Deep Dive #1: Start the Conversation

This is a tough one and I know you are tempted to skip it. But there’s a reason why it’s the first step.

Why?

If you haven’t started the conversation with yourself, or your loved ones, how will you know who should get what?

How will you know what matters to you if you haven’t asked and answered the question for yourself?

If you haven’t taken the time to think about your hopes and dreams for the future as well as those of your family, how can you create your legacy.

There will never be a “right time,” for that conversation, but it can be too late.

“Because no matter how hard a conversation is, I know that on the other side of that difficult conversation lies peace. Knowledge. An answer delivered. Character is revealed. Truces are formed. Misunderstandings are resolved. Freedom lies across the field of the difficult conversation. And the more difficult the conversation, the greater the freedom.”

- Shonda Rhimes

Here are a few things to consider:

  1. Talking about your plans isn’t just talking about death. In fact, most of this work is about your life and legacy and new beginnings. If you’re talking to a partner, ask questions about the life you want them to have when you’re gone. If you have kids, what do you want to provide for them? Who should care for them if something happens to you? How do you want them to remember you? What stories and recipes do you want to pass on?

  2. I often hear from adult children that want to talk to their parents, but aren’t sure how to bring it up or what to discuss. If you’re looking for ideas about memorials, ask them what they liked about “home-goings” that they have attended. Another approach is capture their personal story and history. If you’re concerned about finances, the conversation may start with where they bank. You don’t need to know much they have in their accounts, but you can start a list of those financial institutions.   

  3. Remember: You can share as much or as little as you want about the details of your plans. I encourage everyone to let at least two people know you have a plan, whether it’s a letter, or a list, or a will, and where to find it (a safe deposit box, a thumb drive, with a lawyer, a family friend).

What questions do you have about starting the conversation? Share your ideas, too! We’re always available for a conversation at hello@iamwilling.us.

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Deep Dive #2: What is Wealth?

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Introducing the Deep Dive Series