you learn skills to navigate jobs in the tech sector. Apply here.

6. If you’re an ad/scriptwriter with ecommerce experience, Upshot Creatives would like to hear from you for a part-time, salaried role. Apply here.

7. Finance writer? The Mom Project can get you up to $45/h for one of their clients. Apply here.

8. Pretty easy B2B web content writer gig for up to $37/h. PT, 20 hours a week. Apply on LinkedIn.

9. Get It Recruit is looking for a conversion copywriter. It’s listed as remote and PT, but is a salaried role. Not sure how that will work, but, if you’re interested in environmental causes, it looks like a solid gig. Apply here.

Don’t forget — all the jobs we post here are remote and we privilege gigs with transparent pay.

A handful come from our personal networks and aren’t on any jobs boards… yet. So get on ‘em.

Wait! One more thing… 📣

One last thing while we have you…

When we were talking about relaunching The ProWriter Newsletter, one of the main things we wanted to focus on was participation.

We didn’t want to put out some bland, curated list of crusty gigs you’ve already seen everywhere else and call it a day.

We wanted to build a community.

That’s why we’re asking you to reply to this email with your burning questions about freelance writing.

Remember that we have a unique vantage point on the industry, because we’ve run a content agency for nearly a decade. We hire writers. We talk to employers. We see the other side you don’t get to see.

And we want to share that world with freelance writers, because we believe that when we do, you’ll become better writers who make more money, and employers will get content they’re happy with and stop devaluing our work.

Win/win!

So if you have questions you’ve never gotten a clear answer on, reply to this email and ask us. We’ll turn it into content in future editions of this newsletter so that everyone can benefit.

And seriously, ask us anything. Things like:

• How do I get my pitches read?

• Where will the opportunities be in 5 years?

• What in the hell are employers even thinking?

You can write short, punchy questions, or tell us a whole sob story. Whatever you want!

This is an open invitation, but we’ll ask again every couple of newsletters.

Just reply to this email with any questions you have.

And remember what they told you in school! If you have a question, you should raise your hand and ask it, because a lot of your classmates probably have the same question and are too shy to ask.

Thanks for reading, ProWriters!

Let’s have a great week.

Dave & Dusten

P.S. Want to look smart to all your friends? Forward them this newsletter.

If you’re that friend, subscribe to The ProWriter Newsletter here.

P.P.S. Want to really upgrade your freelance writing career?

🖥 Build your personal brand with a free writer portfolio.

🎓 Learn how to become a freelance writer with our free course.

📝 Get paid to publish content with our free Submissions database.

Until next week, see you on Twitter and LinkedIn.