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The 7 Big Questions to Answer Before You Retire

Jim Martin, RFC, AAMS
October 11, 2026

The 7 Big Questions to Answer Before You Retire

Most people approach retirement with one big question:

Can I retire?

It sounds like there should be a simple answer. Add up your401(k), IRA, savings, and Social Security. Compare that with what you spend. Ifthe numbers look big enough, you retire.

But retirement is rarely that simple.

An account balance is only one piece of the picture. Youalso have to decide when the paycheck stops, when Social Security begins, howyour savings will create income, what happens during a bad market, how taxesfit in, how you’ll pay for healthcare, and what happens if one spouse is lefton their own.

In other words, retirement isn’t one decision. It’s sevenconnected decisions.

Here are the seven questions worth answering before youleave work behind.

1. When Can You Afford to Retire?

There is no magic retirement number.

A couple with $1 million who spends $5,000 a month may be ina very different position from a couple with the same savings who spends$10,000.

Start with the life you want.

What does a normal Tuesday look like in retirement?

Once you understand what retirement may cost, you can beginasking whether your income and savings can support it.

2. When Should You Claim Social Security?

Social Security gives you choices.

But the biggest monthly check isn’t automatically the bestdecision.

Your health, other income, savings, retirement date, andspouse all matter. For married couples, the decision can also affect the incomeavailable to the surviving spouse later.

The goal isn’t to find the “perfect” claiming age. It is tofind the age that fits the rest of your plan.

3. Where Will Your Retirement Paycheck Come From?

For most of your adult life, a paycheck arrived every coupleof weeks.

Then retirement happens, and it stops.

Now you have to create your own paycheck.

Social Security and pensions may cover part of yourspending. Your savings may have to provide the rest.

And they need to do it in good markets and bad ones.

4. How Should Your Money Be Invested?

Retirement changes the job of your money.

While you were working, you may have been focused mostly ongrowth.

In retirement, some money may be needed next year. Othermoney may not be needed for 10 or 20 years.

Those dollars have different jobs.

Instead of asking, “What investment should I buy?” a betterquestion may be:

When will I need this money, and what job does it need todo?

5. What Is Your Tax Strategy?

Most people think about taxes once a year.

Retirement gives you a reason to think further ahead.

The years after work income stops can sometimes createunusual tax-planning opportunities.

The goal isn’t simply to pay the least tax this year.

Sometimes the better question is:

How can I pay less tax over the course of my retirement?

6. How Will You Pay for Healthcare?

If you retire before 65, you may need to bridge the yearsuntil Medicare begins.

Once you reach Medicare, you still have choices involvingcoverage, premiums, prescriptions, doctors, and out-of-pocket costs.

Healthcare also connects back to taxes because income canaffect certain health insurance costs and Medicare premiums.

That is a good example of why these seven decisions can’talways be made one at a time.

7. What Happens to Your Spouse and Family?

A retirement plan shouldn’t only work while both spouses arealive and healthy.

Ask what happens if one of you dies first.

One Social Security benefit may disappear. Taxes can change.Healthcare needs may change. The surviving spouse may suddenly be responsiblefor financial decisions they never handled before.

This may be the least enjoyable retirement question.

It may also be one of the most important.

One Plan, Not Seven Separate Answers

These seven questions affect one another.

Retiring earlier may change your healthcare costs. DelayingSocial Security may mean taking more from savings for a few years. Taking morefrom an IRA may affect taxes. Taxes may affect healthcare costs. And all ofthose decisions may look different after the death of a spouse.

That is why a retirement plan is more than an investmentportfolio.

It is a way of making sure the pieces work together.

For families approaching retirement in Roanoke,Christiansburg, and throughout the country, these are the kinds ofquestions we work through every day at Martin Wealth Solutions.

You don’t need seven perfect answers.

But before you retire, you should know which questions youhave truly answered—and which ones you’ve simply assumed will work out.

We help women & couples 50+ simplify taxes, income, and investments through our signature SmartWealth System™
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