Questions to Help You Start Planning for Retirement

One day, Herman Heyn’s 8^th grade teacher drew the Big Dipper on the blackboard. She told the class: “Go find it.” That moment instilled passion for astronomy in Mr. Heyn. He wanted to become a scientist when he grew up.

Unfortunately, learning disabilities prevented him from achieving his dream. Instead, he jumped from job to job, never staying in one place longer than three years. Yet, his passion for the stars never faded.  

Then one fateful evening in Baltimore with a clear night sky overhead, Mr. Heyn decided to lug his telescope down to a street corner and invite people to check out the moon and distant planets. He also brought along his hat – just to see what would happen.

That night, he made $10. The following night, he made $40. Besides the money, he gained something more valuable: his true calling. For the next 27 years, he practiced street astronomy, earning the affectionate title of “star hustler.”

The story of Mr. Heyn is one of many produced by StoryCorps, an organization whose mission is to “preserve and share humanity’s stories in order to build connections between people and create a more just and compassionate world.” The recorded stories are inspiring, harrowing and often entertaining, exploring themes ranging from love to war to work. (If you’re an avid NPR listener, then you’ve likely heard these stories air every Friday.)

Mr. Heyn’s story and the StoryCorps mission exemplifies an important part of planning for retirement: the act of discovery. For many people, their careers are far removed from their passions. Therefore, retirement becomes the opportunity to pursue one’s passions.

The challenge is discovering your calling, or rather, your ideal retirement.

Of course, you should simply start saving for retirement as soon as possible. But, without personal goals or dreams in mind, how can you know if you’re making the right financial decisions to live the retirement you want?

To find an answer, you should actually ask yourself many questions. A neat feature is the StoryCorps Question Generator, developed to help aspiring oral historians start conversations. Many of the questions found here are applicable to retirement planning.

Here are some that we think will help you find your calling in retirement:

• What was the happiest moment of your life? The saddest?
• Who has been the biggest influence on your life? What lessons did that person teach you?
• What are the most important lessons you’ve learned in life?
• What are you proudest of?
• If you could hold on to one memory from your life forever, what would that be?
• How has your life been different than what you’d imagined?
• How would you like to be remembered?
• Do you have any regrets?
• What does your future hold?
• What did you think you were going to be when you grew up?
• What did you want to be when you grew up?
• If you could do anything now, what would you do? Why?

Asking yourself personal questions is a crucial part of planning for retirement. When you can visualize your future, you’re better able to determine what specific financial steps you need to take to get there. How much you need to save. How many more years you need to work. Whether you need to save more. What investment strategy makes most sense for you.

The sooner you start and the more time you dedicated to planning your retirement, the less financial headaches and more likely you’ll achieve your financial goals.

The mark of a qualified financial adviser – and an important principle of our firm – is the effort to ask questions. At Advance Capital, our goal is to get to know our clients as well as possible so that we may best help them make the right financial decisions for their personal situation.

If you want to start planning for retirement, take some time to consider the questions above. Or, answer Advance Capital’s Dream Questionnaire that is designed to help you explore your dreams for retirement. Your results will be conveniently emailed to your inbox and you can have a financial adviser contact you to help create a roadmap toward your ideal retirement.