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 Retirement Questions Nobody Warns You About
Retirement planning focuses heavily on money, but many of the biggest retirement questions have nothing to do with finances. Loneliness, purpose, friendships, and figuring out what to do each day often become the real challenges. After years of conversations with retirees, I’ve discovered these concerns are far more common than most people realize—and you’re certainly…
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Why Housing Matters More Than Social Security
Two retirees can receive the same Social Security check and have very different retirement experiences. The difference is often housing. Here’s why your housing costs may matter more than your monthly benefit.
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After 60, The “Last Times” Feel Different
Many of life’s most meaningful moments end without warning. A reflection on family dinners, aging, retirement, and why the ordinary moments often become our most treasured memories.
Protect Your Paperwork
Simple checklists and document systems so your family knows what to do in an emergency.
Go to Paperwork →Control Your Monthly Bills
Budget tools and routines that help you control cash flow on a fixed income.
Go to Bills →Living Alone & Stability
Simple routines, mindset, and systems that protect emotional health and daily structure.
Go to Stability →Start with the Free Retirement Paperwork Safety Checklist
👉 “Check your email and click the confirmation link to finish joining.”
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
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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 Retirement Questions Nobody Warns You About
- Why Housing Matters More Than Social Security
- After 60, The “Last Times” Feel Different
- If You’re in Your 50s or 60s, Don’t Make These Mistakes
- 10 Things Retirement Taught Me About Time
- Why Do Retirees Become More Talkative?
- Don’t Pay Medical Bills Until You Do This
Want more laughs and lessons? Explore all posts on the Retired and Trying blog