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I love the title of this article. Mostly because of the hope it implies. As if there were some magical approach that would make something hard to do into something easy to do.

But let’s face it; there are just certain things in life that are difficult. Sometimes you get lucky and they’re a little less difficult then what you expected. And sometimes they end up being more difficult then you had hoped they would be.

Planning for the future of aging family members is just one of those topics where some conversations are going to be tough. And while it’s not really possible to remove all the difficulty, there are some good tips to be had on making hard conversations easy…..or at least easier.



Over the next few weeks I’ll offer up some tips I have found very helpful in having difficult conversations.

Use humor
Humor is one of the most powerful tools there is. Humor binds people together and keeps their attention. It can help you through difficult conversations and having a bit of humor about yourself can keep you grounded when things get rough.

My mother pre-purchased her funeral. An older gentleman came over when mom was in her mid 50s and I in my mid 30s to go over the details of what she wanted. One of her wishes was a headstone with a little locket-like panel where you put a picture. She even knew which picture she wanted. It’s one from her wedding to my stepdad – and I agree, it’s a beautiful photo. But I didn’t want one specific image representing her in my memory.

We went back and forth about it. Then – much to the horror of the nice gentleman trying to help us – I came up with a plan. I told mom she could have the locket feature on the headstone on one condition. Before she died, we were going to arrange for a photo shoot. We would bring a few different Halloween costumes. Have some beach shots in different bathing suits. Maybe dress her up as cupid for Valentine’s Day. Have a fun formal outfit or two for New Year’s Eve. We would turn the little locket photo idea into a calendar and have enough pictures to change them out each month for a few years.

I thought it was genius! Mom laughed. The cemetery rep just giggled nervously.

My mom and I were absolutely cracking up while we planned the details of her funeral and final resting place.


Tell stories

People don’t remember statistics – they remember stories.

Stories connect you to people. They elicit feelings and get your point across. They make you and what you are saying relatable to others.

Stories can help break the ice. Maybe your dad has been reluctant to speak with you about the possibility of having to move out of the family home. The minute you bring it up he checks out. But what if you tried something more like this:

“So I was over hanging out with Joe the other day. Remember Joe who I went to college with? He was just back from the hospital visiting his mom. I guess his mom got up in the middle of the night to go to the bathroom and didn’t turn the light on or something and she tripped on the bathmat and fell while in the bathroom. She was okay but she couldn’t reach up to the sink counter to help pull herself up and she didn’t bring her cane – I imagine because she figured she was just going a few steps.

​”She’s lucky though because she was scheduled to have the air conditioner looked at that next afternoon and Joe was meeting the handyman there so when Joe came in he found her. How scary though, huh? She’s okay but what if they didn’t have that handyman appointment set? It was bad enough spending like 12 hours on the bathroom floor – can you imagine if nobody had planned to be there for a few days?”

Those are just two ideas. Over the next few weeks I’ll be posting additional ways to get you through difficult conversations – both about planning for the future of aging parents – and really any difficult conversation you may be facing.

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