Welcome to Casual Mondays

You know that moment on Sunday night when you'd set your alarm for Monday morning? The mental preparation. Checking your phone for to-dos and flagging critical emails. What clothes do I need? What calls am I on? What’s due?

Now imagine waking up on a Monday with nothing on the calendar except what you put there.
No meetings. No deadlines. No performance reviews.
Just... Monday. Your Monday.
For some of you, that's already your reality. For others, it's the dream you're working toward.
Either way, you're in the right place.
Welcome to Casual Mondays—the podcast for those who've traded their day planner for days to plan.
I'm Kevin Donahue, and this is where we talk about what happens after you step away from the 9-to-5.

Here's the truth nobody tells you about retirement: the hard part isn't leaving work. It's figuring out what comes next.
I spent 25 years in luxury hospitality—driving revenue, building brands, leading teams. I loved it. But here in my early fifties, I made a decision that surprised a lot of people, including myself, in some ways: I walked away.

Not because I was burned out. Not because I hated what I did. But because I realized that the life I was designing for "someday" needed to start becoming the life I was living.
And that transition? It's exhilarating. It's liberating. And it's also... disorienting.

We spend our entire careers building next eggs and preparing to “retire from” … no one ever told us to focus on what we are “retiring to”.

Because suddenly, you have all this time. All this freedom. And if you're not careful, all this anxiety about whether you're using it right.
Am I doing enough? Should I start a business? Travel more? Volunteer? Learn Italian? Train for a marathon?
Or is it okay to just... be?
These are the questions that keep early retirees up at night. And these are exactly the conversations we have on this podcast.

Casual Mondays isn't about wealth management or estate planning—you've got a financial advisor for that. And it's not about chasing some fantasy of permanent vacation.

This show is about living well in retirement. About designing days that feel purposeful, connected, and alive with possibility.

Over the coming episodes, we'll explore:
How to craft a daily rhythm that balances freedom with intention.
How to curate a bucket list that's more than tourist traps and surface experiences.
How to build community when your work friends fade and your identity shifts.
How to pursue second acts—whether that's mentoring, micro-entrepreneurship, creative projects, or something entirely new.

We'll talk about wellness, not as obsession, but as foundation. About travel that transforms, not just entertains. About legacy—leaving a mark that matters without making it your full-time job.

We'll even dive into the stuff people don't talk about: the awkward first months, the relationship dynamics, the unexpected grief of leaving professional relevance behind.

And yes, we'll acknowledge the financial side—because even though I won’t give investment advice, we can talk about how to make sense of your plan, values-based spending, lifestyle design, and making intentional choices with your resources.

Here's what this show isn't: prescriptive. There's no "one right way" to retire. No checklist that guarantees fulfillment.
But there are frameworks. Lessons learned. Wisdom from those who've gone before us.

And that's what we'll unpack together—through interviews, personal stories, expert insights, and honest conversations about what's working, what's not, and what we're still figuring out.

Some of you listening are already retired and looking for fresh ideas to keep momentum. Others are still in the workforce but planning your exit strategy. Maybe you're 45 and targeting early retirement. Maybe you're 62 and counting down the days. Maybe you're 70 and realizing that "retirement" doesn't mean slowing down—it means shifting gears.

Wherever you are in the journey, this show is for you.

Because here's the thing: you didn't spend decades building a career just to spend your days feeling lost. You earned this. Now let's make it count.

Every episode of Casual Mondays will give you something actionable. A new perspective. A question worth sitting with. A story that makes you think, "Yeah, I could do that."
We'll keep it real. We'll skip the platitudes. And we'll remember that the best retirement isn't the one that looks good on Instagram—it's the one that feels right when you wake up on a Tuesday morning with no alarm set.
So whether you're lounging in sandals on a deck chair or still wearing the suit five days a week, I'm glad you're here.

Coming up in our first full episode: Day One in Freedom—how to craft your new rhythm when the structure of work disappears and the blank calendar stares back at you.
We'll talk morning routines, intentional time blocks, and why the first 90 days of retirement might be the most important.
Until then, here's your assignment: think about what you want your Monday mornings to feel like. Not what they should feel like. What you want them to feel like.
I'm Kevin Donahue. This is Casual Mondays.
Welcome to your next chapter.