Because retirement planning isn’t just about money—it’s about making sure every piece fits.
Retirement isn’t something you just walk into—at least not without a little preparation. If you want to avoid surprises (and stress), you’ll need to talk to the right people first. Retirement affects your income, healthcare, lifestyle, and even your relationship with your spouse. Here’s who should be on your pre-retirement checklist:
Your HR Department
Before you leave your job, talk to HR. They’ll help you understand what benefits you’re eligible for, what you’ll lose, and what can be transferred or continued.
If your employer offers a pension, it’s crucial to get clarity on when and how it pays out. You’ll also want to ask about any retiree health benefits, life insurance, or 401(k) rollover options.
Ask:
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What happens to my benefits when I retire?
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How do I start my pension?
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Is there anything I need to do before my last day?
A Medicare & Supplement Specialist
Once you’re no longer covered by your employer’s insurance, you need a plan—literally. A licensed agent who specializes in Medicare and Medicare Supplements can guide you through what’s covered, what’s not, and how to avoid costly mistakes.
They’ll help you sign up at the right time and choose a plan that matches your health needs and budget.
Ask:
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What’s the difference between Medicare and a supplement plan?
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When do I need to enroll?
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Will I face any penalties if I delay?
The Social Security Administration
Whether you’re married, divorced, or widowed, your Social Security benefits are based on more than just your own work record.
Talking to the Social Security office can help you understand what benefits you’re entitled to—and when the best time is to claim them.
Ask:
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What are my benefits and my spouse’s?
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How does my claiming age affect my payout?
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Are there benefits I might be missing?
A Retirement-Focused Financial Advisor
Not all financial advisors are created equal. You want someone who specializes in retirement planning—not just investing. They’ll help you turn your savings, pension, and Social Security into a sustainable income stream that can last 20–30+ years. They’ll also consider taxes, long-term care, and legacy goals. Let us be your Retirement Advisor. Make sure to hit this link and we will meet to discuss how we help our clients stay retired.
Ask:
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Can you build a retirement income plan using my portfolio, pension, and Social Security?
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How do we plan for health care costs and long-term care?
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What tax strategies can help stretch my savings?
An Estate Planning Attorney
It’s time to dust off that will—or create one if you haven’t yet. An estate planning attorney can help you set up or revise your legal documents, including wills, trusts, power of attorney, and health care directives.
Ask:
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Do I need to update my will or create a trust?
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Who should be my power of attorney?
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Are my beneficiaries up to date on all accounts?
Your Spouse
This is the most important conversation you’ll have. Retirement changes more than just your bank account—it changes your daily routine, your shared goals, and sometimes your timeline.
Is your spouse emotionally and financially ready for retirement? Is there a significant age gap that affects benefits or planning?
Talk About:
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Do we both want to retire now?
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How will our routines change?
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How will we handle decisions about travel, spending, and caregiving?
Retirement is more than just stopping work. It’s a full-life shift that affects everything from your finances to your family. Talk to the right people, ask the right questions, and build a plan that makes this next chapter the best one yet.