Zen and the Art of Real Estate Investing with Jonathan Greene

Watching My Family Die Made Me an Expert in Death


When my first relative died I was still pretty young. My mom didn’t even let me go to the funeral. I probably wasn’t ready for it anyway. But I felt like I missed out on something because I never got to say goodbye.

I had no idea that the first funeral that came into my life would be the first of many.

It’s not just that people die. People we love die. And over the course of our lives, most of them will die before us. Or we will die before them.

Fortunately, I am still healthy. But that could change any day. You never know.

Unfortunately, I have become an expert in death. This is how. Through some of the people I loved. That I have lost.

*This is a personalized history of those I have lost. But I think if you read it, you will notice similarities to many people in your own life. That’s why this is a melancholy understanding of the appreciation of life. From what I have learned, maybe you can learn something. Before it’s too late.

Aunt Molly

My Aunt Molly was that first funeral. I was around eight or nine years old when she died. She was my favorite grandmother’s sister. I spent a lot of time with her throughout my early childhood.

She was also my grandmother’s best friend. She could have been my grandmother’s only real friend. My grandfather died well before I was born. And after that, my grandmother packed it in. She called it a life.

Except for me.

Aunt Molly was there for all of it. Whenever I made the trip out from Brooklyn to Short Hills, New Jersey, they were both there. I remember riding in Aunt Molly’s brown car. And spending time at her house.

Molly’s son was my favorite uncle. And his kids were my favorite cousins. But I didn’t pay my respects at her funeral. Because I was too young. Unready for death.

This is where I began to understand death. But it would be a long time before I could understand how death should be appreciated. Really how life should be appreciated.

Aunt Molly and I on what looks like my fifth birthday. P.S. — lower right with the hand over her face is the actress, Jennifer Connelly.

Aunt Molly and I on what looks like my fifth birthday. P.S. — lower right with the hand over her face is the actress, Jennifer Connelly.


I had a long break between my first real funeral and my second. Actually, my best friends’ (twins) mom died a few years before this and it hurt. She was a great lady. And I hurt for them. I knew her well. But she wasn’t my mom. I tried to be there for them. But I didn’t know how it felt. Until I did.

When I was 20 my mom died after a long battle with multiple cancers. I have written about her plenty on Medium.

The Hole That You Left in My Heart is My Strength: An Open Letter to My Mother

The details are in other works. But not about the funeral. My second in a long list of family funerals.

It was at a non-denominational Zen garden to the best of my memory. It was very peaceful. I sat in the front row. I didn’t cry. I was in a daze. I was smiling at how people remembered her.

Without mention of the cancer that followed her for years. And pretended like it would go away. Until it didn’t. And it persisted. In killing her. In front of all of our eyes.

I had cried so much. So hard. I didn’t have much left for her funeral. I was 20, but I wasn’t ready to give a eulogy. I would later learn how to do this out of necessity. I wish I spoke to her then. To everyone. But everyone knew. That she was a beautiful person.

Taken too soon.

My mom and I — two years before she died.

My mom and I — two years before she died.


This one still hurts. They all do. But this one, my favorite grandmother, just burns inside of me. I beat myself up to this day because I could have been there more for her.

I was in law school in Florida and she was in New Jersey. I called her every Sunday, no fail, from my first cell phone. I was literally what she lived for. She was the most exceptional caretaker as a grandmother.

Making me so many cups of hot tea with more sugar than anyone could ever imagine. Getting me bagels and lox and kippered salmon and whitefish before every visit. Trying so hard to get me cool clothes by asking people at The Gap what a young man would like.

I really f*cking miss her. Because I wasn’t there for her when she was dying. Because I didn’t think she would die.

She had been in a bad car accident. Because she was still driving when she should not have been on the roads. She slowly recovered from that, but wasn’t the same. I think she had lung cancer too. Honestly, it’s hard to keep all of these ailments straight.

So she began a cycle that I was all too used to. From being away from my mom when she was sick. I would call and she wouldn’t answer. And then I would find out she was in the hospital. And I would call her in the hospital. And she would say she was fine.

Until she wasn’t.

And I couldn’t have that last call. Because I didn’t know. I should have called more. If you are reading this and have relatives still alive that you love. Call them more. Call them now. You can come back to this after.

Because one day you will kick yourself in the ass over and over again. Over many years. Even if you were an exceptional grandson. Because you could have been better. Even if you know she would forgive you. Because you were everything to her.

But, the funeral. We did something small. Family only. There weren’t many of us. Me, my dad, my uncle (Aunt Molly’s son) and his wife, and his kids. I thought I would be fine. I thought I was a man who had already been able to handle the worst. I was wrong.

As usual.

The rabbi was saying some words. Of which I knew nothing. I never talked to him. Everything was a blur, again. This world of death. And agony. And funerals.

But then he said something. Something like, I was what she lived for. And I exploded out of nowhere into the deep sobbing you see in movies when they are overdoing it. I couldn’t stop. I moved back behind everyone because I couldn’t stop. Because it was true. And I felt the same way about her.

I never got to tell her one last time. But I do take solace in the fact that I was very present. And loving. And there for her. And what she needed. Even when she pretended she was strong.

Gog and I in the early days. Yes, I was a chubby baby.

Gog and I in the early days. Yes, I was a chubby baby.

Aunt Sylvia

My great Aunt was a very interesting lady. She had her only son in her forties and at the time, that was unheard of. She was really a trailblazer. In a lot of ways.

When I was younger she would always send me a watercolor of myself for my birthday. As a bratty little d*ckweed, I scoffed at them. I probably said it didn’t even look like me. But they did. They always did.

I appreciated her in ways I didn’t realize I did. And as I got older and started my own family, I began to show her that I appreciated her for a change. I know that she died knowing that I loved her. And that was and still is very important to me.

I swore off flying after 9/11. But a couple of years later, I got the call that Aunt Sylvia had died. I didn’t think twice about flying to Chicago to go to the funeral. I owed her that.

The funeral was large. She had a lot of friends. She was an icon in Geneva. There was a kind of open eulogy run during her funeral. I wanted to stand up and talk about her.

I was polished now. I had been trying cases as a prosecutor for years and certainly had no aversions to speaking in public. But I didn’t know if could do her justice. So I sat there. And listened.

And now I sit here, in regret. Because I didn’t speak.

Aunt Sylvia, my son and I — 2002.

Aunt Sylvia, my son and I — 2002.

Grandma Charlotte

I honestly don’t remember if Grandma Charlotte died before or after my Aunt Sylvia. And that makes me mad. I felt like death was happening so much in my life that timelines are blurred.

*(Not only did I figure out that she died after Aunt Sylvia, but I also realized that she died after my dad — see below.)

Grandma Charlotte was a very opinionated person. When I was younger I often loved her and hated her at the same time. Because I knew she loved me, but would also tell me I was a p*ssy. She was like that. She was actually really funny.

It’s just that when you are a young boy and an older woman is emasculating you, it’s not that funny. If I was watching a comedy special, I would have laughed. She just didn’t give a rat’s ass. To be honest, I kind of was a p*ssy as a kid. She may have been on to something. At the time.

Grandma Charlotte lost her husband, my step-grandfather and a great guy, at some point. And although she loved to berate him all the time, I know she missed him terribly. Because he put up with her.

After that, in some ways, she gave up. She started having adult accidents at family gatherings. Before Thanksgiving we would move the seats around to try to predict where she would sit so that it would be on a chair without a cushion. She would not wear Depends.

Many people said she was senile. She would just sit there and not say much. But really she wasn’t saying much because no one was talking to her anymore, like an adult. They were doing that thing where you talk really loud and slow. But when someone doesn’t need that.

So one holiday I went over and talked to her. She was the same Grandma Charlotte. She wasn’t senile at all. She was bored. She knew everything. She asked me questions. She probably peed herself just because she could. She probably laughed about it later.

She was the type of grandma who you would get a call about. From the old person’s home she was living in before she died. And they would say she causes a lot of trouble. Because she is hitting on ALL of the men. Yup.

Now that she’s gone, I miss her. I didn’t pay enough attention to her before she died. And I didn’t even go to the funeral. I think I had just had it with death.

While writing this I realized why I didn’t go to her funeral. It was because she outlived my dad, her son. I’m leaving this in place here because I totally forgot. I remembered because we couldn’t tell her that my dad died. Because she wasn’t doing well. And that would have been it.

I still feel bad. I should have told her. I should have flown to see her and told her. But I didn’t. I don’t know if someone told her. I don’t know if I hope they did or not.

This is death. Unanswered questions. Perceived failures. And pain. But with pain comes understanding. Eventually.

Grandma Charlotte, my dad (her son), me and my sister at my law school graduation — 1997.

Grandma Charlotte, my dad (her son), me and my sister at my law school graduation — 1997.


This one destroyed me. My dad was my best friend. Before him, my mom was my best friend. But he was there for me every step of the way when my mom died. And when I was upset about girls. Or college. Or other random stupid sh*t.

I called my dad every day. Sometimes five times a day. Because he always knew just what to say. And he loved hearing from me. And talking to me. But at 33, I would no longer be able to call him. Ever.

I’ve written about my dad a lot as well. A lot.

An Open Letter to my Father: If Only I Didn’t Have To Write This

I am the person I am today because of him. He hustled every day to make sure my life would be ok. He taught me things when I was unwilling to listen. But I remember. I was always listening.

My dad had cirrhosis of the liver. But he didn’t drink. It was probably from rehabbing houses on his own. Carrying chemicals in his car all the time. Never wearing a mask when playing with asbestos. The dude did everything himself. Or with day laborers. Because he was cheap AF. And cool AF.

He got a liver transplant. We were fortunate. And for six months he was back to himself. Hitting the gym. Golfing. Nagging. But then it stopped working. And he died. Just like with my mom, I was right next to him when he died.

His funeral was a stage I wasn’t sure I was ready for. But I was. I had two kids at the time and was still working as a prosecutor. I could handle this. Kind of.

Everyone was going to be looking at me the entire time. I knew this. My step-mom never showed emotion so everyone knew she would be fine. My sister was younger and they knew I would shield her as much as I could. And she wasn’t the social type. Especially not right now. So it was on me.

I decided to give the eulogy and jotted down a list on the plane. My dad died in Miami, near me, but he would be buried in Sag Harbor. Lists were all I needed. I didn’t do speeches. I was an off-the-cuff guy. In trial. In life.

It was bleak in the time getting closer to my eulogy. Everyone loved my dad. People were really f*cking sad. Some were just sad that he wouldn’t loan them money anymore. Or do them favors. But for that, they were truly sad too.

My younger step-brother read something that my older step-brother wrote first and it was nice. Someone else may have said something. I can’t remember. Because this death thing was really starting to piss me off. How much more did I need to endure? I was only 33.

My time came and as I rose from my seat in front, I suddenly realized that now, everyone was really staring at me. Wondering what I would say. They all knew he was my best friend. The person I turned to when everything wasn’t right. When I was sad. When I was mad. When I was happy.

They all thought my dad babied me. Because he liked to. What they didn’t know is how much he taught me. About being a man. About being a good person. About doing things he was uncomfortable doing.

So I stood up. And gave the eulogy to end all eulogies. Or so I have been told. People still ask me about it and talk about it, 15 years later. Because it was raw. And really funny. Because my dad was really funny.

He used to tell me d*ck jokes in the car when I was like five. Or sing me songs with every curse word in them. But he also would ask me if I was regular, as in bathroom regular. Until way into adulthood. He loved me like a father should. And then some.

I got through this. Somehow.

But there are times I go to his grave and just sit there. And wonder what life would be like if he were still here.

My dad, my son and I — 2002. Look at how much he loved that moment. So did I. Except for my chin(s).

My dad, my son and I — 2002. Look at how much he loved that moment. So did I. Except for my chin(s).


My step-mother was an entire separate story. I didn’t really care when she died. For a number of reasons.

But I had a long break before this one. She only died a couple of years ago, if that. I didn’t care because she wasn’t enjoying her life. She loved her family, but she was barely able to do anything any longer.

My sister was taking her to the doctor every day. More than once. My sister had also been taking care of her since she was 14. Her youngest son, my step-brother, was flying in all the time. But he was helpless too. Between his family and his mother. It was time.

It wasn’t sadness at her funeral. It was relief. For her. Because she struggled all her life. Inside. And when the time came, I knew it would be me who would stand up again. To talk about her.

We went off-book on this one and buried her in California so she could be closer to my sister and my step-brother. She has a plot next to my dad in Sag Harbor, but nothing is there. Besides a headstone.

I’m sure my dad is somewhere thanking us because she won’t be nagging him for eternity at his side. But she was the one who stayed by his side every day when he was sick. So maybe not.

I have the whole eulogy on video, courtesy of my step-brother’s wife, but I have never watched it. Because I think it will be harder to watch than I think.

It was a conflicted death. Because as much as I hated her growing up, she was an important, if not completely aggravating, part of my life. And that’s why I remember her here. By writing. Because I think it makes her life feel more meaningful to me. Because it was.

My dad and step-mom.

My dad and step-mom.

Aunt Marilyn

This is the most recent death in my family and it wasn’t unexpected. Marilyn was my dad’s sister and she was in her late eighties. The last time I saw her, she was barely there. And it hurt.

She would tell her husband, my uncle Saul, to let the dog out over and over. Or to let him in. But they hadn’t had a dog in years. There was no dog.

No one warned me. Saul just shrugged in his understanding way and said something like, “You know, she’s not all here.” And I could see how much it hurt him. They had been together for around 50 years. And he was in his nineties. With the spirit of a fifty year old.

When I got the call, I drove out the next day. My Aunt Marilyn was to be buried next to my dad. They are in the same plot of four. I was the only one who knew the process. Because I had already been through it.

When you know the guys at the funeral home and the cemetery this well, you have gone down this road too many times.

My uncle was a mess. You could see it in his face. He hadn’t been without her for 50 years. This was going to test every ounce of his being. To stay with us. And he is. Staying with us, that is.

So I stood up again. As the few of us who were there all said something. While we stood over her open plot, before they lowered the casket in. A sight I was way too accustomed to seeing.

And still in my view, while burying my Aunt Marilyn. Was my dad. I could see his headstone in my peripheral vision. And the headstone of my step-mom. And somehow, some way, this comforted me.

My Uncle Saul, Aunt Marilyn, my daughter, me and my sister — 2003.

My Uncle Saul, Aunt Marilyn, my daughter, me and my sister — 2003.

That’s Death

The more you see of it, the more you learn to understand the appreciation of it. Not understand and appreciate it. You learn to understand how to appreciate it. Death. And life. Through your actions. And your words.

I learned when my mom died to ask my dad more questions. Because one day I wouldn’t be able to. It just so happens that day came way before I was ready. As it did with my mom. As it did with my grandma. And everyone above.

But death happens. And if you are not conscious of this fact of life (and death), you are ignoring someone who you will miss when they are gone. You will forget to tell them you love them. Or to call them on their birthday.

But there will be no do-over. Because they are gone.

So what will you do today to avoid this?

Do something. To understand the appreciation of death (and life). Before it happens. To someone you love.

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