Know If You're On Track — Before It's Too Late to Adjust

The five years before retirement are the most consequential of your financial life. The decisions you make right now — about your 401(k), Social Security timing, Medicare enrollment, and how your portfolio is positioned — will shape everything that comes after. We work with pre-retirees across Central Florida to stress-test their retirement date and close any gaps while there's still time to act.

Are You on Track, or Is Your Retirement Date at Risk?

Most people approaching retirement have a number in mind — an age, a year, maybe a savings balance — but haven't run the actual math to know whether that target is realistic. We start every pre-retirement engagement with a detailed projection that compares where you are today against where you need to be. If there's a gap, we identify it clearly and walk through the specific adjustments — savings rate, retirement date, investment mix — that can close it.

 

This is not a general review. It's a retirement countdown analysis built around your income, your expenses, and your actual target date.

The Decisions That Determine When You Retire

The years between 55 and 64 are where the biggest preventable mistakes happen — and where the right moves can meaningfully accelerate your timeline. Here are the decisions we focus on together:

 

  • 401(k) rollover strategy: Whether to leave funds with your employer plan, roll to an IRA, or consolidate multiple accounts — and how each choice affects your options at retirement.
  • Catch-up contributions: If you're 50 or older, the IRS allows additional contributions to your 401(k) and IRA each year. We identify how much runway you have and whether maximizing those contributions changes your outcome.
  • Social Security timing: Claiming at 62 versus 67 versus 70 can mean tens of thousands of dollars in cumulative income. We model the breakeven points for your specific situation.
  • Medicare enrollment timing: Missing your enrollment window can trigger permanent premium penalties. We map out your timeline well in advance, including how your employer coverage interacts with Medicare eligibility.
  • Employer benefits transition: Health insurance, pension elections, stock options, and deferred compensation all require decisions at or before separation. We make sure nothing is left on the table.
  • Portfolio allocation shift: The mix that grew your savings may not be the right mix for the five years before you stop working. We adjust your allocation to reflect where you are in the journey.

10 Things to Do in the 5 Years Before You Retire

If you're within five years of your target retirement date, here's where to focus your attention:

 

  1. Run a full retirement income projection — not a ballpark estimate, a detailed analysis of what you'll actually have and what you'll actually need.
  2. Maximize catch-up contributions to your 401(k) and IRA every year you're still working.
  3. Model your Social Security claiming options before you assume you know the right answer.
  4. Confirm your Medicare enrollment timeline and understand how your current health coverage interacts with it.
  5. Consolidate scattered retirement accounts so you have a clear picture of your total assets.
  6. Stress-test your portfolio against a market downturn in the two years before retirement — sequence-of-returns risk is most damaging in this window.
  7. Review your life insurance coverage and determine whether your current policies still fit your situation.
  8. Start building a post-retirement income plan, not just a savings target.
  9. Understand your employer's pension options, if applicable, and the tradeoffs between lump sum and annuity elections.
  10. Identify your healthcare cost exposure between retirement and Medicare eligibility at 65.

 

These aren't tasks to delegate to a checklist. Each one involves tradeoffs specific to your income, your timeline, and your household. We work through all of them with you.

Shortfall or Surplus — You Need to Know Which One You're Facing

There are two very different pre-retirement conversations. One starts with "you're on track — here's how to stay there." The other starts with "here's the gap, and here are three ways to close it." Both are manageable. What's not manageable is not knowing which situation you're in until it's too late to adjust.

 

Allen has spent more than 30 years in financial services helping clients answer this question clearly. His planning process identifies whether your current trajectory gets you to your target date — and if it doesn't, what specific changes will. That conversation is available to you now, while the options are still open.

What Comes After Pre-Retirement Planning

Getting to retirement on time is one milestone. Building a plan that keeps you financially secure through 20 or 30 years of retirement is the next. Once your countdown plan is in place, we move into post-retirement income planning — structuring your withdrawals, your guaranteed income sources, and your investment accounts to last as long as you need them to.

 

If Medicare timing is part of your pre-retirement picture, we also work through Medicare supplement planning to make sure your healthcare coverage is in place before you separate from your employer plan.

Frequently Asked Questions About Pre-Retirement Planning

  • What should I do 5 years before retirement?
    The five years before retirement are the time to run a detailed income projection, maximize catch-up contributions, model your Social Security options, confirm your Medicare enrollment timeline, and shift your portfolio allocation to reflect your proximity to retirement. Each of these decisions has a meaningful impact on when you can retire and what your income will look like when you do.
  • Am I ready to retire?
    Readiness isn't a feeling — it's a number. We look at your projected income from all sources (Social Security, retirement accounts, pensions, and any other assets), compare it to your expected expenses, and determine whether the math supports your target date. If it does, we build a plan to maintain that position. If it doesn't, we identify what needs to change.
  • When should I start planning before retirement?
    The earlier the better, but the five years before your target date are the window where planning has the most leverage. Decisions made in this period — about savings, allocation, Social Security, and benefits — have a direct and measurable effect on your outcome. If you're in your mid-50s and haven't had this conversation yet, now is the right time.
  • How does Social Security timing affect my retirement date?
    Claiming Social Security early reduces your monthly benefit permanently. Waiting increases it. The right answer depends on your health, your other income sources, and whether you need the income immediately or can afford to delay. We model the breakeven points for your specific situation so you're making the decision with full information.
  • What happens to my 401(k) when I leave my employer?
    You generally have three options: leave it in your former employer's plan, roll it into an IRA, or roll it into a new employer's plan if you're continuing to work. Each option has different implications for investment choices, fees, and required minimum distributions. We walk through the tradeoffs based on your specific plan and retirement timeline.

Start Your Retirement Countdown With a Clear Plan

You've spent decades building toward retirement. The next step is finding out exactly where you stand — and what it takes to get there on your timeline. Schedule a consultation and we'll run the numbers together.