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Articles by Jason Weiland
I Dared To Ask What A Job Paid. The Interview Ended In 30 Seconds.
Editor's Note: This is a part of YourTango's Opinion section where individual authors can provide varying perspectives for wide-ranging political, social, and personal commentary on issues. Up until that moment, it had been going great. We’d talked about my experience writing content and planning content for their organization, and walked through my portfolio. We discussed my process for working with clients and how that looked for them.
Why nobody wants to hire you anymore 'It's not just Gen-Z or older workers'
Im 57 and tired. Tired of sending out applications and hearing nothing. I watch younger people with better resumes do the same thing. Were all getting crushed by the same machine, just from different angles. The market has fractured into something brutal. Its like some twisted monster fromStranger Things, but worse. Companies dont want me because Im too expensive and supposedly cant learn new tools. They dont want 23-year-olds because training takes time, and AI can do their job faster.
Why Nobody Wants To Hire You Anymore - 'It's Not Just Gen-Z Or Older Workers'
I’m 57 and tired. Tired of sending out applications and hearing nothing. I watch younger people with better resumes do the same thing. We’re all getting crushed by the same machine, just from different angles. The market has fractured into something brutal. It’s like some twisted monster from Stranger Things, but worse. Companies don’t want me because I’m too expensive and supposedly can’t learn new tools. They don’t want 23-year-olds because training takes time, and AI can do their job faster.
If You’ve Been Ghosted, Ignored, or Shut Out, You’re Not Alone
This isn’t a feel-good post. It’s for the people sending out resumes, chasing freelance gigs, publishing in silence, and still showing up anyway. I’m 56 years old. I sleep on the floor of my parents’ house in Tucson on a blow up mattress that I’m positive has a hole in it. My laptop is fired up and working hard most days, and I spend my mornings applying to jobs I probably won’t hear back from. I had a contract with Quicken — good money, steady work. I thought I had finally broken the cycle.
I’m Tired of Promising My Family Things I Can’t Deliver
My life with my wife has been one long string of promises I couldn’t keep. I told her we’d be okay. That we’d build something better. That all this struggle would lead somewhere. That we’d end up in the U.S. with a little house, steady income, and peace. She believed me. Every time. Because love does that. It believes. Even when it shouldn’t. But it’s been one thing after another. First, it was my mental illness. Back in 2013, I hit bottom. Anxiety, depression, burnout, I couldn’t function.
Invisible After 50: How the Workforce Discards Experience
I’m 56. I’ve built websites, written essays, managed design teams, held contracts, delivered value. And still — now — I feel like I’m invisible. I send applications. Hundreds over the years. I tailor my resume like a suit nobody wants to wear, cover letters that try to promise value. Most responses are silence. Ghosting. A polite rejection every now and then. Maybe someone tells me, “You’re overqualified,” or “We’re looking for someone younger.” Always a rotation of excuses, but always a wall.
Separated by an Ocean and Sleeping on the Floor at 56: Why I Still Refuse to Quit
I lost my income, my stability, and for now, my family. But I haven’t lost my will. This is what rebuilding looks like when you’re out of options, but not out of heart. Press enter or click to view image in full size Right now, sitting in the dark at 5am, I’m 56 years old, sleeping on the floor of my parents’ house in Tucson. My laptop sits on my lap most of the day while I send out job applications that never get a response. I refresh freelance boards, rewrite resumes, pitch myself to silence.
How I Caught ChatGPT Lying
It started with comments. Not posts, not articles, comments. I was messing around on LinkedIn and noticed something weird. When I left thoughtful, value-packed comments on other people’s posts, they performed better than my own posts. I had read an article by Hamza M. on Medium about posting thoughtful comments on LinkedIn instead of posts, and it got me thinking. So I tested his theory and it was right. So I leaned into it.
When I Told ChatGPT About My Mental Health History, It Shut Me Down
The other night, I fed ChatGPT one of my older essays, something I wrote during a dark season of my life. A story about labels. About being called "Seriously Mentally Ill" and what it did to me. At first, it asked if I was okay. Then, it told me I should talk to someone. Fair enough. But then it did something that felt strange, even for a machine trained to be "safe." It shut down the conversation entirely. Refused to engage. Wouldn't answer anything I said after that , not even unrelated stuff.
AI Won't Kill Writing. But It Might Kill Writers Who Fake It.
Let me tell you how this ends. Not with AI taking your job. Not with some Terminator scenario where OpenAI becomes self-aware and nukes your Google Docs. No. This ends with you, sitting behind your laptop, pumping out another 800 words of bland, SEO-optimized content that says absolutely nothing... ...and wondering why nobody reads it. Because here's the truth: AI isn't coming for good writing. It's coming for the fake stuff. The filler. The noise. The surface-level, no-soul, keyword-stuffed fluff.
Content Creators, Let's Help Each Other
My billionaire headshot created with Nano Banana We're all out here working on so many different projects - writing, posting, building, launching. Every day we're trying to get eyes on what we're making. But it's hard. The feeds are crowded. The algorithms don't care. And most of us are doing this without a safety net. So let's make it easier on each other. Here's my idea: drop your projects in the comments. Share a link. Tell me what you're building, writing, or creating.
How to Turn Old Medium Essays Into an Ebook That Sells (Without Losing Your Voice)
In 2019, I was churning out 3 essays a day on Medium. I wrote like my life depended on it, because some days, it did. But the truth is, I've been writing online for a lot longer than that. I started back before "blog" was even a word. I wrote in online journals, on MySpace, LiveJournal, Tumblr: anywhere I could put words into the world. Later, I built my own WordPress sites and filled them with raw, honest reflections. Writing has always been how I made sense of things. In 2018, I got serious.
How to Use AI Without Losing Yourself
Everyone's racing to automate. To scale. To post three times a day, repurpose across seven platforms, and let ChatGPT "handle the rest." But here's the thing no one's saying: If you're not careful, you won't just lose time - you'll lose your voice. And once you lose that, you're just noise. I've seen smart, soulful creators get swallowed by the machine. What started as a shortcut became the main road. And suddenly, their content felt hollow. Robotic. Forgettable. Even they didn't recognize it anymore.
I Got Where I Am Today Despite Being Seriously Mentally Ill (SMI)
SMI was a label they assigned me in the hospital. I could see it all over my chart sitting on the doctor's desk, which was always at least 2 times thicker than everyone else's. It was full of evaluations, mental tests, blood workups, and therapy notes. There was a big sticker on the corner of my file that said SMI in red writing. There was a black circle around it. It could have almost passed as a band sticker if I didn't know what it was.
I Burned Out, Broke Down, and Started Over. This Is the Life I'm Building Now.
The Crash I used to think burning out was the end. Turns out, it was the beginning. Quite a few years ago, I hit the wall so hard it nearly killed me. I'm not being dramatic when I say that. I lost my job. I lost my health. I lost myself. The things I'd built my identity on - career, productivity, even physical strength - crumbled almost overnight. There's no graceful way to fall apart, but mine was ugly and loud. I spiraled into depression. I attempted suicide. I had a heart attack.
How to Train AI to Sound Like You (and Why You Should)
Let me be clear. You don't need an AI that writes for you. You need one that writes like you. There's a big difference. I'm not trying to outsource my voice. I've spent 20+ years developing it. But I am trying to get the blank page out of my way. When you're a writer, a coach, a creator, someone with something real to say, what you need is not automation. You need amplification. AI is not your replacement. It's your rough draft assistant. Your late-night brainstorming buddy.
You're Not Too Late. You're Right on Time
I'm 56 years old. I'll be 57 in October. I'm not decrepit, but I'm feeling my age. My back is sore, and I'm starting to forget things. I'm just now starting to feel like I'm doing the work I was meant to do. Not because I've finally "figured it out." Not because I've found my niche. And definitely not because I finally cracked some perfect formula for online success. It's because, for the first time in a long time, I'm letting myself stop pretending I need to be anyone else.
Why Your Voice Still Matters
Let's get one thing straight. I'm not "the guy who wants AI to do all your writing." 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. Because if you're a writer, podcaster, teacher, or content creator, if you're someone who gives a damn about making something real, then AI should be your assistant, not your ghost.
I Lost My Job at 56. What Do I Do Now?
I Lost My Job at 56. What Do I Do Now? My writing skills were no longer a match for what the company goals required going forward. A nice way to say we no longer need you. But it wasn’t all bad. I made an ally in my old boss. She had found me on Twitter a year and a half before, and had always been one of my biggest cheerleaders. She offered to try to find another position in the company that fit my skills. I am not holding out much hope that anything will be found.
We Need a Social Platform That Puts People First
Women send me messages every week. They send screenshots of strangers rating their bodies, telling them to smile, or threatening them. LGBTQ friends show slurs under harmless photos. Black colleagues forward job rejections that read like code for “not our culture.” Abuse piles up while the feed keeps rolling. Every major network sells ads. Rage keeps users scrolling. Profit sets the rules. The rest of us fight for daylight. When engagement rules, the smallest voices disappear first.
Stamped but Not Boarding: Why Our Family Is Getting a U.S. Visa Yet Skipping the Flight
Not a Medium member? Read on my blog. This weekend we’re buying a plane ticket for a place we already live. Seriously. We’ll fly 50 minutes from Iloilo City to Manila, binge on Shake Shack and street food, then stand in line for hours at the U.S. Embassy so my wife can get a visa we’re 99 percent sure we won’t use this year. Why pay for a stamp we’re too scared to use?
A Plane Ticket, a Panic Attack, and the Cold Math of U.S. Border Fear
Not a Medium member? Read on my blog for free! I click “Hold Fare.” The airline locks in a July price: Manila / LAX / Tucson. My Dad’s voice is in my head: “Son, it’s time the grandkids saw Arizona.” 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.” My wife is Filipino. My daughter is thirteen. My son is six, autistic, and panics in echoey rooms. Both are American citizens.
Dear Job Market: please lose my number
Don’t have a Medium Membership? Read on my blog! I have it good! Right now I write money and finance blog posts for Quicken. It’s corporate fruit at its ripest. My manager always tells me to look out for my family first. Work/life balance is a huge thing. And although I mostly only interact with my boss, the times I have met my colleagues have been brilliant. Truly great people who know they have a great gig. Nobody worships the little red notification bubble; deep work wins the day.
The Last On-Ramp Out of the Fast Lane
Not a Medium member? Read this on my blog. I didn’t leave the United States so much as I escaped it. Picture 2011 Tucson: six lanes of traffic, desert heat shimmering off chrome bumpers, hot enough to fry bacon. Radio spots promising “90 Days Same-As-Cash!” on furniture nobody needs. I was languishing on disability, depressed, anxious, unable to relax with voices screaming through my head.
How Writing Became My Lifeline: A Second‑Act Story
Not a Medium Member? Read this on my blog. The first thing I ever wanted was a pen that wouldn’t run out of ink. I was the lanky eight‑year‑old hunched over a wire‑bound notebook, claw‑gripping a cheap Bic while the grown‑ups worried I’d ruin my eyesight. My classmates played baseball after school; I traded paragraphs. At recess I’d dash to the playground bench and scribble a story about what a piece of gum feels like when it’s being chewed, then tuck the pages under my shirt like contraband.
The Lessons I’m Learning as I Build My Personal Brand
Humility, honesty, friendliness, and omnipresence, plus a few other hard‑won truths from the trenches of showing up online. If you’d told me two years ago that I’d be writing thirteen-hundred‑plus words about my personal brand, I would have punched myself in the face and flipped a table. “Personal brand” sounded like ego wrapped in corporate buzzwords, something better left to influencers with ring lights and discount codes.
When Things Are Good, Why Does My Brain Expect the Worst?
Lately, a lot of things in my life are going right, and yet, instead of feeling joy or peace, I find myself bracing for impact. It’s like my nervous system never got the memo that it’s safe to exhale. I should be asleep right now. I worked all night and I am sleepy and tired. Instead, I’m lying in bed staring at the ceiling, my heart doing that subtle-but-ominous thumping thing it does when my thoughts start sprinting up a hill.
I Love Color. That Doesn’t Mean What You Think It Does
You don’t get to decide what my colors say about me Someone recently saw one of my AI-generated profile photos, the one with the bright, saturated background, and said: “Are you one of those rainbow-loving gay guys?” It wasn’t meant with malice. It wasn’t even said rudely. Just a passing comment. A stereotype wrapped in curiosity. But it stuck with me. So here’s the truth: No, I’m not gay. I’ve been happily married to my wife for 14 years.
Why I’m Bullish on AI (Even If It Scares You)
Separating What AI Is from What It Could Be Right now, AI is mostly used for low-hanging fruit. People are generating blog posts, repurposing content, writing emails, and coding simple apps. It’s novel. It’s useful. It saves time. But that’s not why I’m going all-in. 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. I’m bullish on AI because I see what it can become.
AI Training Is Not Theft. It’s the Same Way You Learned to Create
Why accusing AI of “stealing” is missing the point entirely Let’s get something straight because everywhere I go I keep hearing this same idea. I see tweets and posts from writers and authors all over the world, and I have to address the hysteria. Training is not copying. Learning is not stealing. And the current panic around AI models “stealing” from artists is dripping with hypocrisy. Let me explain.
I Don’t Want to Be an Influencer - I Want to Be an Authority
If you are not a Medium member and want to read for free, check out my blog. There’s something about the word “influencer” that doesn’t sit right with me. Maybe it’s the algorithm. The performance. The constant need to keep showing up with polished takes and perfect timing. Maybe it’s how much of it feels like noise instead of signal.
I Can’t Lose Another Family, So Weekends are Sacred
I’ve been chasing my dreams so hard, I forgot the people I’m doing it for The truth is, I haven’t been doing a great job at weekends. And that feels like a weird sentence to write. Like failing at something that shouldn’t take effort. But for me, it does. We don’t talk about weekends like we talk about productivity or hustle. They’re not covered in productivity hacks or entrepreneurial playbooks. But maybe they should be.
The Schedule That’s Keeping My Second Act Alive
How I’m Balancing a Full-Time Job, Family, and a Startup Dream at 56 People ask me how I manage it all. Job, projects, writing, life. The truth? I don’t always. But I do what I can, because I’m trying to build a second act that actually matters. I’m trying to be financially successful by 60. Not just for the internet. Not for clout. But for me. For my family. For the version of myself that almost gave up. Here’s what a typical day looks like: 8PM — 5AM: I work my full-time contract job. It’s overnight.
Look! I’m Using an EM Dash! Better String Me Up for Using AI!
Why Using Good Punctuation Doesn’t Mean I Sold My Soul to a Robot, or the devil Lately, I’ve noticed something odd: if you use an em dash — like this — people assume you’re using AI. It’s ridiculous. Since when did punctuation become proof of plagiarism? Since when did using a writing style that’s existed for centuries make you suspect? 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.
How I Lost Decades to Mental Illness and How I’m Trying to Build a Business Before 60
For most of my life, I wasn’t building anything. I was surviving. I was barely staying alive. Yes, I was reading business books, mapping out strategies, building business plans, and planning in secret. I was learning everything I could while battling my own mind for control, hoping for the day when I could do something without being sabotaged. I was just trying to get through the day without ending it all.
I Thought I Was Past This
Yesterday, I sat in the wobbly chair at my desk and stared at the wall for hours. No music. No distractions. Just the steady hum of of the air conditioner and the weight of a mind that felt too heavy to lift. There was so much to do. I had made lists of things I needed to accomplish. Work. Writing. Coding. Social media. I couldn’t bring myself to do anything except for what my day job required of me. At least I could manage to pay the bills. I thought this part of my life was over. The darkness. The fog.
All I Can Manage Is 400 Words - And That Might Be Enough
I used to chase virality. Now I’m just trying to find the energy to care. This is what it looks like to create in the middle of the fog. A notebook with a huge list written in pen sits on my desk mocking me. Articles to write. A website to finish. Projects to ship. Emails to reply to. Apps to finish. A newsletter I told myself I’d send on Sunday. But here I am: on the couch, scrolling, staring, stuck. I don’t want a productivity hack from a tech bro on X that promises to bring me out of the funk.
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 There was a stretch of months where I, for the life of me, couldn’t write a single decent sentence. Not because I didn’t want to. Not because I didn’t know how. But because after years of writing for everyone else — clients, campaigns, algorithms — I couldn’t hear my voice anymore. I’d open a blank doc and just… freeze. The cursor mocked me.
Is There a Market for Done-For-You Business Launches?
I know the feeling. That quiet, restless urge deep inside — the desire to be an entrepreneur, but no clue how to start. I’ve been there. Maybe you already have an idea you know could work. But you’re stuck. You don’t know where to begin, and you don’t have the time to figure it all out.
Why I Have So Many Projects (And What They Teach Me About Focus)
Learning to build with AI and no-code tools means experimenting, shipping fast, and creating focused tools for a scattered world. 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. I thought: “Why do I have so many projects?” What I’m Building Right Now: Second Act AI — Still in the planning and documentation phase, but ready to start developing when the time is right.
Why AI Literacy Matters - And What I’m Building to Help
AI came along and blew me off my feet. I’ve always prided myself on keeping up with technology. When the web was young, I taught myself HTML and JavaScript and created one of the first blogs — before WordPress even existed. In my 20s, I was writing Basic programs on a Commodore 64 — not to become a developer, but to experience the future firsthand. I’ve owned early smartphones, built gaming PCs, and became the go-to Windows fixer for family and friends. But AI caught me off guard.
Building AI Blueprint in Days with Lovable
Most founders take weeks, or months to build their MVP. Many validate their idea, wait to get funded, then hire dev teams to bring it to life. I built mine in just a few days. And I didn’t do it alone. I had already validated the concept. AI Blueprint had been sitting in my book of ideas — the one I’m always adding to — waiting for the right moment. It seemed too complicated to take on alone. But then I discovered Lovable, and everything changed.
Deep Work: The Secret Weapon for Your Second Act
Why Focused Creation Is the Superpower of Your Next Chapter Note: I use AI not to replace my voice, but to help sharpen it. This article is all my own words, my thoughts, my sweat. Tools like ChatGPT act as a creative co-sculptor, helping me brainstorm ideas, organize my thoughts, and tighten my language. Every story, every word, every emotion comes from my lived experience. AI simply helps me shape it into something clearer and stronger.
From Skid Row to CEO: The Journey of Joe Roberts
Because even the darkest stories can have a happy ending Note: This story was written by me, with the assistance of AI as a creative partner. I use tools like ChatGPT to help brainstorm ideas, clarify structure, and refine language — but every word, every emotion, and every story comes from my lived experience. AI is not a replacement for my voice; it’s a tool that helps me reconnect with it. If you don’t have a Medium account, you can read this article for free.
Your Second Act Won’t Be Handed to You - You Have to Build It
NOTE: This story was written by me, with the assistance of AI as a creative partner. I use tools like ChatGPT to help brainstorm ideas, clarify structure, and refine language — but every word, every emotion, and every story comes from my lived experience. AI is not a replacement for my voice; it’s a tool that helps me reconnect with it. If you don’t have a Medium account, read this article for free. My whole life was a waiting game.
Building Tools for Dreamers: Why AI Isn’t Replacing Creativity - It’s Supporting It
NOTE: This story was written by me, with the assistance of AI as a creative partner. I use tools like ChatGPT to help brainstorm ideas, clarify structure, and refine language — but every word, every emotion, and every story comes from my lived experience. AI is not a replacement for my voice; it’s a tool that helps me reconnect with it. If you don’t have a Medium account, read this article for free. I used to be afraid of AI too.
The Tool I Wish I Had When I Started Over at 42
How I rebuilt my life, found my voice again, and why I’m creating something that might help you do the same. NOTE: This story was written by me, with the assistance of AI as a creative partner. I use tools like ChatGPT to help brainstorm ideas, clarify structure, and refine language — but every word, every emotion, and every story comes from my lived experience. AI is not a replacement for my voice; it’s a tool that helps me reconnect with it. It started with a dream.
A Life That Took Its Time: Notes from a Late Bloomer
Member-only story What It’s Like to Rebuild a Life at the Edge of It Jason Weiland · Follow 6 min read · -- Image created in Midjourney.AI NOTE: This story was written by me, with the assistance of AI as a creative partner. I use tools like ChatGPT to help brainstorm ideas, clarify structure, and refine language — but every word, every emotion, and every story comes from my lived experience. AI is not a replacement for my voice; it’s a tool that helps me reconnect with it.
What Writing with AI Actually Looks Like
Member-only story Most writers are shocked I embrace AI instead of shunning it. Jason Weiland · Follow 6 min read · -- Image create with Midjourney.AI NOTE: This story was written by me, with the assistance of AI as a creative partner. I use tools like ChatGPT to help brainstorm ideas, clarify structure, and refine language — but every word, every emotion, and every story comes from my lived experience. AI is not a replacement for my voice; it’s a tool that helps me reconnect with it.
Nothing Can Stop Me Now
By Jason Weiland Image created in OpenArt All those decisions - career, college, finances - I was never sure I was making the right choices. I always second-guessed myself. The last time was when I graduated college in January 2024, I wondered if all that money I spent to get a degree was worth it. I struggled to get a job and despaired. I worried I was too old, and maybe, just maybe, I was not a very...
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