Estate Planning: Lessons from a Loss

Estate planning isn't just about protecting assets after death. It's about taking ownership of how you use your resources during life. It's about providing direction and clarity so your loved ones have confidence in moments of stress, transition, or incapacity.

I've worked in financial planning and wealth management for several years, writing and talking about legacy planning often. I understand it professionally. When my father passed away in October 2024, though, settling his affairs while grieving made the principles I'd taught suddenly personal and real.

In that process, I learned several key lessons worth sharing—some unsurprising, some humbling, all relevant, I believe, for any investor to consider.

I've found that if you ask a roomful of people what the most important estate planning document is, most will say, "a will." It's important to have a will, of course. But for many people, I don't think that answer is quite correct.

For most investors, beneficiary designations are the highest-priority, highest-impact estate instructions. Legally, they come before a will, before a trust, and far before any verbal instructions.

Beneficiary designations directly control the transfer of retirement accounts (401(k)s, IRAs), life insurance policies, annuities, and many financial contracts. They override every other document. If they contradict your will, the beneficiary designation wins.

Asset titling, or how property is owned, comes next in legal priority. Only after these two layers does a will or trust take effect. This means a simple mistake like an outdated beneficiary, a missing contingent, or an account opened years ago and never reviewed, can derail your entire plan.

Get these right first. Confirm them regularly. Ensure they align with the rest of your estate instructions. This is the foundation.

Probate is the court-supervised process for validating a will and settling an estate. Without a will, the court distributes assets according to state intestacy laws—often in ways the deceased never intended. Avoid that scenario at all costs.

But even with a will, probate has drawbacks that families can underestimate, in my experience.

Lack of privacy. Probate makes estate details public. My father owned a property that required probate. I received intrusive calls asking if I was interested in selling, and people drove by the property repeatedly. That visibility is unsettling and, in our situation, unnecessary.

More than a year later, I still receive unsolicited texts and calls from time to time from investors combing through probate filings.

Time. Probate can be slow. Even straightforward cases drag on for months. If any assets fall outside other transfer mechanisms, probate becomes the bottleneck in an otherwise clean estate plan.

There are tools that help bypass probate: beneficiary designations, joint titling, transfer-on-death instructions, and living trusts. If avoiding delays and preserving privacy matters to you or your family, use them.

Revocable living trusts can be a useful tool to help avoid or navigate probate. I've found, though, that investors can misunderstand them, imagining them as only for the wealthy, serving as a sort of "trust fund," or involving complex tax strategies. In reality, a basic revocable living trust can be an effective and often straightforward tool for property transfer.

A revocable living trust allows you to retain full control of assets during life while designating how they'll be distributed at death—without probate. It can be changed anytime. At death, it becomes irrevocable, and your successor trustee executes your instructions.

A living trust:

• Limits or avoids the need for probate
• Preserves privacy
• Serves as a centralized instruction manual
• Coordinates with beneficiary designations
• Can include provisions for minors or complex situations

However, many people skip an important step: They create the trust but never fund it.

Funding means transferring legal title of assets, like real estate, into the trust. Without this step, the trust can't direct those assets at death. They fall back into probate.

This was our biggest mistake. We created a solid living trust for my father but never transferred title of one key property into it. As a result, I've had to initiate probate in his home state and ancillary probate in a second state where the property is located. That process is still unfinished today. It's the final unresolved step of the estate.

The lesson is blunt: A trust is only as good as its funding. Don't skip this step. Don't assume you'll get to it later. Transfer and then verify every title for property you'd like distributed from the trust now.

Most people think about their legacy as something that activates when they're gone. But a legacy can be reinforced as powerfully during life, as it can be after it.

After reviewing my father's financial plan and showing him he had more than enough to maintain his lifestyle and cover potential health care costs through his remaining years, he felt more confident and in control to create a structured gifting plan. He established an annual gifting plan for his eight grandchildren, contributing $18,000 per year per child (at the time, the annual individual gift tax exclusion amount) to 529 education accounts for each grandchild.

But the money wasn't the only point.

The most powerful part, for him and each grandchild, was the personal note he wrote to each of them about how education shaped his life and why he wanted to support their education. The letters mattered as much to my father as the funds themselves.

It was one of the most satisfying decisions I saw him make in his final year. Education was very important to him, and the letters allowed him to express that value directly while he was alive to see the impact.

Many people delay gifting because they fear they won't have enough. That fear is understandable but often unfounded once you analyze the actual numbers.

Gifting is one of the clearest ways to convey values, love, and intention while you're still here to shape the experience.

This is one of the most difficult aspects of estate planning, and often one of the most necessary.

A health care directive defines your wishes if you become unable to make medical decisions. Every hospital will ask for one. Very few people prepare one in advance, and even fewer discuss it openly with their family.

My father, a physician, asked me to make final medical decisions for him when the time came for end-of-life decisions. My brothers are both doctors, but the legal responsibility fell to me. His directive was explicit: no extraordinary measures, no prolonged suffering, no artificial extension of life without meaningful recovery.

When that moment came, having the health care directive in writing certainly mattered. But what was even more meaningful was the conversation that document forced us to have months earlier.

That conversation made the choices clear. It removed doubt. It prevented conflict at the worst possible time.

I am sad about the decisions I had to make, but I do not regret them. I would not have had that clarity without that directive and those conversations.

Everyone needs one of these documents. And everyone needs the conversation that comes with it.

Similarly, a financial power of attorney gives someone the ability to make financial decisions on your behalf, such as depositing and withdrawing money from bank accounts, signing checks, and managing brokerage accounts.

I learned that the power of attorney is helpful during life, but as soon as you inform a financial firm that the person is deceased, the power of attorney expires. The firm turns off access to the deceased's accounts and either begins to follow the beneficiary instructions to distribute the funds or waits for a probate court, executor, or other account or property titling for instructions on what to do next.

Estate planning is where technical precision and human emotion collide most directly.

The "math" of the process is the logic: documents, titling, tax implications, legal structure, asset transfer.

The emotion covers the values: fear, confidence, family dynamics, hopes for the next generation.

Many people focus on the details, avoiding the emotion. A strong estate plan requires both—clear documents and honest conversations. It's not about paperwork. It's about purpose. Losing my father clarified this in a way no professional experience ever did. The technical elements mattered, but the emotional preparation mattered more.

Estate planning is not merely about passing on wealth. It's about passing on clarity, control, and confidence. It's about leaving your family equipped, not overwhelmed. It's about taking ownership and sharing a legacy of values and love to help use your assets wisely during life, and for a legacy as well.