Retirement Planning for Central Florida Retirees and Pre-Retirees
We're a retirement planning firm in Winter Haven, FL helping pre-retirees and retirees across Central Florida answer the question that matters most, will my money last as long as I do, through a documented four-step process that turns a lifetime of savings into income built to last.
Reviewed by Allen Thomas, independent financial advisor practicing since 1991, author of Wealth Beyond Work.
What Retirees Worry About Most
The Real Question Behind Retirement Planning
Almost every conversation we have with a new client starts with the same fear, sometimes spoken out loud and sometimes not:
what if I run out of money?
That fear is reasonable. People who retired in 1995 could lean on traditional pensions, modest healthcare inflation, and a Social Security trust fund that wasn't yet under stress. People retiring today are walking into a market that swings on geopolitics, healthcare costs that rise faster than nearly anything else in their budget, and a longevity curve that makes 30-year retirements increasingly normal. The retirement planning playbook from a generation ago doesn't answer the questions this generation is actually asking.
Our work as a Winter Haven retirement planning firm is to replace that fear with a number. Not a marketing number. The actual number that comes out of running your real spending, your real Social Security election, your real healthcare costs, and your real longevity assumptions through a documented framework. Once you can see what you have and what you need, the planning starts to feel like math instead of dread.
How We Build Retirement Plans Step by Step
A Four-Step Retirement Planning Process
We use the same four-step process with every household. Each step has a specific output, and you see deliverables in writing before you ever decide whether to continue.
Step 1: Assessment
We run a full retirement income gap analysis, comparing what you have against what you'll actually need given your spending, healthcare costs, and longevity assumptions. You walk out of the first working session with a clear number, not a generic projection. If there's a gap, you see exactly where it is. If there isn't, you see what's protecting you from one.
Step 2: Strategy
We build a written retirement income plan covering the levers that matter: Social Security timing, withdrawal sequencing, tax-aware decumulation, the role of guaranteed lifetime income strategies, and how your investments sit alongside any fixed insurance pieces. You see the strategy in writing, with worked examples, before you sign anything.
Step 3: Management
Once the strategy is in place, we manage the investment portfolio actively at Charles Schwab as your independent custodian, adjusting positioning based on economic fundamentals rather than locking your money into a static allocation. Your assets are held in your name. We never take custody of client funds.
Step 4: Support
Retirement isn't a one-time decision. We review your plan on a regular cadence, adjust as the economy and your life change, and stay reachable in between for the questions that come up on a Sunday afternoon. For senior clients with urgent financial or insurance questions, Allen is available outside business hours.
Will I Have Enough to Retire?
This is the question almost everyone asks first, and the honest answer is that we can't tell you until we've run the numbers.
Enough depends on what you spend, what you expect to spend after retirement, when you claim Social Security, what your healthcare picture looks like, and how long the plan needs to support you.
What we can tell you is that the gap analysis we run in the first working session is built to give you a real answer, not a hopeful one. We use realistic longevity assumptions (often into the early 90s for healthy clients), conservative return assumptions, and your actual spending data rather than a generic 80%-of-income heuristic. If there's a shortfall, we'd rather show you now while there's still time to address it than nine years into retirement when there isn't.
When Can I Actually Afford to Retire?
The retirement date that fits your numbers isn't always the date you had in mind, and it's almost never a single fixed point. We model multiple retirement timelines side by side, factoring in Social Security claiming age (62, full retirement age, or 70), healthcare coverage from your employer versus the ACA marketplace versus Medicare, and the income each scenario delivers.
The output is a comparison you can read at a glance: retire at 64 and the plan looks like X, retire at 66 and it looks like Y, retire at 68 and it looks like Z. You make the decision based on tradeoffs, not guesses. Many clients are surprised to find their feasible retirement date is sooner than they thought. Others discover that one or two more working years dramatically reshape the back half of retirement.
The Three Stages of the Retirement Arc
A retirement plan is really three connected plans, one for each stage of the arc. Most advisors focus on the middle. We work the whole curve.
Pre-Retirement:
The Final Approach
The five to ten years before retirement are where the most consequential planning decisions happen. Asset allocation needs to begin shifting. Withdrawal strategy needs to be designed before you stop earning. Social Security timing and Medicare enrollment timing need to be coordinated. And the question of
what your retirement actually looks like needs to get specific.
The Transition: When You Actually Retire
The year you stop working is a hinge year. Your income source changes, your tax picture changes, and the first five years of withdrawals carry disproportionate weight because of sequence-of-returns risk. This is the period where careful planning matters most and rushed decisions cost the most.
Post-Retirement: Income That Has to Last 25 to 30 Years
Once you're retired, the work shifts to income management. How much to draw, from which account, in what order, with what tax consequences, and what to adjust when the market moves or your situation changes. This is where we spend most of our ongoing time with clients.
Principles Behind Our Investment Approach
How We Build Retirement Portfolios
Our investment methodology rests on three principles, and we walk every client through them before any money moves.
- Risk-tolerance-driven allocation. Your portfolio is built around your tolerance for volatility, your income needs, and your time horizon, not a generic model based on age alone. A 70-year-old with a guaranteed pension and modest spending has a very different risk profile than a 70-year-old drawing 5% from their portfolio with no other income.
- Active management based on economic fundamentals. We adjust positioning based on what's actually happening in the broader economy: monetary policy shifts, interest rate environments, fiscal actions, and global events that meaningfully change the risk picture. We don't trade reactively. We don't market-time on headlines. We do think the static buy-and-hold model that worked in the 1990s isn't well-suited to today's market.
- Layered income strategies. For clients whose plans benefit from it, we layer fixed index annuities with lifetime income riders alongside the managed portfolio. The annuity provides a contractual income floor, structured to continue paying for life even if the underlying account value drops to zero. The managed portfolio handles growth and flexibility. Most retirement plans benefit from both, in the right proportions.
How Does Florida Change the Retirement Math?
Florida retirees plan differently than retirees in other states, and a national content site or out-of-state advisor often misses the specifics that matter most for retirement planning in Central Florida.
- No state income tax.
Florida doesn't tax personal income, which changes the math on traditional IRA withdrawals, Roth conversions, and the geography of where it makes sense to recognize gains. We work this into the tax-aware withdrawal sequencing for every client.
- Homestead and property tax considerations.
Florida's homestead exemption and Save Our Homes assessment cap create planning opportunities that compound over a long retirement, particularly for clients who downsized into the state.
- Hurricane and insurance cost realities. Property insurance costs in Florida have risen sharply, and the line item shows up in retirement budgets in a way it didn't a decade ago. We factor it into the spending projection rather than ignore it.
- Healthcare access in Central Florida. Polk County and the surrounding region have strong access to AdventHealth, BayCare, and Orlando Health systems, which matters for Medicare Supplement and Advantage decisions. We help clients understand which networks their plan choices actually cover.
We serve clients across Central Florida, including those working with us as their retirement planner in Polk County and families who travel down from their primary retirement advisor relationships in Lakeland, Orlando, Tampa, and Davenport.
Straight answers to the most common retirement planning questions in Central Florida.
Common Retirement Planning Questions
Who is the best retirement planner near me in Central Florida?
The right retirement planner is the one who specializes in your stage of life, works as an independent fiduciary rather than a captive product seller, holds your assets at an independent custodian, and is genuinely reachable when you have a question. Thomas Advisory Services has been built around exactly that profile in Winter Haven, with 30+ years of practice behind it and a focus specifically on retirement-stage households.
How do I plan for retirement in Florida?
A Florida-specific retirement plan starts with the standard fundamentals (income gap analysis, Social Security timing, withdrawal sequencing, healthcare planning), then layers in the state-specific pieces: the absence of state income tax, homestead and property tax planning, the rising insurance cost line item, and the Medicare network considerations in your part of the state. Working with a Florida-based advisor matters more here than in most states because of how many of these levers are local.
When should I start retirement planning?
The best window is five to ten years out from your intended retirement date, when the decisions you make still have time to compound and the strategy can be implemented without rushing. That said, post-retirement clients regularly come to us in their late 60s or 70s after a frustrating experience elsewhere, and we can still meaningfully reshape the plan from there. The honest answer is as soon as you start wondering about it.
What is the difference between financial planning for retirees and general financial planning?
General financial planning is built around accumulation, the saving years, and tends to emphasize asset growth, contribution strategies, and long-time-horizon investment behavior. Financial planning for retirees is built around decumulation, the spending years, and emphasizes income reliability, sequence-of-returns risk, tax-aware withdrawals, healthcare cost management, and longevity protection. They're related disciplines, but they require different priorities and a different planning framework.
Do you offer free initial consultations?
Yes. The first conversation is free, runs 20 to 30 minutes, and carries no obligation to continue. It's meant to give both sides enough information to decide whether a longer planning meeting makes sense.
Experience-driven, independent retirement advice.
Who's Behind Thomas Advisory Services
Thomas Advisory Services is led by Allen Thomas, an independent financial advisor based in Winter Haven, Florida who has practiced in financial services since 1991 and is the author of Wealth Beyond Work. Allen holds the FINRA Series 66 registration along with Florida Life, Health, Variable Annuities, and Property and Casualty licenses, and has held FINRA Series 6, 7, 24, 79, and 99 over the course of his career. The practice is independent and fee-based, with client assets held at Charles Schwab as an independent custodian.
Let's Build Your Retirement Plan
If you're within ten years of retirement on either side, the most valuable thing you can do is replace the fear with a number. Call us or send a message, and we'll set up a free first conversation.