20 Questions to Ask Before Retirement (and Answer)


The thought of retirement can make one excited and anxious. Why have anxiety? Because of the ‘what-ifs’ about the future – the unknowns. You might have questions about retirement and whether it will live up to what you hope for, especially after decades of work.

Now, before you break out the party hats and leave the workplace hustle, make sure that your plan is ready to go. Retirement planning isn’t all about money, although that is a big part of it. Your financial plan should also spell out how you will make the most of your newfound free time. Whether you want to travel, spend time with loved ones, pursue hobbies, relax at your leisure, or do something else, your retirement plan will serve as a roadmap and GPS for keeping things on track.

Here are 20 questions to help ensure you have your retirement ducks in a row. From finances to lifestyle, you can use these questions to frame your overall goals and expectations for your golden years. You have worked hard to reach this point. Now is the time to confirm that you have everything you need to enjoy it fully.

Questions for Retirement Planning

Let’s dive into these 20 questions that will help you navigate that long-anticipated journey into retirement!

1. Will you have enough money for retirement?

Money, money, money. It’s the fuel that keeps your retirement vehicle going. Before you say goodbye to your career, take a good look at your savings, retirement accounts, and investments. Will they be enough to pay for your dream retirement?

If not, you might look at ways to keep working and saving more to reach your goal. Or you might align your goals for retirement more with your current financial situation. No matter what, it’s good to take some time to evaluate this before making any decisions. The follow-up questions that build on this can help bring clarity.

2. What will your lifestyle be in retirement?

Everyone has a certain vision of what they would like for their retirement to be. What does yours look like? Will you travel the world? Venture from state park to state park? Volunteering or enjoying a hobby that you have long favored? Or simply spending some lazy days at home?

If you have a spouse or partner, what are their expectations of retirement? It’s good to have a conversation about their goals for retirement, the timing for that, and what they would like to do. If how you spend your time has been pretty independent until this point, you might talk about how to mesh your lifestyles together. The bottom line? Knowing what you want out of retirement will help you tailor your financial plan to fit your desired lifestyle, like a perfectly tailored suit.

3. Do you want to work in retirement? What will that be like?

Retirement doesn’t have to mean a complete departure from the workforce. Some folks want to stay engaged with part-time work or pursue passion projects. Maybe it’s hard to say goodbye to your specific work that brought you joy and satisfaction. Of course, you might also be up for something different from what you did in your career.

Do you want to start your own business? Pursue consulting opportunities where others can benefit from your knowledge and experience? Stay active in job roles that you had, but in a part-time capacity? Retire for a bit and then unretire? There are many ways in which you can keep a toe in the working world. It’s a matter of deciding whether you still want to work (or if, financially speaking, if you have to), and what type of work would be fulfilling for you.

You can talk to friends and acquaintances that know you about opportunities and things to think about. They can give you feedback based on your skill set and what they know you enjoy (and don’t as much).

4. What are your income needs?

Crunch those numbers! In retirement, income is the most crucial outcome. You have to replace the income that you earned from your career somehow. You have your lifestyle in mind. Now, how much will it cost to fund your desired quality of life in retirement?

Calculate how much income you will need to cover your expenses. First, start with breaking down your expenses into monthly living expenses and non-essential spending. Then, factor in everything, from housing, healthcare, and insurance to leisure activities, entertainment, and charitable goals. Run your income projections for at least a 30-year span. Don’t forget to include inflation, which can be as simple as increasing your expected spending by 2-3% per year.

Knowing your income needs will help you create a solid financial plan for the future. A well-thought-out plan will also give you room to be flexible and adapt if changes are needed over time. Secure tomorrows start today, so carving out time to know your retirement numbers will pay off.

5. How will you spend time in retirement?

Retirement isn’t just about the Benjamins; it’s also about how you will fill your days. Think about the activities and hobbies that bring you joy and fulfillment. Whether it’s traveling, volunteering, or mastering something like scuba diving, having a plan for your time can make retirement that much sweeter.

If you have a general idea of how you would like to spend your time, but not quite so much of a hold on what your weekly schedule might look like, invest some time there, too. Will you want to do anything with your spouse? Will you continue working in some capacity as we discussed earlier? Do you anticipate that you will be spending a lot of time where you live, or will you be on the road for some time with travel?

It’s also good to think about what you would like to do in early retirement versus later years. Some split retirement into three phases: go-go, slow-go, and no-go years. The go-go years are when people’s energy and physical health tend to be strong. So, at that point, they do those long-held goals that will be hard to get around to in later years.

If you aren’t sure about what you would like to pursue, test-drive different possibilities! Try out a particular activity or a certain lifestyle aspect for a week, see how it goes, and evaluate whether you like it. This can be a great way to see how you will enjoy spending your free time in retirement.

6. What will your major sources of retirement income be?

You have a sense of what your income and spending needs will be. From where will you get the money? Social Security? Do you have a pension? Will you count largely on your investments?

Take stock of your primary sources of retirement income. Start with Social Security. According to the Social Security Administration, your benefits payouts are intended to replace 40% of your career income. Of course, that might not apply to everyone. Either way, you still have an income gap to cover.

Depending on how much you have in retirement investments and savings, you can use a variety of withdrawal strategies to ensure your income lasts. If the risk of outliving your money concerns you, you can turn to lifetime income-generating vehicles including annuities to make sure your cash-flow doesn’t run empty. Again, it’s about filling the gap and making sure that your income lasts as long as you need it to.

7. When will you take Social Security, and why?

In many respects, Social Security is the golden ticket of retirement income. But when should you start your benefits? There is no one-size-fits-all answer for everyone, but if you would like to receive 100% of your benefit payout, consider waiting until full retirement age. And if you would your payouts to be bigger and you can wait, delaying until age 70 can let your benefit accrue another 32% roughly.

When does it make sense to claim early or wait? Consider factors like your health, life expectancy, family history, and financial needs when deciding the right time for you. An experienced, retirement-knowledgeable financial professional can also map out different ages for taking Social Security for you – and let you see what those look like.

8. What about risk with your retirement investments?

Risk – it’s a four-letter word that can be a “dealbreaker” for financial security in retirement. When you are in the span of 10 years before and in early retirement, you are in what we call the “retirement risk zone.”

Investment losses during this period can be hard to bounce back from, and if you are taking out money for withdrawals, those losses compound. You might even have to change your long-term goals if you suffer steep losses at the wrong time

On the other hand, you also don’t want to take too little risk, especially if you were behind on saving for retirement, and your investments need to perform well. So, take some time to assess your risk tolerance and also the level of risk in your asset holdings. Does it align with your comfort level? Do you need to take less or more risk?

Generally, the more we move into our retirement years, the more we should put the brakes on investment loss risk. However, this will be different for every person depending on their personal situation, tolerance for risk, financial timeline, and more. The bottom line – it’s all about finding that sweet spot between growth and security.

9. What are your spouse’s or partner’s goals?

Retirement isn’t about flying solo. It’s a team effort. Sit down with your spouse or partner and discuss your retirement goals and aspirations. Understanding each other’s priorities can help you create a retirement plan that works for both of you.

In particular, you may want to talk about how you will spend your free time, if you both have been independent until now. What activities do you enjoy together? What activities do you like to do individually? If you both are independent, how will both of your schedules jive in retirement? Would your spouse like to continue working, and what will that look like? Will their choices affect your retirement goals? These are good questions to consider.

10. How is your health, and what will it look like in retirement?

As the old saying goes, “health is wealth.” Especially in retirement! Take stock of your current health and consider how it might change as you age. It’s also good to think about other factors that can come into play.

To what ages did your parents live? May you face the prospect of a long-time retirement? Or do you expect a shorter retirement span? If they loved for a long time, that means that you may have more years of retirement income to plan for.

Did your parents have any medical conditions that may be prudent to consider? For example, while it’s not a pleasant topic, parental history of heart disease, cancer, dementia, Alzheimer’s, or other conditions is good to think about for health possibilities in your future.

That being said, medical and wellness advances have moved the needle in healthcare. While our family history may be a clue-in to what our future health looks like, it’s no longer sure destiny. You may live longer than you think with those healthcare gains. If you are also mindful about your personal wellness before and in retirement, your health expenses will likely be lower than what they could have been.

And of course, don’t forget to include potential healthcare costs and long-term care needs when planning for retirement.

11. What will your relationships with loved ones, friends, and others be in retirement?

Retirement is a time for nurturing relationships and creating lasting memories. Consider how your relationships with loved ones might evolve in retirement. How will you go through life changes together?

Does your family live near you, or are they some distance away? Do you plan to visit them more frequently? Would you consider moving to be closer to them?

How is your social circle of friends? Do you want to make new friends and peers who are within your age range and have similar interests? How will you seek those opportunities out? Consider possibilities with friends from your workplace, people in your faith community (if you have one), health and well-being groups, social meetups that share your personal interests, causes or organizations that matter to you, and similar groups.

No matter what, prioritizing relationships can enrich your retirement years. Making them a top goal can help bring new, exciting potential and enjoyment to your lifestyle.

12. How will you deal with unexpected financial or life emergencies?

Life is unpredictable, especially in retirement. Prepare for the unexpected by building an emergency fund and having a solid contingency plan in place. Whether it’s a sudden health crisis or a market downturn, having a financial safety net can help you weather the storms of life with confidence.

You can talk to a financial professional for guidance on what a solid emergency fund would look like for you. (More on finding the right financial professional later.)

13. How will inflation affect your retirement finances?

Ah, inflation, a.k.a. the silent thief of retirement income. Inflation is one of a few things that you can’t control, and it does take its toll over time. How will you take heed of the impact of inflation on your money’s purchasing power?

Nothing is ironclad, but you can make a variety of moves to combat the rising cost of living and make your retirement dollars count. First, take inflation into account when planning for retirement. When you have your long-term income and spending projections (again, at least 30 years’ worth, ideally), have your spending rise by 2-3% per year. That is what historical inflation has averaged out to be over the past few decades. It can give an idea of how much money you might need with an increasing cost of living.

As for having inflation-adjusting strategies as part of your overall retirement plan, you can choose from a variety of options. Inflation-protected securities, such as TIPs, can help your money keep up its purchasing power. If having an assured monthly income will bring peace of mind, an annuity can set a floor of guaranteed income that is unchanging. That will pay a baseline income. Then the rest of your assets could be in market-based investments that grow at a pace that keeps up with inflation.

Other options include laddering bonds, CDs, or other financial products used in a diversified fixed-income strategy.

14. What will your plans be if you outlive your retirement money?

Outliving your retirement savings is a fear many retirees face. Some surveys show that people fear running out of money more than public speaking or even death. You can beat back this risk by exploring options like annuities to provide a steady stream of income in your later years.

Another risk is that long-term care and high-cost healthcare will drain your retirement assets. Long-term care insurance, life insurance with living benefits, and other insurance products might be something to look into before you get into later retirement. These options can pay multiples in benefits for each dollar of premium that you put into them.

If you do wind up outliving your money, make a contingency plan in advance. Will you live with adult children? What will that look like, and how will they support you? If that isn’t an option, could you live with close friends? What would living arrangements be? Then take some time to discuss with your family or friends what that might look like, although it’s probably an uncomfortable topic.

The bottom line is that planning for longevity in advance can help you be ready for what lies ahead.

15. What is your plan for taxes in retirement?

Taxes don’t magically disappear in retirement. In fact, they might even increase depending on your income. Develop a tax-efficient withdrawal strategy for your retirement accounts and explore tax-advantaged vehicles to minimize your tax burden in retirement.

There are three accounts that you might pull from in retirement: qualified (pre-tax, principal and gains are taxable), non-qualified (after-tax principal, gains are taxable), and Roth (tax-free). Some other options may also give you potential income tax-free cash-flow. Talk to your tax advisor and an experienced financial professional about what order of accounts can maximize your income net of taxes.

 A little tax planning now can lead to big savings later on. It’s possible that your tax bracket may be lower in retirement than it was during your career. But taxes may well go up due to growing national debt (and financial pressures to pay it off). In your tax planning, you can see if strategies such as Roth conversions and other tax-smart moves make sense for your specific financial situation.

16. What is your plan for taxes in retirement?

Taxes don’t magically disappear in retirement. In fact, they might even increase depending on your income. Develop a tax-efficient withdrawal strategy for your retirement accounts and explore tax-advantaged vehicles to minimize your tax burden in retirement.

There are three accounts that you might pull from in retirement: qualified (pre-tax, principal and gains are taxable), non-qualified (after-tax principal, gains are taxable), and Roth (tax-free). Some other options may also give you potential income tax-free cash-flow. Talk to your tax advisor and an experienced financial professional about what order of accounts can maximize your income net of taxes.

 A little tax planning now can lead to big savings later on. It’s possible that your tax bracket may be lower in retirement than it was during your career. But taxes may well go up due to growing national debt (and financial pressures to pay it off). In your tax planning, you can see if strategies such as Roth conversions and other tax-smart moves make sense for your specific financial situation.

17. Do you want to leave assets to loved ones?

Leaving a legacy is a noble goal for many retirees. Decide whether you want to leave assets to loved ones or charitable organizations. Include your wishes in your estate planning. Whether it’s funding your grandchildren’s education or supporting a cause close to your heart, leaving a lasting impact can be a meaningful part of your retirement legacy.

Make sure that your estate plan leaves ways for your wealth to be passed to your heirs in the most efficient ways possible, including for taxes. Some states also have estate taxes, so keep that in mind as you plan for your legacy wishes.

18. What will you want to happen to your estate when you are no longer here?

Estate planning isn’t the most glamorous part of retirement planning, but it’s oh-so-important. Create a will, establish a power of attorney, and designate beneficiaries for your retirement accounts. If you worry about probate, talk to an estate attorney about what different trusts can do for you.

Planning ahead can spare your loved ones unnecessary stress and uncertainty during an already difficult time. What’s more, you can also help keep over-the-top family drama and conflict to a nil by proactively planning.

19. Have you worked with a financial professional to answer these questions and more?

Retirement planning can be complex, but you don’t have to do it alone. An experienced financial professional can benefit you in multiple ways.

They should know the most important “what-ifs” to work through for your financial situation, saving you time and energy. Their experience in helping other clients navigate the financial pitfalls of retirement can bring assurance in the solutions they recommend to you. They will build a customized plan around your goals, needs, concerns, and financial situation.

They are also your financial quarterback. They can be a coach for you to stick to your plan when times are tough or things go off-kilter. And if you need to pivot or change your plan, your financial professional can give you options for what changes might make sense. In short, they can be your trusted partner on the road to retirement.

Don’t hesitate to explore what a working relationship with the right financial professional can do for you. Even if you have been a DIY investor to date, there are upsides. Retirement and income planning are very different from investment planning. See how they might be able to assist you!

20. Have you considered trade-offs or other possibilities apart from what you have planned?

Flexibility is key when it comes to retirement planning. Be open to exploring alternative strategies and considering trade-offs to achieve your retirement goals. Whether it’s delaying retirement a few years to boost your savings or downsizing your home to free up cash, thinking outside the box can lead to new possibilities and a more secure retirement future.

Working Through Your Retirement What-Ifs for a Bright Future

Retirement may seem like a distant dream, but with careful planning and consideration of these 20 questions, you can turn that dream into a reality. Grab a pen, pour yourself a cup of coffee, and start mapping out your path to retirement bliss. Take some time to work through these questions, how they apply to your situation, and what you can do to make the most of your retirement planning.

Your future self will thank you for it! And remember, you don’t have to go this alone. An experienced and versatile financial professional who understands retirement can help you make some huge gains in your goals and keep you financially on track.

If you are looking for someone to help you, many independent financial professionals are available here at SafeMoney.com. Get started by visiting our “Find a Financial Professional” section, where you can connect with someone directly. If you would like a personal referral for a first appointment, please call us at 877.476.9723.

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