“The world’s longest coffee break.”

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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.

Older man relaxing on a bench with mountain view – representing simple retired life.

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.

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.

Blue book cover for “From the Floor to Six Figures” – a guide to career success and leadership growth.

Six Figure Plan

Green minimalist book cover for “Gratitude Journal” by Don Romans – a daily reflection guide.

Grattitude Journal

Navy blue T-shirt with the slogan “Retired, Not Expired,” part of the Retired and Trying apparel line.

Retired & Trying T-Shirts

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LegalShield Services

Embrace Retirement Joy and Simple Pleasures

Discover engaging stories, practical tips, and humor crafted to enrich your retirement lifestyle.

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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.

Dotted circle icon symbolizing simplicity, balance, and minimal living in retirement.

Simplified Living

Practical tips on decluttering, cutting costs, and focusing on what really matters so you can retire stress-free and enjoy more freedom.

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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.

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Catch up on the latest laughs, lessons, and side hustles from Retired and Trying.

Latest Posts from Retired and Trying

Want more laughs and lessons? Explore all posts on the Retired and Trying blog