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.
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A short, real email once a week from Don at Retired & Trying—with a quick story, one simple money or side-hustle tip, and a reminder that you’re not the only one still trying to make this season of life work (with plenty of coffee along the way).
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If you’d like, you can treat me to a coffee — it helps keep Retired and Trying caffeinated and creating. ☕
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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Why Quiet Days Matter More Than Busy Ones After Retirement
Quiet days in retirement aren’t empty or wasted. They give space for rest, reflection, and clarity—often bringing more peace and balance than a busy schedule ever did.
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Why Less Really Does Feel Like More After Retirement
Retirement has a way of softening life. Fewer commitments, simpler routines, and quieter days often create more comfort and satisfaction than having more ever did.
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What a Simple Retirement Actually Looks Like Day to Day
A simple retirement doesn’t mean doing nothing. It means slower mornings, gentler routines, and days shaped by comfort and intention rather than urgency or constant activity.
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
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
- Why Quiet Days Matter More Than Busy Ones After Retirement
- Why Less Really Does Feel Like More After Retirement
- What a Simple Retirement Actually Looks Like Day to Day
- Simple Ways Retirees Spend Less Without Feeling Deprived
- Letting Go of Old Expectations in Retirement
- Why Retirement Can Feel Lonely Even When You’re Not Alone
- What No One Tells You About Having More Time in Retirement
Want more laughs and lessons? Explore all posts on the Retired and Trying blog