Your Roadmap to Retirement That Actually Works: Season 1 of Casual Mondays

A 16-episode journey from "Now what?" to "Now THIS."

You've spent decades building your career. You've got the nest egg. The freedom. The endless Mondays stretching ahead.

So why does it feel equal parts exhilarating and terrifying?

Welcome to Casual Mondays - the podcast for those who've traded their suit for sandals and their desk for a deck chair. I'm Kevin Donahue, and over 12 episodes this season, we're tackling the real questions early retirees face when the structure of work disappears, and life becomes a blank canvas.

This isn't about bucket lists and beach photos. It's about designing days that matter.

Episode 0: Welcome to Your Next Chapter

The show premise, the promise, and why the hardest part of retirement isn't leaving work - it's figuring out what comes next. Your introduction to a different kind of Monday morning.

Stream Now:   Apple Podcasts | Spotify | YouTube

Episode 1: The Identity Shift - Who Am I Without a Business Card?

You spent 30 years building a professional identity. Now at cocktail parties when someone asks "What do you do?" your mind goes blank. This episode explores the psychological disruption of losing your career identity and provides seven research-backed strategies for rediscovering authentic purpose beyond your job title.

Episode 2: Finding Your Ikigai – Your Reason for Being Beyond the Paycheck

You can fill every hour with activities and still feel empty. Golf, volunteering, travel—you're busier than when you worked, but something's missing. This episode introduces the Japanese concept of ikigai (your reason for being) and explores how to discover genuine purpose beyond staying busy. Learn the four-circle framework adapted for retirement and walk through a practical three-month experiment to cultivate what gets you out of bed in the morning.

Episode 3: Creating Structure Without the 9-to-5

It's 10:47 AM on Tuesday. You're still in pajamas, scrolling your phone, wondering where the morning went. You have all the time in the world, yet none of it feels like yours. This episode tackles the paradox of retirement: freedom without structure is just chaos in disguise. Discover the Four Pillars Framework for building meaningful daily routines that provide purpose without rigidity, and learn why the first 90 days of retirement set your pattern for years to come.

Episode 4: Resolution Reset - Making This Year Actually Different

For 30 years you crushed every Q4 target at work. But your personal New Year's resolutions? Failed by February. Again. This episode explains why corporate goal-setting frameworks fail in retirement and introduces a values-first approach to creating meaningful change. Learn the Three-Resolution Maximum, discover what to subtract (not just add) from your life, and explore why fewer goals sustained beats more goals abandoned.

Episode 5: The Social Network Reboot - Building Community Post-Career

Your work friends are fading. Your social calendar feels empty. This episode addresses the isolation epidemic in early retirement and provides actionable strategies for building authentic connections, maintaining friendships, and creating meaningful community outside workplace relationships. Loneliness isn't inevitable - but connection requires intention.

Episode 6: Health as Your New Career - Preventive Wellness Strategies

What if you treated health maintenance with the same strategic focus you once gave quarterly targets? This episode reframes wellness as your primary "job" in retirement, covering preventive care, fitness routines, mental health, and creating healthcare advocacy systems that keep you thriving for decades.

Episode 7: The Bucket List Myth - Purposeful vs. Aimless Adventure

Skydiving. Machu Picchu. Safari in Africa. But whose bucket list is it really? This episode challenges the traditional retirement adventure checklist and explores how to create meaningful experiences aligned with your values rather than Instagram expectations. Purpose beats tourism every time.

Episode 7: The Encore Career - Working on Your Terms

Retirement doesn't mean stopping work - it means stopping work you don't want to do. Explore options for continued contribution that align with personal values and lifestyle goals: consulting, part-time work, volunteering, entrepreneurship. This is about designing work around life, not life around work.

Episode 8: The Encore Career - Working on Your Terms

Explores options for continued work that aligns with personal values and lifestyle goals, including consulting, part-time work, volunteering, and entrepreneurship in retirement. Not about needing money but about designing work around life instead of life around work. Addresses when work serves purpose versus when it's just filling time out of fear.

Episode 9: Relationship Rebalancing - When Both Partners Are Home

You've spent 30 years with separate work lives. Now you're both home. All day. Every day. This episode addresses relationship dynamics when couples transition to shared retirement time, including communication strategies, space negotiation, maintaining individual identity, and why "together time" doesn't mean "all the time."

Episode 10: Time Wealth - You Know Your Net Worth, But How Are You Measuring Your Time?

You can recite your investment portfolio allocation to the decimal point, but where did last Tuesday go? Most retirees track every dollar but can't account for how they spend their 8,000 waking hours per year. This episode introduces the Time Wealth Portfolio with four categories of time use, walks you through a one-week time audit that reveals where your hours actually disappear, and provides a 60/20/20 framework for optimizing your most valuable asset: time itself.

Episode 11: Money Mindset Shift - From Accumulation to Strategic Spending

For 40 years, you saved. Now you're supposed to spend. But that scarcity mindset doesn't flip overnight. This episode tackles the psychological and practical aspects of transitioning from saving mode to strategic spending, including overcoming "portfolio guilt" and creating spending plans that align with retirement values, not fear.

Episode 12: The Learning Renaissance - Education as Recreation

Your brain doesn't retire just because you did. This episode explores lifelong learning opportunities - from formal education to creative pursuits and intellectual engagement - as sources of fulfillment and cognitive health. Learning isn't something you leave behind in your career; it's something you reclaim.

Episode 13: Geographic Freedom - Where to Live Your Best Life

Suddenly, your address isn't tied to your office location. This episode explores retirement relocation options - from downsizing locally to international living - including practical considerations, lifestyle alignment factors, and why "where you live" might be the most important retirement decision you make.

Episode 14: Legacy Building - Making Your Mark Beyond Career

Your professional legacy is written. Now what? This episode explores ways to create meaningful impact through mentorship, volunteering, family engagement, and community contribution. Legacy isn't about monuments - it's about moments that matter to people who matter to you.

Episode 15: The Five-Year Vision - Designing Your Retirement Decades

Retirement isn't one phase - it's multiple chapters spanning potentially 30+ years. This episode provides strategic planning frameworks for navigating from active years through evolving needs, including regular life reassessment, adaptation strategies, and why flexibility beats rigid planning every time.

Ready to Trade Your Planner for Days to Plan?

Season 1 of Casual Mondays drops soon. Each 22-minute episode delivers research-backed frameworks, real stories, and actionable strategies for designing retirement that feels as good as it looks.

Because you didn't spend 40 years building a career just to spend your retirement feeling lost.

Subscribe now: Apple Podcasts | Spotify | YouTube

Follow along: @casualmondayspodcast on Instagram

Trade in your suit for sandals. Your desk for a deck chair. Your Mondays for something better.