CASUAL MONDAYS PODCAST

Retired? Working towards retirement? Click to join the Casual Mondays Club!

Welcome to Casual Mondays, the retirement podcast for those who’ve closed the office planner and opened the door to tomorrow. Whether you're planning for retirement or already made the transition, join us for conversations about what happens after you step away from the 9-to-5: from day one plans to shaping a second act that’s as fulfilling as it is flexible.Expect expert advice, inspiring stories, and actionable tips for designing a life that’s rich in experiences, purpose, and joy. Trade your desk for a deck chair. This is the retirement podcast for living your best life - every single day.

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The Podcast for Early Retirees (and those preparing to be!)

Expect expert advice, inspiring stories, and honest conversation about the good, bad, and all the in betweens of life in retirement.

Trade your desk for a deck chair. This is the retirement podcast for living your best life - every single day.

NOTE: This is not an investment advice podcast. Consult a Certified Financial Planner for investment advice.

Retired? Working towards retirement? Join the Casual Mondays Club!

Recent

April 13, 2026

The Social Network Reboot - Building Real Community After Your Career

Your work friends are fading. Your social calendar feels empty. And asking someone to grab coffee at 53 feels like middle school all over again. This episode tackles the isolation epidemic that nobody warns you about in early...

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March 23, 2026

Resolution Reset - Abandoning Your Failed Plans and Making This Year …

You crushed every Q4 target for 30 years. Hit your numbers. Delivered projects. Earned promotions. But your personal resolutions? Failed by February. Again. Here's the thing: the framework that made you successful at work doe...

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Feb. 9, 2026

Creating Structure Without the 9-to-5

It's 10:47 on a Tuesday morning. You're still in your pajamas, scrolling your phone. You had vague plans—organize the garage, call a friend, hit the gym. But there's no meeting at 11. No deadline at noon. No boss wondering wh...

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Jan. 19, 2026

Finding Your Ikigai - Your Reason for Being

You've retired. You can fill every hour with activities—golf, volunteering, travel—and still feel empty. You're busier than when you worked, but something fundamental is missing. This episode introduces the Japanese concept o...

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Dec. 25, 2025

Who Am I Without A Business Card? The Identity Shift

"So, what do you do?"Three weeks after leaving my 25-year career in luxury hospitality, I froze at this simple question. According to Harvard Business School research, I'm far from alone—the retirement identity crisis is one of the most profound psychological challenges that nobody talks about.…

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Dec. 9, 2025

Welcome to Casual Mondays

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Retirement Success Graph

Stress test your retirement plan against 100+ years of market data with Retirement Success Graph.

Secure by design, the Retirement Success Graph app brings advisor-level analysis to your device without ads, subscriptions, or privacy compromises. The fully-functional, free-for-life app provides 50 simultaneous Monte Carlo model runs to measure your retirement plan against decades of economic data.

Unlock Premium features with a one-time $4.99 purchase, including support for multiple withdrawal methods, social security strategies, model retirement income and windfalls, and compare results over 10,000 simultaneous model runs.

Recent Blog Posts

April 13, 2026

When Your Work Friends Fade: Rebuilding Social Connection in Retireme…

Three months into retirement, you send a text to your former colleague: "Coffee next Tuesday?"The reply comes four days later: "Swamped this week, maybe next month?"Next month becomes three months. Three months becomes silenc…

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April 13, 2026

Why Your New Year's Resolutions Keep Failing (And How to Fix It)

February 14th. Valentine's Day. Also the day when approximately 80% of New Year's resolutions have already been abandoned.For thirty years, you crushed quarterly targets. You managed complex projects, navigated corporate politics, and …

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April 13, 2026

From Career to Blank Calendar: How to Design Your Days Without the 9-…

You open your eyes Monday morning. No alarm. Just the natural rhythm of waking up when your body is ready.You reach for your phone—not to check urgent emails, but just... because.Your calendar app shows nothing. No meetings. No deadlines. …

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About the Host

Kevin Donahue

Author. Podcast Host. Pilgrim Backpacker. Aspiring Racer.

With a 25+ year track record of driving revenue, creating and repositioning brands, and developing leaders, Kevin Donahue is regarded as one of the elite marketing strategists and sales leaders in the luxury hospitality industry. He left the industry in his early fifties to prioritize intentional time as a husband and father, a pilgrim backpacker, an author, a digital developer, and a podcast host.

In his "retirement era", Kevin serves on the College of Business Advisory Council at Florida Gulf Coast University and is pursuing new passions, including auto racing and mobile app development.

For more on Kevin's active projects, please visit KevinDonahue.com and ChezMerStudios.com