That final stretch—the six months before you leave your job behind—is often a wild mix of anticipation and a bit of "wait, did I check everything?" panic. You've spent decades building this financial structure, and now it's time for the ultimate final inspection. This isn't just a countdown; it's a critical window for moving past estimates and making concrete decisions.
Getting these details right now can smooth your landing considerably and genuinely help set yourself up for retirement success, turning those final jitters into confident excitement.
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Pin down your Social Security details
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If you're planning to start receiving Social Security benefits soon, don't just assume the check will arrive on time. You'll want to confirm your specific filing date and the precise amount you expect to receive. A quick call to the Social Security Administration or a deep dive into your online account can clear up any lingering questions. Think of this as your last chance to iron out any discrepancies in your earnings history that could affect your first payment.
Confirm the money that's coming in
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It's time to stop relying on calculator projections and confirm the real numbers that will hit your bank account. Removing this uncertainty is key to feeling stable. Consider all places you expect your income to come from in retirement, including retirement accounts and pensions. You should have a good idea of what you can expect to hit your bank account each month.
Talk to your former employer about your payouts
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For those with a pension, reach out to your plan administrator now. You need to confirm your chosen payout (whether that's a lump sum or monthly checks )and when those payments officially begin. For 401(k)s, figure out the logistics: Will you roll the money over into an IRA? How are you setting up those first systematic withdrawals? Every institution has its own paperwork and timeline, so getting a jump on this might prevent a stressful gap in your cash flow.
Get a protection plan on all your appliances
Did you know if your air conditioner stops working, your homeowner’s insurance won’t cover it? Same with plumbing, electrical issues, appliances, and more.
Whether or not you’re a new homeowner, a home warranty from Choice Home Warranty could pick up the slack where insurance falls short and protect you against surprise expenses. If a covered system in your home breaks, you can call their hotline 24/7 to get it repaired.
For a limited time, you can get your first month free with a Single Payment home warranty plan.
Get brutally honest about your retirement budget
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Your spending habits are likely going to change dramatically. That daily commute cost disappears, but travel expenses and maybe that premium gym membership might take its place. It's time to build a truly realistic budget for life without a salary. Move beyond simple guesswork. Detail the expenses that could fluctuate: higher Medicare premiums, the budget for visiting the grandkids, or the cost of that new pottery hobby. It's helpful to map out two scenarios: your calm, average month, and the month when your annual car insurance or property taxes are due.
Set aside a comfort cash bucket
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Many retirees find immense peace in having a liquid pool of money (say, six to twelve months' worth of expenses) in a safe place like a high-yield savings account. This "cash bucket" helps you avoid being forced to sell off long-term investments during a market dip just to pay the electric bill.
Make peace with healthcare paperwork
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Healthcare is often the biggest unknown expense in retirement. Handling the paperwork now can save you significant stress later. Yes, medical paperwork can seem overwhelming, and insurance can be complicated. But, the time to handle your future healthcare is now, not after you're retired.
Don't miss the Medicare window
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If you're turning 65 or leaving employer-sponsored coverage, getting your Medicare enrollment right is vital. The Initial Enrollment Period (IEP) is set in stone, and missing it could result in delayed coverage and, permanently, a higher premium (the late enrollment penalty). Beyond Part A and B, you'll need to make a firm decision on your Part D drug plan and whether you want a Medicare Advantage Plan (Part C) or a Medigap supplement. These decisions are huge, so allow yourself the time to research them thoroughly.
Perform a full insurance review
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This is a great moment to look at all your insurance policies. Are you still paying for the same car coverage now that you might only be driving for pleasure? Do you need to update your home insurance to reflect new valuables or home improvements? Most importantly, confirm your life insurance still aligns with your goals for your estate and your family's future.
Give your legal and financial files a final polish
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Start by double-checking your beneficiaries. The beneficiaries listed on your IRAs, 401(k)s, and insurance policies are the legal word on where that money goes, often trumping your will. An outdated name on one of these forms could send a large sum to an ex-spouse or an unintended relative, which is a stressful mess no one wants.
Compile a simple, secure list of every financial account, including the institution's name, the account number, and contact details. This single document will be invaluable to your spouse or a trusted family member should they ever need to step in to help manage your affairs.
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That's right. According to the FTC, Americans lost over $10 Billion to fraud and identity theft in 2023.
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Prepare for the emotional shift
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Money is important, but a happy retirement is built on more than just numbers. The shift from a busy working life to open, unstructured time is huge. The lack of a work schedule could leave you feeling unmoored. Start thinking about what a "typical" week might look like. Schedule non-negotiables: volunteer work, exercise, time for travel planning, and time for simply relaxing. Having this blueprint often makes the transition smoother.
Bottom line
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The six months leading up to your retirement are a window for action, not just planning. This period should be dedicated to confirming your income sources, verifying legal documents like beneficiaries, and making final, concrete healthcare decisions that will govern your life for decades to come.
Ultimately, this preparation helps you transition from saving money to reliably generating income, and it is the ideal time to check up on your retirement readiness beyond just the numbers by creating a fulfilling daily routine. While most people anticipate lower expenses, data suggest that spending often remains high (sometimes 80% or more of pre-retirement levels) during the initial "go-go" years, driven by travel and new leisure activities.
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