Questions That Can Help You Make Better Retirement Decisions

William Lloyd
4 min readApr 20, 2022

You face a series of key decisions as you approach retirement, as well as shortly after you retire, that are typically more complex and have larger stakes than the saving and investment decisions you had to make throughout your working years. You have a better chance of making the proper decisions if you ask questions of yourself and people with hard-won life experience.

In this article, we explore a number of important questions to consider in the evaluation process.

Question 1: What would you consider to be a successful retirement?

Question 2: How would you spend a “ordinary day” in retirement if you weren’t completing things on your bucket list?

Question 3: What’s on your “bucket list” to do after you retire?

Question 4: How did you (or will you) decide when to retire?

There’s evidence that asking these questions is important: you’re more likely to make better decisions if you’re emotionally invested in tackling potentially difficult retirement decisions. When to retire, when to claim Social Security, how to invest your retirement money, and whether to relocate to a place or property that better supports your retirement life are all examples of potentially difficult decisions.

These questions are meant to help you imagine yourself in retirement. This can motivate you to devote the time necessary to figure out how to fund the retirement lifestyle you desire.

Below are a few more questions to consider:

What’s the Grand Plan?

When they retire, some people dream of buying a boat, while others choose to spend their days on the golf course. Others desire to tour the globe. You need a goal before you get too far ahead of yourself in thinking about how you’ll save for retirement. As a result, deciding what you want to do in retirement is critical. You can start making your dream a reality once you know what it is.

For example, if your desire is to wake up every morning and play golf all day, you should research what it takes to join a club (some charge significant upfront costs) and whether the area you live in-or want to live in-has sufficient golf courses.

Similarly, if you want to explore the world, you’ll want to live near an airport (or seaport if you prefer to cruise). You’ll also want to make sure there aren’t any additional roadblocks in the way of your plans. You may mold the rest of your plans to make your dream retirement life a reality by determining what you want to do after you retire.

Do You Have the Cash?

It’s fantastic to have goals, desires, and ambitions, but they mean nothing if you don’t have the financial resources to realize them. Rather than hoping for the best, do some soul-searching to figure out what your future expenses will be and whether you’ll be able to live comfortably and enjoy your retirement years.

For decades, financial planners have debated how much money the average person or couple requires in retirement. According to some estimates, you’ll need 60 percent to 80 percent of your pre-retirement salary per year to maintain your lifestyle. However, many of those projections are just that: projections.

The objective is to do some research if your retirement aim is to tour the world. Calculate the cost and be sure you’ll have enough money to live your aspirations (and pay your debts) for the rest of your life. To make it work, you might need to adjust your dreams or cut back on your spending in other areas.

Do You Need a Better Place to Live?

People tend to live in more metropolitan regions when they are young and working. Seniors, on the other hand, sometimes find it extremely expensive to live in or near big cities. People who plan to retire in the next several years should therefore consider relocating to a more affordable region. There are numerous options available, but how can you analyze them all?

When looking for a new home, there are several variables to consider. For instance:

  • Proximity to family members
  • The cost of housing (and owning versus renting)
  • Access to healthcare facilities
  • Access to entertainment (such as shows and sporting events)
  • Proximity to a major airport
  • Year-round weather conditions
  • Taxes (state income, property, and estate taxes)

    It is almost impossible to find a location that fits every need, so the best strategy is to settle on an area that meets the bulk of your needs, particularly those related to long-term health and well-being.

Have You Made an Estate Plan?

It seems sense to perform some estate planning to guarantee that your assets are appropriately transmitted to your heirs and to reduce estate taxes. As unpleasant (and tedious) as the concept may be, it’s critical to sit down with your attorney and accountant to figure out the most cost-effective way for your estate to be handed to beneficiaries after you die.

To begin, you need a will. But that could only be the beginning. Setting up a trust and/or custodial funds for children or grandchildren may be the best option.

Do You Have a Personal Plan?

As you approach the risks of advanced age, take some time to plan for your own care — and that of your partner, if you’re married. Make healthcare proxies, powers of attorney, and other forms well in advance of when you may need them, so you can think about your needs and preferences.

Don’t put off making these important decisions until an emergency strikes, when your energy and abilities may be limited. Others may make decisions that are not in line with your preferences. Make sure you’re first in line and that you make your own decisions.