10 Financial Questions Everyone Over 60 Should Ask

10 Financial Questions Everyone Over 60 Should Ask

September 1, 2020 All Articles Healthcare Investments Retirement Taxes 0

Did you realize that reactive and creative are an anagram? We’ve realized that far too many people fail to ask the “right” questions regarding their unique situations. The result: reactive. We encourage you to spend a little time being creative so you don’t have to be reactive. You can begin by asking these 10 questions:

  1. When do I begin taking social security? Sadly, there is no stock answer – but be aware that by being off by one year could mean 6 figures of benefits lost! There are many variables and strategies behind Social Security and you need to ask questions. Taking it at 62, like most people choose to do, is usually not the best answer. Good news: We have a Social Security calculator to help assess your unique situation with all the variables and assist you in making an educated decision.
  2. How do I battle rising healthcare costs? There are 10,000 baby boomers turning 65 every day…so it’s no wonder healthcare costs are on the rise. And by 2030, all of them will have reached that magical age. Did you know it is estimated that the average boomer will spend $295,000 on out-of-pocket healthcare costs? Is your plan prepared? Over 60% of people believe this doesn’t apply to them! 2.   A good friend of mine with cancer once said, “you don’t have anything if you don’t have your health.” This won’t be an optional expense.
  3. What does it take to be comfortable in retirement? “Comfortable” is different for everyone, but results in the same thing – how you sleep at night. I think we’ve all spent enough sleepiness nights raising our kids or being stressed at work, and don’t need or want any more. Unfortunately, there is no denying that we live in an uncertain economy and governments around the world are changing. Does it or could it cause you unrest? Have you stress tested your retirement plan?
  4. How do I protect my assets? We used to say there were 3 thieves after your money – Uncle Sam, Lawsuits, and You. Today, it’s more like seven! How about taking care of your aging parents and/or your adult kids who are struggling in this economy? We already talked about health care. But, what about who you can trust if your health begins to fail you? And last, but certainly not least, re-marriage…touchy subject, but a BIG one!
  5. How do I combat increasing taxes? Historically, when people retire they pay less in taxes. Their income is lower and not all taxable. However, and a big however, our tax system is rapidly evolving. We are an aging country with a lot of debt. The chance of your taxes staying status quo or going down is slim. Every plan should have tax diversification. Tax you will pay now, tax you will pay later, and tax you will pay never. And most import: you need to make sure you will only pay tax once, not twice, three times or more – as most retirees do.
  6. How much money can I afford to lose with my investments…aka- how much risk should I take? Could you afford to lose income during retirement? My bet is no. But taking no risk really is a risk. Think about this. They used to call Wal-Mart the “century store.” This was because every time you went you dropped a $100 bill on goods. Your cart was loaded, but you still paid $100. When was the last time that your cart was loaded with $100 worth of groceries? I can’t remember. Now imagine you only had $100 to spend. What are you willing to put back on the shelf? Your investments need to keep you sleeping at night, but they also need to be funding your future grocery bill. There is a fine line to walk for the solution to this question.
  7. What will inflation do to my lifestyle? The government tells us inflation has been 1.76% on average since These are currently favorable times regarding inflation, as they are much lower than the historical norm. The problem is that no matter where inflation rates fall, CD rates are most likely lower. Since 2010, one-year CD’s peaked at 0.91%. Worse, that was in 2010. Even three-year CD’s didn’t overcome inflation. They also peaked in 2010 at 1.64%.3. Even worse, this doesn’t take into consideration what taxes would do to your CD return. If you were in the 24% tax bracket, this 1.64% turns into a whopping 1.25% return.  What does all of this mean? Simply put, if you don’t try to outpace inflation, you will spend more than you’re earning and you will eventually go broke safely.
  8. What will I do if I live longer than I expect? I have decided the most sought after tool in our business is a crystal ball. Too bad there isn’t one. Can you really put an expiration date on your life? Yet at the same time, it’s not financially feasible to plan for eternity. So how do you plan for both?
  9. How will my spouse be taken care of when I die? Many people do not realize that a surviving spouse will lose, on average, 33% of their household Social Security income at the death off a spouse. To make matters worse, the surviving spouse will also be filing as single on their tax return, which can have a severe impact on taxes. This is not to mention other planning concerns that may already exist, such as a single life pension that the surviving spouse will not receive.
  10. What are the questions I don’t know to ask that I should ask? Everyone’s situation is unique, which means you can’t cookie cut planning. Yale and Oxford’s Future of Humanity Institute polled hundreds of industry leaders in artificial intelligence. Their goal was to gather a consensus of when artificial intelligence will be as smart or smarter than the human mind. The answer: 2060. So, until you have your own robot to quiz you, this will be the wisest question you can ask about your future.


If you are 60 or older, there is a very good chance that retirement – or something like it – has crossed your mind. Whether it has or hasn’t, and you want to or you don’t want to retire, the end result is the same.  You need to plan for this period of your life. So, which word do you choose? Reactive or Creative….


  1. https://www.fidelity.com/viewpoints/personal-finance/plan-for-rising-health-care-costs
  2. https://www.cnbc.com/2019/04/09/baby-boomers-face-retirement-crisis-little-savings-high-health-costs-and-unrealistic-expectations.html#:~:text=The%20average%20amount%20spent%20by,than%20that%20to%20live%20on.
  3. https://www.nerdwallet.com/article/banking/historical-cd-rates
  4. https://www.inc.com/kevin-j-ryan/elon-musk-and-350-experts-revealed-when-ai-will-overtake-humans.html


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