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.
-
10 Things Retirement Taught Me About Time
A movie clip from 2010 made me realize how quickly time passes in retirement. Here are 10 lessons retirement has taught me about time, aging, family, health, and making the most of today.
-
Why Do Retirees Become More Talkative?
Have you ever walked away from a conversation with a complete stranger and wondered, “Why did I tell them all that?” Since retiring, I’ve noticed I’m much more likely to strike up conversations and share stories with people I barely know. It turns out I may not be alone. Here’s why many retirees become more…
-
Don’t Pay Medical Bills Until You Do This
I almost paid a $79.83 medical bill without question. After checking my Explanation of Benefits (EOB), I discovered I owed nothing. Here’s what every retiree should know before paying a medical bill.
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.
75
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
- 10 Things Retirement Taught Me About Time
- Why Do Retirees Become More Talkative?
- Don’t Pay Medical Bills Until You Do This
- I Almost Canceled My Life Insurance in Retirement
- I Thought My Condo Was Bigger… Turns Out It Didn’t Matter
- How I Ended Up Single for 35 Years (And Why I Stayed That Way)
- If You’re Close to Retirement and Didn’t Save Enough… Don’t Panic
Want more laughs and lessons? Explore all posts on the Retired and Trying blog