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Welcome to Retired and Trying
The world’s longest coffee break doesn’t mean slowing down—it means living on your own terms. Here, you’ll find laughs, lessons, and side hustles that keep retirement interesting. From coffee-fueled thoughts to shirts, books, and resources, this is about enjoying freedom while still trying new things every day.
☕ Get “The Trying Times” — Your Free Weekly Note from a Retiree Who’s Still Figuring It Out
A short, real email once a week from Don at Retired & Trying—with a quick story, one simple money or side-hustle tip, and a reminder that you’re not the only one still trying to make this season of life work (with plenty of coffee along the way).
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If you’d like, you can treat me to a coffee — it helps keep Retired and Trying caffeinated and creating. ☕
Coffee-Fueled Stories & Tips
Retirement isn’t the end of the story—it’s the best chapter yet. Grab a cup of coffee and enjoy quick reads on living simply, trying new things, and finding humor in the world’s longest coffee break.
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If I Could Start Retirement Over — Here’s What I’d Do Differently
If I could begin retirement again, I’d do it differently — with more purpose, more movement, fewer possessions, deeper connections, and more courage to live fully. Here’s what experience revealed.
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The 7 Surprising Ways a Side Hustle Makes Retirement Better (Even When It Makes No Money)
A side hustle can make retirement more fun, more purposeful, and surprisingly fulfilling—even when it brings in little money. Here are seven reasons why.
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10 Simple Habit Changes That Make Retirement Happier
Retirement happiness isn’t about big changes — it’s about the small daily habits that make life calmer and more meaningful. Here are ten simple shifts that transformed my days.
Smart Strategies for Embracing Retirement Joyfully
Discover our curated selection of retiree-friendly finds and exclusive offers designed to add simplicity and fun to your days.
Six Figure Plan
Now available on Kindle — From the Floor to Six Figures by Don Romans.
Gratitude Journal
Gratitude Journal
LegalShield Services
Embrace Retirement Joy and Simple Pleasures
Discover engaging stories, practical tips, and humor crafted to enrich your retirement lifestyle.
Side Hustle Inspiration
Discover easy, low-risk ways to earn extra income in retirement—from creative projects to smart side hustles that keep life interesting.
Simplified Living
Practical tips on decluttering, cutting costs, and focusing on what really matters so you can retire stress-free and enjoy more freedom.
Lighthearted Perspectives
A dose of humor and encouragement for the retired life. From coffee jokes to daily laughs, find joy in the world’s longest coffee break.
Join the Retired and Trying Community
Share laughs, ideas, and side hustles with others living their best retired life. Discover tips, humor, and resources that make every day feel like the world’s longest coffee break.
Retirement with Purpose and Plenty of Laughs
From coffee chats to side hustle experiments, Retired and Trying is where humor meets practical tips for living your best retired life.
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Side Hustles Explored
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Simplicity in Action
400
Joyful Moments
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Retirement Tips
Keep the Coffee Break Going ☕
Retirement doesn’t have to be quiet — join me on YouTube for weekly laughs, side hustle ideas, and simple living tips.
Catch up on the latest laughs, lessons, and side hustles from Retired and Trying.
Latest Posts from Retired and Trying
- If I Could Start Retirement Over — Here’s What I’d Do Differently
- The 7 Surprising Ways a Side Hustle Makes Retirement Better (Even When It Makes No Money)
- 10 Simple Habit Changes That Make Retirement Happier
- My Retirement Budget Has a Sense of Humor… Too Bad It Isn’t Funny
- Affiliate Marketing for Retirees: The Simple Way I Do It
- The Art of Doing Nothing—and Enjoying Every Minute of It
- How I Use ChatGPT as My Business Partner (No Tech Skills Needed)
Want more laughs and lessons? Explore all posts on the Retired and Trying blog