Kiley Fleming, director of the Iowa Mediation Service, recently shared with me and other participants during a managing difficult conversations training some advice once given to her: “Care enough not to care.”
Kiley offered this advice during a conversation on a difficult session I once had with a client’s attorney. He did not take kindly to my answer when he asked who in the room I represented. I simply answered: “The farm.” My sarcasm didn’t land well with him, and he spent the rest of the meeting attempting to bully and discredit me. Although I was intimidated, I held strong until the end, and Kiley said: “Mike, that’s because you cared enough not to care.”
Care enough not to care applies in everyday situations, too. It’s a way of expressing deep investment or commitment to something to the point where you’re no longer bothered by the potential negative consequences or criticisms it may bring.
Some examples:
- I care enough about my friends’ wellbeing that I don’t care if they’re upset with me for telling the truth.
- I care enough about my project to not worry about what others think.
- I care enough about my child that I don’t care if they get a bad grade.
Farmers are no different. They hold strong grit, passion and loyalty to the farm. However, when it comes to planning for the future of the farm, there’s no shortage of advice: podcasts, webinars, legal updates, tax strategies and expert opinions fly in from every direction. It’s difficult to sort through the options and decide what is right or wrong.
The very commitment to “doing it right” can leave families paralyzed, second-guessing every decision and delaying action for years. That’s where this phrase comes in: “Care enough about the farm that you don’t care.”
It’s a paradox, but a powerful one. It means you care so deeply about the long-term future of your farm that you're not easily swayed by every outside opinion or headline. You stop trying to make a perfect plan that pleases everyone and instead start building a plan that works for your family and your future.
Step one: Define your long-term goal
Before sorting through legal entities or gifting strategies, pause and ask the most important question: What do I want this farm to look like in 10, 20, or 50 years?
Then answer these questions:
- Is your goal to keep the farm intact for the next generation to operate?
- Do you want it to be financially sustainable without your daily involvement?
- Are you trying to treat multiple heirs fairly? Or is your goal to ensure one child has the tools to succeed in production agriculture?
Without that vision in place, any advice you receive – no matter how good – will feel disconnected or overwhelming. But once your goal is clear, every planning decision can be filtered through that lens.
Step two: Expect conflicting opinions
When you start talking to professionals – attorneys, CPAs, financial planners – you quickly realize something: even the experts don’t always agree. One advisor might urge you to set up a trust. Another may warn against it. A tax expert might suggest gifting assets during your lifetime, while your attorney cautions about control and risk. It’s tempting to jump from one strategy to the next, hoping to land on the “right” answer.
Here’s the truth: No plan is perfect.
Every option has pros and cons. Your job isn’t to chase the most popular tool but to choose the one that best supports your goal. Once you’ve made that decision, trust it. The best plan is the one you actually will complete.
Step three: Stay the course
That’s where the second part of the saying comes in: “...that you don’t care.” Once you’ve anchored yourself in your values and goals, you have permission to stop caring about every new idea that comes along. Not because they’re wrong—but because they’re not right for you.
Succession planning requires resilience. At some point, someone in the family might disagree. An in-law may question your fairness. A neighbor might tell you what they did, and why your plan is “risky.” This is where clarity and conviction become your biggest assets.
You care enough about the farm to push through the noise. You don’t care – at least not too much – about criticism that doesn’t come from those who are helping carry the vision forward.
Step four: Value progress over perfection
There will always be a better trust. A more tax-efficient strategy. A new trend in entity structuring. But waiting for the perfect solution can cost you the most important asset of all: momentum.
Care enough about the farm that you're willing to act. Even if the plan isn’t flawless, it’s a step toward protecting your legacy. You can refine and adjust over time – but only if you start. One decision at a time.
Want to learn more about the “Common Traits of Highly Successful Farm Transitions?” Please join me as the American Society of Agricultural Consultants hosts a free webinar at 11 a.m., May 15.
Downey has been consulting with farmers, landowners and their advisors for nearly 25 years. He is a farm business coach and the succession planning lead at UnCommon Farms. Reach Mike at mdowney@uncommonfarms.com.