Jason Weiland

Medium, course, writing

You’ve Been Writing on Medium for Months. Maybe Years. And You’re Still Making Pennies. I Know Why.

I was authentic. I was vulnerable. I was real. And I made nothing. $50 one month. $12 the next. My best month in seven years was $300 and I thought I’d finally figured it out.

Medium, course, writing

I’m Building the Medium Course I Wish Someone Had Taught Me 7 Years Ago

But if you’re only writing to process your own feelings, nobody’s going to pay you. You have to give them something. A takeaway. A solution. A reason to come back.

I Use AI-Generated Art for My Medium Articles. Here’s Why I Don’t Feel Bad About It.

They suggested I sketch my own images. Or snap photos on my phone. Or use free stock photos from Unsplash.

family

I'm Running Out of Time, and My Family Can't Wait Anymore

My wife is alone in the Philippines. I’m in the U.S., trying to find work, again. Trying to keep the promise that one day, I’ll bring her and the kids here, that one day we’ll build something better, together.

Writing

How to Turn Old Medium Essays Into an Ebook That Sells (Without Losing Your Voice)

In 2018, I got serious. I started publishing on Medium. I had $3,000 months. I had $0 months. I wrote through sickness, heartbreak, burnout. I published three times a day, chasing the dream of being one of those top writers who made it big. I wrote like hell to get noticed.

manifesto

I Burned Out, Broke Down, and Started Over. This Is the Life I’m Building Now.

So I moved across the world. I left everything familiar behind—my routines, my city, my assumptions—and went to the Philippines. For love, yes. But also for something I couldn’t name at the time. Space? Clarity? A reset button?

AI

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.

AI

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.

skool

Help Me Build Something New: Join Second Act AI

I just launched a new online community called Second Act AI, and I’m inviting a small group of people — creators over 40 who want to explore writing and content creation with AI, not in competition with it — to help me build it.

AI

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.

unemployment

I Lost My Job at 56. What Do I Do Now?

I am not holding out much hope that anything will be found. New management moved in and suddenly there was concern that the contractors were providing value for the money they spent.

credit

Your Second Act Needs Good Credit: How I Raised My Score 50 Points in a Year

As a young man, I signed up for high-interest credit cards without a second thought. My first wife and I spent money like it was endless, never thinking about what would happen when the bills came due. When they did, I couldn’t keep up.

jobs

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.

social media

We Need a Social Platform That Puts People First

Women, queer communities, racial minorities, and older workers drown in attacks while the platform charges advertisers billions in blood money.

travel

Stamped but Not Boarding: Why Our Family Is Getting a U.S. Visa Yet Skipping the Flight

So we’ll treat Manila like a mini‑honeymoon — hand‑holding, street food, zero kid chaos — and leave with Plan B glued into her passport. Plan A is to keep our family, and our vacation money, right here in Asia.

Customs and Border Security

A Plane Ticket, a Panic Attack, and the Cold Math of U.S. Border Fear

But the cursor hovers over “Purchase.” I picture a different scene: fluorescent hallways, back‑to‑back benches, an officer in Kevlar repeating “Secondary — this way, ma’am.”

business

Dear Job Market: please lose my number

Yet, at 56, I’m old enough to hear the trapdoor click somewhere under my rolling chair. I want the next five years (or however long they’ll have me) to feel luxurious without pretending the hatch isn’t there.

Philippines

The Last On-Ramp Out of the Fast Lane

So I saved for a few months, eating ramen and stale peanut butter sandwiches, sold the rust-brown sedan for parts, and booked a one-way ticket to Manila: no plan, no backup, just a hunch that anywhere had to be saner than the all-you-can-eat American buffet that passed as life.

Newsletter

A Few Weeks in the Trenches of My Second Act

Three weeks ago I ripped the plastic off a brand‑new banner for my LinkedIn profile-neon circuitry, rainbow letters, the whole fever‑dream palette. Writer. Founder. Builder of Second Acts. Those words stared back at me like a dare: prove it.

story

How Writing Became My Lifeline: A Second‑Act Story

I don’t remember the exact date, trauma scoops out the middle of time like a melon baller, but I remember the blood. I’d lost a job that paid for my house and cars and somehow kept my life stitched together for the sake of my family. They cut me loose without a thought, and I spiraled.

brand

The Lessons I’m Learning as I Build My Personal Brand

Then the freelance roller coaster dipped into oblivion (again), my contract gig wobbled like jello, and I realized that if I didn’t treat myself like the most important client on my list, my future income would always depend on someone else’s mood.

mental health

When Things Are Good, Why Does My Brain Expect the Worst?

Work is going well. I’m writing, and using AI to help me create content. I’m treated with respect and my boss loves me. What more could you ask for out of a job?

color

I Love Color. That Doesn’t Mean What You Think It Does

When I make blog images or AI avatars, I crank the saturation, mess with the hues, make everything pop. I want it to jump off the screen. I want it to reflect what I’m trying to say, even if what I’m saying is messy, raw, imperfect.

AI

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

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.