Five Questions to Ask Before You Retire

Retirement isn''t a date on the calendar — it''s a shift in how your money has to behave. Before you make the leap, work through these five questions with your advisor.

1. What will my income actually look like?

Payroll stops. Social Security, pensions, portfolio withdrawals, and (sometimes) part-time work step in. Model the full picture month by month for the first ten years, not just an annual average.

2. Where will the taxes land?

Traditional IRA, Roth, brokerage, HSA — each bucket is taxed differently on the way out. The order you draw from can add or subtract years of longevity from your portfolio.

3. How am I bridging to Medicare?

If you retire before 65, health coverage is often the single largest new line item. Plan it before you resign, not after.

4. What if I live to 95?

Longevity risk is the quiet one. Stress-test your plan against a 30-year horizon and a couple of ugly market sequences.

5. What is this money ultimately for?

Kids, grandkids, causes, a second home. Your estate plan should match the answer — and it should be written down, not assumed.

If any of these feel fuzzy, that''s the signal to plan before you retire, not after.