For many people, receiving mail addressed to someone who has died is jarring. The first envelope is hard. You see their name and everything feels off. When someone dies, we expect grief, sadness, loss, and memories. What we don’t expect is how much of that grief gets tangled up in ordinary things. A trip to the mailbox, or a name on an envelope or a stack of papers that no one has the energy to face.

When I tell people just how much organization goes into dying, most folks get skittish and think they can opt out. I like to tell people: “You want to leave memories, not a mess.” People nod in agreement, yet getting them to actually put the pedal to the metal is a challenge. Have you penned your obituary? Thought about a service of some sort—or not? Remember—this is your life. Have it be yours to the very end – and beyond.

A month after my mom died, I put a quart-sized bag of loose and ringed keys into my aunt’s hands. One set stood out: they were the keys to my nana’s last apartment. Being curious about that bag of keys didn’t just help me remember Nana’s cooking or humor. It reminded me of a turning point—a moment of disruption that brought Nana more fully into my life.

Too often, the phrase “estate planning” suggests legal appointments, costly documents, and an abstract notion of preparing for death. However, when the legal and financial map is already laid out, loved ones can spend their time remembering the person who died instead of filling out the next required form or hunting for documents. Think of estate planning not as an intimidating legal process, but as an act of love.

When her husband Paul died suddenly, Rebecca learned the hard way that one unchecked box or one outdated form can unravel into years of unnecessary stress. We cannot control everything, but we can make things easier for the people we love by paying attention to the details—today, not later.

After Ethan’s unexpected death, his husband Daniel was shocked to find an error on Ethan’s 401(k) beneficiary paperwork. A simple mistake opened the door to bitter lawsuits, prejudice and heartbreak during the hardest chapter of Daniel’s life—dramatically illustrating the importance of carefully updating your paperwork after every major life change.

My mother planned her death carefully—body donated to medical research, final documents in order, and she chose when to stop taking her medication. But it was up to me to carry out her final request: for her ashes to be spread around a tree in upstate New York’s Hudson Valley.

Death is a universal experience, as are the feelings of grief and loss when loved ones die. Unfortunately, this period of grief and loss comes with unfamiliar paperwork. There is more paperwork to close out a person’s life than we would expect—and it can be overwhelming and confusing.

After my mother passed away in March 2023, I found myself sorting through the familiar clutter of her home—papers, photos, keepsakes. But it was a bag of spare keys that unexpectedly opened the door to parts of her life I never truly knew.