AI - Jason Weiland

Jason Weiland

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AI

A collection of 16 posts

AI Shouldn’t Replace You—It Should Sound Like You

AI Shouldn’t Replace You—It Should Sound Like You

I’ve said it before: AI is a tool, not a replacement. The end product—your words, your ideas, your story—has to come from you. If you let AI do all the work, you lose the very thing that makes your writing worth reading: your voice.

Don't Let AI Do All the Work: Why Your Voice Still Matters

Don't Let AI Do All the Work: Why Your Voice Still Matters

I’m the guy who wants it to help you do your best work faster, but not replace the part that only you can do. The part where you bleed a little on the page. Where your voice shows up, raw and alive.

I Wrote a Book About Using AI for Content Marketing (But Keeping It Human)

I Wrote a Book About Using AI for Content Marketing (But Keeping It Human)

I’ve been a writer for more than 20 years. Not saying it to brag, but to let you know that I’ve been around the block a time or two.

When Life Shifts: My Second Act and the Search for Collaboration

When Life Shifts: My Second Act and the Search for Collaboration

I’ve been freelancing off and on for more than 20 years. In that time, I’ve written about everything from mental health and finance to technology, expat living, and business strategy.

Why I’m Bullish on AI (Even If It Scares You)

Why I’m Bullish on AI (Even If It Scares You)

Yeah, some of the stuff it’s doing can be done by humans and frankly, should be, because they do it better. Art. Design. Music. But AI is learning to become better.

AI Training Is Not Theft. It’s the Same Way You Learned to Create

AI Training Is Not Theft. It’s the Same Way You Learned to Create

No one accuses you of copyright infringement when you read Joan Didion and then write a personal essay with similar rhythm. No one calls it theft when a jazz musician riffs on Coltrane’s phrasing after listening to him for 10 years straight.

Look! I’m Using an EM Dash! Better String Me Up for Using AI!

Look! I’m Using an EM Dash! Better String Me Up for Using AI!

I’ve been a writer for decades. I love the em dash. I love how it punches in, how it disrupts, how it lets you break rhythm and inject a thought or change direction. It’s not AI. It’s voice. It’s craft. It’s me.

I Co-Write With a Robot, and Somehow, It Still Feels Like Me

I Co-Write With a Robot, and Somehow, It Still Feels Like Me

After two decades of typing in my own voice, I let AI join the process. Here’s what surprised me, what scared me, and why I still hit ‘publish’ with pride

Why I Have So Many Projects (And What They Teach Me About Focus)

Why I Have So Many Projects (And What They Teach Me About Focus)

It was 3 a.m., and I was putting the finishing touches on Deep Work Timer, my third no-code AI development project. I built the whole MVP in just seven hours.

Your Second Act Won’t Be Handed to You — You Have to Build It

Your Second Act Won’t Be Handed to You — You Have to Build It

Building your second act means getting your hands dirty. It means taking drastic action, trying things that might not work, learning new skills, and being willing to start small and imperfect.

Building Tools for Dreamers: Why AI Isn’t Replacing Creativity — It’s Supporting It

Building Tools for Dreamers: Why AI Isn’t Replacing Creativity — It’s Supporting It

I was on Bluesky the other day, and the level of hysteria around AI was breathtaking. Artists, writers, and creators were furious that AI had trained on their work, not realizing that they themselves learned by studying the work of those who came before them.

The Tool I Wish I Had When I Started Over at 42

The Tool I Wish I Had When I Started Over at 42

For weeks, I had barely left my bed. Depression hung over me like a wet blanket. The silence in my apartment was deafening. I was sleeping too much, eating too little, and telling myself I was just “resting.” But I was unraveling.

You Don’t Have to Know the Whole Plan — Just the Next Step

You Don’t Have to Know the Whole Plan — Just the Next Step

We’re told these days that we can’t start anything unless we’ve got a polished five-year plan, a business strategy, or some perfect vision. I bought into that for way too long. I held off on dreams because I thought I wasn’t ready.

AI Isn’t Replacing My Voice — It’s Helping Me Find It

AI Isn’t Replacing My Voice — It’s Helping Me Find It

There’s this unspoken stereotype floating around the tech world: that if you’re over 50, you don’t “get it.” You’re too old to understand AI, not adaptable enough to use the tools shaping the future.

What Writing with AI Actually Looks Like

What Writing with AI Actually Looks Like

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 become key to my process.

From Voice to Page: How AI Helped Me Remember How to Write Again After 50

From Voice to Page: How AI Helped Me Remember How to Write Again After 50

Eventually, I stopped writing for fun. I stopped starting anything. I let go of entrepreneurial dreams. I abandoned Medium, Substack, even my personal journals — except for a few hastily scribbled notes.