End-of-Life Planning
There’s a conversation happening across Gen X right now. It doesn’t have a name. It shows up in texts between old friends, at birthday dinners that used to be easier, in the parking lot after a memorial service. It usually starts with “Did you know he didn’t have a will?” or “She handled everything herself and I had no idea where anything was” and ends somewhere in the range of “I really need to get my stuff together.”
Then life resumes and nothing gets done.
This is not laziness. It is a structural problem, and Generation X is caught in the middle of it in a way no generation has been before.
The Sandwich Generation, But Make It Terminal
Gen X — roughly anyone born between 1965 and 1980 — is now between 45 and 60. Which means, in terms of mortality, they are:
Managing the last years of aging Boomer parents, many of whom planned nothing and expect their children to sort it out. Watching peers — people their own age — get sick, die unexpectedly, leave messy estates. Raising adult or nearly-adult children who may or may not be financially independent. Carrying more student debt, at this age, than any previous generation did. Preparing — or failing to prepare — for their own retirement.
In the language of financial planning, this is called the sandwich generation. In practice, it means Gen X is managing mortality from both directions at once, while also being significantly underplanned for their own.
The generation that came of age during the AIDS crisis, watched grunge musicians die at 27, and learned early that life could end without warning has, as a cohort, done remarkably little to document their own wishes for when it does.
Why Gen X Avoided This (A Fair Assessment)
Before this becomes a lecture, the avoidance is understandable.
Gen X grew up largely unsupervised — literally. The latchkey generation. The kids who came home to empty houses, raised themselves through afterschool TV and weekend independence, and were praised for self-sufficiency. They learned to handle things, but they also learned to defer feelings. The two skills are not unrelated.
Add to this the fact that Gen X entered adulthood during recessions, navigated two market crashes before 50, and is statistically more financially stressed than either the Boomers before them or the Millennials after them, despite being the cohort that built the modern internet and the companies that run on it. They have been too busy surviving to do planning.
And then there’s the genuine cultural failure: nobody teaches this. No high school class, no onboarding packet, no parenting book covers what to do when you or someone you love is about to die. The skills required — the paperwork, the conversations, the decisions — are learned on the fly, in the worst possible circumstances, with the least possible preparation.
What Actually Needs to Happen
This is not a think-piece that ends with a feeling. Here’s the situation on the ground and what it requires.
Your parents’ planning (or lack of it): If your parents are still alive and have not documented their wishes, the time to have that conversation is now, before a health crisis forces it. What they want for their medical care. Where their documents are. What they want done with their things. This conversation is uncomfortable and they may resist it. Have it anyway.
The alternative is making decisions for them in an emergency — guessing about their wishes, fighting with siblings about what they would have wanted, discovering accounts and assets no one knew existed, finding or failing to find a will in the hour after they die.
Your own planning: The same logic applies. If you have not documented your wishes — not just a will, but your actual wishes, for your ceremony, your belongings, your last words, the people who should know what you wanted — you are leaving that work to the people who are already going to be dealing with your absence.
Planning your own death is not morbid. It is the most functional thing you can do for the people you’ll leave behind.
The conversation with your family: At some point, your family needs to know where things are. Not because you’re going to die soon, but because at some point you will, and the difference between a family that knows where to look and one that doesn’t is a significant amount of additional pain in an already painful moment.
What Gen X Is Actually Good At
Here is the thing about this generation: they are, in practice, well-suited for exactly this kind of work.
Gen X raised itself. It is comfortable with difficulty. It is not precious about uncomfortable conversations. It is deeply skeptical of systems and experts, which makes it well-positioned to take ownership of its own affairs rather than delegating them to institutions it doesn’t trust anyway.
The generation that fixed its own problems, figured things out before the internet, and never expected anyone to hand them anything is exactly the generation that can look at death planning — with all its paperwork, its conversations, its uncomfortable logistics — and say: fine, I’ll handle it.
They just need to actually do it.
The Document That Holds All of It
There is no single piece of paper that covers everything, but there are a few that matter most:
A will. The baseline legal document. Covers your assets, names an executor, designates guardians for minor children. Without it, the state decides.
An advance directive. Your medical wishes if you can’t communicate them. The form that tells doctors what “everything possible” actually means to you, and where your line is.
Beneficiary designations. These are on your retirement accounts, life insurance policies, and certain bank accounts. They override your will. They must be current.
A letter of instruction. Not a legal document — just the practical guide. Where the will is. Where the accounts are. What the passwords are. What you want done, by whom, with what.
Your wishes. Not just the legal and financial layer. What kind of ceremony, if any. What you want said, or not said. Who gets the things that matter most to you but wouldn’t survive a legal appraisal. The letter to your kids.
Adiosly is built to hold all of this. Not as a vault, but as a living document — something you build over time, update as things change, and trust will reach the right people when it needs to.
The Only Thing Worse Than Having This Conversation
Is being the one who has to reconstruct what someone wanted after they’re gone.
Every Gen X adult has been in that role, or watched someone be in it. It is among the most painful ways to grieve — carrying the logistical weight of someone’s death while also mourning them, guessing about things they should have known, managing conflict that wouldn’t exist if there had been a document.
The conversation is uncomfortable. The planning takes an afternoon. The alternative is harder than either.
Adiosly is built for exactly this: helping you plan your departure, document your wishes, and make sure the people you leave behind know what you wanted.
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