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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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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Letting Go of Old Expectations in Retirement
Retirement can feel heavier than expected when old expectations linger. Letting go of how retirement “should” look often creates space for calmer, more honest days to take shape naturally.
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Why Retirement Can Feel Lonely Even When You’re Not Alone
Loneliness in retirement isn’t always about being alone. Even with people around, retirement can feel isolating as routines and connections change. Here’s why that feeling is common — and what it really means.
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What No One Tells You About Having More Time in Retirement
Having more time in retirement sounds ideal, but it can feel strange at first. Here’s what really changes when time slows down and how many retirees quietly adjust to it.
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 →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
- 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
- What I Spend Money on Now That I Never Did Before Retirement
- Why Retirement Feels Strange at First (And Why That’s Normal)
- Things Retirees Waste Money On Without Realizing It
- How Much Money Do You Really Need in Retirement?
Want more laughs and lessons? Explore all posts on the Retired and Trying blog