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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10 Choices That Let Me Live on Social Security
Can you really live on Social Security? People ask me that all the time. The truth is, there wasn’t one magic trick that made it possible. It was a series of decisions—some easy, some difficult—that helped me reduce expenses, simplify my life, and build a retirement I could actually afford. Here are the 10 choices…
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Why Dr. Google Is My Worst Retirement Habit
Retirement gives us more time to notice every ache, pain, forgotten word, and unusual symptom. Here’s how one crooked parking job sent me down the Dr. Google rabbit hole—and what my doctor said that instantly put my mind at ease
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Things to Give Up in Retirement (That You Won’t Miss)
Retirement isn’t just about what you gain. Sometimes the biggest surprises are the things you’re happy to leave behind. From ironing and alarm clocks to meetings and owning too much stuff, these are the things I gladly gave up in retirement—and why I don’t miss them at all.
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
- 10 Choices That Let Me Live on Social Security
- Why Dr. Google Is My Worst Retirement Habit
- Things to Give Up in Retirement (That You Won’t Miss)
- Retirement Isn’t a Destination: Why Life Keeps Changing After You Retire
- How Downsizing My Life Made Retirement Feel Easier
- The Retirement Questions Nobody Warns You About
- Why Housing Matters More Than Social Security
Want more laughs and lessons? Explore all posts on the Retired and Trying blog