Prepare Your Finances Before You Stop Working
Pre-Retirement Planning in Winter Haven for individuals five to fifteen years from retirement who need to close income gaps and finalize their transition strategy
Thomas Advisory Services provides pre-retirement planning in Winter Haven to help you identify what still needs to happen before you can afford to leave your job. This service is for people who are close enough to retirement that their decisions now directly affect their income later, but still have time to adjust their savings rate, refine their investment approach, and address any shortfalls. You receive a detailed assessment of whether your current trajectory will support your intended retirement date, and a clear action plan for the years remaining.
The work includes calculating the gap between what your savings will generate and what you will actually need to spend each month, then determining how much more you need to contribute or how many additional years you may need to work. If you are still contributing to an employer retirement plan, the review covers whether you are maximizing available matches, using catch-up contributions if you are over fifty, and whether a Roth conversion strategy makes sense given your current and future tax brackets. The planning also addresses how to reduce taxable income now to lower your Medicare premiums later, and how to position your portfolio as you move closer to the date you stop earning a paycheck.
If you want to know whether you are on track or need to make changes, contact Thomas Advisory Services to schedule a pre-retirement strategy session in Winter Haven.
Our Services
Building a Timeline That Connects Today's Actions to Future Income
Your pre-retirement plan is organized around a specific target date and includes annual milestones that show what needs to be completed each year. This includes when to shift your asset allocation, when to begin estimating your Social Security benefits more precisely, and when to finalize decisions about healthcare coverage if you retire before age sixty-five.
After the planning session, you will know how much you need to save each month to meet your goal, which accounts to prioritize for contributions, and whether you should delay retirement by one or two years to significantly increase your monthly income. Thomas Advisory Services shows you the financial difference between retiring at your target age versus working longer, and what that means for your withdrawal rate and the longevity of your savings.
The plan also includes strategies for paying down high-interest debt before you retire, deciding whether to pay off your mortgage early, and determining how much liquidity you need in taxable accounts for the transition period. It does not provide investment management or ongoing portfolio adjustments unless you separately engage those services, but it does outline how your current investments should be repositioned as you approach retirement. The plan also identifies tax exposure from required minimum distributions and whether Roth conversions during lower-income years can reduce future tax liabilities.
Common Questions About Preparing for Retirement
The planning process starts with a full review of your current savings, employer benefits, projected Social Security income, and anticipated expenses in retirement. You will also discuss any planned changes such as relocating, downsizing, or continuing part-time work after you leave your primary job.
What happens if I realize I am not saving enough?
The plan will show you how much additional monthly savings you need to reach your goal, or it will outline how working an extra year or two changes your income and allows your portfolio more time to grow without withdrawals.
How do I know when to stop contributing to a traditional retirement account and start using a Roth?
The decision depends on your current tax rate compared to what you expect in retirement, and whether you have room to convert traditional assets to Roth during years when your income drops, such as between retirement and claiming Social Security.
When should I finalize my retirement budget?
You should create a detailed monthly budget at least two years before your planned retirement date so you can test whether your projected income covers your actual expenses, including property insurance and healthcare costs in Winter Haven.
Why is it important to plan for healthcare before Medicare starts?
If you retire before sixty-five, you will need to pay for private health insurance or COBRA coverage, and those premiums can be significantly higher than what you paid through your employer, which affects how much income you need to withdraw.
How does pre-retirement planning differ from general retirement planning?
Pre-retirement planning focuses on the final actions you need to take in the years immediately before you stop working, including maximizing contributions, adjusting risk, and closing any remaining gaps, rather than long-term accumulation strategies.
Thomas Advisory Services works with clients in Winter Haven and surrounding areas who want to enter retirement with confidence that their savings, Social Security, and other income sources will support their lifestyle. If you are within a decade of your planned retirement date and want a clear timeline, reach out to schedule a pre-retirement strategy session and get a realistic assessment of where you stand.