Episode 87: 5 Years From Retirement? Here’s Your Must-Do Checklist

Are you five years out from retirement? If so, you’re in one of the most critical financial windows of your life. What you do—or don’t do—during this period can have a massive impact on your retirement lifestyle, income security, and peace of mind.

In Episode 87 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Rob and Archie Hoxton lay out a step-by-step checklist designed for people entering the final stretch of their working years. Whether you’re feeling confident or overwhelmed, this episode is packed with practical moves that make a difference.

Why Five Years Out Matters

It may seem like there’s still plenty of time—but five years is the perfect moment to tighten your plan, fix any gaps, and start rehearsing your future lifestyle. At this stage, you still have flexibility. But that flexibility will begin to close as you approach your last paycheck.

Here are the must-dos.

1. Understand Critical Ages

You’ll want to be ready for the following key milestones:

  • Age 50: Eligible for catch-up contributions to retirement accounts.
  • Age 59½: You can begin withdrawing from retirement accounts without penalty.
  • Age 62: Earliest possible age to claim Social Security (with reduced benefits).
  • Age 65: Medicare enrollment begins—miss it and you may pay lifelong penalties.
  • Age 73–75: Required Minimum Distributions (RMDs) begin depending on your birth year.

These dates matter for taxes, income, healthcare, and how long your money will last. Make sure your strategy reflects them.

2. Audit Your Spending

This is one of the most overlooked parts of retirement readiness. Most people underestimate their expenses, especially for discretionary items like travel, home improvements, gifts, or hobbies.

Rob and Archie recommend:

  • Reviewing 12 months of spending
  • Categorizing expenses into needs, wants, and obligations
  • Looking for subscription creep or lifestyle inflation
  • Building a realistic retirement budget based on actual behavior—not idealized versions of it

3. Visualize Retirement

Retirement isn’t just about leaving your job—it’s about what you’ll do next. Ask yourself:

  • What will your daily routine look like?
  • Will you travel, volunteer, start a business, or take care of family?
  • Where will you live—and will that change?

Defining these answers now helps you align your financial plan with your lifestyle plan.

4. Business Owners: Begin Succession Planning Now

If you own a business, Rob and Archie stress that exiting takes longer than you think. You’ll need time to:

  • Value your business
  • Groom a successor or explore buyers
  • Create a tax-efficient sale structure
  • Plan your income strategy post-exit

Starting this five years out gives you breathing room and negotiating power.

5. Prepare for the Unexpected

Life happens—even to the best-planned retirements. Rob and Archie urge listeners to prepare for:

  • Long-term care expenses
  • Market corrections just before or after retirement
  • Health challenges that affect timing
  • Family needs like helping aging parents or adult children

Having an emergency buffer and flexible spending strategy can help you adapt without panicking.

Final Thought

Five years may feel like the home stretch—but it’s also your best opportunity to fine-tune your plan and lock in confidence. Think of this checklist as your financial pre-flight routine. You want to know that everything’s working before you take off.

Want to go deeper?

Get the full Pre-Retirement Checklist—free. Or schedule a one-on-one planning session with our team at www.hoxtonpm.com/schedule to make sure you’re ready for what’s next.
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Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 86: Barriers to Wealth – 6 Common Mistakes That Undermine Your Financial Future

You’re working hard, saving consistently, and trying to make smart choices. But if building wealth still feels like an uphill battle, it’s worth asking: What’s getting in your way?

In Episode 86 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® Archie Hoxton and advisor Jimmy Sutch explore the hidden habits and overlooked decisions that quietly erode financial progress. These barriers don’t always make headlines—but they can have a massive impact on your long-term financial security.

If you want to accelerate your wealth-building path, the first step is identifying what’s holding you back.

1. Bad Debt Decisions

Not all debt is created equal. A low-interest mortgage can be a smart tool. But high-interest consumer debt—especially car loans and credit cards—can drain your savings potential.

Jimmy shares the example of a $740 monthly car payment. Over 15 to 20 years, that expense could translate to hundreds of thousands in lost retirement savings if invested instead.

2. Lifestyle Inflation

Earning more shouldn’t automatically mean spending more. But for many families, income increases are quickly matched—or exceeded—by lifestyle upgrades: a bigger house, fancier cars, private schools, or luxury vacations.

The result? No matter how much you earn, you feel like you’re just getting by.

Archie and Jimmy recommend being intentional about upgrades. Are they supporting your long-term goals—or just feeding short-term gratification?

3. Divorce

Divorce is both emotionally and financially disruptive. It often cuts retirement savings in half, reduces long-term security, and triggers expensive legal fees.

While it’s not always avoidable, couples nearing or in retirement should prioritize proactive planning, open communication, and clear documentation—especially when dealing with blended families or separate assets.

4. Emotional Investing

Fear and greed are the two biggest threats to long-term investment success. Panic selling during downturns or chasing “hot” stocks rarely ends well.

Archie emphasizes that staying invested is often more important than picking the perfect investment. A disciplined strategy—aligned with your goals and risk tolerance—is your best defense against emotional decision-making.

5. Hoarding Cash

Holding too much money in low-interest accounts might feel safe—but it’s a hidden risk. Inflation erodes purchasing power over time, and uninvested cash often misses the compounding opportunity of long-term markets.

Keep enough for emergencies and short-term needs, but make sure your savings are working for you—not just sitting idle.

6. Poor Tax Strategy

Taxes are your single largest lifetime expense—and most people pay more than they need to.

Jimmy and Archie point out that strategic tax planning—from Roth conversions and account withdrawals to donation timing and Social Security strategies—can save six figures over the course of retirement. But you have to plan ahead.

Ask Yourself:

  • Do I know my biggest financial blind spot?
  • Am I tracking lifestyle changes or just letting them happen?
  • Is my investment plan driven by goals—or by headlines?
  • Have I optimized my tax strategy over the next 10 to 20 years?

Final Thought

Wealth isn’t just about what you earn. It’s about how you manage, protect, and grow what you already have. Eliminating these common barriers won’t just increase your net worth—it will boost your confidence in the process.

Which of these barriers are affecting you?

Download our free Barriers to Wealth Self-Audit and start making smarter decisions today. Or schedule a consultation at www.hoxtonpm.com/schedule to talk through your personalized roadmap.
Download the Self-Audit
Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.

Episode 82: These 5 Retirement Risks Could Derail Your Plan (And Most People Miss Them)

Retirement planning often focuses on savings goals, investment returns, and withdrawal strategies—but what about the threats that could quietly knock your plan off course?

In Episode 82 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Archie and Rob Hoxton explore the hidden risks that derail even well-funded retirements. These risks aren’t always obvious, but they can have a profound impact if left unaddressed.

If you’re approaching retirement—or already in it—this is the checklist you didn’t know you needed.

1. Inflation: The Rust of Retirement

Even at 2 to 4%, inflation eats away at purchasing power over time. A modest 1% change in your inflation assumption might not seem like much—but over 30 years, it can be the difference between a comfortable lifestyle and an unexpected shortfall.

Archie describes inflation as “the rust you don’t see—until your plan starts to fall apart.”

2. Rising Healthcare Costs

Healthcare is one of the most underestimated retirement expenses. Rob and Archie cite research showing that the average 65-year-old couple could face $300,000 or more in lifetime healthcare expenses—not including long-term care.

With Medicare premiums, out-of-pocket costs, and supplemental insurance all on the rise, your plan needs to account for both predictable and unpredictable medical costs.

3. Behavioral Investing Mistakes

Markets go up. Markets go down. But how you react during those downs can do more damage than the downturn itself.

Rob explains that “investing is more about managing your emotions than your portfolio.” Common missteps like panic-selling or chasing performance can sabotage decades of good planning.

4. Greed: The Other Side of Emotion

Fear isn’t the only emotional threat. Greed can be just as dangerous. Whether it’s chasing the next big stock, jumping on crypto hype, or overcommitting to a “sure thing,” speculative behavior often stems from good intentions—but poor discipline.

If your plan is built on long-term goals, don’t let short-term noise pull you off course.

5. The Wrong Kind of Risk Management

Ironically, avoiding all risk is one of the riskiest things you can do in retirement. Many retirees shift too conservatively and end up falling behind inflation. The real goal isn’t to eliminate volatility—it’s to manage it in alignment with your needs and time horizon.

Rob and Archie recommend maintaining an appropriate level of market exposure to support long-term growth—even in retirement.

Ask Yourself:

  • Am I stress-testing my plan for inflation and healthcare shocks?
  • Is my portfolio structured to avoid emotional decision-making?
  • Have I built in enough growth potential to outpace rising costs?
  • Am I reacting to fear or greed—or following a disciplined plan?

Final Thought

A successful retirement isn’t just about how much you’ve saved—it’s about protecting what you’ve built. Ignoring these risks won’t make them go away. But addressing them now? That’s how you build confidence for the decades ahead.

Which of these risks are hiding in your retirement plan?

Download our free Retirement Risk Audit Tool or schedule a one-on-one session at www.hoxtonpm.com/schedule to ensure your plan is ready for what’s next.
Download the Tool
Certified Financial Planner Board of Standards Center for Financial Planning, Inc. owns and licenses the certification marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the United States to Certified Financial Planner Board of Standards, Inc., which authorizes individuals who successfully complete the organization’s initial and ongoing certification requirements to use the certification marks.