15 Questions Couples on the Brink of Retirement Should Ask Themselves Now

Before you stop working, make sure you and your partner are on the same page about retirement.

couple talking on couch at home
Updated July 18, 2024
Fact checked

We receive compensation from the products and services mentioned in this story, but the opinions are the author's own. Compensation may impact where offers appear. We have not included all available products or offers. Learn more about how we make money and our editorial policies.

Are you or your partner considering retiring soon? Before you do so, make sure you're ready for such a big switch.

Retiring isn’t a decision to make lightly — or alone. Here are 15 essential questions to discuss with your partner as the two of you craft your retirement plan.

Eliminate your late tax debt

Each year, the IRS forgives millions in unpaid taxes. If you have more than $10,000 in tax debt, or have 3+ years of unfiled taxes, you could get forgiveness too. You might be eligible to lower the amount you owe, or eliminate your tax debt completely.

Easy Tax Relief could help you lower or get out of your tax debt for good. They’re well respected in the industry and have been recognized for their ethical standards when dealing with tax debt. While most tax companies just put you on a payment plan and file your taxes for you, Easy Tax Relief talks to the IRS directly. They can help you pay off your tax debt faster while potentially reducing what you owe.

Important: Not everyone will qualify. To take advantage of this special program you must owe more than $10,000 in past-due taxes.

Fill out this form to get started

‘Do we know when we want to retire?’

bernardbodo/Adobe making plans for the future

This is a personal, multifaceted question. To come to a firm answer, you may need to have some honest conversations with your partner about your financial situation.

If you haven’t saved a lot of money, retiring too early can jeopardize your financial fitness. Meeting with a financial planner might be helpful before you make a decision.

Also, don’t forget to weigh your mental and physical health and think about your long-term goals prior to making this big decision.

‘Have we thought about how we will spend time during retirement?’

rocketclips/Adobe couple having a conversation

Don’t let fantasies of playing golf all day cloud your judgment here. That will be fun for a week or two.

But once the thrill wears off, how will you spend your time? It’s important to think about how you will derive meaning and purpose from your life.

‘Do we have the money to live out our retirement dreams?’

fizkes/Adobe woman talking with man

Simply “getting by” in retirement is one thing, but do you have the cash to fulfill your retirement dreams?

If you have specific plans for retirement — such as travel or buying a new home — it’s imperative that you have enough funds to make them happen. Include these expenses as you calculate the money you will need each month during retirement.

Earn $200 cash rewards bonus with this incredible card

There's a credit card that's making waves with its amazing bonus and benefits. The Wells Fargo Active Cash® Card(Rates and fees) has no annual fee and you can earn $200 after spending $500 in purchases in the first 3 months.

The Active Cash Card puts cash back into your wallet. Cardholders can earn unlimited 2% cash rewards on purchases — easy! That's one of the best cash rewards options available.

This card also offers an intro APR of 0% for 15 months from account opening on purchases and qualifying balance transfers (then 20.24%, 25.24%, or 29.99% Variable). Which is great for someone who wants a break from high interest rates, while still earning rewards.

The best part? There's no annual fee.

Click here to apply now.

‘Should we move to somewhere new for retirement?’

C Coetzee/peopleimages.com/Adobe senior couple enjoying summer

The driver behind a desire to move is often to be close to family, but there are many financial implications to weigh here.

As the source of your income shifts from wages to living off savings and Social Security, pay attention to how a new state’s cost of living and tax situation might impact your money.

‘Do we have a plan for when to file for Social Security benefits?’

Maria Vitkovska/Adobe couple having conversation while driving

You can begin receiving Social Security benefits at age 62, but you will receive a larger monthly payment the longer you wait to file up to the age of 70.

Figure out how much income you can generate from other sources and then decide when it makes the most sense to begin taking Social Security.

‘Do we have a plan for financing health care costs?’

kieferpix/Adobe couple sitting at home talking

Generally, people qualify for Medicare at 65. So, if you are retiring earlier than that, you need to have a plan for how to pay for health insurance.

Options may include purchasing an Affordable Care Act marketplace plan, paying for COBRA coverage to extend the insurance from a former employer, or joining your spouse’s insurance plan.

Also, remember that Medicare itself does not cover all health care expenses and that you will still need to cover many costs out of pocket.

‘Should we dial back on investment risk?’

PheelingsMedia/Adobe couple talking in street

Many investment experts advise dialing down your risk as you enter retirement. Market downturns are much scarier when you rely on investments to fund your day-to-day lifestyle.

As you age, you also have fewer years to recover from market downturns.

‘Should we work part time during retirement?’

LIGHTFIELD STUDIOS/Adobe couple having conversation during date

Working part time during retirement can decrease your reliance on investments, supply you with health insurance, and give you a productive way to spend your time.

It can also prevent you from becoming socially isolated. But working is not the right fit for all seniors, particularly if they have serious health issues that limit their ability to work.

‘Will we travel a lot during retirement?’

Rawpixel.com/Adobe couple having a serious conversation

Traveling is a dream of many aspiring retirees. Whether or not travel is important to you will determine a lot about your retirement plan.

Do you want to retire early while you have the stamina for globetrotting? Or does it make more sense to stash away cash and build a larger nest egg so you can retire later and see the world in style?

If you’re over 50, take advantage of massive discounts and financial resources

Over 50? Join AARP today — because if you’re not a member you could be missing out on huge perks. When you start your membership today, you can get discounts on things like travel, meal deliveries, eyeglasses, prescriptions that aren’t covered by insurance and more.

How to become a member today:

  • Go here, select your free gift, and click “Join Today” 
  • Create your account (important!) by answering a few simple questions 
  • Start enjoying your discounts and perks!

You’ll also get insider info on social security, job listings, caregiving, and retirement planning. And you’ll get access to AARP’s Fraud Watch Network to help you protect your money, as well as tools to help you plan for retirement.

Important: Start your membership by creating an account here and filling in all of the information (Do not skip this step!) Doing so will allow you to take up 25% off your AARP membership, making it just $12 per year with auto-renewal.

Become an AARP member now

‘Have we crafted a budget?’

Bliss/Adobe couple in casual clothes

Just because you are not working doesn’t mean you no longer need a budget. In fact, a budget can be even more important during retirement than it was during your working years.

Outliving your money is a real risk during retirement. Keeping track of and reining in your monthly expenses will help ensure your nest egg lasts.

‘Have we paid off our debts?’

JackF/Adobe family couple having serious conversation

While it’s not a requirement to be completely debt-free before you call it quits on working, have a plan in place to repay any outstanding debts during retirement.

Downsizing your home, selling an extra car you no longer need for commuting, or choosing to live in an area with a low cost of living can help with this goal.

‘Have we made an estate plan?’

Evrymmnt/Adobe young couple on a date

Retirement is the time when you need to consider what you want for your partner and heirs after you die.

A good start is to take inventory of all your assets and then decide who should inherit each one. You might also consider who you want to take care of your finances and medical decisions later in life if you become unable to do so yourself.

‘Should we downsize?’

BullRun/Adobe couple in love having conversation

Once children are grown and flown, you might consider downsizing your home. If you downsize, your equity could help you move into a smaller home you can buy in cash.

Downsizing to a single-story home also can be helpful in the event that you have mobility issues as you age. Downsizing won’t make sense for every situation, but it’s worth considering.

‘Do we still need life insurance?’

DimaBerlin/Adobe couple having serious talk

During your working years, life insurance might have been essential for protecting your family in the event of your premature death. Once you retire, you will need to decide if this coverage still makes sense.

Life insurance can help provide for the needs of a spouse or children after you are gone. It also can help you leave a legacy to a charity you love or pay for your funeral expenses. Discuss with your partner whether the ongoing expense of life insurance still makes sense for you.

‘Do we have a plan for long-term care?’

Nomad_Soul/Adobe family couple having nice conversation

Up to 70% of people who live to the age of 65 will develop severe long-term services and supports needs at some point, and 48% will pay for care, according to the U.S. Department of Health and Human Services.

With these statistics in mind, long-term care should be a part of a holistic retirement plan. As you prepare for retirement, make sure you have a plan to pay for long-term care services should you need them.

Bottom line

InsideCreativeHouse/Adobe couple drinking wine

When to retire is a personal choice. Financial considerations will inform your decision, but so will emotional, health, and family factors.

Exploring and discussing the many facets of your life with your partner and family will help you better gauge your retirement readiness so you can decide whether this is the time to finally leave work behind.

Lucrative, Flat-Rate Cash Rewards


Wells Fargo Active Cash® Card

Current Offer

$200 cash rewards bonus after spending $500 in purchases in the first 3 months

Annual Fee


Rewards Rate

Earn unlimited 2% cash rewards on purchases

Benefits and Drawbacks
Card Details

Author Details

Jenni Sisson

Jenni Sisson is a freelance writer and editor who focuses on personal finance, real estate, and entrepreneurship. She has been published in Business Insider and The Ways to Wealth. In addition to writing, Jenni hosts the Mama's Money Map podcast to help fellow stay-at-home moms on their journey to financial freedom.