As a former legal administrator, and someone very aware of the importance of advance preparation, I thought this section would be a breeze to move through.
It wasn’t.
As I worked through this part of my planning, I realized I wasn’t as organized as I thought I was. While all the pieces were there, they weren’t necessarily in the same place, or even in what might be considered a logical place. Things had been created at different times, stored in different locations, and organized in ways that made sense to me at the time, but not necessarily now.
I also realized I hadn’t reviewed my documents in seven years, and there were, in fact, things that needed to be changed or updated.
Looking at My Planning as If I Were My Own Executor
I made a conscious decision to walk through everything as if I were my own executor. I tried to look at what I had, and what I didn’t, through their eyes.
That’s when it became very clear that there were gaps between the information I had shared and the information my executor will need to know. There were things I had never talked about. There were decisions I had made based on circumstances that no longer applied. In some cases, it wasn’t even that the circumstances had changed, but rather that as life evolved so had my views.
This was especially true when it came to my health care wishes.
Over time, my personal views have evolved and so has my understanding of what my loved ones might need when the time comes, not just legally, but emotionally. Reviewing this section gave me the opportunity to make updates that better reflected my values now, and to think more carefully about how those decisions might feel for the people I love.
This is one of the real benefits of planning in advance and then taking the time, every few years, to review. It allows you to make sure your documents still align with your life as it is now.
Personal Items: A Bigger Project Than Expected
I also wanted to bequest certain personal items outside of my will. I initially thought this would be simple, but it turned out to be a much bigger project than I anticipated.
The first question was: Where are these items actually located? And then it occurred to me that it’s very likely those items may be located somewhere else when the time comes.
That led to the next question: How do you describe an item with enough detail to be clear, especially when it’s something personal or sentimental?
In the end, I chose a different approach. I took a picture of each item and printed the photo. On the photo, I made notes about what the item was, who I wanted it to go to, and the story or significance behind it.
This process had a surprising feel-good benefit. It gave me time to think back on beautiful memories and to share stories or details that may provide additional comfort to my family and to the recipient. It was a very pleasant, and very nostalgic, walk down memory lane!
Why These Items Aren’t in My Will
Because it’s entirely possible that these items may be given away, lost, or sold prior to my death, I chose not to include them in my will.
Instead, I left guidance in a memorandum as part of my planning.
Updating a will usually takes time, money, and paperwork, so it’s not always the best place for personal items that might move around, be gifted, or no longer exist years down the road.
A memorandum, sometimes called a letter of wishes, is different. It’s not legally binding, but it offers flexibility. You can update it as life changes. You can add to it, revise it, or rethink things without having to redo your entire will.
Essentially, it’s guidance rather than instructions. It gives your executor insight into your intentions and helps them understand what mattered to you, especially when it comes to sentimental items.
This approach isn’t right for every situation, but when used thoughtfully, it can reduce confusion and make the administration process feel a little more human.
A Final Reflection
What this part of my planning reminded me of is that being organized doesn’t always mean being prepared.
Even with a legal background, I found things that needed updating, clarifying, or rethinking. Walking through my documents as if I were my own executor was incredibly helpful, and it reinforced the value of regular reviews.
Planning isn’t something we do once and forget about. It’s something we return to as our lives, circumstances, and values change.
And sometimes the most meaningful part of planning is giving ourselves permission to revisit old decisions and choose differently, with the wisdom we have now.