Estate Planning Conundrums and How to Make Progress

Many of us know we need to put estate planning documents in place, but time and again, I observe clients having a hard time getting started. It is easy to procrastinate because the process feels overwhelming and emotionally loaded. The decisions feel big. You must choose who will handle your affairs and who will receive your assets. None of this is legal advice, but what follows are the real questions and situations people wrestle with as they work toward an estate plan that feels right.

Choosing Your Executor, Agent, and Trustee

Deciding who should be responsible for carrying out your wishes can be just as much of a roadblock as deciding who gets your stuff. People commonly freeze at this stage because it involves assessing others in sensitive ways. You need someone trustworthy, organized, and willing to take on the responsibility because handling your affairs is real work. I cannot stress that enough.

Consider whether the person has the capacity to handle what can be a multi-year process. Someone who is already stretched thin or dealing with their own challenges might not be the ideal choice. You also want to consider someone who is likely to outlive you and remain capable, so age becomes a factor.

Some families try to assign roles to multiple children so everyone feels involved. This can come from a place of love, but it can also create logistical complications when it’s time to act. It is important to remember that your goal is to create clarity at a difficult time. You do not need to hand out jobs to everyone to avoid hurt feelings. There will be plenty of other opportunities besides being named in a legal document.

Interpreting the language of the legal documents, knowing exactly what to do and when, and the intricacy of your situation should not be underestimated. Be open to the idea of appointing a third party to execute your final instructions. Yes, there is a tradeoff in cost, but a professional executor or trustee can remove emotional strain and reduce the risk of making a mistake, all of which can bring a sense of peace to a family grieving loss or navigating family dynamics.

How to Divide Assets in a Way That Balances Fairness and Equality

Once you move past the structural decisions of who to name as your representative, the next task is determining how to divide what you own. This is often where the concepts of fairness and equality come into conflict. Here are some questions to ask yourself:

How healthy are my family relationships?

Do your children and family generally get along, or is there underlying tension? Does anyone have a sense of entitlement or a habit of keeping score? These dynamics influence how your decisions will be received.

It is important to remember that these are your assets, and no one gets to guilt you into choices that don’t feel right. Even so, you may worry about what your choices might trigger. A child who receives more may feel guilty. A child who receives less may feel resentful. Being concerned about this is human and common.

Is equal always equal?

Many parents lean toward equal division because it feels objective and simple. Yet is equality always the right choice?

• One child may be far better off financially than another.

• A family member with a medical condition or special need may require support to ensure quality of life over the long term.

• One may have received significantly more help during your lifetime, perhaps to start a business, buy a house, or cover college.

In these and other situations, an equal split might not reflect real life.

What if I have a blended family?

Blended families add a layer of special consideration. People often want to provide for a surviving spouse while also ensuring that their own children eventually inherit their remaining estate. Structuring an estate plan for a blended family requires careful coordination. The best outcome will be achieved when both partners are on the same page, and transparency is essential.

What about misbehavior?

Parents struggle with what to do when a child is struggling with addiction, poor spending habits, or other risky behaviors. In these cases, a trust structure can protect the child from themselves and protect the assets from quick depletion.

What if one kid supported me?

If a child supported you financially or with day-to-day care, you likely want to make them whole. In my own family, my mom wrote into her trust that the siblings who provided for her would be paid back first with interest. That felt right to her, and it worked well because none of us felt entitled.

What about others?

Your estate plan doesn’t have to be limited to family. Charities and causes you care about should be part of the conversation. Charitable gifts can be structured in flexible ways, such as a fixed amount, a percentage of what is left, or naming a charity as a contingent beneficiary.

A Framework to Get Started

Here’s a plan you can use to help you move through the process.

1. Get aligned with your spouse. Share why planning matters to you and listen to what is important to them.

2. Find the right attorney. Choose someone who specializes in situations like yours. As your financial advisor, we can help point you toward a good fit.

3. List your assets. This is strictly a numbers thing, but don’t aim for perfection. Note ownership and beneficiaries. The goal is to give your attorney information to recommend the right plan.

4. Choose your executor, agent, and trustee. Get a top candidate list going. Literally write it down. Refine as you have conversations. Using the same person throughout could streamline your plan.

5. Consider your powers of attorney. Decide whether they should be effective now or only if you become incapacitated. This also includes decisions about whether quality, comfort, or length of life is more important.

6. Communicate with everyone involved. This will avoid surprises and reduce the chance of misunderstandings. You probably would not want to be chosen for handling a huge responsibility and only find out when someone dies.

A couple of other tips:

Do not overthink decisions at this initial stage. Give your attorney your best preliminary answers. You can easily revise anything before signing your documents (don’t forget this critical step) and even afterward through amendments.

Avoid micromanaging personal items. Don’t get too meticulous with bequeathing your stuff. Most people don’t find your stuff as valuable as you do. If you really want someone specific to get something, talk to them ahead of time.

Follow Through

Estate planning brings up practical questions and emotional reactions. Progress begins with first steps, honest conversations, and a willingness to keep the process moving, even though you’re not always excited about it. It’s one of the most loving gifts you can leave behind.

A financial advisor who stays involved throughout the process can add real value. Estate planning support reflects a deeper level of service that goes far beyond monitoring an investment account.