Five to ten years out — time to build a real plan.

Why the pre-retirement decade matters most

The five to ten years before retirement are some of the most consequential in the whole arc of your financial life. DROP eligibility windows open and close. Social Security filing decisions carry decades of downstream impact. Medicare enrollment windows matter. Deferred-comp contributions and allocation need to shift as the timeline shortens. These decisions can't be made on autopilot — and unlike the early career years, there's little time left to absorb a misstep.

What makes this decade unusual is how many decisions interact. The DROP entry date you choose can change when your pension income starts, which changes whether you delay Social Security, which changes how hard your deferred-comp savings have to work in the gap. Pull one lever and the others move. That's exactly why a written plan — one that holds all the pieces at once — tends to be worth far more in these years than any single product or account. We help pre-retirees build that plan before the decisions arrive, not in the middle of them.

Start with a real benefit projection

Almost everything downstream depends on one number you may not have looked at closely yet: your actual projected FRS benefit. A real projection means confirming your class (Regular Class for teachers and general state and county staff, or Special Risk Class for law enforcement, firefighters, EMS, and corrections — which carries earlier eligibility and a higher benefit multiplier), your years of creditable service, your average final compensation, and the payout option you intend to elect. Then we model the benefit at several candidate retirement dates so you can see how an extra year or two of service changes the picture.

Because the exact figures depend on your individual record, members should confirm the current specifics through MyFRS.gov or FRS directly. Our role is to turn that data into a clear, written estimate you can actually build an income plan around. If you're still mapping the fundamentals, our overview of FRS retirement planning and the differences between the Pension Plan and the Investment Plan is a useful starting point.

The DROP decision window

For Pension Plan members, the Deferred Retirement Option Program (DROP) is often the single highest-stakes timing decision of the decade. DROP lets eligible members keep working while their monthly retirement benefit accumulates — commonly for up to about eight years — instead of being paid out. The date you enter affects how long you can participate and how much accumulates, and once the window passes it generally can't be reopened on the same terms.

The common mistake is treating DROP as a yes-or-no question answered at the last minute. In practice it's a "when, and how does it fit the rest of the plan" question that rewards being modeled years ahead. We walk through how an entry date interacts with your pension start, your savings, and your tax picture. Our dedicated DROP planning page goes deeper on how the program works and what to weigh.

Ramp up deferred comp and catch-up contributions

The final working years are usually your highest-earning ones, which makes them the best time to ramp up deferred-compensation savings. Members age 50 and over generally have access to catch-up provisions that allow higher annual contribution amounts, and some plans offer an additional pre-retirement catch-up in the years just before normal retirement age. Whether to use that capacity depends on your cash flow, your tax situation now versus in retirement, and the role these savings play alongside your FRS benefit.

This is also the moment to revisit how those dollars are invested. A portfolio built for a 35-year-old with decades to recover looks different from one funding income that may start within a few years. Right-sizing risk as the runway shortens — without abandoning growth entirely — is part of the conversation.

Preview your Social Security timing

For most public employees, the filing decision is less about the earliest age you can claim and more about how claiming interacts with everything else. Benefits claimed earlier are generally reduced, while delaying past full retirement age can increase the monthly amount — so the question is how a few years of pension or DROP income might let you wait, and what that's worth over a long retirement.

There's also good news worth knowing: the Social Security Fairness Act, signed in January 2025, repealed the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) that historically reduced Social Security for some public pensioners. If you'd previously been told your benefit would be cut, it's worth a fresh look. Our Social Security education page covers the timing trade-offs in more detail.

Draft your first retirement income plan

All of these pieces come together in a first draft of a written income plan: your projected FRS benefit, any DROP accumulation, deferred-comp withdrawals, Social Security, and the modest Health Insurance Subsidy (HIS) that supplements many FRS retirees based on years of service. The plan also needs a healthcare bridge from your retirement date to Medicare at 65, since that gap is one of the most commonly overlooked costs.

A first draft five years out won't be the final version — and it isn't meant to be. The plan you build at year nine looks different from the one you need at year three, and different again in the last twelve months. We stay with you through that tightening timeline, revisiting the numbers as decisions get closer. You can see how the finished picture fits together on our retirement income planning page.

Everything here is educational and general in nature, not individualized advice, and Benowitz Wealth Management is not affiliated with or endorsed by the Florida Retirement System or the State of Florida. As a fee-only fiduciary, our only job is to help you see the trade-offs clearly and decide on purpose.