Current Trends - What Pumpkin Pie Teaches Us About Estate Planning - Episode 224

Hey there, Legal Tea Listeners – This is your host, Jenny Rozelle. Welcome back for another episode, which is a “current trends” topic where we talk about things going on currently that are relevant and pertinent to my estate and elder law world, and/or maybe things I’ve seen on the news or stumbled across on social media. Well today’s episode is going to release the Tuesday before Thanksgiving and it got me thinking about a story / joke that I sometimes share when I give presentations on all this estate planning stuff. It involves Thanksgiving, pumpkin pie, and inheritances – and I’m sure you are like, “WHERE is the intersection of those things?!” Well … I use Thanksgiving and pumpkin pie as a way to talk about “controlling from the grave” or maybe a nicer way to describe it is that you can easily set up an estate plan to govern your money – even after you have passed away. Let’s talk about it…

So here's the scenario I like to paint for people. Imagine you are working with an estate planning attorney, and you tell them, "You know what? I want to make sure my family stays connected after I'm gone. They are already starting to drift apart, and I am worried that once I am not around, they will never see each other." Now, some people would say, "Well, that is sweet, but there is not much you can do about that from beyond the grave, right?" Wrong! This is where estate planning gets really fascinating – and maybe a little bit controlling, but some people are control freaks (like me … so just hear me out on this episode!). You could actually structure your estate plan so that your beneficiaries only receive their inheritance if they show up to Thanksgiving dinner every year. And here is the funny part – they have to be there in person to get their check, which gets handed to them along with a slice of pumpkin pie. No attendance, no pie, no inheritance check. It is like the ultimate family reunion enforcement mechanism!

Now, before you think I have completely lost it, let me be clear – I am not necessarily recommending this exact approach. In fact, it is a pretty extreme example, and there are some family dynamics where this would be a disaster rather than a blessing. But here is why I love sharing this story: it perfectly illustrates just how much power and flexibility you actually have when it comes to estate planning. Most people think of a Will or a Trust as just a simple document that says "give this to this person, give that to that person." But it can be so much more than that! Estate planning allows you to set up rules, conditions, and structures that govern how your assets are distributed and managed long after you're gone. You can literally control your money from the grave – though I prefer to think of it as "providing guidance and structure" rather than "controlling," because that sounds a little less creepy.

The pumpkin pie example might sound a bit silly, but it opens up a much bigger conversation about what is actually possible with thoughtful estate planning. You can set up distributions that happen over time rather than all at once. You can create incentives for education, like releasing funds when beneficiaries graduate from college or complete a trade program. You can protect assets from a beneficiary's creditors or from a potential divorce. You can support charitable causes you care about for generations to come. You can even set up provisions that help a family member with special needs without jeopardizing their government benefits. The possibilities really are endless, and most people have no idea just how customizable and creative estate planning can be. It is not just about avoiding probate or minimizing taxes – though those are important to some people – it is about creating a lasting structure that reflects your values and protects the people you love, even when you can't be there to do it yourself.

So as you're sitting around the Thanksgiving table this year, maybe take a moment to think about your own estate plan – or the fact that you have been meaning to create one and haven't gotten around to updating your current one yet. No judgment here; most people put it off! But remember the pumpkin pie principle: you have more power and more options than you may realize. Whether you want to encourage family gatherings, support your grandchildren's education, protect a loved one from their own poor financial decisions, or simply make sure your assets go exactly where you want them to go, estate planning gives you the tools to make it happen. And who knows? Maybe your legacy won't involve mandatory Thanksgiving attendance, but it can absolutely involve the values, priorities, and protections that matter most to you. That's the real power of estate planning – not control for control's sake, but the ability to care for your family and shape your legacy long after you're gone.

Now let's get a little more technical for a moment, because understanding the mechanics of how this works is really important. When we talk about conditional things like this or incentive planning – which is what that pumpkin pie Thanksgiving example really is – you actually have a few different options for how to structure this. You could create what's called a testamentary trust, which is a trust that's built right into your will. The downside there is that your will has to go through probate before that trust gets activated and funded.

The other route – and often the preferred one – is to set up a living trust during your lifetime that includes these conditional distribution provisions to “kick in” after you pass away. That way, when you pass away, the trust is already in place and funded, it avoids probate, and your trustee can start implementing your wishes fairly quickly (after getting through the immediate administrative stuff). Either way, whether it's a trust built into your will or baked into a standalone trust document, there are different ways to skin the cat. The key is that you are creating a legal structure where a trustee – the person or institution managing the trust – has the authority to distribute funds based on whether certain conditions are met. In our Thanksgiving example, the condition is attending dinner. The trustee becomes the enforcer of your wishes, making sure that your beneficiaries actually comply with the terms you have set up before they receive their distributions..

One thing that is not only important, but maybe also interesting to mention is the difference between conditions that are legally enforceable and those that are not. Courts generally allow you to place conditions on inheritances, but there are limits. You cannot, for example, require someone to do something illegal, or create conditions that violate public policy – like requiring someone to get divorced. The Thanksgiving attendance requirement would likely hold up because it is not asking anyone to do anything harmful or illegal; it is simply incentivizing family connection. However, you would want to build in some flexibility. What if someone is sick? What if they are traveling abroad or traveling for work? What if there's a global pandemic? A well-drafted trust would include provisions for these kinds of exceptions, and it would give the trustee discretion to determine whether someone made a good-faith effort to comply.

Another technical consideration is potential tax issues of structuring distributions over time rather than as lump sums. When you distribute assets through a trust with ongoing conditions, those assets remain in the trust and may (emphasis on MAY) be subject to trust income tax rates, which are usually higher than individual rates. However, there are ways to structure these trusts to minimize tax burden – for instance, using distribution standards that allow the trustee to distribute income to beneficiaries, who then pay taxes at their individual rates. These are the kinds of details that separate a cute idea from a actually workable estate plan.

Finally, let's talk about the role of the trustee in all of this, because it is absolutely critical. The trustee is the person who is going to be responsible for enforcing your pumpkin pie provision – or whatever conditions you have established. This means they need to be someone who is organized, responsible, willing to potentially say "no" to family members, and comfortable with the administrative burden of managing a trust that might last for years or even decades. Some people choose a family member they trust, while others opt for a professional trustee like a bank or trust company, especially if they are worried about conflicts of interest or family drama. Professional trustees bring expertise and objectivity, but they also charge fees. For trusts with unusual conditions, having professional management can be worth every penny, because they will handle the documentation, tax filings, and difficult conversations that come with enforcing your wishes. The bottom line is this: creative estate planning is powerful and possible, but it requires thoughtful design, expert legal drafting, and the right people in place to make it work.

So here's what I want you to take away from today's episode, whether you're enjoying pumpkin pie this Thanksgiving or not. Estate planning is so much more than just a legal formality or a box to check off your to-do list – it's one of the most powerful tools you have to express your values, protect the people you love, and create a lasting impact that extends far beyond your lifetime. Yes, the pumpkin pe Thanksgiving dinner example is a bit strange and maybe a little controlling, but it illustrates something profound: you have options and flexibility that most people never even consider. But whatever you choose to do, the important thing is that you are being intentional about it.

Ultimately, you are creating a plan that reflects who you are and what matters most to you. So if you have been putting off your estate planning, let this be your wake-up call. You don't need to have all the answers right now – that's what estate planning attorneys are for – but you do need to start the conversation. Because the power to shape your legacy is in your hands, and the decisions you make now will echo through your family for years to come. That is not control for control's sake – that's love, thoughtfulness, and responsibility in action. And that, my friends, is worth much more than a slice of pumpkin pie.

Alrighty, let’s wrap this episode up, shall we? Next week, we’re back to the “celebrity estate planning” type of episode – so, for this episode, I’m probably going to do an episode on the estate of THE Hulk Hogan. I have been seeing some headlines about his estate pop up, so there must be stuff going on there that is worth a Legal Tea episode … so yeah, next week will be on him, so tune in next week, Legal Tea Listeners. Talk to you then!

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