5 Questions to Ask Before You Retire

Aug 12, 2026
5 Questions to Ask Before You Retire
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Introduction

Retirement is an exciting milestone, but deciding you’re ready involves more than choosing your last day of work.

Before making the transition, here are five important questions worth asking.

1. Where Will My Retirement Income Come From?

Start by identifying the income sources you’ll have available. These might include Social Security, a pension, 401(k)s, IRAs, investments, savings, or other assets.

Then consider whether those sources can reasonably support your expected expenses throughout retirement.

2. When Should I Claim Social Security?

You may be eligible to begin Social Security retirement benefits as early as age 62, but that doesn’t necessarily mean you should.

Your claiming decision can affect the amount you receive, making it important to consider your overall financial situation and retirement goals before deciding when to file.

3. How Will Taxes Affect My Retirement?

The amount you have saved isn’t necessarily the same as the amount you’ll have available to spend.

Depending on where your retirement income comes from, withdrawals may create taxable income. Looking ahead at potential taxes can help you better understand what your retirement income may actually look like.

4. What Happens if the Market Drops?

Market volatility doesn’t end when you retire. In fact, significant market declines can feel even more important once you begin taking withdrawals from your portfolio.

Consider how your retirement plan would respond if a major downturn occurred during your first few years of retirement. Having a strategy ahead of time can help you avoid making emotional decisions during periods of uncertainty.

5. Do I Have a Written Retirement Plan?

You’ve spent years accumulating assets. Retirement is when the focus begins shifting toward how those assets will support your lifestyle.

A written plan can help bring your income, investments, taxes, Social Security, healthcare considerations, and long-term goals together in one place.

At Retirement Advocates, we help individuals and families look at the complete retirement picture and understand how the different pieces work together.

The goal isn’t to predict every detail of the future. It’s to enter retirement knowing you’ve taken the time to prepare for it.

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