In Arthur Miller’s Pulitzer Prize–winning 1949 play, Death of a Salesman, the central questions of the drama revolve around Willy Loman—a sixty-something salesman—and his sons, Biff and Happy. As the plot develops, we learn that Willy is nearing the end of his life and, apparently, his sanity. He is frustrated that neither of his sons appear to be taking steps toward the goal he has striven for his entire life: the “American Dream”—which remains rather poorly defined, even in Willy’s last days.
As we’ve mentioned before, nothing is more vital to a successful journey than having a good understanding of where you’re trying to go. So, maybe the most important questions you can ask yourself about retirement are those that help you visualize what you want, where you hope to end up.
Of course, depending on your age, your station in life, your experiences, and a host of other variables, the idea of “retirement” can look very different. For someone in mid-career who spends their days raising kids and building professional success, “retirement” may seem like a hazy picture that they’ll start thinking about “someday.” For others, retirement is just whatever you do when you quit working: you work and try to save as much as you can, and then, when you can’t or don’t want to work anymore, you retire.
But retirement doesn’t have to be either a hazy dream or a default that you sort of fall into when you stop working. Retirement can be something you move toward with excitement. It can be the culmination of your own, individual version of the “American Dream.” In order for that to happen, though, you need to have a picture in mind. You need to understand what retirement looks like to you.
Asking the Right Questions
Most of us, when we’re young, instinctively have the right approach to learning about the world: we are curious and ask questions. In fact, anybody who has raised toddlers or pre-teens can probably remember getting frustrated by the never-ending stream of queries: “Why do cats climb trees and dogs don’t?” “How does the heater in the house know when to turn on?” “What’s inside a soccer ball?” The questions kids ask are limited only by their vocabulary and imaginations.
But sometimes, when we get older, we forget how to stay curious and ask the right questions. However, the key to envisioning what a successful, satisfying retirement looks like to you is asking good questions and thinking carefully about the answers. So, imagine that you’re sitting across the desk from me, wanting to figure out a plan to help you prepare for retirement. Here are some of the things we encourage you to think about.
- What is most important to you?
- As you’ve gotten older and more experienced, what things or ideas are most important to you? Why do you think they matter so much? Do you think your attitude toward them could change, either now or when you retire? If not, what do you think you should do to get ready?
- Is there anything about retirement that worries you?
- Why do you think that is? How would your life be different if that fear were eliminated?
- As you think about the time when you aren’t going in to work every day, what would you most like to achieve during that part of your life?
- What is something you’ve always been interested in or wanted to do more of: something that you’d like to do, once you retire? What would it take for you to be able to do that?
- What motivates you the most right now?
- Do you think that will change after you retire? Why do you think that is?
- Can you think of someone whose retirement you really admire, for some reason?
- What about someone whose retirement looks like a failure to you? What are the main differences between the two?
- If you were to close your eyes and imagine what a really good day or week would look like in retirement, what do you see?
- What does a successful week in retirement look like for you? A Month? A Year?
- Who are the people you most want to spend time with in retirement?
- Is there a theme or quality that connects them? Is there anything specifically you want to do with them?
- How would someone you know describe your retirement?
- Imagine that you’re retired, and one of your friends, whom you haven’t seen in a while, asks someone close to you about how things were going in your retirement. What would that person say?
Maybe you’ve noticed something interesting about these questions: they don’t involve money—at least, not directly. Instead, they are more about the “why” of retirement: what it means, what it looks like, how it feels, why it matters. From that perspective, money is a tool—a means to an end, but not the end itself. The mistake too many people make when planning for retirement is focusing always on the tool—the “how”—and not nearly enough on what they want to build—the “why.”
At Curio, our main goal is helping you discover what really matters most to you. We do that by asking questions and encouraging you to do the same. This matters, because only when you—and we—fully understand what your retirement means to you can we help you build the financial infrastructure to make your vision a reality.
To learn more about Curio and our “Curated Curiosity” approach, visit our website to read our article, “Your Fabulous Fifties.”
