Hi, I'm Jason Weiland
This Is What Freelancing Really Looks Like
Copy Over Coffee is a blog for freelance writers, designers, and creative business owners navigating self-employment with purpose. I write about freelancing tips, client management, SEO writing strategies, building WordPress websites, and making a living on your own terms—whether you’re just getting started or getting back in the game like I am.
Find Out More About Jason Weiland and the Blog
I’m a long-time freelancer, writer, and web designer who’s hit reset more times than I can count (and somehow keeps bouncing back). This blog is where I share the real stuff — not the influencer version of freelancing, but the quiet wins, awkward client calls, big comebacks, and lessons learned from two decades of doing this work off and on.
Web Design That Works—Without the Bloat
I build clean, fast, and functional WordPress websites tailored to your brand and business goals. Whether you’re launching a blog, promoting services, or building authority in your niche, I’ll help you stand out with thoughtful design, SEO-ready structure, and responsive performance. Let’s turn your vision into a digital home that gets results.
Blog Posts That Speak Human (and Rank)
I write blog content that bridges the gap between people and search engines. With over two decades of experience, I combine SEO strategy, engaging storytelling, and conversion-focused structure to create posts your readers (and Google) will love. Whether you’re building authority or boosting traffic, I’ve got you covered.
I Bet You Are Looking for the Blog...
On the blog, we talk about the real life of freelancing. From landing clients to managing burnout, building websites to chasing invoices, this is where I share the ups, downs, and lessons learned from running a solo business—with caffeine in hand.
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....
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...
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...
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...
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...
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...
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...