Preparing to Die, So You Can Live in Peace

Justin Berry |

This article is an updated version of one I originally wrote in 2016. I was thinking about this topic a lot recently, so I wanted to share. Those of you I work with on a regular basis know that I spend a lot of time discussing topics outside of the logistical nuts and bolts of finance. How our financial system works and how it applies to you is important, but figuring out how a Roth 403b functions, setting up automatic savings, maximizing the efficiency of your student loan repayment plan, or protecting your income with proper insurance is not always the most valuable part of a comprehensive financial strategy. Sometimes the conversations than can have the biggest effect are focused on making sure our actions support the things we say are most important to us.

There is nothing more important to me than the close relationships I have in my life. A combination of my own personal experience, professional experience, and many academic studies have shown me that strong relationships are the most important factor in leading a happy life. Health, career, money, and even your daily commute all factor in as well, but the relationships with family, friends, and the people you interact with through work are at the core.

What happens to those people and the relationships when you die? I understand it is awful to think about, but I believe it is important for all of us to plan for an event that we know is physically impossible to avoid. There are three things I have done to ensure that when I pass away there will not be any unnecessary pain, hassle, or regret.

#1 – I financially protected them
There are people I love who depend on me for financial support. Therefore, I have life insurance. This is simple and straight forward, so I do not need to spend more time on this topic.

#2 – I will not be a physical or emotional burden
I have an advance directive and I had conversations with my family about my health care choices. In my opinion, the most important reason to complete an advance directive is not about you even though you are the one in the not-so-great medical condition. It is for your loved ones who are going to have to make decisions on your behalf. I have heard too many stories about people living with the regret and uncertainty of not knowing if the healthcare decision they made on behalf of a family member was the decision their loved one wanted. My mom, brother, and I have been in the situation of having to make a decision regarding life support for a family member following an accident. Thankfully, my dad was very clear about his wishes so while it was still a difficult situation, the burden and potential guilt from the decision was not put on my mom’s shoulders. I will never forget walking out of our final meeting with the palliative care physician and the trauma surgeon thinking, “I’m so glad my dad was explicitly clear about what he would want us to do in a situation like this.” Put your wishes down on paper and have the conversation with loved ones, especially your parents, so you know what their desires are when the time comes for a decision.

#3 – Notes to remember me by
I have written letters to my loved ones and stored them securely with my life insurance policy. The letters talk about my favorite memories with them. The letters describe how much they mean to me. The letters tell how much I love them. For my daughters I have also created email accounts for them that I have been sending pictures and notes to since they were born. I recently logged in to Sydney’s and there are over 120 messages in there. If something happens to me, I hope those emails bring them some comfort as they grow up. I hope the emails help remind them of who their dad was and how much he loved them.

I want to make it clear I am not suggesting you write down all your true feelings about a person, tuck it away in a safe for 40 years and never tell them how you feel. That sounds like a recipe for regret. What I am saying is that by choosing to responsibly plan for your inevitable death, I believe you can enjoy life more and worry less. I also want my daughters, my nieces, my wife, my mom, my brother, and a few of my friends to have something final to remember me by.

It is a small thing that does not take much time or effort, but I cannot quantify how much better I feel knowing these things are taken care of. If my life ends up being much shorter than anticipated, no one is going to have to make horribly difficult medical decisions without knowing what I want. No one is going to financially suffer. Most importantly, no one is going to wonder how I felt about them. By properly planning, I have shown how much I love them by not leaving a mess behind.


The cost and availability of life insurance depend on factors such as age, health, and the type and amount of insurance purchased. Before implementing a strategy involving life insurance, it would be prudent to make sure that you are insurable by having the policy approved. As with most financial decisions, there are expenses associated with the purchase of life insurance. Policies commonly have mortality and expense charges. In addition, if a policy is surrendered prematurely, there may be surrender charges and income tax implications.