Copy Over Coffee Blog
Welcome to Copy Over Coffee — if you’ve found your way here, chances are you’re navigating the wild, unpredictable world of freelancing… and you’re not alone. This blog is your spot to slow down, sip something warm, and get real about the work, the hustle, and the life that comes with running your own thing.
Whether you’re just starting out, coming back after a break, or trying to level up your creative business, you’re in the right place. No fluff, no fake guru talk — just honest stories, useful strategies, and the kind of insight that comes from someone who’s been in it for two decades (with a few detours along the way). Glad you’re here.
From Freelancing to Content Creation: Why I’m Pivoting (and You Might Want To, Too)
For years, I made my living as a freelancer — writing for clients, juggling deadlines, hopping between tools, Slack channels, and revision requests. Some days, it felt like I had three different bosses. Other days, it felt like I had none — which somehow was worse.
What Writing with AI Actually Looks Like
No, I don’t tell ChatGPT, “Write an essay for me,” while I scroll YouTube and sip coffee. That’s not how this works. At least, not for me. I’m a writer, and I write everything I publish under my name. But here’s what you need to understand: AI is my writing partner. Research, outlining, editing, brainstorming: AI has...
How Writing Became My Lifeline: A Second‑Act Story
From childhood notebooks to mental‑health freefall, through twenty years of freelance survival, to finally writing for myself — the brutally honest origin story behind my so‑called “personal brand.” 1. The Kid With the Notebook The first thing I ever wanted was a pen that wouldn’t run out of ink. I was the lanky...
How I Use AI as a Writing Partner (And Why It’s Still Me on the Page)
Yesterday, I received an email from a long-time reader and fellow writer on Medium. It moved me more than I can say. They said they’ve been reading my stories for years, since before my heart attack, and even though they’re a self-described lurker, my latest newsletter about AI pulled them out of the shadows. They were...
Behind the Blog: How I Write (and Why It Works)
Writing isn’t magic. But it can feel like it when it clicks. After 20+ years of freelancing, I’ve learned that great content—whether it’s for a tech startup, solo founder, or small-town bakery—starts with structure, strategy, and empathy. It’s not just putting words on a screen. It’s getting into the reader’s head,...
How the Internet Thinks You Should Price Your Freelance Rates
This story was written November 17, 2023. ... Are your freelance writing rates set so high that nobody wants to hire you? I thought mine were. I was a full-time freelance ghostwriter and web designer for 20 years before I started writing full-time on Medium and my blog. I pride myself on being able to write about any...
Do You Need a Niche or Specialization to be Successful?
Really? Is there such a thing as a successful generalist? Okay, I’m sorry. This started all wrong. Allow me to unscrew myself. We shouldn’t start an article about success unless we talk about the nature of success and what it means. I shudder to discuss it because it means something different to everyone. For some, it’s...
I’m Jason Weiland. Let’s Talk About Freelancing (Again)
You ever feel like you're starting over, even when you’ve done the thing before? That’s me right now. I've been freelancing off and on for more than 20 years. I started back in the days when HTML was still considered a marketable skill by itself. Built websites. Wrote content. Ran a design team. Managed clients from...