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“The world’s longest coffee break.”

Retired & Trying on YouTube

📺 Welcome to Retired and Trying on YouTube

Welcome to the official Retired and Trying video hub — the place where I share my real-life journey to build an extra $1,000 a month in retirement. Like many people, I didn’t save enough during my working years, so now I’m showing exactly how I’m figuring it out one side hustle at a time. My channel is all about honesty, experimentation, and encouragement. I share what’s working, what’s failing, and what I’m learning along the way — so you can try these ideas too or just follow along for inspiration.

Every week, you’ll find new videos here, from practical side-hustle updates and frugal living tips to motivational “Morning Coffee Thoughts” and behind-the-scenes looks at how I’m building small streams of income. This isn’t about overnight success — it’s about slow, steady progress and real-world results. Whether you’re retired and want a little more financial breathing room or just looking for ways to simplify life after work, you’ll find plenty here to keep you motivated.

Start by watching my video below on why I started this channel — then explore more episodes on side hustles, retirement lifestyle tips, and lessons learned from both wins and missteps. And if you like what you see, be sure to subscribe on YouTube so you don’t miss new uploads every week.

Videos

The world’s longest coffee break — now streaming fresh stories every week.

🎥 Morning Coffee Thoughts

Quick daily reflections, retirement humor, and little motivational sparks — perfect with your first cup of coffee.

👕 T-Shirt Hustle Updates

Behind-the-scenes of building a retirement side hustle through merch. See designs come to life, progress updates, and the occasional funny flop.

💡 Retirement Tips & Stories

Enjoy humorous and relatable tales that celebrate the quirks and joys of retired life.

📚 Books & Journals Spotlight

Updates about my published books — from From the Floor to Six Figures to the Gratitude Journal — plus insights on writing in retirement.

Helpful Links