Jason Weiland (@jasonweilandsr) 's Twitter Profile
Jason Weiland

@jasonweilandsr

Writer. AI Consultant. Creator of Second Acts.
Building content, community & comeback stories.
Join me on Skool — we’re making real stuff again.

ID: 1966559957073227777

linkhttps://www.skool.com/second-act-ai/about?ref=23c91c0f147f4366a55cd75b6cf5bf23 calendar_today12-09-2025 17:50:14

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28 Followers

63 Following

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

What’s an AI Strategist & Consultant? I don’t just prompt ChatGPT, I train it to think like you. I help writers, founders & teams use AI without losing their voice. Workflow design. Voice training. Real content. Real results. #AI #consulting #chatgpt #openai #contentstrategy

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

I’m 56. I’ve been a writer, a designer, a freelancer, a college student, a husband, a dad, and a guy who almost gave up. Now? I’m building content every day. Not for clicks—but for connection. If you’re over 40 and trying to build your second act as a writer, creator, or

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

I’ve applied to over 300 jobs at 56. Most end in silence. Ghosted. Ignored. Erased. I’m sleeping on the floor of my parents’ house in Tucson, far from my wife and kids in the Philippines, trying to rebuild a life. Every morning I open my laptop, fill out another application, hit

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

At 56, I’ve been told without words that I don’t matter. The silence of the job market is louder than any rejection. But here’s the truth: I’m not done. I’m building my second act in public, one post, one essay, one imperfect piece of content at a time. Because if I wait for

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

I’ve failed more times than I can count. Lost jobs. Lost money. Lost people. But I haven’t lost the part of me that keeps trying. And as long as that part’s still alive, I’m not done. Not today.

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

Some days, trying feels impossible. But quitting feels worse. So I write. Even when I’m tired. Even when I feel invisible. Because if I stop, I disappear completely.

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

I'm 56. Sleeping on the floor. My family’s across the ocean. My inbox is full of silence. And yet—I still write. Because creation is the only fight I haven’t lost.

Jason Weiland (@jasonweilandsr) 's Twitter Profile Photo

I've been ghosted by jobs. Broken by poverty. Estranged from people I love. But I’m still here. Still showing up. Still trying to build something that matters. That counts for something.