Top Estate Planning Challenges

Estate planning is a responsibility most adults recognize but often neglect or stall on. What challenges block this healthy, mature task, and what are the solutions? Knowing solutions exist is half the victory. If you feel your estate plan is incomplete or outdated, this article is for you. If you’re among the rare few who always plan perfectly and on time, you can skip it.

Get a Plan

The worst plan is no plan. Without one, politicians, tax authorities, and plaintiffs’ attorneys eagerly claim your estate. Over half of estates end this way. Comedian Bob Newhart, in a humorous skit, tells a patient with severe disorders to “Stop it!” Likewise, start planning.

Kill the Procrastination Bug

Delaying planning causes complications and missed opportunities. James Clear, author of Atomic Habits, suggests avoiding the overwhelm of the entire project. Set a tiny goal: make one phone call to a trusted source for a referral or to a confident attorney. The rest will follow.

Once Is Never Enough

Like a husband claiming, “I told you I loved you when I married you. If that changes, I’ll let you know,” neglecting updates harms marriages and estate plans. Regular reviews are essential; their absence sabotages wealth and family. Locate your documents and keep them visible.

Come to Terms With Conflict

As a child, I joined a bully in teasing another student. My mother disciplined me, but the other boy’s mother denied his actions, saying, “My son would never do that.” He smirked, learning a different lesson. Parents who think “my child would never” fight over an estate are naive. Estate litigation matches divorce rates. Conflict is inevitable; lawsuits are optional. A well-crafted estate plan can eliminate family lawsuits. If your advisor can’t achieve this, seek a second opinion.

Know Who You’re Dealing With

Family complexity—blended families, multiple marriages, diverse relationships, uncertain parentage, in-laws, or special needs—heightens conflict risk. Excluding family members without explanation or not justifying allocation differences fuels discord. Choosing the wrong executor or trustee sparks trouble; those most eager are often least suitable. Disinheriting someone or reducing their share via charity, then appointing them to lead, invites disaster. Be honest about family dynamics with advisors to reduce conflict.

Know What You’re Dealing With

People often misjudge their assets, undercounting or undervaluing them. Start with an accurate balance sheet, including overlooked items like inheritances, life insurance benefits, digital assets, personal property, business entities, and retirement accounts. Plan explicitly for each asset. Unplanned assets invite trouble; incomplete or conflicting instructions breed uncertainty, fear, and hostility. Track assets via a diagram (as our firm does) or a spreadsheet, e.g.:

Know Yourself

Estate planning isn’t just about post-death assets; it’s about your life. It involves naming decision-makers for medical events, addressing long-term care, and planning for incapacity or disability—vital components of a complete plan.

Know the Role of Time

Time challenges estate planning, as it’s hard to think beyond mortality. Focusing solely on death ignores the ripple effects of your plan across generations. You can’t control the ripple, but you can choose the stone and where to throw it. A single-use, throw-away plan ripples differently than a lasting, protective one. Do your advisors understand this?

Know Your Advisors

Estate planning is a team sport. A solo “hotshot” may profit but cost you the game. Advisors in accounting, investing, insurance, and law are essential. Missing players or lack of coordination leads to loss. Integrated planning, where advisors collaborate, ensures victory. Multiple contributors to this newsletter reflect this approach.

Jump Over the Legal Hurdles

Legal planning shapes your family’s future, fueling or disrupting wealth cycles. It impacts taxes, risk, and business survival—85% of family businesses fail by the third generation. How your lawyer defines issues determines solutions. Avoid part-time dabblers or outdated documents copied from past plans. Trusts range from simple to complex; the right one depends on your needs, as does your legal counsel.

The first step to overcoming these challenges is small. You know what it is. Take it. These challenges and solutions are general; your situation requires specific advice. Consult qualified advisors. 

Top Estate Planning Challenges © 2025 by Rick Durfee is licensed under CC BY 4.0