How do I talk to my family about what I want when I die?

So much of it depends on having open communication through the course of one's life. One of my teachers used to say, "we die the way we live". If we know how to talk to people we love about things that are important to us, we won't have a problem talking to them about how we want to die. If not, there are people in medical settings, like chaplains, who can be helpful.  Palliative care teams talk about goals of care. 

Sometimes family members find it really hard to speak in a forthright way about the coming death of someone they love, so family members tend to try to take care of one another by not bringing up things that are hard. But one thing that helps in the talking about it is the more we're able to put our wishes into words, the more connected we will be in this process. Ultimately, that will bring greater relief and comfort even though the experience of starting to put it into words can be frightening.

This is arguably the most difficult thing to do. 

When I was diagnosed with cancer, I took it in stride for the most part. I did not breakdown. My wife and I were very candid with one another. The only instance in which I got emotional was when I had to tell family members.There's just so much context there. Obviously, you've got a lifetime with these people. It's so difficult to have to tell them that you could be dying, let alone something as awkward as what your wishes are. 

When you're talking about your wishes, I'd like to think that you can connect with them and say, "If you were to be in the same situation, I would want to know what you truly want, and unfortunately, I'm now in this position or I will be. And it's important for you to understand what I truly want." 

I have to believe that no family member, however awkward they may feel, can do anything but engage when that is the context.