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A Gentleman’s Guide to Preparing for Your Inevitable Death

Because it’s gonna happen—just hopefully not for a while

Roger Ebert once said, “There’s nothing like impending death to rouse you from existential boredom.”

And that’s just making sure you get to as much bucket/fuck-it-list entries as possible — Joe Versus the Volcano-style (a movie Ebert gave 3.5 stars btw).

But there’s a lot of other stuff — most of it banal and/or involving serious decluttering and paperwork — to take care of before you go, too, and while it may seem scary, complicated or just plain depressing, planning for death is an essential part of life, whether you expect to pass soon or are simply taking care of things “just in case.”

Yet although dying is inevitable for everyone, only a small percentage of us do the proper planning to prepare for it. According to a 2017 study by, just 42 percent of American adults have a will — for adults with young children, this drops to 36 percent. This latter stat is particularly troubling: If you’re a family man — as I am — there is a veritable laundry list of things a spouse has to take care of after their partner dies.

Even for singles, though, there’s still the question of what will happen to your body and your belongings, questions that will have to be answered by your loved ones if you don’t set things up in advance. Grief is hard enough without it being compounded by overwhelming new responsibilities, so do your family a favor and…

Organize — or Just Throw Out — Your Shit

That stack of old Zip Disks; the two drawers full of old concert tickets; the sack of vintage Transformers toys that you’ve had since 1988: Whatever your collected treasures are, know that someday, when you die, someone is going to have to go through them, and most likely, throw them right in the trash. But do you really want your loved ones to have to go through all your junk after you kick your collection of vintage buckets?

Instead, recognize that there are a few different approaches you can take when trying to declutter your life. “We encourage our clients to pay it forward to families in need,” says Amanda O’Reilly, CEO of Balance InStyle, a company that recommends people gift items to the needy or family members before they go. For more general downsizing, you might consider the words of Japanese minimalist guru Marie Kondo, who advises you to ask yourself if something you own makes you feel joy; if not, she says, let it go. A more pragmatic approach still is the practice of Swedish death cleaning, whose driving ethos is that you should consider how the objects you own might burden your family after your death.

Alternatively, consider this nugget of wisdom — perfect for the compulsive collector — that was imparted to me by a guy named Ralph in a vintage record store about 15 years ago. He encouraged me to, “Represent, not collect.” In other words, when looking at that pile of old Transformers, you can get rid of Grimlock, Bumblebee and Ultra Magnus, and hold onto Optimus Prime alone, letting him single-handedly represent your entire, once-glorious, Autobot army.

Take Care of the Legal Stuff

According to the survey referenced above, the stats on wills get even more staggering when you break them down: While 81 percent of those over 72 have a will, it’s just 36 percent for Gen Xers and 22 percent for millennials.

Age and anxiety about the topic aren’t the only barriers, either. Twenty-nine percent of the survey participants said they didn’t have a will because they “don’t have enough assets to leave anyone,” which, says estate attorney George Kontogiannis from White Plains, New York, is flawed thinking. “Some people think you only need a will if you have thousands of dollars in the bank, but there are lots of reasons to have all that planning done, even if you have almost nothing,” he says.

Here’s the thing: Your will doesn’t just clarify who gets your stuff, your house, your kids, and if you have any, your cash — it also appoints people to be in charge of your stuff after you go. “If you don’t create a will, the state will impose a will on you when you die,” warns Kontogiannis. This means that, for example, your spouse may not just “get everything” as you’d expected. Lacking clear instructions from you, people may sue each other to get what they want, so it’s better to formalize your wishes and spare your family the aggravation.

Also, you really should get an attorney to draft it. “There is a bias in the courts for attorney-drafted wills,” Kontogiannis says. “Some people think they can just go to a website and sign a will, then have a notary notarize it and they’re done. But there are certain formalities that need to take place when signing and drafting a will, and those formalities need to be followed.”

Organize Your Money (Again, Even If You Don’t Have Any)

An important thing you’ll want to consider when planning your affairs is finding the right person for each individual job. So maybe your sister looks after the kids, but your cousin the CPA may be in charge of your trusts for your children. Overall, you should worry less about hurt feelings after you die and more about what’s best for everyone, especially your spouse and kids. “I’d rather have someone pissed at me when I was dead than have my child suffer after I’m gone,” remarks financial advisor Adam Ditsky. Ditsky adds, “It’s a lot of work to be an executor or a trustee, so most people are pretty thankful they don’t have to deal with it, once they find out the work involved.”

If you’re steeped in credit card debt, be aware that while some of that debt may die with you, those companies can claim your assets before they get distributed to your family. That means even if you’re cash-poor, they may go after your house, etc. That’s why you want to do your best to see what you can do about paying off your debt before you die. Be sure to update the beneficiaries on your retirement plans, 401Ks and your life insurance plan, too, as many people put their siblings as beneficiaries and forget to change it after they get married.

Speaking of which, life insurance is a very, very good idea. While there are a few different kinds of life insurance plans, the most common is a “Term Life Insurance Plan,” which works like this: Say you take out a $100,000, 20-year plan, if you die within the next 20 years, your beneficiaries get $100,000. Now, if you don’t die within that time, you get nothing, but buying a plan that at least covers the time your children are with you, or at college, will ensure some financial stability to your family if you pass.

Sadly, you can’t get life insurance if you’re terminally ill, but if you’re healthy and worried about the “just in case,” Ditsky says, “For just a few hundred dollars a year, it will provide tremendous protection to ensure funeral costs and education costs for your children, etc., are covered.” While he understands that even a few hundred bucks may be a hardship, compared to the immense costs of a funeral, it can be a big help. “Life insurance is ‘Planning 101,’” says Ditsky.

Decide What You Want To Do With Your Body

“I would suggest anyone over the age of 18 set up a pre-plan,” says Barry Bernstein of Morse Funeral Home in Middletown, New York. Funerals can easily cost $5,000 to $10,000 — a hell of a burden on your loved ones — whereas a pre-plan may be opened at your local funeral home for whatever amount set by the state (it’s $500 in New York, for example). After that initial amount, you pay on the plan regularly, and you can pay as little or as much as you like. Once it’s paid in full, your funeral is covered and your wishes will be clearly stated in the plan.

You want an elaborate service complete with marching band and light show? A simple cardboard box? To be cremated, then have your remains mixed with pig shit and thrown in Piers Morgan’s face?* All of that goes in the pre-plan, and as long as it’s paid for, it’ll be done (provided someone can stomach getting that close to Piers Morgan).

Give Directions for Your Digital Afterlife

Professional organizer Judith Kolberg recommends getting a “Digital Estate Plan,” which is a place to put all of your important usernames and passwords, state your wishes for your online presence and name a digital executor. Consider PayPal accounts with money in them, or the eBay seller IDs where you’ve listed all your old Transformers: All of those important accounts should be in there.

Meanwhile, do you want your Facebook page memorialized, or should it remain untouched, like some sort of digital ghost? Do you want your final tweet about Donald Trump’s tiny, Big Mac-clutching hands to be your last official digital words? Your social media wishes also should go into your digital estate plan, Kolberg advises.

For her money, though, you should seriously consider taking it all down: “Keeping up your social media after you die increases the chances that you’ll be phished or hacked,” she explains, which may end up with your family having to deal with it later. But if you’re determined to keep your accounts active, Kolberg recommends at least removing any identifying information like addresses, schools attended, etc., thus sparing your family the aggravation.

Another thing to consider in the digital realm falls under the same advice of finding the right person for each job. You may want to consider not having your spouse be your “digital executor,” especially if you have something to hide. Be it your DMs with your ex-girlfriend or all of the booty shots you’ve “liked” on instagram, if you’re worried about maintaining your image post-mortem, you may want to appoint someone to be the modern equivalent of a “Porn Buddy” and spare your spouse any unneeded anguish.

Share with Others What’s Important to You

One final piece of advice is to talk about your goals, dreams and desires with the ones closest to you. While some of us keep our dreams to ourselves, worrying that they may be silly or juvenile, sharing them with others may help them come true — even if you aren’t around to see it happen. Just recently, for example, a good friend of mine reached out to me to connect him with an illustrator I knew. My friend, Justin, had just lost his good friend Val unexpectedly, and because Val had shared an important goal with him, Justin felt compelled to see it through.

“I knew Val for 12 years, and about a month before he died, he had come to me with a script he had for a children’s book that we wanted to get published,” says Justin. “It was only eight pages, but it was very important to him as it was about his Nigerian heritage as told through the eyes of a young girl, representing his daughters. At the time, no one knew he was going to die — including him — but he told me that this was specifically about legacy.

“I remember being at the wake and thinking, I have to get this done for him. So soon after, I went to his wife and made sure it was okay with her. Since then, I’ve been taking the steps to make it happen. As his friend, and the guy he had shared this goal with, it feels like a necessity — for Val, for his wife and for his daughters.”

So, if you’ve got a children’s book, an invention or anything else that you’d like to accomplish “someday,” you really should open up to the ones around you about making those things happen.

Who knows, maybe you’ll get to leave that little bit of legacy behind after all.

*For legal reasons, we are obliged to point out that funeral homes will not** really do this.

**Although they should.