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.