#121: Estate Planning, Hard Conversations, and the Future of Your Farm
“Imperfect planning is still better than no planning. If you don’t talk about it now, the people you love are going to be in a really hard spot.”
Estate planning and transition planning tend to be the two conversations farm families avoid the most — and the two conversations that shape whether the next generation can continue the work at all.
I sat down with Jessica Groskopf, a Nebraska Extension Economist, farm wife, and daughter-in-law in a fourth-generation operation, to talk about how families can approach these decisions with honesty, clarity, and courage. Jessica has worked with farm families for more than a decade and understands the emotional, legal, and financial layers behind passing an operation on.
In this episode, Jessica breaks down the difference between estate planning and succession planning, how to get started when everything feels overwhelming, and what every family should gather before meeting with an attorney or advisor. Her insights are both practical and deeply human — especially as she shares her own family’s journey navigating a major buyout at age 32.
Whether you’re the generation stepping back or the one stepping forward, this conversation is one every ag family needs to hear.
The Path to Farm Business Management
Jessica didn’t plan to work in farm transition. Originally on a path toward international ag trade, she eventually returned to rural Nebraska and found herself helping producers navigate the business side of their operations. Today, she blends her university work with her lived experience farming alongside her husband north of Scottsbluff.
As she puts it:
“My 9–5 is teaching this stuff. My 5–9 is discussing it around our own kitchen table.”
Her dual perspective lets her meet families where they are — overwhelmed, confused, avoiding conflict, or unsure which steps to take first.
Understanding the Difference: Estate Planning vs. Succession Planning
One of the biggest misconceptions Jessica sees is families believing a will alone will “take care of everything.”
Estate planning handles:
What happens when you die
Who makes decisions if you cannot
Your medical care preferences
Succession planning handles:
How the farm transitions
Who will manage it
When ownership shifts
What happens in divorce, disability, retirement, or conflict
A will distributes stuff.
A succession plan protects the business.
And both are necessary.
Ranching Through the Reality of Family Dynamics
Many families hit a wall not because of legal logistics — but because of emotions.
Generations want different things.
Some members avoid conversations.
Some fear losing control.
Some don’t know how to start.
Jessica shared the phrase she uses often:
“You can’t push a rope.”
If the ownership generation refuses to engage, the younger generation can’t force them. What they can do is prepare: build savings, understand entity structures, document their own assets, and establish realistic expectations.
And sometimes, they must ask hard questions like,
“Is staying here the right thing for my family if nothing ever changes?”
The Six Things Every Family Should Gather Before Meeting Advisors
Jessica outlined the six items that can save families thousands in legal fees and months of stress:
A written vision for what you want to happen
A list of concerns (addiction, conflict, spending issues, spouse concerns, etc.)
A complete balance sheet of everything you own and owe
A family tree
A list/map of all entities and how they operate
All existing legal documents (leases, agreements, POAs, wills, operating agreements)
Most families already have pieces of these — they’ve just never gathered them in one place.
Navigating Transition with Confidence — Not Fear
Transition is messy. Unexpected deaths, illness, disability, divorce, or financial strain change the path quickly. Jessica explains the importance of “stress-testing” the plan: pulling a name from a hat and asking what happens if that person dies first.
Because life rarely happens in order.
But even when it’s uncomfortable, Jessica says the real peace comes when families face the conversations rather than run from them.
Building a Future with Intention
Jessica and her husband lived this firsthand when they stepped into a major family buyout. At 32, they signed their first seven-figure loan — not because it was easy, but because they’d prepared for years.
Her message to young producers:
“Build your own empire. Saving and preparing doesn’t hurt you — it positions you for opportunity.”
Inheritance isn’t a guarantee.
Preparation is.
A Final Word of Hope
The hardest conversations often lead to the strongest relationships.
Jessica’s encouragement to families is simple:
Don’t avoid the uncomfortable topics.
Say what you mean with kindness and clarity.
Involve advisors instead of carrying the burden alone.
And trust that honesty builds healthier families and healthier operations.
If the legacy matters, then the conversation matters.
You can follow Jessica on Instagram for more free tools, resources, and guidance.
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About the Host of Farming On Purpose, Lexi Wright:
I’m your host, Lexi Wright. I started the Farming on Purpose Podcast from a passion for sharing the future of production agriculture.
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