The Hidden Costs of Doing Nothing: Why Waiting to Plan Could Cost Your Family Everything

by | Jan 5, 2026 | Aging Parents, Elder Care Advising

Why Waiting to Plan Is So Costly

  • Delaying estate and elder care planning almost always leads to higher taxes, legal fees, family conflict, and emotional stress.
  • High-profile cases like Prince, Aretha Franklin, and Stan Lee show how even wealthy, successful people can leave chaotic legacies.
  • A simple Will is a start, but often not enough: Powers of Attorney, medical directives, and sometimes Trusts are critical.
  • Under-preparing can force the sale of family property and permanently damage sibling relationships.
  • Our free workshop, Planning to Age: What Every Family Needs to Know BEFORE a Health Crisis, walks you step by step through what to put in place and when.

Table of Contents

Why Waiting Is So Dangerous

I think most of us had teachers with posters or signs near their desks that read, “Failing to prepare is preparing to fail.” And they’d point to it every time a student complained about a bad grade they had earned, reminding them that their discomfort was a direct result of their failure to plan.

Estate planning works the same way. Failing to plan—or even delaying—eventually catches up with us and our loved ones. What feels like “I’ll get to it later” can quickly turn into:

  • Expensive court battles and legal fees
  • Unnecessary taxes and delays in inheritance
  • Confusion about your wishes
  • Family conflict that sometimes never heals

Our newest free workshop, Planning to Age: What Every Family Needs to Know BEFORE a Health Crisis, is designed to walk you through the steps necessary to plan for your family’s future.

But is planning really that important? What actually happens if we don’t?

Let’s look at a few real stories that show how waiting to plan for your financial future can cost your loved ones almost everything.

When No One Plans

Prince: No Will, No Plan

When famous musician Prince died unexpectedly, he left no clear plan for the distribution of his estimated $156 million estate. His six half-siblings were declared his heirs, but two of them died before the probate process was resolved.

In the end, after losing tens of millions of dollars to taxes and legal fees, half of what was left went to three of his siblings, and the other half went to a music publishing company.

After six years of court battles, the advisor to the three beneficiaries said he was, “relieved and thrilled to finally be done with the Probate Court system and bankers who do not know the music business and did not know Prince.”[1]

Key lesson: Dying without a Will can cost your loved ones a huge portion of their inheritance in taxes and legal fees, and it hands control of your legacy to courts, creditors, and, sometimes, strangers.

Aretha Franklin: Two Wills, Twice the Confusion

When singer Aretha Franklin died, it seemed as if she, like Prince, had failed to plan for her assets. About a year later, her children discovered two different handwritten Wills hidden in her home.

Her sons disagreed about which Will should control the estate. The tension became so intense that her executor—who was also her niece—walked away from the job after one year, saying, “Given my aunt’s love of family and desire for privacy, this is not what she would have wanted for us, nor is it what I want.”[2]

Key lesson: Dying with a confusing, handwritten Will can create years of conflict, public court battles, and deep rifts in family relationships.

The Solution: Make a Plan

A well-written, legally binding Will should be the bare minimum when it comes to planning for the future. It doesn’t have to be complicated, but it does need to be clear, valid in your state, and actually signed.

Step-by-step: Getting Your Basic Plan in Place

  1. Meet with an estate planning attorney. They’ll help you understand what documents you need for your situation, not just a one-size-fits-all form.
  2. Draft a Will that fits your finances and your wishes. This includes naming who should receive what, who will serve as executor, and who will care for minor children, if you have them.
  3. Review beneficiary designations. Make sure your retirement accounts and life insurance policies name the right people—and that those designations match your Will.
  4. Store documents safely. Let your executor or a trusted family member know where your Will and key information can be found.

If you don’t have a relationship with an attorney, take advantage of free workshops to help you find one you trust and think you’ll work well with.

And remember: It’s never “too early” to plan. Prince died at 57.

When the Basic Plan Isn’t Enough

Stan Lee: Protect What’s Yours

Marvel creator Stan Lee created an extensive plan for his estimated $50–70 million estate. On paper, it looked thorough. But he left the management of his finances to his wife, who died in 2017.

After her death, his agent allegedly coerced Stan into giving him Power of Attorney, then misappropriated millions of dollars. Lee accused him of elder abuse. The lawsuits dragged on for years. After his death, Lee’s daughter inherited what was left of his estate, but continued pursuing lawsuits, saying she wanted “everything that’s mine.”[3]

Key lesson: Even a detailed estate plan can fall apart if you don’t plan for elder care, incapacity, and protections against financial exploitation.

Closer to Home: Selling the Farm

A close friend of mine saw this play out in his own family. His mother passed away with a basic Will in place, but:

  • She left no instructions for her burial.
  • She hadn’t planned ahead for taxes and expenses on her 200+ acre farm.
  • She named my friend and his sibling as co-executors, assuming they would “just work it out.”

They didn’t. The stress of making decisions in grief, combined with unexpected costs, created deep conflict. In the end, they had to sell the family farm to pay for her funeral and estate taxes. Decades later, my friend and his sibling still don’t speak. The loss of the farm—and the relationship—is still a source of sorrow for him 30 years later.

Key lesson: Underpreparing for the inheritance process can lead to severed relationships and the loss of cherished family property, even when a “simple Will” exists.

A well-written Will is a great place to start. But for many families, it’s not comprehensive enough.

The Solution: Make a Comprehensive Plan

A well-written will is a great place to start. But for many families, it’s not comprehensive enough.

What A Comprehensive Plan Should Include

  1. Clear, updated Will or Trust. Especially if you have real estate, blended families, a business, or specific goals for how and when children or grandchildren inherit.
  2. Financial Powers of Attorney. So someone you trust can manage your finances if you are incapacitated—and so the wrong person cannot step in and take over.
  3. Medical Powers of Attorney and advance directives. So your medical wishes are honored, and your family isn’t left guessing in a crisis.
  4. Thoughtful executor and trustee choices. One person, or a clear structure, not an accidental recipe for sibling conflict.
  5. Plans for major assets. Family homes, farms, or businesses often need extra planning if you want to avoid forced sales.
  6. Regular reviews. Update your plan after major life events: births, deaths, divorce, remarriage, selling a business, or moving states.

How Our “Planning to Age” Workshop Helps

Our newest workshop, Planning to Age: What Every Family Needs to Know BEFORE a Health Crisis, is the perfect introduction to comprehensive estate planning and to our family here at Edwards Group.

In this free session, we’ll help you:

  • Understand the difference between a basic Will and a comprehensive plan
  • Spot the gaps in your current planning (or lack of planning)
  • Learn how Powers of Attorney and medical directives actually work in real life
  • See when a Trust may be better than a Will for your situation
  • Know what to do this year to protect your family from a future health crisis

We encourage you to bring your questions. This is an educational workshop, so no high-pressure sales, just clear explanations and practical next steps.

Frequently Asked Questions

1. When should I start estate planning?

Most people should have at least a basic Will and Powers of Attorney by the time they own a home, have children, or have any savings or retirement accounts. You don’t have to be “old” or “wealthy” to need a plan. The earlier you start, the easier it is to update over time.

2. Is a handwritten Will ever a good idea?

Some states recognize handwritten (holographic) Wills, but they’re often unclear, incomplete, or easier to challenge in court. As Aretha Franklin’s case shows, multiple handwritten Wills can create years of confusion and conflict. A professionally drafted, properly signed Will is far safer.

3. Do I really need more than a simple Will?

It depends on your situation. If you own real estate, have a blended family, run a business, or want to control how and when heirs receive their inheritance, you probably need more than a one-page Will. Powers of Attorney, medical directives, and a Trust give much stronger protection.

4. What happens if I become incapacitated without Powers of Attorney?

If you can’t make decisions and you haven’t named trusted agents through financial and medical Powers of Attorney, your family may need to go to court to appoint a guardian or conservator. That process can be slow, expensive, and emotionally draining—and the court might appoint someone you never would have chosen.

5. How often should I update my estate plan?

Review your plan every few years, and definitely after major life changes: marriage, divorce, birth or adoption of a child or grandchild, death of a spouse or heir, a significant change in health, selling a business, or moving to a new state.

6. What’s the difference between a Will and a Trust?

A Will directs how your assets are distributed after your death and typically goes through probate. A Living Trust holds assets during your lifetime and can help avoid probate, provide more privacy, and offer more control over how and when assets pass to your beneficiaries. An attorney can help you decide what fits your goals.

7. How can I get started if I feel overwhelmed?

You don’t have to figure everything out at once. Start with education. Attend a workshop, read a basic guide, and then meet with an attorney who will walk you through your options. Our Planning to Age workshop was created specifically to make this first step less intimidating.

Sources and Further Reading