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Episode 88: Are You Really Ready to Retire? Use This Checklist to Find Out

You’ve saved. You’ve planned. Maybe you’ve even circled your retirement date on the calendar. But before you walk away from your last paycheck, ask yourself: Are you really ready to retire?

In Episode 88 of the Last Paycheck podcast, CERTIFIED FINANCIAL PLANNER® professionals Rob and Archie Hoxton revisit their comprehensive pre-retirement checklist—helping you assess not just whether you can retire, but whether you’ll retire well.

Retirement isn’t just a date. It’s a full transition—financially, emotionally, and logistically. This episode breaks down the key actions to take in the final stretch to make sure you’re truly prepared.

Key Milestones to Watch

Certain birthdays trigger important financial rules, benefits, and penalties. Are these on your radar?

  • 59½: You can withdraw from retirement accounts without the 10% early withdrawal penalty.
  • 62: You’re eligible to begin Social Security—but your benefits will be permanently reduced.
  • 65: Time to enroll in Medicare. Miss it, and you may face lifetime penalties.
  • 73 to 75: Your Required Minimum Distributions (RMDs) begin, depending on your birth year.

Each of these age-based triggers carries planning implications for income, taxes, and healthcare. Ignore them, and you could leave money—or protection—on the table.

Test Drive Your Retirement Budget

One of the biggest risks in retirement? Spending more than you think.

Rob and Archie encourage listeners to do a “budget test drive” before their final paycheck. That means living off your projected retirement income for several months. Track every dollar. Account for:

  • Property taxes
  • Insurance premiums
  • Home maintenance
  • Travel, hobbies, and holiday spending

This exercise will show whether your retirement income is truly sustainable—or if adjustments are needed.

Reevaluate Your Investment Risk

Your portfolio doesn’t retire just because you do. But your risk tolerance might change. Too conservative, and you risk falling behind inflation. Too aggressive, and a market drop could derail your withdrawals.

Rob and Archie recommend reviewing:

  • Your current allocation
  • Time horizon for each pool of money
  • Whether you need to implement a retirement “glide path” that gradually reduces volatility

Final Tune-Ups Before You Retire

As you count down to your final paycheck, don’t overlook the details:

  • Cancel unused subscriptions and recurring charges
  • Evaluate long-term care insurance options
  • Pay off high-interest debt
  • Strategize your Social Security claiming plan for maximum lifetime benefit

Ask Yourself:

  • Have I accounted for healthcare costs and Medicare gaps?
  • What happens if my spouse outlives me by 10 to 15 years?
  • Do I have a strategy for drawing from different account types (IRA, Roth, brokerage)?
  • Is my plan stress-tested for inflation or market volatility?

Final Thought

Retirement is not just about having enough money. It’s about having the clarity, confidence, and control to enjoy your next chapter on your terms. With a thoughtful checklist and the right guide, you can retire not just comfortably—but powerfully.

Get the full Pre-Retirement Checklist—free.

Or schedule a conversation with our team at www.hoxtonpm.com/schedule to personalize your path forward.
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.