5 Emotional Roadblocks that Could Halt a Successful Estate Plan

07/11/2024 12:01 PM By Mike Halper, CFP®, MPAS®, SE-AWMA®, CDAA, CBDA

You’d be hard-pressed to find any family that would rather sit around the table discussing estate plans than going out to eat, enjoy the day outside, or doing just about any other activity as a family. No one likes to think about our inevitable mortality, but we all know that it is just that — inevitable. Estate planning can be an immense blessing to any family at a time of great loss. Below, we discuss five of the most common emotional blocks family members face when trying to establish a successful estate plan.

Roadblock #1: Discussing Death

Talking about one’s own mortality isn’t a particularly fun thing to do, especially in the company of a partner, spouse, children, or grandchildren. But the reality is, not discussing it doesn’t keep it from happening. Instead of trying to sit down and talk about your future death with your family, try to use gentler terms like “when I’m gone” or “once you’re on your own.” Finding other, softer ways to frame it can help you and your loved ones move past the negative feelings and on to thinking about the next steps and how to move forward efficiently.

Practical Steps:

      • Set a Comfortable Setting: Choose a calm and comfortable setting for these discussions, such as during a family meal at home.
      • Use Positive Language: Emphasize the positive outcomes, such as ensuring family security and fulfilling personal wishes.

Roadblock #2: Assessing Assets

In order to craft a successful estate plan, you need to account for every asset. And if you’re well established and have lived a long life, you’ve likely accumulated quite an estate. It can be overwhelming to think about assessing each and every account, property, car, painting, piece of jewelry and more — so overwhelming, in fact, that you find yourself putting it off altogether.

If you’re able, work together with your spouse or a loved one to start two lists: financial and physical. As you think of things you own, start jotting them down in their appropriate category. Once you have a fair amount listed out, you can begin working on the next set of details: breaking the categories down into smaller, more specific subsections, listing the prices or values and thinking about who you’d like to have what. Move through this process one small step at a time to help reduce the feeling of being overwhelmed while still making progress toward your estate plan.

Practical Steps

      • Start Simple: Begin with a broad list and gradually add details. Use two main categories: financial and physical assets.
      • Break It Down: Divide these categories into smaller subsections. For example, under financial assets, list bank accounts, investments, and insurance policies.
      • Use Tools: Consider using online tools or software designed for asset tracking.

Example: One couple started by listing their main assets during a weekend, then spent the following weekends adding more details and assigning approximate values. This step-by-step approach made the process less daunting.


Roadblock #3: Working With a Lawyer

This is one roadblock you may not have even realized even existed — working together with a lawyer. If you’ve worked with a trusted attorney in the past, this may not be an issue for you. For those who need to work with a lawyer for the first time, the search can be intimidating, nerve-wracking and confusing. Estate plans can be complex, and you need to make sure you’re drafting one that offers tax benefits for your loved ones and protection for the things you love.

If you’re apprehensive about hiring an attorney, asking friends and family or other trusted professionals for referrals may be a reassuring step in the right direction. And if you find one who isn’t listening, speaking over your head, or you just have a bad feeling about them, don’t be scared to pick up your things and go. Developing an estate plan that addresses your needs and concerns is far too important to settle with the wrong professional.

Practical Steps

      • Ask for Referrals: Seek recommendations from friends, family, or other trusted professionals.
      • Conduct Interviews: Interview a few attorneys to find one who listens well and explains things clearly.
      • Trust Your Instincts: If an attorney makes you uncomfortable or isn’t meeting your needs, don’t hesitate to look elsewhere.

Example: A friend referred Susan to a highly recommended estate lawyer. During their first meeting, the lawyer’s clear explanations and empathetic approach reassured Susan, confirming she had found the right professional.


Roadblock #4: Deciding Who Gets What

Uncomfortable truths can start to surface when you begin thinking about who should be left with what. Even happy parents and kids with no family issues need to be realistic about the future — what’s the likelihood the widow will remarry, what happens if a child dies unexpectedly, what if there’s a divorce in the family, etc. And things can get even harder to discuss for families who may be struggling. Do you leave the child who's battling addiction a large sum of money, or do you give the majority of your wealth to your more stable child? If things have gotten rocky between you and a loved one, do you disinherit them altogether? There’s no shortage of emotional decisions to be made around who should get what, but you can’t let that stop you from pushing forward in determining who will receive what in the event of your passing — or else you may lose control of who receives what altogether.

Practical Steps

      • Open Conversations: Have open discussions with family members to understand their needs and expectations.
      • Seek Professional Advice: Consult with your lawyer about setting up trusts or stipulations that can address specific concerns, like addiction.
      • Document Decisions: Clearly document your decisions to prevent misunderstandings or disputes later on.

Example: John and Mary used a family meeting to explain their decisions and the reasoning behind them, ensuring transparency and understanding among their children.


Roadblock #5: Paying For an Estate Plan

Establishing a successful estate plan doesn’t come cheap. But if that’s keeping you from creating one, it may help to think of it as establishing a legacy for your family and leaving a gift to your beneficiaries. Taking the time to work with a professional now can help save your family members from costly tax obligations or other fees associated with dividing up your property. 

Practical Steps

      • Budgeting: Include estate planning in your financial planning budget.
      • View as an Investment: Consider the long-term benefits and potential savings from reducing tax burdens and legal fees for your heirs.

Example: Sarah saw the upfront cost of her estate plan as an investment in her family’s future, ensuring they wouldn’t face unnecessary financial or legal challenges.


Discussing an estate plan is no walk in the park, but it may be easier to address when you think about what it truly is — the gift of passing on a legacy in a tax-efficient manner to your loved ones. Take your time working through the emotional roadblocks discussed above, and keep moving forward in developing a successful estate plan now to protect your family in the future. By addressing these emotional roadblocks with practical steps, you can make the estate planning process more manageable and ensure that your wishes are honored and your family is protected.

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This content is developed from sources believed to be providing accurate information. The information in this material is not intended as investment, tax, or legal advice. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. The opinions expressed and material provided are for general information, and should not be considered a solicitation for the purchase or sale of any security. Digital assets and cryptocurrencies are highly volatile and could present an increased risk to an investors portfolio. The future of digital assets and cryptocurrencies is uncertain and highly speculative and should be considered only by investors willing and able to take on the risk and potentially endure substantial loss. Nothing in this content is to be considered advice to purchase or invest in digital assets or cryptocurrencies.





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