Planning Ahead: From Finances to Feelings, How Estate Planning Can Help You Cope with Loss and Grief

In Trust & Will’s study of twenty thousand individuals, ranging in ages from twenty-five to forty, 78% of respondents created a will in 2020. Since COVID-19 has confronted our world with our inevitable mortality, it makes sense that so many millennials would want to create a safety net for their loved ones. And their pets, of course. In quintessential Millennial fashion, 78% of respondents in their study appointed pet guardians. 

Only 16.67% of respondents cited the all-encompassing “2020” and “Pandemic” as their reasons for creating a will. The majority, 37.99%, cited having a child as their main reason and 13.19% chose general life planning. Here at we love to see everyone dealing with financial stress – estate planning is up there as one way to reduce financial anxiety and improve quality of life. 

However, when we talk about estate planning (and later generational wealth), we often don’t highlight the emotional toll that not having a plan can have on loved ones, especially spouses or long-term partners. It could be that it’s a taboo topic or takes too much energy to recount these sad tales. I firmly believe that we can reduce anxiety over money by sharing these more challenging topics. Without them, we can’t convince our families and friends how important it is to protect those left behind. I know all about this subject because I am one of those people whose partner passed away without any end of life planning. 

I want to highlight the lessons I learned as the almost-fiancĂ© of a wonderful man who died too early, so others don’t make the same mistakes. Mistakes that I and those impacted by his death only corrected because we lost him, not because we were financially responsible. I highlight two main points: know their wishes and know their assets. 

Know Their Wishes: Because if You Don’t, Someone Else will Decide for your Loved One. 

This is probably the hardest part. Talking about death automatically depresses us, reminds us there is an end. No one wants to talk about their parents or spouse dying. That’s so many decades in the future that a few more years won’t make a difference, right? 56% of the population in 2016 didn’t communicate their end of life wishes, according to The Conversation Project. (This number has undoubtedly gone down, but it took a global pandemic for it to happen.)

We personified that statistic. We talked about everything: our hopes, dreams, our financial stress and wanting to develop good financial habits, lottery winning distributions (because who doesn’t?), why no one buys ugly produce, which cat litter is best, and most importantly for two budding archaeologists, who did it better, the Greeks or Romans? (He chose the Romans every time.)

But we never talked about what we wanted when we died. Of course, neither of us could have thought the other would die anytime soon. In fact, like most people, it wouldn’t happen to us. Only our grandparents had to worry about that.

He died before both his grandmothers and my maternal grandparents. 

Reduce Financial Stress with’s Wealth Check

Left Wondering

To this day, I don’t know what he wanted. Did he want to be cremated, his ashes spread out among the mountains he loved so much? If not, did he want to be buried? Where did he want to be buried? Near his grandpa, or somewhere completely random, since his mind wandered to so many different places over the years? 

His family chose all of his funeral arrangements. He didn’t design his funeral. Those who knew him said that the funeral didn’t reflect his personality at all. This has always been one of the hardest pills for me to swallow. If his funeral didn’t reflect him, what was the point? Funerals are for the living, and the funeral reflected his family, not what I think he would have wanted. This detail will always hurt me, and the guilt I carry won’t ever go away. 

Use a Checklist

This is the first lesson I learned: talk about what someone wants when they die. Know precisely, down to the tiniest detail their wishes. Talk about it with everyone, especially your long term partner. Ask them these critical questions so that if that time comes, you can execute their wishes. Because their desires matter. Not knowing what he would have wanted haunts me whenever the idea comes up, which is often now. Thanks, COVID.

Knowing everything but…

I mentioned I was the “almost-fiancé” because we talked about our “getting married” timeline. We knew what year we wanted to get married in; we knew where we wanted our wedding, we knew the when, how, and who. But I didn’t know what to do if he died. This is human nature: we construct our existence around life’s joys, rejecting any hint of sorrow that could dampen our happiness. We lift up accomplishments like getting married, crying to the highest rafters our love because in doing so, we somehow chase away the dark. Death can be that dark, so we don’t mention it unless we absolutely must deal with it. 

Know Their Assets: Don’t be Blindsided by Anything Unexpected.

This one is a no-brainer, supposedly. This would naturally fall under something that goes into a will, and usually, it’s evident amongst long term partners. You will talk and see the cars, benefits, properties, etc. But I want to point out the psychological effects of not knowing. 

Whatever resilience I had built up, about fifteen days after his death, was prepared for calls about him. But the lady on the other line explained she was from the life insurance company and needed to discuss his policy. They wanted to remit the funds as quickly as possible.

What Life Insurance?

His job had the remarkable foresight to offer life insurance as a benefit to the employees. Which I should have known, as I also worked there. In fact, I eventually found the copy of what I filled out in my papers, designating my sister and brother as the recipients of my insurance money. (Something I didn’t notify them of and promptly forgot about, obviously.)

His sister and I would be receiving his life insurance money. Money that probably set her up on her path to becoming a doctor. Money that allowed me to pay the fine for breaking our apartment lease, find a new place to live, obtain a car, take care of our cats, put some money in savings, pay off a significant amount of medical debt, and accumulate a retirement cushion.

The Impact of Things We Don’t Talk About

He never told me I would be a recipient, and we never talked about it. Knowing him, he probably didn’t think it was necessary. I certainly didn’t. This phone call utterly broke me. I took care of the first four things on my list because life never stops, especially for grief, and checked myself in for a voluntary psychiatric hold for suicidal ideations. 

Every single thing that happened leading up to this point caused this, not just the phone call. But the absolute knowledge that I was suddenly financially stable was too much. My financial stress, my high-interest medical debt I could never pay off would be gone in one fell swoop. I received that money because he died, I shouldn’t be relieved. Being relieved was wrong. He was gone, and all of my anxiety over money was nonexistent? Nothing made sense, nothing was fair, and I just couldn’t deal with anything. 

Coping with Grief

I know that I am not alone in my reaction: coming into a life-changing amount of money doesn’t happen often. The relief is a sudden, visceral reaction that is as psychological as it is physical. But the knowledge that the money is because a loved one died produces guilt, whether that person’s passing is a known possibility or completely unexpected. In my case, his death was violent, traumatic, and never in a million years would anyone have predicted it could happen. That call, that guilt, my reality without him, was just too much. 

Transferring Wealth – Reducing Financial Anxiety

Even if it’s hard, talk about it.

Talk to your partners, no matter how hard the conversation ends up being. Don’t commit to marriage or a long term partnership unless you understand the other person’s finances, including their life insurance. We had no idea, the silly twenty-five-year-olds we were, that this was even something important. Neither one of us was financially literate at the best of times, so please don’t make the same mistakes we did. 

Grief is an awful ride, to begin with, but adding in financial stress as part of or in addition to suffering just makes everything harder. I wrote this story to highlight two important lessons I learned when I lost my partner, but there are many more. Estate planning can blunt the impact of some of the problems I described, so I encourage everyone to have a plan in place. 


The National Suicide Prevention Lifeline has a direct number – 800-273-8255.

The National Institute of Mental Health has a guide on  

The Grief Rollercoaster explains the ups and downs that some will experience after losing a loved one. 

Trust and Will, Online Estate Planning


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