5 Critical Questions That Could Make or Break Your Retirement

One unexpected health bill. A sudden drop in income. A tax surprise you didn’t see coming.

These are the kinds of moments that can quietly unravel years of careful retirement planning. And they don’t just happen to people who didn’t plan—they happen to people who thought they had everything in place.

Many retirees reach this phase of life assuming the hardest decisions are behind them. But what actually happens is the pressure shifts—from saving and growing money to protecting it, using it wisely, and making it last. That’s when the real test begins.

The retirees who stay in control often have one thing in common: they asked the right questions while there was still time to act.

If you’re ready to take control of what comes next, these five questions can help you stay ahead of the challenges—before they turn into problems.

1. How do I make sure I never outlive my income?

The market goes up. The market goes down. But your expenses? They just keep coming.

Too many retirees try to “wing it” by withdrawing from their portfolios without a clear plan. That’s a risky way to approach 20 or 30 years of retirement. The goal isn’t just growth anymore—it’s stability and predictability.

Ask yourself: What portion of your income is guaranteed for life? Are you relying too much on the market? Are you withdrawing in a way that minimizes taxes and preserves principal?

These early decisions can set the tone for the decades that follow.

2. What happens if my healthcare needs suddenly change?

Medicare doesn’t cover everything—especially not the long-term care many retirees eventually need. Without a plan, a sudden diagnosis or care need can drain your savings quickly.

Start by getting clear: Do you have a strategy to cover long-term care if it’s needed? Have you looked at care options in your area and what they actually cost? Are you expecting family to step in—and have you talked to them about that?

Waiting until you’re in a health crisis to make decisions can leave you with fewer choices and much higher costs.

3. Can my spouse stay financially secure if something happens to me?

The loss of a spouse is difficult enough without financial instability added to the mix.

Many couples are caught off guard by how much income disappears when one partner passes. Pensions may be reduced. One Social Security check may stop. And the surviving spouse faces an income gap—at the very moment they need financial clarity the most.

Have you reviewed how your household income would change if one of you passes away? Are there gaps you can fill now, while you still have time to plan?

4. Are my assets set up to go where I want them to go?

Estate planning is more than just having a will. It’s about the full picture: how your assets are titled, who your beneficiaries are, and whether your plans are clearly communicated.

Many retirees assume everything is in order—only to discover years later that a retirement account still names an ex-spouse or that a trust hasn’t been updated. Others never share their legacy goals with family, which can lead to confusion or conflict.

When was the last time you reviewed your estate documents? Are your beneficiaries aligned with your current wishes? Don’t leave your legacy up to chance—or to the court system.

5. Am I paying more taxes than necessary?

Retirement doesn’t end your relationship with the IRS. In fact, your tax liability may go up—thanks to required minimum distributions, taxable Social Security, and investment income.

Smart tax planning doesn’t stop at retirement. It just looks different.

Could Roth conversions lower your future tax burden? Are there charitable strategies that align with your giving goals? Are you drawing from the right accounts, in the right order? Small adjustments today can add up to meaningful savings over time.

Don’t Wait for a Crisis to Act

These five questions aren’t just financial checklists—they’re keys to long-term security, independence, and peace of mind.

If you’ve been putting off these conversations, don’t wait for the market to drop or a medical event to force your hand. Proactive planning gives you options—and options give you control.

Start with clarity. Call Barb Swiatek at 719.597.2179 to talk through your retirement strategy and make sure your next steps are in place—before life makes those decisions for you.