Editor's note: It's one of the toughest questions you must answer as an investor...

How do you know when to sell?

But it's not the hardest question you'll need to face in your lifetime.

Today's Masters Series essay is adapted from our colleague Dr. David "Doc" Eifrig's Big Book of Retirement Secrets. In it, he details a difficult conversation you should have with your loved ones while you're gathered together during the holiday season...

Six End-of-Life Questions You Must Discuss With Your Family

By Dr. David Eifrig, author, Big Book of Retirement Secrets

It's the first day of December... That means it's time for me to ruin your holidays.

Through the years, readers have accused me of putting too much of a damper on the joyful season. That's because I always encourage folks to have the hard discussions while all the family is together. And by hard discussions, I mean end-of-life planning.

It's shocking... But over and over, the medical establishment is denying people the right to die peacefully or with dignity. The facts about the end of life are alarming...

Medicare spends 30% of its dollars on people in their last 12 months of life. And worse, people aren't dying peacefully or with dignity. About 41% of people in their last three months of life receive a "burdensome intervention." These are things like tube feedings, emergency room visits, and heart shocks. Where is the comfort... dignity... or even common sense?

People don't need to be admitted repeatedly to the hospital when they're dying or gripped by advanced dementia. It creates a sense of false hope for friends and loved ones and discomfort for the patient. Worse, it's just feeding the hospital's coffers with money it doesn't deserve. I understand that in the heat of the moment, it seems like the right thing to do, but that's the point. It doesn't change the outcome... All it does is waste money at the end of a loved one's life.

So this weekend, if you're still gathered with family for the extended Thanksgiving break – or over the next month as you celebrate the holidays – take control of the circumstances surrounding your death.

Read these six questions with your friends and family. Talk about the issues and plan for the future. Don't let some cold, faceless hospital dictate how you or your loved ones will spend those last months on Earth.

And if death seems like a remote concern... all the better. You can discuss these six questions now without the anxiety or emotions that come when death seems imminent.

Urge your family members to create living wills, health care proxies, and powers of attorney. And do it for yourself, too.

1. Do you and your family (parents, siblings, etc.) have a living will? This document spells out what your wishes are regarding ventilators, heart shocks, and other interventions if you're sick. It's hard to know. But imagine you had dementia, didn't know your husband's name, and couldn't feed yourself. Would you want extraordinary measures done to keep you alive? Would you want to be treated for pneumonia (a leading cause of death in the U.S., especially in the elderly)? Or just left to die?

2. Do you have a health care proxy? This is a document that says who you want making decisions for you if you're incapacitated. Talk about it. I've known of families where two kids thought dad wanted everything done to keep him alive and two thought the exact opposite. You can't have both. Someone will make the decision, and relationships can fracture over it.

Be sure and sit down with your designees and make your wishes clear. I recommend doing it with at least two family members and have them write out your wishes so you're sure they understand.

3. Have you thought about where you want to die? At home? The nursing home? Don't forget about "hospice care," which provides pain medication but nothing else. No treatments, no tests, no interventions in your last months of life... This is how I'd like to go: At home with little pain. But everyone's decision is personal. If you expect to care for a loved one through this last stage of life, please ask him or her now.

4. Have you considered nursing homes and assisted living centers? If so, be sure and look at the fine print.

And be sure to look online at the federal government's website on nursing homes. The site allows you to compare ratings and locations among thousands of nursing homes. For a U.S. government site, it's surprisingly useful and chock-full of information to help you decide what's best for your situation.

5. What's covered by insurance when someone is dying? Once you or your family member is in a nursing home, who pays for a hospitalization? What will be your out-of-pocket expenses for each major decision? If you had $250,000 to leave to your daughter but you were in your final year of life, would you want to be treated out of pocket or forgo it and let your child get the money?

It doesn't seem like a big deal now, but you and your daughter should talk about it. Imagine if you discovered she felt the exact opposite... You should know these things before you're in the midst of it and don't have any control to take your time and consider what is best for you.

6. Have you addressed your spirituality? Whatever your beliefs, make them known to your family and loved ones. Do you want your priest coming by? Do you want music? Do you want to give or get forgiveness from anyone? These issues should be discussed if not explicitly planned for. Is there anyone you want to talk to about love? Again, all things to talk about.

I hope these six topics open up a dialogue with at least yourself... and that this essay has added a little something to your life. I truly hope that as you contemplate your or another's mortality, you can talk about it safely with friends and loved ones.

Begin the dialogue this week and continue it throughout the upcoming holiday season.

Here's to our health, wealth, and a great retirement,

Dr. David Eifrig

Editor's note: Regular readers know Doc is one of the smartest and most accomplished people we've ever met. And in his Big Book of Retirement Secrets, Doc shares countless nuggets of wisdom and well-researched ideas to help you lead a healthier and wealthier life. If you're interested in learning more of these "life hacks," claim your copy for just $5 right here.