The 3 Biggest Retirement Questions You’ve Been Afraid to Ask

You know that feeling at 2 a.m. when your mind won’t shut off? When you’re staring at the ceiling, running through the same worries on repeat? Many retirees share that experience — not because they regret leaving work, but because retirement brings up questions they’ve never said out loud.

Asking those questions doesn’t mean you’re unprepared. It means you care enough to face what really matters. Everyone wonders about them — the difference between people who sleep soundly and people who don’t often comes down to whether they’ve faced these concerns or kept pushing them aside.

Let’s look at the three questions that surface most often during those restless nights — and, more importantly, what you can do about them starting today.

1. What if I outlive my money?

This one keeps more retirees awake than anything else. You’ve saved for decades, watched your accounts grow, maybe even hit your target number. But now you’re watching it flow out instead of in, and every market dip feels different than it used to.

Here’s the struggle: you’re caught between two fears. 

1. Spend too freely now and you might regret it later. 
2. Hold back too much and you risk missing the retirement you’ve earned.

A better way to approach this? Focus less on your total balance and more on your monthly income floor — the amount you can count on no matter what the market does.

Start by adding up your guaranteed sources: Social Security, a pension if you have one, or perhaps an annuity that pays a set amount each month. Then compare that income to your essential monthly expenses — mortgage or rent, utilities, groceries, insurance, property taxes.

If your guaranteed income covers those basics, you’re already on stronger ground than you may think. The rest of your savings can fund the flexible parts of your life — travel, gifts, or those spontaneous “why not?” moments that make retirement enjoyable.

Here’s a realistic example. Suppose your Social Security and pension cover most of your essentials, but there’s still a small gap. That gap means you’re pulling from investments every month just to keep up. Over time, market downturns will sting more because you’re forced to withdraw during losses.

But if you restructure so your guaranteed income covers your base expenses, your investments can ride out market swings without panic. You get back something even more valuable than returns — peace of mind.

Your next step: List every income source you have and mark which ones are guaranteed versus market-dependent. If too much sits on the market side, talk with a retirement income advisor about creating a steadier foundation. You shouldn’t have to check your portfolio before buying groceries.

2. What if my health declines and the costs catch me off guard?

Nobody enjoys imagining themselves needing help with daily tasks. But pretending it won’t happen doesn’t make it less likely — it just makes you unprepared if it does.

Here’s what surprises many retirees: Medicare doesn’t cover ongoing long-term care. If you need help bathing, dressing, eating, or managing medications — whether at home or in a care facility — those costs are on you. And they add up fast, often several thousand dollars per month depending on your area and level of care.

Even the healthiest person can face unexpected health events. A fall. A stroke. Dementia. And when that day comes, bills arrive before emotions settle.

You don’t need to know exactly what the future holds. What matters is building flexibility into your plan now. Some people dedicate part of their portfolio to future care costs. Others explore hybrid long-term care insurance that combines life coverage with care benefits. A few use health savings accounts strategically during their working years.

The specific method matters less than having a plan. Without one, a health event can drain decades of savings faster than most imagine.

Start with a simple calculation. Add up your current medical costs — Medicare premiums, supplemental coverage, prescriptions, regular visits. Then assume they’ll rise every year. In ten years, those same routine expenses could nearly double, before any major medical event even happens.

Your next step: Write down this question and answer it honestly: “If my health changed next month, what money would I use to pay for care?” If the answer feels vague or uncertain, that’s your cue to create a strategy. A simple plan now can protect both your savings and your family later.

3. What happens to my spouse or loved ones if something happens to me?

This might be the hardest question to face because it means thinking about what happens after you’re gone. But having this conversation now is one of the kindest things you can do for the people you love.

In many marriages, one person naturally takes the lead on finances. If that person passes first, the surviving spouse can be left trying to track down passwords, policies, and income details during an already painful time.

Here’s the truth: some income sources stop or shrink after one spouse passes. Certain pensions end entirely unless a survivor option was chosen. Social Security shifts too — the survivor keeps only the higher of the two benefits, while the smaller one disappears. That can mean a real loss of monthly income right when emotions are raw.

The solution isn’t complicated, but it does require a little intention. Start by making a simple document that lists your accounts, insurance policies, income sources, and where key papers are kept. Store it safely, but make sure at least one other person knows where it is.

Then, have a calm, honest conversation. Sit down over coffee and walk through what would continue, what would stop, and what would change. No legal jargon — just clarity.

And don’t forget to check your beneficiary designations. They override your will. If your IRA still lists someone from decades ago, that’s who receives it regardless of your current wishes. Review these at least once a year.

Your next step: Block out one hour this week for a family financial talk. Go over your accounts, policies, and documents together. If you’d like a professional to help guide the discussion, a trusted advisor can ensure nothing slips through the cracks.

You’ve Earned the Freedom to Feel Secure

These questions only hold power when they stay unspoken. Once you bring them into the open, they become solvable. Running out of money, facing unexpected health costs, leaving loved ones uncertain — each fear softens when you have a plan that reflects your life, your priorities, and your goals.

You’ve worked too hard for too long to spend retirement worrying about what-ifs. The freedom you’ve been building toward includes financial calm, reliable income, and confidence in the future.

If you’re ready to talk through these concerns and create a plan designed around your real life, reach out to Barb Swiatek at 719.597.2179. Together, you can build a retirement strategy that gives you what you’ve truly earned — peace of mind that lasts.