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Sunshine, Sand, and a Solid Plan: My Florida Retirement Wealth Game Plan

Why I Decided to Get Serious About Wealth Management in Florida

Okay, real talk—there comes a moment where you’re sipping coffee on your lanai, staring at the palm trees swaying like they’ve got it all figured out, and you realize… you don’t.

That was me. Just another day in Sarasota, barefoot in flip-flops and feeling way too casual for the state of my finances. Retirement was no longer some fuzzy concept—it was here. And let me tell you, Florida might be paradise for weather and lifestyle, but if your money’s not managed right, it can be a mirage of peace with a surprise thunderstorm.

So I decided: no more winging it. I needed a real plan for managing my wealth during retirement—one that let me sleep easy at night and order an extra Key lime pie without guilt.

The Illusion of “I’ve Got Time”

Back when I first moved down from New York (cue eye-rolls from locals—yeah, I’m one of those transplants), I thought I had time. I figured my 401(k), a few rental properties, and some random mutual funds were enough.

Spoiler: they weren’t.

Florida retirement isn’t cheap. Between rising insurance premiums, HOA fees that seem to grow like weeds, and the temptation to hit every seafood joint along the Gulf Coast… it adds up fast. And let’s not forget healthcare—aging joints come with aging bills.

Building My Florida Retirement Wealth Strategy (Without Losing My Mind)

Here’s where things got real.

1. Inventorying Everything—Yes, Even the Junk Drawer

First, I went through everything. Bank accounts I forgot existed. Subscription services silently draining me $8.99 at a time. That one stock I bought because I liked the company’s commercials (don’t judge me).

I needed to see the full picture. It wasn’t pretty—but it was honest.

2. Switching from “Saving” to “Strategizing”

Retirement isn’t about stacking cash anymore. It’s about distribution, taxes, risk management, and making your money last. I worked with a wealth planner who didn’t just toss charts at me—he actually asked about my lifestyle.

Want to golf four times a week? Cool. Want to leave something for the grandkids? Even cooler. But let’s make a plan that works.

He helped me:

• Convert some taxable accounts to more tax-efficient vehicles (hello Roth conversions).

• Reallocate investments to protect against downturns (no more YOLO on tech stocks).

• Factor in Florida-specific stuff like property tax caps, homestead exemptions, and hurricane reserves.

Yep, I now have a “hurricane reserve fund.” That’s just adulting in Florida.

3. Healthcare: The Retirement Elephant in the Room

I used to think Medicare would handle everything. I also used to think frosted tips were a good idea. I’ve been wrong before.

We built in real numbers for long-term care, supplemental insurance, and potential emergencies. Because one thing you don’t want? Selling your Naples condo just to pay a hospital bill.

4. Making It Fun (No, Seriously)

I gamified the process. No joke. Every time I hit a financial milestone—like maxing out an IRA or cutting $200 in monthly waste—I’d reward myself. Fancy dinner. New fishing gear. A weekend trip to the Keys.

Wealth planning doesn’t have to be dry and soul-crushing. You’re not prepping for Armageddon. You’re designing a life.

Lessons I Learned the Hard (and Humbling) Way

Let me give it to you straight—because no one told me this when I was in my 40s.

• Retirement doesn’t mean your money problems disappear. It just means they evolve.

• A laid-back Florida lifestyle still needs a buttoned-up financial plan.

• Doing nothing is a choice. And not the good kind.

I had to confront some uncomfortable truths: like the fact that I wasn’t as diversified as I thought, or that inflation wasn’t just some abstract headline—it was showing up in my grocery bills. (Have you seen the price of oranges lately? In Florida??)

What Peace of Mind Looks Like (and Feels Like) Now

Fast forward a couple of years. I’m not stressing about whether I can afford to replace the A/C unit. I’ve got cash flow that doesn’t make me panic every time the market hiccups. And I know—deep in my very sun-kissed soul—that I can live the life I want without going broke or burdening my kids.

It’s not just about the spreadsheets and estate documents (though I’ve got those too). It’s about waking up and choosing between beach walks and boat rides, not between cutting meds or cutting dinner out.

Key Takeaways: Wealth Planning for Florida Retirement

Here’s the CliffsNotes version, in case you’re skimming on your phone from a pool chair ️:

• Track everything: Know where your money’s going—and what’s just leaking.

• Work with a pro: DIY is fine for IKEA furniture, not for retirement wealth.

• Plan for Florida-specific risks: Storms, insurance, taxes—don’t ignore them.

• Make your plan flexible: Life isn’t static. Neither is the market.

• Enjoy the process: You earned this phase of life. Don’t white-knuckle it.

Final Thoughts: Don’t Just Retire—Thrive

If you’re living in Florida or planning to retire here soon, listen to someone who’s made the mistakes and corrected course. You can sip margaritas and still manage money like a boss. One doesn’t cancel out the other.

Take the time to do it right. Be the chill retiree with a sharp financial backbone. Because wealth management isn’t about hoarding dollars—it’s about designing freedom. And if you ask me, that’s worth every spreadsheet.

Now if you’ll excuse me, I’ve got a tee time to make—and not a single financial worry on my mind.

Let me tell you a little story.

Picture two people—my wife and me—sitting in a mahogany-clad office, sipping espresso that costs more per ounce than the wine we drank in our 20s (not by choice, mind you). We were smiling, nodding at our wealth advisor like we understood every single chart and graph he threw on the screen. But internally? My brain was screaming: “We’re flying blind here, man.”

We’d built wealth, sure. Decent portfolios, some real estate, a business or two. But managing it as a family? That’s where things got tricky.

The Moment We Realized “Money” Meant Two Different Things

Here’s the kicker: my version of “managing our wealth” looked a lot like spreadsheets and tax strategy. Hers? More about impact, legacy, making sure the kids didn’t turn into jet-set slackers.

Let’s be honest. Most high net worth couples aren’t arguing over whether to invest. The real heat shows up when you start talking how, where, and why. She wanted to fund a nonprofit incubator. I was stuck on whether our Roth conversions were optimized.

Cue the tension.

What broke the cycle was this question: “What does success look like for both of us, 20 years from now?”

That question flipped the script.

Step One: Get on the Same Page Before You Touch a Dime

I used to think family wealth planning was about hiring the right team—estate attorney, tax advisor, investment manager, the usual suspects.

Wrong.

It starts at the dinner table. No advisors. No spreadsheets. Just two people, talking goals like:

• Do we want to leave an inheritance, or focus on charitable impact?

• What kind of lifestyle do we want in 5 years? 10?

• Are we supporting adult kids? Grandkids? Cousins? Everyone and their dog?

When we finally hashed this out—over a weekend getaway, actually—things clicked. We had different goals, yes. But once they were all out on the table, we could start designing a plan that honored both of us.

That’s wealth management step zero: alignment.

Step Two: Build a Real Strategy (Not Just a Stack of Accounts)

Let me tell you what didn’t work: checking our net worth every month and assuming it meant we were doing great.

What worked?

• Creating “buckets” for different goals: legacy, lifestyle, liquidity.

• Allocating based on purpose, not just performance.

• Separating our personal portfolios from the family wealth structure.

We built an investment policy statement—not just for our advisor, but for us. It spelled out our risk appetite, values (like avoiding certain industries), and target allocations. Once that was set, we could finally stop second-guessing every little move.

There’s freedom in clarity. Trust me on that.

Step Three: Treat Your Family Like a Business (The Healthy Kind)

This one took us a while to embrace. But eventually, we started running our household wealth like we’d run a successful company.

• Quarterly reviews: Yes, we literally put it on the calendar. Wine helps.

• Family meetings: Not just with the kids, but also siblings, parents—anyone connected to trusts or shared assets.

• Roles and responsibilities: One of us handles philanthropy. The other tracks investments. We both weigh in on big decisions.

No more “Oh, I thought you were handling that…” awkwardness. And surprisingly, the kids appreciated being looped in. Even if they mostly came for the snacks.

Step Four: Don’t DIY the Deep End

I’m a big fan of rolling up my sleeves, but I’ve learned this the hard way—there’s a point where DIY wealth management becomes expensive.

• Tax strategy? You need a ninja who eats IRS code for breakfast.

• Estate planning? One word: dynasty. (Trusts, not Game of Thrones.)

• Asset protection? You’ll want someone who’s seen a courtroom up close.

We finally assembled a “family office lite”—no marble floors or private jets involved. Just a tight crew of pros who actually talk to each other. That’s key. Your CPA, estate planner, and advisor need to work like a jazz trio, not soloists.

Step Five: Legacy Isn’t Just About Money (But It Helps)

Here’s the emotional bit.

When we talked legacy, we didn’t mean just “how much are we leaving behind?” We meant: what kind of people are we raising?

So we got intentional.

• We started a donor-advised fund together. Each year, we let the kids vote on where the funds go.

• We wrote a “family mission statement” (cheesy, but powerful).

• We started documenting family stories, lessons, even failures. Stuff money can’t buy—but wealth can preserve.

That’s when this whole thing stopped being about net worth and started being about meaning.

The Bottom Line (Because I Still Love Numbers)

If you’ve built wealth with your partner, don’t assume managing it will be easy.

It’s like owning a yacht—without a map, you’re just adrift on a really expensive boat.

Here’s what I wish we’d done sooner:

• Had the “what do we really want” conversation—without advisors in the room.

• Created a written strategy with purpose-driven buckets.

• Built a trusted team before things got messy.

• Involved the kids early—and made it fun.

• Focused less on control, more on connection.

We didn’t get it right at first. But once we stopped chasing returns and started chasing clarity, everything changed.

Now? Our wealth feels like a tool, not a trap.

And honestly… I sleep better.

Key Takeaways for High Net Worth Couples

• Talk first, invest second: Get aligned on goals, fears, and dreams.

• Think in buckets: Lifestyle, legacy, liquidity—each has its own plan.

• Run it like a business: Regular reviews, defined roles, and open communication.

• Outsource the complex stuff: Especially tax, legal, and multi-generational planning.

• Make legacy about more than money: Include values, family history, and impact.

And if you’re reading this wondering whether it’s too late to get on the same page with your spouse?

Let me just say this: I thought that too.

Turns out, the best time to plant a tree was 20 years ago. The second-best time? This weekend.