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.
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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The New Retirement Mindset: How to Make the Most of Your Next Chapter
Retirement is no longer just about slowing down. It’s about reinvention. Here’s how to embrace the new retirement lifestyle and make the most of every day.
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How to Live Well on a Retirement Budget: Frugal Tips That Don’t Feel Like Sacrifice
Retirement doesn’t mean giving up the good life. Learn how simple shifts in spending, saving, and mindset can help you live well on a retirement budget — without sacrifice.
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Smart Side Hustles for Retirees: Earning Without Stress
For most retirees, the idea of “working again” doesn’t sound appealing — but what if work looked totally different? What if it was enjoyable, on your terms, and helped fund a few adventures or hobbies? That’s the power of a smart side hustle.
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

Grattitude Journal

Retired & Trying T-Shirts

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 & 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 & 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
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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
- The New Retirement Mindset: How to Make the Most of Your Next Chapter
- How to Live Well on a Retirement Budget: Frugal Tips That Don’t Feel Like Sacrifice
- Smart Side Hustles for Retirees: Earning Without Stress
- How to Build a Fulfilling Retirement Routine
- Why Retirement is the Best Time to Shine
- How to Balance Relaxation and Recreation
- Living Every Day Like It’s the Weekend
Want more laughs and lessons? Explore all posts on the Retired and Trying blog