Start Before You're Ready03/24/2021

Start Before You're Ready

What challenging conversations about aging are you putting off? None of us, myself included, wants to willfully look at the reality of our own diminishing capacity to care for ourselves. None of us.

In my early 20s, I was fortunate enough to get a job working for a tax attorney/estate planner, and it changed my life forever. I watched as informed and educated families put plans into place that addressed illness, incapacitation, death and disposition of assets. On the flip side, I also got to see the colossal mess, arguments and lost money that occurs when people fail to plan. It is not pretty, trust me.

Thirty years have passed since I had that particular job, and life hasn’t gotten any easier. In fact, it has gotten far more complicated. The reality is that those who fail to plan well ahead of when they are going to need assistance, usually end up holding the short end of a shockingly small stick. Without the foresight of good legal planning, your options to have opinions about your outcome shrink dramatically.

In some cases, in order to qualify for government assistance for long term care, you must first use all of your own assets, which makes sense, right? Maybe you want to qualify for some help so that your money will last longer? People who think they are going to sell Momma’s house, bank the money for the long haul and get government subsidized care are in for a big surprise. In order to be eligible for assistance and to protect your assets, some states are requiring that the assets be moved up to five years prior to applying for assistance, making last minute scrambles a moot point.

Plan ahead. Don’t wait until it’s too late to protect your assets. We are all living longer and making your dollars stretch further takes some planning.

As a professional organizer, I’m working with quite a few people who are organizing for their final season of life. For some, they need help gathering their important documents before making their way to their attorney. For others, they’ve completed that task and are now needing assistance going through their personal effects and deciding what to do with them. Someone who isn’t emotionally involved or attached to their outcome can make the process easier.

Letting go of cherished belongings can be challenging for anyone. Here are three creative ways you can share your treasured possessions with someone you love. Watching them receive and enjoy these gifts can be a joyful event for you both.


When I was in my late teens, my maiden aunt Mary did something incredibly cool for Christmas. She ended up with a slew of family heirlooms and decided that it was time to let them go. She wrapped and boxed them all carefully and brought them to my sister’s house for our annual celebration and gift exchange. All the items were then unpacked and displayed on long tables for us to look over. She gathered up her nieces and nephew and passed a hat between us and we each drew a number. We then took turns choosing the items we wanted. We kept picking (in order) until eventually the tables were bare. We swapped as we wanted to, and it ended up being great fun. She intimated that it just made things easier. By letting folks have what they wanted, she didn’t have to sweat over the details. She also loved watching us enjoy the mementos that had given her so much joy, something she would have missed had this all waited until she passed away.


Have you ever had a friend or family member comment on how much they love a certain item in your house? Why not just make it a random gift to them? You already know they like it, why not give it to someone you are certain would appreciate and love it? Invite them for lunch, wrap it in a nice package and include a thoughtful card. What a lovely way for you both to enjoy a cherished item.


A client who had been collecting notes and cards from her nieces and nephews for years decided it was time to do something with these bits of memorabilia. When these kids became adults and started having families of their own, we got together to decide what to do with it all. There was artwork, letters from summer camp, invitations, graduations and photos all gleaned from events during 30+ years. We went through everything carefully and separated items by child. Photos took a little longer but it all worked out well.

The final step was boxing them in a beautiful creative way and attaching a lovely hand written note. For the next year each adult child got their own box for their birthday. It was a huge family hit.

Going through your treasure can be a fun process. Watching someone else get joy out of these things as well—even better.

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