Hello Reader!

I just did the math.
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Over my 16-year career, I’ve written ~4,000 assets (blogs, reports, case studies, ebooks, newsletters, ads) and edited over 10,000,000 words.
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I’m doubling down on this saying I have:
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I do homework for a living. 🤓💰
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And a lot of it.
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Here are the top lessons I've learned:
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​1. Start every project with a GOOD, human-created brief​
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Every project that’s gone off the rails either had no content brief (you can’t just take a topic and run), had a bad brief (not capturing the right or clear enough expectations), or an AI-generated brief.

Need one? This is the content brief I use on every project.
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​2. Always have a second set of 👀 on your content before you send it to a client
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It doesn’t matter how good a writer or editor you are. When you own a piece of content, your brain adjusts and will accept mistakes as part of the narrative.
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That’s why you may hit “send” on a newsletter and then realize you’ve screwed up an its/it’s.
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It’s okay. It happens to the best of the best.
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But get an editor on your team. You'll be glad you did.
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​3. Learn on-page search optimization and invest in a tool for it ​
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On-page optimization isn’t difficult, and there are SEO tools that will give you the data you need to rank (I use Clearscope... also an affiliate of mine).
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If you can deliver good content AND strategy, you can charge higher prices.
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​4. Don’t let yourself burn out​
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It is beyond easy to burn out as a professional homework do-er.
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Your brain is thinking a million miles and hour every day.
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Eventually, it will say “nope, I’m done.”
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If you let yourself get to that point, you’ll either stop caring or your writing will be bad.
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Take breaks. Go on vacations. Split up the cognitively demanding tasks.

I wrote a detailed article about how I manage this for Copyhackers. You can see it here.
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​5. Set up processes ​
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It’s hard to stay in demand if you’re all over the place.
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Create an onboarding process..
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Develop writing systems.
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Learn how AI can automate the mundane (but don't use it to do the creative stuff).
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Develop marketing and sales systems.
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Have a process for collecting data and testimonials.

Thanks for reading,

Ashley R. Cummings

Partner | Lettuce

As content creators and strategists, we're masters at planning for our clients. But when it comes to our own businesses? Most of us never actually sit down to strategically plan our year ahead. We're so focused on the next deadline, the next client deliverable, the next piece of content that strategic thinking about 2026 feels like a luxury we can't afford.

But what if you had one day dedicated entirely to building your roadmap forward?

That's what the Lettuce Solo Summit is on November 6, 2025. This free virtual event is designed to help sophisticated solopreneurs—including content professionals who've built thriving independent practices—think bigger about what's possible and then give you the actual frameworks to make it happen.

You'll explore building financial infrastructure that minimizes taxes and maximizes wealth, implementing AI and automation that scales your creative capabilities without sacrificing quality, creating systematic lead generation that fills your pipeline with ideal clients, and breaking free from the time-for-money trap.

Whether you're a content strategist, writer, creator, or consultant, this time investment will pay off in how you approach your business with the CEO-level strategic thinking it deserves, giving you the tools, insights and clarity that separate solos who thrive from those who stay stuck.

Register for your 2026 planning session.

Expert Interview | Lars Lofgren

1. Tell me more about you and your journey into content.

Always enjoyed writing since I was a kid. During college, blogs were a hot, hip thing, so I naturally gravitated to them. Tried building a few that never went anywhere. Then I quickly discovered that the skills I learned building the blogs were way more valuable than the blogs themselves. So I started freelancing, got my first marketing job at a SaaS startup with a very well-known blog, and been doing it ever since.

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2. What are the biggest mistakes you see companies make when trying to build a sustainable content engine?

The biggest mistake companies make is by flip-flopping on whether or not their content is a priority. Every top-tier content engine I've been a part of took 5-10 years before it became a major marketing lever. You gotta commit. And the ROI won't be visible for a LONG time. Even worse, many companies start to take it for granted after it does work, then cut the budget at some point. Things can coast for years, but do eventually decline. Once it's a visible problem, it's a multi-year turnaround to get back. Content programs are not an engine, they're a garden. They need constant nourishment.
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​3. Your recent posts show you’re not afraid to call out BS in the industry—from Google’s AIOs to affiliate “parasites.” What’s driving that shift toward investigative content for you—and do you think it’s where t

No idea if the best voices will focus on investigative-type content. All I know is that if I don't tell some of these stories, they're not going to get told. Especially when good people or good companies are being harmed by others. Someone needs to stand up and call it out. In my opinion, all the dominant platforms stopped putting the users first years ago. These days, change doesn't happen unless the powers that be have a PR crisis on their hands.

Must-Read Industry Content

Think smarter, faster: Each week, I share the articles that are shaping where content marketing is going, so you don’t have to dig.

1/ Ragebait is everywhere. Should marketers lean in?

2/ How to know if your GEO is working

3/ Inside advertising's most grueling new genre: 'You have zero social anxiety' (I'm kinda obsessed with the live content trend right now. I keep thinking of ways B2B brands could make this successful)

AI Updates + Tools To Watch

Don't get left behind: The most useful AI updates and content tools worth paying attention to this week.

Become a Content Connect VIP

Are you ready to be part of the Cool Content Club? As a Content Connect VIP member, you get:

• All the goods. Every product, template, and asset we’ve ever created ($700 value). See some of them here.
• Job leads. Curated, high intent, and fast to your inbox.
• Discounts. Save on courses, workshops, and future drops.
• Deep dives.Thoughtful breakdowns that help you level up your work.

Don’t miss your shot to be part of the most useful, no-BS space in content. This is where the good stuff happens first.

Resources

Let's Connect!

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