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

Life has a funny way of surprising you and waking you up. One moment, you think you’ve found steady ground, and the next, the earth shifts under your feet. Like a slap in the face, you are cruising along happily and then reality smacks you like a semi-truck.

For me, that moment came recently when changes at Quicken, where I’d been writing and shaping blog content, pushed me to reimagine my own path forward. I'm still there for now, but the landscape is changing and I need to change with it.

Instead of looking at it as an ending, I’ve chosen to see it as the beginning of my second act: a new chapter where I can lean on everything I’ve learned as a writer, web designer, and creative professional, and turn it into fresh opportunities.

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.

One of the projects I’m most proud of was my work with AnxietyBoss.com, where I created mental health content aimed at helping people struggling with anxiety. Writing for that audience required empathy, clarity, and the ability to translate medical and psychological concepts into plain language people could actually use.

It taught me how powerful writing can be when it meets people at their most vulnerable and offers both guidance and hope.

I’ve also built websites. From those early HTML and CSS static builds back in the late ’90s to modern WordPress and Webflow blogs and websites. Alongside all that, I’ve guided teams and designers and writers, managed creative projects, and learned how to balance storytelling with strategy.

My career has never been a straight line, but the twists and turns have prepared me for this exact moment.

Why This Matters Now

The way people search and consume content is changing fast. We’re living in a world where AI-driven tools like ChatGPT are becoming just as important as Google.

At Quicken, I didn’t just write finance articles, I helped shape the new direction of their blog. We transitioned from traditional SEO-focused content to writing that also works for AI-driven discovery.

That meant refreshing old posts, reorganizing the content library, and creating new material that’s not just keyword-rich, but structured so AI bots can easily pull accurate, useful answers.

This was a shift into an AIO (Artificial Intelligence Optimization) mindset, and I had a front-row seat in helping move a major financial brand into that future.

That experience showed me that the future of content isn’t just about writing, it’s about writing for discovery, relevance, and connection across multiple platforms. And now, I want to take that knowledge and partner with people who need it.

How I Use AI in My Work

I’m not just talking about AI in theory, it’s part of my daily writing process. I use it every day.

I use tools like ChatGPT and Claude to brainstorm topics, generate outlines, and accelerate research. They help me find gaps, surface new angles, and speed up repetitive tasks like rewriting or formatting. But I never hand over the final product to AI alone—every word gets shaped, refined, and polished by me.

I see AI as an assistant, a helper, a guide, not a replacement: it gives me the efficiency to produce content at scale while leaving room for my experience and voice to guide the work. This balance is how I stay both fast and authentic in today’s fast-changing content world.

What I’m Looking For

As part of my second act, I’m looking to collaborate with businesses, entrepreneurs, and creators who need help in two key areas:

1. Content Creation & Strategy
   Whether it’s blog posts, website copy, or a content plan that makes sense for your audience, I can help you find the right words and structure them for maximum impact. I believe in writing that’s not only well-crafted but also works—driving traffic, building trust, and helping you connect with the people who matter.
2. Website Design & Development
   Your website is your digital home base, and I’ve spent years building sites that are clean, modern, and easy to use. From simple business websites to more complex builds, I can design and develop a site that reflects your brand and supports your goals. I use tools like Webflow, WordPress, and Figma to bring ideas to life.

Let's connect!

jasonjamesweiland@gmail.com

Collaboration, Not Just Contracts

I’m not looking for one-off gigs where the work ends as soon as the invoice is paid. What excites me are partnerships: collaborations where we build something together, whether it’s a content engine that powers your business month after month or a website that grows alongside you. I want to bring my skills to the table, but I also want to work with people who have a vision and are ready to take action.

Why Work With Me

• Experience Across Fields: From mental health to finance, I’ve adapted my writing to reach audiences where they are.
• Balance of Strategy & Creativity: I see the big picture but also sweat the small details.
• Future-Focused: I helped Quicken move toward an AIO-focused content strategy, and I build content with AI-driven discovery in mind.
• Human First: At the core, I believe in honest communication, simple design, and writing that connects.

My Second Act, Your Next Step

This isn’t just about me finding work. It’s about me finding the right people to work with. I know from experience that when collaboration clicks, the results are bigger than what either side could do alone. So if you’re building a business, growing a brand, or simply tired of trying to do it all yourself, maybe we should talk.

Life doesn’t always go the way we plan, but that’s not necessarily a bad thing. Sometimes, a shake-up is exactly what you need to step into something better. For me, that’s what this second act is about: turning change into opportunity, and finding the people who are ready to build something meaningful together.

If you’re looking for content that speaks or a website that works, I’d love to connect. Let’s see what we can build in this next chapter.