I spend a lot of time thinking about how people avoid estate planning, not because they don’t care, but because they genuinely don’t know where to start. And nothing captures that better than a question I got recently while checking out at Trader Joe’s in Michigan.

A cashier named Ron noticed my Death Readiness sweatshirt and asked the question almost everyone has wondered at some point: “If I want to leave everything to my brother, can I just write it down and sign it?”

The short legal answer, at least in Michigan, is yes. A handwritten Will (called a holographic Will) is valid if it’s dated, signed, and the material portions are in your handwriting. But when it comes to planning for real-life families, real-life assets, and real-life drama, the better answer is: this gets messy fast.

When you go through a major life change, you think the moment of “finalizing” something will bring a sense of closure. But usually, it doesn’t. When my husband and I bought our house this fall, I was convinced I’d feel relieved the minute we signed the paperwork. Instead, we immediately plunged into the real work—packing, moving, cleaning out the old place, dealing with inspection repairs, and pretending we’d get around to changing the keypad code “tomorrow.” Weeks later, most of that list is still waiting for us. That weird gap between being “done” on paper and nowhere near done in reality is exactly where one of my listeners, Amy from Nashville, finds herself right now.

Amy is newly divorced after ten years of marriage. The court has signed off. The marital dissolution agreement is official. She is, in theory, “legally done.” But like so many people who reach this point, she quickly realized there’s a long list of loose ends that don’t magically handle themselves. One of the questions at the top of her list was: does she need to update her Will to remove her ex-spouse?

If you spend enough time in trusts and estates, you eventually learn that the law and common sense don’t always travel together. A recent Michigan case illustrates this perfectly, raising a question most people never imagine needing to answer: Can someone inherit from a person they were once accused of trying to kill? It’s an uncomfortable question, and the answer is not what most people expect.

This case centers around a trust created by a man named Donald shortly before his death in 2017. His wife, Elaine, became the sole beneficiary after he died, and their son, Donnie, was next in line. The trustee at the time, Michael, was not a family member but had been named in the trust documents as a future beneficiary after Donnie’s death. Within months, however, the probate court removed Michael as trustee, a notable action that suggested the court had concerns about how the trust was being managed.

You’d think “filing” your Will would be simple. But as one listener, Jazmine from New Jersey, found out the hard way, it’s not that simple. She thought she had “filed” her Will with her attorney. When her house was burglarized and her important papers were stolen, she wasn’t worried about her Will. She assumed her attorney still had the original. Except, he didn’t. He’d been disbarred and his law firm no longer existed. And her original Will was gone. So, what does it even mean to “file” a Will? And what happens if yours goes missing?