The author suggests that when it comes to retirement decisions, we may not be asking the right questions.

As the Jodie Foster character in True Detective likes to say, “You’re not asking the right question.” Then for a successful retirement, what is the right question? It’s “Do the decisions I make now matter?” Clearly the answer is “Yes” when we think of ourselves and our impact on our immediate environment and in our immediate time frame. But that doesn’t reveal much so our next question then is “What are the right decisions?”

That’s still not the right question. In this case, the right questions have to be much more specific. It might be, “Is the reason I’m not sleeping well because I’m not comfortable with my current investment strategy?” That can certainly lead you down the path to actually determining whether your finances or housing are keeping you up at night. And it will likely lead you to analyzing your finances and evaluating your financial advisor.

Let’s continue on this journey of determining the right questions to ask.

We start with looking at your life now: What are you least happy about? If the answer has anything to do with your future, read on.

Asking the Right Questions

  1. Whether you’re retired or still working, and barring something catastrophic, do you think you’ll have enough money for the rest of your life? If so, congratulations. But the next question is, are you spending enough time and money now so that you can enjoy your life more? What could you do and what could you spend more money on that would improve your quality of life without jeopardizing the certainty of having enough? What about your time? Could you spend more time doing what you like without affecting your life?
  2. If you don’t think you’ll have enough money, what changes could you make that would alter that? Could you work more, have a side hustle, or invest better? Could you reduce your expenditures without harming your quality of life? What could you do without? Should you seek advice from a professional?
  3. How’s your health and physical activity? If you’re relatively healthy, aside from the normal aches and pains, are you physically active? Is that something you enjoy or, at least, get satisfaction from? If you’re into some sports activity, could you increase the number of hours or days that you play without jeopardizing either your health, relationships, or finances? Do your hobbies and/or outside activities take up about the right amount of time?
  4. How’s your social life? Do you have friends with whom you get together and enjoy each other’s company? Is the time you spend on social activity and time by yourself or with your family at about the right balance? What would it take to get it more in line with what’s comfortable for you?
  5. Do you like where you live? Is your house the right size and location, the right number of floors, and are you near your loved ones and friends? If not, does the idea of moving make you run and hide in your closet? Is there someplace you’d rather live? Have you spent much time there beyond a vacation? Does your partner feel the same?

Of course the questions are limitless. But the exercise of asking more and more questions, as Jodie Foster’s character figured out, helps you narrow down the possible solutions. Or, at the very least, leads you to determining the right questions.

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