They say you’re not supposed to speak ill of the dead, but I was really angry at my Dad.

My stepmother and I had already spent days digging through his office. Her worry-prone brain was spinning into a financial panic about the future. Everything felt difficult. She was having trouble transferring accounts to her name. We couldn’t find the password to his computer. There was an unlabeled safe deposit box key that didn’t say which bank it was for, let alone which branch. And in the mixture of his important papers and memorabilia and old grocery lists, I came across yet another life insurance certificate. From the looks of it, this one was going to be just as worthless as the first two I’d uncovered earlier.

I was recognizing a pattern: My father seemed to get inspired by who knows what to start a process—and then fail on the follow-through. After my mother died, he wrote out a Will by hand, but didn’t update it as the decades passed and the circumstances of his life changed. He would intend to get organized and label folders and envelopes, then just stuff everything into random boxes and shove them out of sight. He purchased life insurance…and then didn’t pay the premiums.

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It was infuriating.

I expect I would have been more forgiving if, like my mother, he died suddenly and unexpectedly, but his health had been precarious for decades. He was a smoker and a sedentary bookworm with diabetes brought on by years of grief-induced drinking. In truth, I found it more surprising that my father had lived into his 70s than that he had died.

His disorganization made grieving him feel chaotic. It was painful to watch my stepmother struggle so much. I knew from my own experience that the only way to move through grief is to actually move through it, to feel the feelings fully. That was clearly something my stepmother was unwilling to do. Instead, she stayed busy, focusing her energy on funding her remaining years. She cleaned and packed, obsessed with readying the condo to sell. I understood this strategy, but was concerned that her busyness had an edge of panic.

Then, during this flurry of errands, in a surprise twist, she had a fatal heart attack. It was only five weeks after my father’s death.

After one trip to close up their house, as I was driving home from LA to San Francisco, I kept thinking about how frustrated I was with my dad. I blamed him for causing unnecessary stress for my stepmother. Part of me even blamed him for her death. My mind was filled with “if only” and “why didn’t you.”

I was feeling quite righteous in my anger until suddenly I realized I wasn’t any more together than my father. If anything, I was worse. Sure, I wasn’t elderly or ill, but that didn’t excuse me. Anyone can get into an accident. If I died that day, I would have left behind a mess, too. I didn’t even have a Will. No one had access to my financial accounts or passwords. My physical stuff was in multiple locations and my online life was even worse. My family and friends didn’t know each other. I wasn’t even sure that they had each other’s phone numbers.

I imagined all the extra pain and struggle I would be causing for the ones I loved—struggle that didn’t need to happen. I also felt like I, of all people, should know better. I’ve known so many who’ve died throughout my life at all ages—from my mom dying suddenly when I was a teenager, to athletic friends dying doing sports they loved, to deaths by car accident, to having lost far too many during the AIDS crisis, to one young friend’s sudden death with no apparent cause. There was no reason for me to think that planning for death was something that could wait until I was older. My own history showed me the truth that none of us knows how long we have.

I thought about those who would have to clean up after my life here on earth was done. I resolved right then that I would take care of what I could in order to be kinder to them. I knew I couldn’t make it easy, but it felt mean for me to make it harder. It was time to get my own act together.

Little did I know how much I would learn going through this process. It even shifted how I felt about my father.

Writing down what’s important

I don’t own much so I figured I could go the DIY route. Everything I read online said that the most important documents to complete were a basic Will, an Advance Care Directive, and a Power of Attorney for Finances, so I started there.

I found helpful resources from NOLO Press to get those done without a lawyer. As soon as they were complete and made legal through witnesses and notarizing, I felt a wave of relief. If anything unexpected happened to me, my friends and family would have answers to the most basic questions they’d be asked by doctors, lawyers, and banks.

It was time to tackle more. I wrote lists of phone numbers and told everyone where to find them. I logged on to my retirement accounts and finally named my beneficiaries. I set up the “payable upon death” option on my bank accounts so my family and friends would have immediate financial resources to cover any expenses for a funeral and a memorial.

Then I went a step further and wrote out my vision for that memorial, including my desire that it would feel more like a party in which they would be sharing stories in celebration of all that I was able to do while I was here. I imagined my best possible legacy is to leave behind a caring community that gave each other support. I still hadn’t decided on what to do with my body, but I had several conversations with my closest friends and my brother so they knew what I was considering and why. I relaxed knowing they’d feel empowered making that call if they needed to.

These conversations made me feel closer and even more trusting of my inner circle. As someone with no partner and no children, I had been carrying an image of either being a burden or being alone if I needed a lot of care. Naming this fear helped release its hold over me. Others shared their fears with me, as well, and I started to see how similar we all were, no matter what our life circumstances.

Dying felt harder than death

Of all these documents, completing the Advance Directive was the toughest for me. It was difficult to visualize myself in the process of dying—even harder than imagining being gone. My Will is for when I’m already dead, but the Advance Directive is for when I’m still alive but not able to speak for myself. I found it hard to consider different versions of my body and mind becoming incapacitated. That one document forced me to get clear on my values and desires for the dying process.

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I filled it out slowly, taking time to think about not just my needs but what impact caring for me would have on those that I love. It brought me back to the 1990s, when I was the primary caretaker for my roommate as his body was progressively disabled by AIDS. Our home was overtaken by the needs of the disease. Hospital bed. Hospice workers. Medicine cycles. Visiting friends. Weeping family. Even what I ate changed when he could no longer smell certain foods without feeling nausea.

And I remembered the grace in my roommate’s way of thanking people who came to help. I recalled how we both relied on our dark humor to ease discomfort as we trained friends to empty a catheter bag or rotate his body to relieve bed sores. I flashed back on how exhausting it was to get to and from the hospital for every doctor’s appointment. And I smiled thinking about the drag party we threw to celebrate who he was, before he lost half his body weight and the ability to walk. One of his eyelids had started to droop, but that night it looked more like a wink accentuated by glitter eyeshadow and a cocky headwrap.

I took all the lessons from that experience and pulled them into my own Advance Directive. I forced myself to think about my greatest fear: Lingering on with a healthy body while my mind fell apart. I had to write down what I wanted my friends and family to do—and what responsibilities I would be releasing them from—should that ever become my reality.

Most people want to die at home but don’t take the steps needed to get the equipment and outside help to make that possible and ease the strain on their caretakers. I know that I want my people around—but I don’t want to completely derail their lives, so I wrote explicitly about welcoming hospice. And I identified trigger events that would give my loved ones permission to transfer me out of my home and into a care facility if I am no longer able to make that decision for myself.

Then I went deeper, thinking about how I wanted to feel while I was dying. I noted that I don’t want any television in my room, preferring silence or music and conversation. I requested that people read to me out loud. And to laugh. I know I will always want to hear laughter.

It’s easier to do with friends

I found great comfort in completing these documents, so I started telling my friends what I was doing. Many of them shared that they also intended to do this work but “hadn’t gotten around to it yet.”

I started a Facebook group so we could all share resources. Several who joined the group were also supporting elderly parents and relatives; we all shared questions and ideas on how to get their relatives to do this work, too. So many were stressed thinking about dealing with probate court or family in-fighting or making decisions about when to get care or just all the extra work of sorting out disorganized finances.

I hated that this lack of advance planning was getting in the way of them being able to simply be sad about losing their parents. The process of dying can be a precious time for connecting and showing love. It shouldn’t be overshadowed by logistics and a lack of clarity around key decisions. I felt that we should all do what we could as soon as we could in order to help.

I wished that my father had given this gift to me and to my stepmother. But even as I wished this, I found myself softening toward him. Completing my own documents, I experienced firsthand how difficult every decision can become and how easy it is to get overwhelmed. I thought about how hard it must have been to imagine leaving his children behind. And I found myself less focused on Dad’s disorganization and more in touch with his pain.

Dad’s true legacy

When I was cleaning out his condo, I did find one letter from my father that is more precious to me than any of the missing paperwork. It was addressed to me and my brother, in an envelope labeled, “To be opened only in the case of my death.”

Nine months after my mom died, when he was about to take an overseas trip, Dad wrote:

The two of you are among the most outstanding young people I have ever known—and, being a teacher, I have known many. You cannot let adversity dim your own hopes and dreams. You have too much to live for, and there is too much to do that perhaps only you can do. Mom and I have tried to do what we could for peace, understanding, cooperation and social justice. Each of you has to do what you can to make your own contributions in your own special way…I want you to understand that each of you has been a total delight to both Mom and me for all of your lives. We have loved you dearly, and we have been very proud of you.  [emphases his]

Reading this, I remembered long conversations with my dad and how animated he would get about something he’d read, or about any sign of progress toward a more just world. I flashed back on playing in the orchestra and how loved I felt when I looked out into the audience and saw his smile beaming back at me. I glowed with memories of him at each of our graduations.

That was the father I loved and wanted to hold on to. That was who I grieved. I got so caught up in the financial and legal mess, I had almost forgotten.

So. Now, I’ve taken all my frustration, my many experiences of death, my practical nature, and my wry sense of humor—and I’m using them to forge a new path. I am devoting myself to helping others think differently about their own deaths, to recognize the impact it will have on those around them. I quit my corporate work and launched a podcast to spread this message beyond my circle of friends. I think my father would approve: I’m doing what perhaps only I can do.

Most of our society’s conversation around estate planning centers on the desires and needs of the deceased, but that’s not who will have to live with those decisions. Avoiding planning for dying is tantamount to offloading our hard decisions onto the shoulders of our loved ones when they are already stressed and struggling to think. If we expand how we think about our own deaths to consider those we love, we may be surprised to discover that having these conversations are acts of kindness, ones that can bring us closer.

I firmly believe that when we die, the people who loved us should be allowed to grieve. We can support them by making key decisions now and being organized. This dying kindness would be our final expression of love.

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