From the Slopes to the Settlements: Why Estate Planning Requires More than Math

Being open to trying new things is essential for personal and professional growth. New experiences challenge our assumptions, expand our perspectives, and often reveal strengths we didn’t know we had. This year I opted to challenge myself to try downhill skiing. I signed up for lessons knowing I’d need someone to guide me through the basics. Following my lesson, I stood at the top of the slope, albeit the smallest slope offered at the resort. The crisp winter air filled my lungs, but my breath came short, jagged. Kids half my size zipped past, their confidence mocking my nerves.

“Just lean forward and let gravity do the work,” my instructor had said. Gravity? I trusted gravity too well—that was the problem. With a deep breath, I pushed off. Immediately, my knees wobbled, my balance teetered. Then—disaster. A rogue bump, a miscalculated shift, and suddenly I was airborne. For one brief moment, I felt like I was flying. Then, I was tumbling, limbs tangled, snow flying, a ski detaching like it couldn’t get away from me fast enough. I came to a stop in a heap. Silence, except for my own ragged breathing. Then laughter—mine, breathless and relieved. Bruised but not broken. I sat up, shaking snow from my jacket, and looked back up the slope.

“Okay,” I muttered, retrieving my ski. “Time for round two!”

Stepping outside our comfort zone, whether on the slopes or in life’s bigger challenges, teaches us resilience and adaptability. Just as my first attempt at skiing showed me that falling isn’t failure but part of the learning process, navigating complex situations—like estate planning—requires a willingness to recognize that what seems fair on the surface may not always feel fair in practice. The same way I had to adjust my approach to skiing, families must carefully consider the dynamics at play when structuring their estate plans, ensuring that their intentions align with the realities of their children’s relationships and expectations.

Parents often distribute their estate equally to avoid conflict, but this approach doesn’t always ensure fairness. One couple, for example, chose equal shares for their three children, hoping to prevent disputes caused by in-laws they saw as disruptive. They believed this plan would eliminate resentment and legal challenges, yet equal division doesn’t always mean equal treatment. Control over the trust and its administration can create tensions, especially when emotions run high after a parent’s passing. True fairness requires considering not just equal shares but also the unique family dynamics at play.

Trust administration can create unintended inequalities, even when assets are divided equally.

Trustee Control: Naming one child as successor trustee grants them full control over trust assets, payments, appraisals, and legal decisions, often leading to resentment from siblings with less access and oversight.
Trustee Compensation: If one child serves as the trustee, they may take a legally entitled fiduciary fee, causing tension among siblings who see this as an unfair financial advantage, despite the work involved. Conversely, a trustee who declines the fee may feel burdened and unappreciated.
Trustee Responsibilities: Managing the trust can take a toll on the trustee’s personal and professional life, while their siblings remain free of responsibility.
Trustee Liability: The trustee may bear personal financial risk, such as IRS claims for unpaid estate taxes, furthering feelings of unfairness.
Specific Bequests: Equal cash gifts to grandchildren can feel unequal when children have different numbers of offspring, leading to perceived favoritism.
Personal Property Division: Items like artwork and jewelry, meant to be split “equally,” often cause disputes due to varying financial and sentimental values.

Some options to consider as remedies for the above potential pitfalls are the following:

Trustee Control: Parents can appoint co-trustees or a neutral third-party corporate trustee like Greenleaf Trust to ensure shared decision-making and prevent conflicts. Requiring periodic reporting to beneficiaries can also enhance transparency and trust. Additionally, a trust protector can be designated to oversee the trustee’s actions and intervene if necessary.
Trustee Compensation: The trust document should clearly define the terms of compensation if an individual is named. An alternative approach is to provide the trustee with a stipend or an extra inheritance in lieu of a fiduciary fee. Open discussions with beneficiaries about the trustee’s role and compensation can also help set expectations and avoid resentment.
Trustee Responsibilities: Managing a trust can be time-consuming and burdensome for a family member, so allowing the trustee to delegate tasks to professionals—such as accountants, attorneys and investment managers—can alleviate some of the workload. Establishing a beneficiary advisory board can foster collaboration among siblings, ensuring that decisions are made with input from all parties. For those seeking a completely impartial approach, a corporate trustee can handle administrative duties while a family member oversees more personal decisions.
Trustee Liability: The trust should retain sufficient funds to cover tax obligations before making distributions. Indemnification clauses can be included to protect trustees from personal financial risk, and trustee liability insurance can provide an extra layer of security against unforeseen claims.
Specific Bequests: Concerns over specific bequests, whether real or perceived, can be addressed by structuring gifts as percentages rather than fixed amounts, ensuring fairness across varying family sizes. Another option is to establish a shared family pool for grandchildren’s education or other collective benefits, which can help reduce perceived favoritism. Clear communication about the reasoning behind these decisions is crucial to maintaining family harmony.
Personal Property Division: When dividing personal property, parents can create a memorandum of personal property specifying who should receive sentimental items. A rotating selection process among beneficiaries can also ensure a fair distribution. For valuable assets such as artwork and jewelry, obtaining professional appraisals can help maintain fairness and prevent disputes.

Fairness in estate planning, like learning a new skill, requires careful consideration, flexibility, and an understanding that equal is not always equitable. Just as I adjusted my approach to skiing after my first fall, families must be willing to adapt their plans to reflect the nuances of their relationships and the realities of trust administration. A well-thought-out estate plan goes beyond equal shares—it accounts for responsibilities, emotional dynamics, and potential conflicts to create a structure that fosters harmony. By recognizing these complexities and implementing thoughtful mitigating strategies, parents can craft a legacy that truly supports their children, not just in numbers, but in fairness and intent.