A reader dropped a note after reading Can your on-farm heir afford to buy you out? Her family’s farm has passed through three generations — bought in the early 1900s, held on to through multiple family and sibling buyouts. Her father was the second generation to buy the farm.
Her father did have a will. But in his final version, he left a portion of the estate — including farmland — to someone outside the family. The result was a legally contested will and the kind of drawn-out probate fight that drains a farm from the inside: tens of thousands of dollars in legal fees, court costs and time nobody had to spare.
Her mother wasn’t on the deeds. She wasn’t on the accounts. Now the family is waiting for a court to decide what’s “fair” — and if the ruling doesn’t go their way, the family will need to pay again for a farm already paid for multiple times. This time, they certainly will pay full market value. Again.
Here’s how she opened her letter: “Wills are worthless.”
Here’s her close: “Our family farm will sadly be bought by three out of four generations.”
Wills are worthless
I want to be clear: Her father’s will wasn’t worthless because it didn’t exist. It was worthless because it didn’t reflect what the family actually built, worked for and talked about. This new direction was lined out on paper — and cost them everything a good plan is supposed to prevent.
And so, for that reader, “Don’t make each generation buy the farm” resonated so deeply that she wrote to tell me her family’s story. Given the impact on her, it probably hits home with others, and her response hit hard with me, so let’s dive into this again.
This matters, because a lot of the documents built to protect your farm are designed around tax strategy first, equal distributions second and family intent last.
Take step-up in basis — the tax benefit that resets an asset’s value at death and wipes out capital gains for the next generation. It’s real, and it’s valuable. But it also quietly encourages families to wait, avoid transferring early, hold everything until death and pray it all goes as planned.
Think about this. Is step-up in basis your No. 1 priority? For more family farms, it is not. Harmony is. Clarity is. A successor who isn’t managing the operation and an estate fight at the same time is. When I sit with families and play out what their will or trust does — line by line, dollar by dollar, acre by acre — the distribution language often doesn’t match the succession plan they’ve spent years talking about at the kitchen table. The documents were built to save on taxes. To treat everyone equal. They weren’t built around the conversations the family had about the future of the farm.
Customize your documents
Here’s the piece I want you to walk away with: It’s OK to personalize your documents.
I constantly hear farm families heard “You can’t do that” or “Why would you want to do that?” from an adviser who was optimizing for a standard outcome. My response: “Why not?”
If you’re curious whether something is possible — unequal ownership splits that still feel fair, a phased transfer instead of an all-at-death transfer, language that protects a non-farming heir differently than a farming one — it likely is. And you can probably find a way to build it.
Here’s how: Ask the question. Push on the “no.” A good adviser should be able to tell you not only why, but also why not, rather than “this is how you do it.”
The moral of the story isn’t that wills don’t matter. It’s that a will or trust is one component of a comprehensive succession plan — not the whole plan.
Preserve the farm and the family
So, play out your will or trust, on paper, with real numbers. Know your farm’s actual transition numbers — what it can afford, what it owes and what it’s worth. Find the balance between preserving harmony in the family and keeping the farm financially viable, because you can rarely protect both if the only planning you’ve done is the kind that happens in a lawyer’s office once, quietly, at the end.
So, do I think wills are worthless? No — but they’re only worth the time, effort and conversations you actually have about them.