Legacy Plan

How You Can Rest Assured

Legacy is a matter of life — and death. And if you’ve made plans for how you live, there’s no excuse to leave without a plan. Thankfully, such end-of-life conversations aren’t staying buried any longer.

How You Can Rest Assured
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One life, it seems, ain’t quite enough for Dolly Parton. Already, the country music icon is making plans for her afterlife.

“I am trying to put songs down for that very purpose,” she said in the final episode of the Dolly Parton’s America podcast, which aired in January.

“There’s enough stuff to go on forever with my music — to do compilation albums, to do new and original stuff.” It’s her way of solidifying her gold-plated legacy, while readying herself for her inevitable promotion to heaven. “I don’t wanna ever leave my stuff in the same shape like Prince or Aretha [Franklin],” she added. “I’m one of those people who believe in being prepared.”

Even for the rest of us, there’s something about being prepared for the coming end. That idea of end-of-life planning, however, doesn’t always sit comfortably with everyone. And why would it? Personal fears, cultural superstitions and other taboos keep us from dwelling on death — especially our own. Not for nothing did Aristotle reckon dying to be “the most terrible of all things”, and the Chinese studiously avoid the number four, which in Mandarin, sounds like the word for death. It’s also why a 2019 study by the Institute of Policy Studies found that while most Singaporeans would like “a good death”, robust end-of-life care and decision-making are still wanting.

But as Parton points out, no one wants his or her legacy left in chaos. Notably, Prince and Franklin did not compose official wills, and their respective estates continue to be fiercely contested long after their passing. Proactively making plans sure beats passively awaiting our long sleep. Folks have been doing so since the medieval ages: note the Ars Moriendi (or The Art of Dying), 15th-century Latin texts that armed Christians with theological tenets and practical tips for the impending task of “dying well”. They made death a manageable affair, empowering readers with some measure of control over matters uncontrollable.

Today, such end-of-life guides come in the form of digital services that have surfaced in the Western world to help users get their affairs in order before they kick the bucket. Have specific instructions for your assets and funeral? Try Cake. Want to gather your wills and insurance policies in one place? There’s Everplans. Need to share your advanced healthcare plans? Go for MyDirectives.

“People are getting used to these kinds of services in other parts of their lives. Instead of making it harder, in many cases, it makes it simpler,” said Mark Duffey, CEO of Everest, a digital funeral concierge service.

These tools have increasingly gained traction with a younger crowd, whose end-of-life plans encompass their so-called digital legacy. They may not have amassed estates, but their digital data — social media profiles, online subscriptions, e-commerce accounts — needs accounting too. While sites like Facebook and Gmail may offer succession options, services from SafeBeyond to Afternote make it their business to secure and preserve your digital footprint. There, you can gather passwords, record farewells in multimedia files or assign trustees for your myriad online accounts. For the intrepid, there’s also Eternime, which combs your existing online activity to construct you an intelligent digital avatar that will persist longer than you ever will (yes, Black Mirror already went there).

No surprise: tech and the Internet have made death easier to consider, confront and possibly live with.

“The Industrial Revolution, with its hospitals and suburban cemeteries, enabled us to keep death at arm’s length,” Elaine Kasket, psychologist and author of All the Ghosts in the Machine, told The Guardian. “But the internet is tailor-made for continuing bonds; it makes it exceptionally easy, because the dead live in tech already.”

Vanitas Still Life (1668) by Maria van Oosterwijck, a Dutch Golden Age painter who explored the transience of earthly life.

That same connectivity has spawned and spurred death positivity, a movement that urges candid thought and discussion about death and dying. In blogs, YouTube videos, death salons and other offline programmes, death positivists boldly tackle everything from grief to human remains to end-of-life care. If all that sounds macabre, it’s only because dying has always been something unspeakable.

“We’re not supposed to be curious about death now. But how can you not be?” Joanna Ebenstein, founder of Morbid Anatomy blog, told The New York Times. “It’s the thing that defines our life, but we’re supposed to pretend it’s not interesting to us?”

Lately, death positivity has coalesced around the Order of the Good Death, a platform that has burnished the idea of eternal rest with some manner of gothic chic. Founded in 2011 by mortician Caitlin Doughty, the Order strives to change the culture around death — to promote open advocacy, to check fears of our certain demise, to make death a part of life. “Accepting that death itself is natural,” reads part of its mission statement, “but the death anxiety and terror of modern culture are not.”

In this, the Order finds a kin in WeCroak. Five times a day, the app sends its users notifications that simply read, “Don’t forget, you’re going to die,” followed by a death-related quote (sample: Charles Wright’s “Let go, live your life, the grave has no sunny corners”). It’s not trying to be morbid; rather, WeCroak acts as a memento mori, a reminder of our mortality, making death recollection a daily, regular exercise.

Five times a day, WeCroak sends you reminders
of your mortality.

“It’s just a little way of making a micro-adjustment so that your whole day — which, remember, is one of your limited days on earth — isn’t taken up with BS,” WeCroak co-founder Hansa Bergwall told tech business journalist Kara Swisher last year.

That’s one way of putting our lives in perspective, while dealing with the dread surrounding dying itself. But let’s face it: death will always be terrifying. Making peace with our eventual end, though, demands that we first face up to our worst death anxieties.

“How do we get ready to die?” end-of-life educator Sallie Tisdale wrote in Advice For Future Corpses. “We start with not being ready. We start with the fact that we are afraid. A long, lonesome examination of our fear.”

Any conversation about death might then best be initiated with a frank dialogue about those fears and the fact that they’ll always be there. As Tisdale noted: “Anxiety about death is a part of being human.” To be divorced from that terror, you’ll have to be, well, dead. But to shun the realities of death and end-of-life planning out of personal or cultural discomfit does a disservice to your life and legacy. Let your final act be yours.

When David Bowie released Blackstar in 2016, he knew it would be his last missive. He’d been battling cancer for over a year by then; but in the many decades before that, he’d charted a course in art and pop so formidable, it was bound to endure. The record, then, wasn’t just his valediction, but was a plucky grappling with his mortality and legacy. “I’ve got drama, can’t be stolen / Everybody knows me now,” goes the album’s centerpiece Lazarus, before concluding, “Just like that bluebird / Oh, I’ll be free / Ain’t that just like me?” It’s a poignant piece that agitates with fuzzy, jazzy experimentation — a Bowie creation through and through. With it, he celebrated living in the face of dying. Then he died just as he lived.

This story first appeared in the May 2020 issue of A Magazine.