It’s Five O’Clock Somewhere
Last month, I found myself in a place where the sun was shining, the people were chatty, and the vibe was unmistakably joyful. I visited Latitude Margaritaville, a 55+ retirement community in South Carolina inspired by the laid-back lifestyle of Jimmy Buffett. My aunt and uncle moved there earlier this year (ages 59 and 54), and I wanted to see for myself what this lifestyle community was all about.
Margaritaville did not disappoint. From the Buffett music piped in from speakers all over the village, to roads filled with golf carts tricked out and decorated to represent each resident’s unique personality, the place was unlike anything I had ever seen.
I’ll tell you: it was more than just flip-flops and Hawaiian shirts. Latitude Margaritaville is a real-life example of what it looks like to embrace aging within a community that focuses on vitality, activities, and happiness.
Here’s what struck me most: Everywhere I turned, people were smiling. Residents were buzzing. From line dancing to pottery class to pickleball, the social calendar everyday is full. And more importantly, so are the hearts of the people who live there. They aren’t just living — they are thriving.
After three days, I left there thinking, “I need to start planning differently for retirement—not just for myself, but also in how I’m strategizing with my clients.”
As a financial advisor, I often focus on helping clients retire from something. But what if I started focusing more on helping them retire into something? What if part of our planning process includes helping clients envision a life they don’t feel the need to escape from — a life full of connection, activity, and joy?
I think Margaritaville is onto something that matters to so many of us. Laughter, leisure, and community — these are not just luxuries. They’re necessities for a long and meaningful life. So how do we begin to find our own version of Margaritaville? How do you start to think about your own future a little bit differently? Here are six ways to get started:
Find your tribe. Whether it’s a yoga retreat, an artist colony, or an RV caravan that crisscrosses the country, start to explore places or groups where you’ll meet like-minded people. Belonging is one of the biggest predictors of long-term happiness.
Focus on activity-based retirement plans. Margaritaville isn’t about sitting still — it’s about doing more of what you love. Brainstorm what lights you up: Live music? Volunteering? National parks? Grandkid road trips? Build these highlights into your plan like you would any asset.
Begin thinking about the concept of “pre-tirement.” Not everyone needs or wants to fully retire. Many people thrive with part-time consulting, mentoring, or passion projects. This can support both your income needs and your mental well-being.
Create a “fun fund.” In addition to traditional budgeting, why not start to set aside money specifically for joy? A travel account, a concert budget, or even a Monthly Margarita line item. It’s easier to stick to a financial plan when it includes things that make life worth living.
Emphasize purpose and connection. Being in a community is the antidote to isolation. Whether it’s co-housing, clubs, spiritual communities, or group travel, we should all be intentionally designing a life that keeps us socially connected and purpose driven.
Planning for the inevitable: At some point in a couple’s journey, one spouse will outlive the other and this can be devastating. But the sadness and grief may be lessened when the widow or widower is already living in a community that embraces them, supports them, and continues to provide friendship and connection during a challenging transition.
Here’s what I learned from visiting Margaritaville: happiness isn’t just a feeling — it’s a lifestyle choice. No one living in Margaritaville grew up there. They all sought out the community and proactively chose to move there for what it offers. What if we all started to think about designing a life that’s rich in both financial security and joy. Who do you want as your future neighbors? What activities and social options are you going to be surrounded by in your later years? You better believe I started making my list on my flight home…
As we think about our futures, think in terms of the celebrations we want to experience. What lights you up? What keeps you feeling youthful? What makes you smile? As Jimmy Buffett said: “Wrinkles will only go where the smiles have been.” Let’s all figure out a way to retire with more smiles, more laughter, and enjoying more days where it really does feel like five o’clock somewhere.
This Week’s Resources & Ideas
Don’t Just Take My Word for It
When you live in Margaritaville, you dine at the Bar & Chill, work out at Fins Up! and go to movies at The Last Mango. Want to hear more about a New Yorker reporter’s experience in the Buffett Community—and what happened to his skepticism on his visit? Read all about it in Retirement the Margaritaville Way.
Find Your Tribe
What retirement communities might be right for you, or for your parents? When you think about who your tribe is, and what activities your people enjoy, specific theme retirement communities are popping up everywhere, for yogis as well as RV enthusiasts! Check out this Kiplinger’s article to find out if a themed retirement community is right for you!
Ready to Escape?
Maybe a move to Escapees CARE Center is the place for you! Escapees CARE Center in Livingston, Texas caters to full-time RVers who want to maintain their mobile lifestyle even in retirement, offering both medical support and a built-in community. Think of it as a hybrid between a retirement home and a national park campground with potlucks, group travel, and shared maintenance bays.
CRN202806-8894033 Disclosure: Securities and investment advisory services offered through registered representatives of MML Investors Services, LLC, Member SIPC. The Jamrog Group is not a subsidiary of MML Investors Services, or its affiliated companies. Supervisory Office: 330 Whitney Ave, Suite 600 Holyoke, MA 01040 Telephone: (413) 539-2000.
