Hello Reader!

You've heard the advice:

Write a crappy first draft.

The main idea is that to overcome writer's block, you should get something down on paper—no matter what it is. The act of writing your thoughts down—no matter how garbage they are—will propel you forward.

This is meh advice to give a content writer.

Here are some of the reasons writing a crappy first draft in the face of writer’s block is a bad idea:

It’s time-consuming. Instead of writing one decent draft that requires little editing, you end up doing the same assignment twice or thrice. What could have been accomplished in 2.5 hours takes 5-6 hours.
It’s frustrating. If you’re not feeling it and your brain and heart aren’t in the zone, you’re going to hate your life. It’s kind of like forcing yourself to eat a yucky protein shake when your body is craving a steak. You end up drinking a protein shake and then going to bed HANGRY, or drinking the gross shake and having the steak too.
It tears down your confidence. I’ve written my fair share of crap drafts, and it always makes me feel like I suck at writing. I’ve also written some killer articles that result in inner high-fives, extra confidence, and growth. I prefer the latter.
It causes resentment. Why did I accept this assignment? + It’s too hard + I can’t do it = resenting yourself. Why did this client send over such a challenging topic + They need to communicate better? + I don’t even know where to start = resenting your client. No one needs that.

These are the main reasons why writing a crappy first draft is a bad idea. But this begs the question, “how do I write a decent first draft every time?”

Great question! I’ll tell you.

1. Write when you’re fresh

You’re already a great writer. I’d be willing to bet that the times you experience writer’s block are when you’re overwhelmed physically, emotionally, or mentally.

Instead of trying to push through the down times, schedule your daily writing when you’re most energetic and rested. For me, this is early morning.

Like everyone, I have a busy life with a lot of demands. If I try to save the tasks that pay for my life when I’m least energetic, confusing writing ensues.

2. Schedule time to rest and play

Writing is just like exercising. If you want to get stronger, you have to do it a lot—almost every day. BUUUUT…you also have to schedule in time for recovery.

And this is what's cool about freelancing. You can *mostly* control your schedule. Don't pack it so tight that you never have time to breathe.

3. Channel that “crappy first draft writing” into a less pressing writing task

Every writer gets writer's block. It isn't easy to organize your thoughts and get them on a page cohesively and powerfully.

If you run into writer’s block with a particular client task, it's good to start writing. However, turning toward a creative writing project, or even another client project that’s like clockwork, is a more effective way to get the wheels turning.

4. Work from a content brief

Writer’s block is often the result of not understanding what your client wants. Maybe you don’t know what their content marketing goals are. Perhaps you don’t understand the client’s target audience and their pain points. Maybe there are a thousand different directions you could take the article, and you don’t know what points the client wants you to highlight.

If you don’t use a content brief, it’s no wonder you have writer’s block. You’re walking in the dark.

You should send a content brief to your client for every project. Period.

(Did you know a proven content brief—and the one I use—is one of the many resources. You can get my content brief here.)

5. Write an outline

If you’re trying to write the whole first draft all at once with no direction, your draft is going to be bad.

Even the Cheshire Cat says so:

Alice: Would you tell me, please, which way I ought to go from here?
The Cheshire Cat: That depends a good deal on where you want to get to.
Alice: I don’t much care where.
The Cheshire Cat: Then it doesn’t much matter which way you go.
Alice: …so long as I get somewhere.
The Cheshire Cat: Oh, you’re sure to do that, if only you walk (write) long enough.

The Cheshire Cat is onto something here. If you don’t know where you’re going, you’re going to get lost.

This sage advice from literature’s favorite wackadoodle cat applies perfectly to the writing process.

If you want to get somewhere with your work, you have to plan and prepare. Don’t start writing a soliloquy. Start with the bare bones of the project, outlining the intro, main ideas, calls to action, etc.

Once you have a good skeleton, PUT SOME MEAT ON THOSE BONES.

If you start with an outline, chances are you’ll end up with a decent first draft.

There you have it! I hope your next draft is fantastic, or at least not crappy.

Thanks for reading,

Ashley R. Cummings

In Partnership With Superhuman

(Every click supports Content Connect.)

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Expert Interview | Liam Carnahan

1. Tell me more about your journey into content.

I graduated in 2008 with a degree in writing and literature and a dream in my heart to be paid to write. It was a bad year to be a college graduate! But I found a job at a content agency, back when I didn't know what "content marketing" or "SEO" meant. I'll be honest, my first few agency jobs were terrible. I was churning out so many keyword-stuffed articles and being paid pennies to do so, but that was the style back then, unfortunately. Eventually, that job sent me to Sydney, Australia, where I worked for 5 more years until I eventually became the director of content at an agency there. It was still a terrible job, but the beaches were nice! After they promoted me to director, I got a look at the amount of money I was bringing in for the company, and decided I'd rather work for myself and bring in the same amount of money, but keep 100% of the profits. So I quit my job and started freelancing in 2019, and have been growing my freelance SEO and content marketing business ever since! Today, I focus on content strategy and SEO training for businesses with in-house teams, and helping other freelancers achieve success through mentorship and a community. Nowadays, if I'm actually producing content, it's probably for my own business, not someone else's.

2. What's one way content strategy has changed in the past year?

You want just ONE way? That's going to be tough! I feel like every day I wake up, something drastic has changed in the content world. I think the biggest change has to be the way people are continuing to grapple with AI. The initial wow-factor/honeymoon period of AI is over, but also, we all know it's here to stay and only going to get better. So we're in this weird period where everyone kind of hates AI, and everyone uses it at the same time. That includes me! I think people are becoming more cautious about AI and more vocal about the dangers it poses to the workforce, and I love that. Look at what's happening with Duolingo right now. They crowed loudly about replacing their contract workers with AI, and now, instead of being a marketing juggernaut, they are getting flamed in their own comments. Ouch. But I love to see people standing up to it! We have to, because the alternative is too dark to consider.

3. What can marketers do to make their content stand out in the age of AI?

Simple: Put some damn human emotion into it. Be vulnerable, because vulnerability is relatable, and relatable content is what resonates with people. When you're reviewing your own content, the question shouldn't be "Did AI write this?" but rather "Could AI have written this?" If the answer is yes - even if it was written by a human - then you're in trouble. Experience, personal knowledge, strong opinions, original ideas, and most of all, creativity. That's what will stand out now.

Connect with Liam on LinkedIn.

Snapshots | Best In Content This Week

This week's sharpest content marketing, search, and social articles.

1/ How LLMs Interpret Content: Structuring for AI Search (CHSEL).

To show up in AI search, structure your content clearly—LLMs favor clarity, not cleverness.

2/ How To Uncover and Improve Broken Content Experiences (CMI).

If your content frustrates people, they won’t tell you. They’ll just leave. Fix the friction before they bounce. Ann Gynn covers the how well here.

3/ Top ways to ensure your content performs well in Google's AI experiences on Search (Google Search Central).

To show up in Google’s AI results, focus on creating helpful, unique content with great UX. Because AI Mode favors clarity and value over clever tricks.

4/ Engineering Relevant Content: Tips to Get Your Content into LLMs (ipullrank)

In Francine Monahan’s piece, optimizing for context means making your content machine-understandable, semantically relevant, and topically authoritative so LLMs can easily retrieve and reuse it in generative search. Monahan shares this to explain it visually:

Newsletter Rec

If you're a freelancer or consultant, you'll love the Freelance Cake newsletter. Every Friday, Austin L. Church helps freelancers settle in to their income-lifestyle sweet spot with 3-5 snackable links or reads and 1 longer article focused on getting better results with less effort. Click here to subscribe.

AI Updates | Bot News

Google AI Mode Live In US: Tests Deep Search, Live Search, Personalization, Custom Charts, Shopping & Agentic (SER).

Google’s AI Mode is no longer experimental. It’s the future of search, and it’s doing the searching, comparing, and buying for you.

Implications of AI Mode and Personal Context – 2025 Google I/O Hot Takes (ipullrank).

Google’s AI Mode is shifting search from one-size-fits-all results to infinite, personalized journeys. SEO now means optimizing for context, not just clicks.

You're now optimizing for how AI understands, personalizes, and uses your content in real-world user scenarios. This includes:

User intent
Query specificity
Personal data (location, interests, search history)
Conversational phrasing
Task completion (not just answers)

How to Optimize for Context (according to the article):

1. Cover Broad Topics, Not Just Keywords

Become the go-to source across an entire theme.
Don’t focus on single keywords—focus on owning a domain of knowledge.

2. Create Context-Rich, User-Specific Content

Anticipate multi-layered, detailed queries (e.g., “best protein powder for women over 40 with joint pain who run 3x a week”).
Build full answer paths, not just surface answers.

3. Match Conversational Tone and Intent

Use natural language that mirrors how people talk.
Reflect phrasing like: “What should I do if…”, “I’m looking for…”

4. Structure for Extractability

Use clear headings, FAQs, lists, and schema so AI can lift and reuse answers easily.
Design your content to be agent-friendly (e.g., clear CTAs like “book,” “buy,” “compare”).

5. Account for Personalization

Realize that different users will see different results based on their data.
This makes rankings irrelevant and shifts focus to:
- Brand presence
- Engagement metrics (time on page, scroll depth, repeat visits)
- Visibility in AI summaries and conversations

6. Prepare for Agents

Your content should be usable by AI agents that take action (e.g. book a ticket, place an order).
Keep product data, pricing, and availability structured and accessible via schema, APIs, or product feeds.

7. Measure Differently

Move beyond traditional click-through rates and rank tracking.
Focus on:
- Topical authority
- User engagement
- Brand mentions in AI outputs
- Attribution modeling (e.g. brand lift or direct traffic trends)

💡| "Zero-click everything"

It's a little hard to see the image, so here it is typed out (so ya don't have to get binoculars):

"We’ve had data on declining click-through rates in Google for the last 7 years; some of the steepest declines were prior to the advent of the current AI craze but didn’t receive external coverage or interest because there wasn’t a hype cycle topic attached (no offense to traditional media outlets, but… 😎)
Last year, Google’s search volume growth offset the drop in click-through rates — they had one of their highest query growth years in the last decade (22%) and crossed 5 trillion searches
The signals this year are that the growth is plateauing and continual declines in click-through rate will affect total traffic available from the engine
But, Google is both far from alone and far from the worst culprit. Thirteen years ago, Facebook was a major driver of traffic to websites and publishers, until they decided to tweak their feeds in favor of native content and keeping people on the site. Twitter, LinkedIn, Reddit, YouTube, Instagram, TikTok, and Threads all followed this direction, and nowadays, despite massive use of these platforms, they send almost no traffic to the open web.
The same is true for so-called AI tools (real talk: they’re just sophisticated versions of Spicy Autocomplete with a shockingly effective brand manager 😏), which send out less than 0.2% of all the traffic they receive
New research suggests that even though the rest of the customer journey is being stolen/hoarded by these platforms, homepage traffic is actually up (because people still need to transact on your website, something they can’t do on Google or ChatGPT)
As I’ve said for years, the job of digital marketers has to change. Traffic is now a vanity metric, and is alone only to optimize for. People are consuming content about your brand, industry, and the problems you solve on other platforms; the goal of earning traffic to your own website at the top and middle of the marketing funnel is a Sisyphian fight against a growing boulder. Instead, marketers need to work on influencing people in the places they already pay attention: the social networks, search engine answers, and AI tool responses.
To be effective, digital marketing needs to go back to the 20th Century mindset: nudge people to know, like, trust, and remember your brand through smart messaging, positioning, and channel choices. Measure based on experimentation and lift, not attribution modeling."