3 Game-Changing Questions to Ask Before You Retire

If you have made it to the point where you are ready to retire, you should give yourself a big round of applause, as there are millions of workers still out there hoping to be you one day. Of course, if you have decided to retire, you must ensure you are set up to live […] The post 3 Game-Changing Questions to Ask Before You Retire appeared first on 24/7 Wall St..

May 12, 2025 - 14:39
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3 Game-Changing Questions to Ask Before You Retire

If you have made it to the point where you are ready to retire, you should give yourself a big round of applause, as there are millions of workers still out there hoping to be you one day. Of course, if you have decided to retire, you must ensure you are set up to live comfortably and successfully. 

Key Points

  • These three essential questions around retirement should have answers before any decisions are made.

  • If you can answer these three questions, it will help you ease into retirement.

  • One of the most important things to do is to have an estate plan all settled, so there is no fight over assets.

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Before you call it quits for good, you have to stop and think through everything that could impact your retirement. This goes beyond good financial planning, which you hopefully have done, but also thinking about where to live and how to handle your estate for future generations. 

Where Do I Want to Live During Retirement? 

It’s true that for most people, the financial questions around retirement come before anything else, but knowing where you want to live shouldn’t be far behind. Surprisingly, most people don’t think more about this until after they retire, but you should have your plans finalized beforehand. 

Lifestyle Preference

Thinking about your lifestyle preference may be the most significant factor in figuring out the “where” part of where you want to live. The lifestyle you want to have will directly dictate how you live, including what type of weather you prefer and if you wish to live near or move closer to family. Are you a golfer, hiker, biker, or swimmer? If so, you might want to be somewhere that allows this type of activity year-round. 

Cost of Living

Cost of living is another big consideration, and it might be worth researching how it plays a role. If you retire to a state like Tennessee or Florida, you have to consider that you have no income tax, which is positive, but you might have higher insurance and property costs in Florida. The same goes for healthcare costs and the purchase price of a home, as these costs can greatly impact where you want to live. 

Proximity to world-class healthcare facilities should likely be at the top of the list, especially if you have known health issues when retiring. In addition, you might want to explore where you can live that offers public transportation or walkable neighborhoods. 

Quality of Life

If you choose the right location, it will positively impact your mental health and social life. All these things will play a big role in having a long and fulfilling retirement, which is why choosing where to live plays a much larger role in retirement decisions than most people give it credit for. 

How Do I Want to Handle My Estate and Legacy? 

This is a big question you need to have some answers to before you put your feet up for good once and for all. Ask yourself if you have a will and or trust, and, if you don’t, make sure you get one before retirement. The last thing you want is any question about where your estate will go post-retirement. 

Wills and Trusts

The top reason to establish a will and trust is that it can help your beneficiaries out in a big way. Establishing who will inherit what can help eliminate the need for family disputes and/or probate. Better yet, these documents ensure that your wishes are honored and that a structured plan is in place for handling your assets, regardless of how much there is. 

Beneficiary Designations 

If you want to leave money to charity or ensure that a specific family heirloom ends with one person, you must designate your chosen beneficiaries. It’s also important to review these plans regularly if a new grandchild arrives or there has been a divorce between one of your children and their spouse. Anything that might impact who is outlined to receive what in a will as a beneficiary should be reviewed at least once or twice a year. 

Protecting Loved Ones

Whether your assets are considerable or comfortable, properly setting up your legacy will protect the ones you love. Clear estate plans can eliminate any need for legal battles between living descendants and ensure peace of mind in your final days, as everything is settled long before you get sick or something else happens. 

The most important thing you want with an estate is to preserve your financial legacy and memory. The last thing anyone wants is to remember you as the source of internal family struggle because the proper paperwork wasn’t filed, leading to family infighting over who deserves what and why. 

Are My Legal and Financial Documents Organized and Up-to-Date? 

Last but not least, the third most crucial game-changing question you need to ask about retirement is all about ensuring everything you have is appropriately organized. This ties closely with the estate and planning, as the more organized everything you own is, the less likely there will be any concerns if you get sick and cannot make health or financial decisions independently. 

Power of Attorney

As part of any will, a power of attorney should be designated to someone who can help manage your finances and major medical decisions. This might be a spouse initially, but should the spouse also be unwell, a child or multiple children might be designated as the power of attorney. There is no understating the importance of having this settled around healthcare, especially if you have specific wishes during emergencies, like a do-not-resuscitate order. 

Retirement Account Records

As part of your retirement planning, organizing every record of the type of financial accounts you have should be mandatory. This includes every 401(k), IRA, annuity, and life insurance documentation. You might consider paper copies available at a lawyer’s office and digital documents with multiple backups. 

Tax Documents

In addition to financial documents, there should also be a file that contains mortgage records, deeds, and up-to-date tax returns. The last thing you want is for your family to fight with a bank or the IRS to get all necessary documents to comply with other legal obligations in the worst-case scenario. 

The most important thing about all of these documents is that you A) can prevent legal complications down the road because the proper documents, like a power of attorney, don’t exist, and B) There is clear documentation outlining exactly what exists regarding retirement accounts so that any will can be appropriately executed regarding asset division. 

Final Thoughts

There is a definite hope that answering these questions will help anyone ease into retirement with a focus on spending the most of their golden years. The last thing anyone wants to do is worry during retirement, so be prepared with these questions before leaving the workforce and just focus on enjoying the easy life. 

 

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