by Jason Weiland | Sep 5, 2025 | Freelancing
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....
by Jason Weiland | Sep 1, 2025 | AI
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....
by Jason Weiland | Aug 31, 2025 | writing
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...
by Jason Weiland | Aug 30, 2025 | AI
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...
by Jason Weiland | Aug 30, 2025 | writing
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...
