Five Years from Retirement? These 5 Tips Could Make All the Difference.

If retirement is on the horizon—say, within the next five years—you’ve entered what we call the retirement red zone. This is a critical window where small financial decisions can have a big long-term impact. It’s also a time to start shaping your post-career lifestyle with as much intention as your investment strategy.

Whether you're looking to solidify your numbers or sketch out your vision for daily life after work, these five actions will set you up for a more confident and meaningful retirement.

1. Know Your Expenses — Without Overcomplicating It

Let’s face it, the word “budget” makes most people want to click away. But knowing your spending is the cornerstone of any solid retirement plan—and it doesn’t have to be painful.

Skip the spreadsheets and hours of number crunching. Instead, total all the debits from your bank and credit card statements over the last two years. Divide by 24. That’s your average monthly spending.

Why does this matter? Because you can’t determine if you're financially ready to retire—especially in the next five years—without understanding what it costs to live your life today. Most people want to maintain their lifestyle in retirement, not downsize it.

And remember: retirees often increase their spending in the early years. With seven Saturdays a week, the travel, hobbies, and projects you put off now become priorities—and that comes with a price tag.

2. Plan for Health Care Costs — They’re Bigger Than You Think

One of the most underestimated retirement expenses is health care. If you're currently working, your true health costs are likely buried in your paycheck as pre-tax deductions. In retirement, they show up in full force.

Here’s what to consider:

Retiring before 65? You’ll need a bridge to Medicare, which could mean private insurance or ACA marketplace plans—both potentially expensive.
Turning 65 and enrolling in Medicare? Costs vary widely depending on income. Medicare Part B and D premiums are subject to income-related surcharges (IRMAA), which can be surprisingly high if your investments are generating significant income.
Have a large retirement account? Required minimum distributions (RMDs), Social Security, capital gains, dividends, and interest all contribute to your taxable income—and potentially your Medicare premiums.

A comprehensive financial plan can help you forecast and prepare for these costs. It won’t be perfect—because it’s projecting decades into the future—but it will identify potential blind spots and let you test different “what if” scenarios.

3. Take Care of Home Repairs Before You Retire

Been procrastinating that bathroom remodel or replacing that ancient roof? Do it before you retire.

Why? Because many new retirees end up spending a surprising amount during their first few years—often to tackle long-deferred home improvement projects. The risk is that you’ll need to pull from investment accounts at inopportune times, which can increase sequence-of-returns risk (withdrawing while the market is down can permanently reduce your portfolio’s longevity).

Another bonus: Getting the work done now means you won’t have to listen to power tools all day while you’re trying to enjoy your newfound freedom. Get it out of the way while you're still working and spending your days elsewhere.

4. Travel Early — While Health and Energy Are On Your Side

That bucket-list trip to Italy? Don’t put it off.

The early years of retirement—often called the "go-go years"—are your best shot at doing the things you’ve always dreamed about while your health, energy, and mobility are still working in your favor.

Plus, while you're still working, those travel splurges are softened by the security of a regular paycheck. Once you’re retired, those same expenses can feel heavier—especially if markets are down or you're trying to stretch every dollar.

Ask retirees in their late 70s and 80s about their biggest regrets. More often than not, they’ll tell you it’s not about the money they spent—it’s about the trips they didn’t take.

Don’t fall into the trap of waiting to live your life until after you retire.

5. Create a Model Week — Structure Still Matters

Ever come back from a dream vacation and say, “It’s good to be home”? That feeling isn’t just about sleeping in your own bed—it’s about returning to the comfort of routine.

Retirement removes three things that gave your life rhythm: identity, relationships, and structure. Without a plan, that lack of structure can quickly become disorienting.

Here’s a simple but powerful exercise: Draw a grid for your week with three sections per day—morning, afternoon, and evening. First, fill it in with how you spend your time now. Then create a second version with how you’d like to spend your time in retirement.

This “model week” helps you visualize your ideal lifestyle and identify gaps. Spoiler: even the most die-hard golfers realize that golf alone can’t fill 21 time blocks a week. The more blank spaces you see, the more you’ll want to think ahead about what brings you purpose, connection, and joy beyond your career.

Give me a call so those “I wish I had known…” moments won't be in your retirement future, (480) 513-1830.

All the best, Charles

Charles C. Scott AIF®, CDP®

ACCREDITED INVESTMENT FIDUCIARY®CERTIFIED DEMENTIA PRACTITIONER®

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