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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Generation Jones: It’s Our Time to Thrive in Retirement
Generation Jones grew up in the shadow of the older Baby Boomers, facing different economic challenges and opportunities. But we worked hard, adapted, and made it to retirement. Now it’s our time to enjoy life, embrace new possibilities, and make the most of our golden years—regardless of how much money we’ve saved.
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Can Working After Taking Social Security Increase Your Benefits? What I Learned After an Unexpected $133 Raise
An unexpected $133 Social Security increase led me to discover that working after claiming benefits can sometimes raise your monthly check. Here’s how it works and who might benefit.
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Why Introverts Actually Win in Retirement
Retirement advice says to stay busy, make friends, and socialize. But what if you’re happier alone? After 39 years of living alone and 10 years of retirement, I’ve discovered why being an introvert can actually be an advantage in retirement.
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
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🤔 Still thinking about your own retirement?
Every retirement is different. If this article raised questions about your own situation, continue the conversation with the Retired and Trying Companion.
Simply type your question, just as you would ask a friend.
- Downsizing
- Social Security
- Housing
- Purpose
- Budgeting
- Travel
- Any retirement question on your mind
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
120
Simplicity in Action
400
Joyful Moments
60
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
- Generation Jones: It’s Our Time to Thrive in Retirement
- Can Working After Taking Social Security Increase Your Benefits? What I Learned After an Unexpected $133 Raise
- Why Introverts Actually Win in Retirement
- Should You Start Investing at 66? My Retirement Without a Nest Egg
- 5 Things I Absolutely Love About My Retirement After 10 Years
- Don’t Leave Money on the Table in Retirement: Sometimes You Just Have to Ask
- Should I Get a Gun in Retirement? Why I’m Afraid of Making the Wrong Decision
Want more laughs and lessons? Explore all posts on the Retired and Trying blog
