Charting a Course Past Procrastination: From "Homework" to Peace of Mind
By Melinda Gustafson Gervasi
January 9, 2026
There are constants in life. I am not sure who gets more inquiries this time of year, the gym on the lower level of my office building, or my estate planning office. Many people resolve “this is they year I create (or update) my estate plan”. All too often, however, after we sketch out the steps involved over the phone, I hear a familiar refrain: "Well, I guess I have some homework to do."
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| Lecture Hall - University of Wisconsin - Madison campus |
There is usually a chuckle in their voice, but I hear the mental weight of the "To-Do" list settling in. I understand the feeling. Collecting account numbers, tracking down titles, and making life-altering decisions about guardians and executors feels like a daunting project. Sadly, for many, this "homework" becomes a roadblock. Days turn into months, and the plan—the very thing intended to provide security—remains unfinished on a corner of the desk. But estate planning isn't a final exam you have to ace alone; it’s a collaborative roadmap. If you’re feeling stalled by the homework, here are three strategies to help you turn the page and get your plan across the finish line.
The "10-Minute Inventory" Kickstart: Most people procrastinate because they think they need a box full of perfect documentation before they can take the next step. Don't wait for perfection. Spend just 10 minutes jotting down your "Big Three". First: What are the high-level list of what you own (you don't need exact balances today). For example, your home, your retirement account, and your life insurance. Second: Who do you want to protect? This may be your spouse, your child, your parents, your best friend from college who is the sister your never had, or your 3 cats. And third: Who is the first person you’d trust to handle your affairs? Aim for Switzerland in your choice - who is neutral, precise, and efficient.
Prioritize Your "Living Documents": Death is a difficult topic to face, and focusing solely on what happens when you’re gone is a common reason for "homework fatigue." Reframe the project by starting with your Power of Attorney and Healthcare Directives. These aren't about your passing; they are about your life. They ensure that if you are ever incapacitated or unable to speak for yourself, the people you trust are legally empowered to help you. When you view estate planning as "disability insurance for your autonomy," the homework feels much more urgent and personal. If you are alive but too sick to make your health care decisions, who should speak for you? Moreover, if you are living but unable to manage your finances, who do you trust with your checkbook? You do not want a health crisis to spark a financial crisis. Take control and appoint the people appropriate for these roles.
Use a "Life Milestone" Deadline: Open-ended deadlines are the natural enemy of progress. If "someday" is the due date, the work will never get done. Tie your planning to a real-world event on your calendar. Whether it’s an upcoming vacation, a milestone birthday, or a child heading off to college, use that date as your firm deadline. There is a unique sense of relief that comes from boarding a plane or celebrating a birthday knowing that your "legal house" is fully in order. Keep in mind that a quality plan can take several weeks or even months to finalize. Every year, my office receives calls from clients eager to sign a plan 10 days before flying off on an international adventure. At that point, there simply isn't enough time to create an adequate plan. Most often, those best intentions are pushed off to “when I get back” and, unfortunately, stay there.
The only "failing grade" in estate planning is a plan that never gets signed. If your homework is sitting on your nightstand or the corner of your desk, remember: you don't have to do it all at once. It’s a new year, the perfect time to circle back and complete this task.
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