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The Plan That Was Perfect — Ten Years Ago

A well-crafted estate plan from ten years ago might look complete — but if it hasn’t kept up with your life, it may cause more harm than help. This is the story of one family’s painful lesson in what happens when a plan doesn’t evolve with the times.

The Plan That Was Perfect — Ten Years Ago

A Real-Life Reminder That Estate Planning Isn’t “Set It and Forget It”

When Jim passed away, his children brought in a tidy folder labeled “Estate Plan – 2013.”
Inside: a revocable trust, wills, durable powers of attorney, and an asset summary.

Everything looked organized. Prepared. Thoughtful.

Jim had met with a trusted attorney a decade earlier and carefully crafted his plan. It checked all the boxes. His kids — two adult children, Peter and Leah — felt a wave of relief.

But as they began working through the details, that sense of relief slowly unraveled.

What Went Wrong

Old Location, New State
Jim had created the plan up north — but moved to Florida seven years ago. His documents hadn’t been reviewed or updated to reflect Florida law or residency.

Family Circumstances Changed
One beneficiary listed in the trust had passed away. Another, a son-in-law, was no longer in the family. But they were still named — and nothing had been adjusted.

Outdated Financial Picture
The asset summary referenced accounts and investments that had long since been closed or moved. New accounts — including a Florida homestead and a brokerage account — weren’t tied to the trust at all.

The Fallout

Court Involvement
Because key assets weren’t retitled into the trust, they had to go through Florida probate.
The very process Jim thought he’d avoided.

Legal and Administrative Costs
Attorney fees. Court filings. Appraisals. Delays. Costs added up — especially for real estate outside of Florida.

Emotional Strain
Instead of focusing on remembering their dad, Peter and Leah were untangling red tape, tracking down paperwork, and correcting problems that could have been easily avoided.

The Missing Step
Jim had built the structure.
But no one had checked it for wear and tear.

Documents, like homes, need upkeep. A well-drafted plan isn’t permanent unless it’s reviewed and refreshed when life shifts.

The Takeaway

A good estate plan is a living thing.
It has to match your life — and your laws.

Review regularly.
Every few years or after major life events.

Update intentionally.
Moves, marriages, deaths, new laws, and asset changes all matter.

Don’t assume it’s “done.”
Even solid documents can fall short if they’re frozen in time.

Jim’s family learned that lesson the hard way.
What started as a perfect plan… turned into a costly clean-up.

You don’t need a new plan every year. But you do need to make sure the one you have still fits.

Because when life changes, your plan should too.

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Craig R. Hersch

  • Senior Partner,
    • Sheppard Law Firm
  • Florida Bar Board Certified Estate Planning Attorney / CPA
  • Editorial Advisory Board Member,
    • Trusts & Estates Magazine
  • Founder & Board Member,
    • State Chartered Trust Company