What I’ve Learned This Year Helping Families Plan for the Unexpected

Every year brings new reminders of why planning matters. This year was no different.

Working with families, business owners, and individuals across many stages of life, I’ve seen the same truth surface again and again: it’s not the complexity of someone’s life that causes problems, it’s the lack of preparation when the unexpected happens.

Here are a few lessons that stood out most this year.

1. Most Planning Breaks Down During Incapacity, Not Death

People often focus on what happens after they’re gone. In reality, the most disruptive moments occur when someone is still alive but unable to act for themselves.

Without proper powers of attorney and healthcare directives, families can find themselves locked out of accounts, unable to make medical decisions, and forced into court involvement during already stressful times.

Planning for incapacity is just as important, if not more so, than planning for inheritance.

2. Documents Alone Are Not a Plan

I’ve seen technically “complete” plans fail because no one explained how they were supposed to work.

Who should be called first? Where are documents stored? Which accounts pass by beneficiary versus by will or trust? Who coordinates between advisors?

A good plan is not just legally sound; it’s understandable and executable.

3. Coordination Matters More Than Complexity

The biggest problems don’t come from a lack of advanced strategies. They come from misalignment.

A will that doesn’t match beneficiary designations.
A trust that doesn’t own the assets it’s supposed to control.
A business succession plan that isn’t coordinated with personal estate documents.

Planning works best when legal, financial, and business decisions are aligned; not separated from each other.

4. Waiting Often Costs More Than Acting

Families sometimes delay planning to “save money.” Ironically, those delays often lead to far greater costs later in legal fees, court involvement, taxes, and family conflict.

Proactive planning is almost always less expensive, emotionally and financially, than reactive problem-solving.

5. Planning Is Ultimately About People, Not Paper

Behind every plan is a family, a relationship, a business, or a set of values someone cares deeply about.

The most successful plans I’ve seen this year weren’t the most complex. They were the ones where people took the time to think clearly about who they wanted to protect, who they trusted, and what they wanted life to look like for those they leave behind.

The unexpected doesn’t announce itself. Planning ahead is how families create stability in moments that would otherwise feel overwhelming.

As this year comes to a close, it’s worth asking a simple question: If something changed tomorrow, would my plan support my family? Or would it leave them searching for answers?