What Do You Regret?
What is your biggest regret and how can your loved ones avoid the same? What do you wish you had done, why, and what will doing that thing hopefully bring to your loved ones’ lives that you missed out on?
We start with this question for a reason. Beginning with regret demonstrates fearlessness and truth-telling. It shows vulnerability and honest reflection that add credibility and depth to our answers to all of the questions that follow.
Most of all, beginning by honestly acknowledging what we did not do but wish we had may well enable our loved ones to avoid, at least a little more than they otherwise would have, living to meet others’ expectations at the expense of their own dreams, the fear that keeps so many of us from reaching out for help, and missing opportunities to celebrate life and share more love, not only at important moments but every day. Speak openly of your regrets with truth and vulnerability so that your loved ones learn from you now and when you are gone.
When Was a Time You Led with Your Heart?
When was a time you led with your heart rather than your head? Why and how did that change your life?
As we mature, we factor in the potential downside of nearly all of our decisions. We become more risk averse and less spontaneous. How ironic then that for most of us the people and pursuits that bring us the most meaning are those we choose with our hearts.
Leading with our hearts won’t always work out, at least not the way we’d hoped. For some of us, even if it would work out, it’s hard to let go of the many ways in which we are raised and taught by society to be conventional and make the safe bet. The good news is that it is never too late to listen to your heart. Even once can change your life in a beautiful way.
If you have already been fulfilled by a heartfelt choice, tell your loved ones about it so they too might be inspired to do the same.
What Makes You Happy?
What makes you happy, and what lesson is there in the things that make you happy that you can share with your loved ones?
There is an old Chinese proverb about happiness: “If you want to be happy for an hour, take a nap. If you want to be happy for a day, go fishing. If you want to be happy for a month, get married. If you want to be happy for a year, inherit a fortune. If you want to be happy for a lifetime, help another person.”
In order to find happiness, we have to find others for whom we make sacrifices born of love and with whom we share our lives. Happiness really is togetherness. It is who, not what, we have that makes us happy, and so often happiness is in the most ordinary moments with the ones we love. Tell the people you love about those moments great and small when happiness filled your heart because of them. Show them the way so that they too can find happiness now and when you are gone.
What Was Your Biggest Failure?
What was your biggest failure and what lesson did you learn that is worth sharing with your loved ones?
A lot of people think the hardest thing to say is “I’m sorry,” but it is even harder to say, “I was wrong.” It’s hard to say those words to others and often even harder to ourselves.
At some point every one of us has been punished for being wrong rather than encouraged for trying. We all spend a lot of time in our lives pretending we have not erred in ways immoral, foolish, unkind, or simply human. That denial and withholding of the truth about our lives keeps terrible feelings bottled up within us and robs others of the opportunity to learn from our mistakes as we hopefully have. In nearly every example, reckoning came far later than people wished. Here again, the simple message seems to be “Don’t wait.”
The columnist David Brooks points out that the people he admires most have reckoned with their “core sin” by identifying it and then humbly trying to correct the bad behavior that resulted from it. Take some time to consider your greatest failure and what lesson lives within it. This may well be the most important truth and invaluable gift you can bequeath to the ones you love.
What Got You Through Your Greatest Challenge?
What enabled you to withstand and move on in the face of your greatest challenge? What advice can you offer your loved ones to guide them when they encounter real adversity?
The most important thing to know about life’s greatest and most painful challenges is that we do somehow endure them and learn to live and love more fully because of them. This is not to say that these challenges are worth the pain, merely that they are ultimately not worthless if they ennoble us with a greater sense of gratitude for all that we still have and for what we have learned.
Sooner or later we are all wounded and scarred, often badly, in ways ugly and frightening. Yet we have a remarkable ability to survive, heal, and grow in the aftermath of life’s most terrible blows. Join here in sharing your most difficult challenges and how you have overcome them, learned from them, and made peace with them. Your faith, your truth, your courage, and your self-compassion are powerful lessons for your loved ones who need you now by their side when they are in pain and by their side too even when, especially when, you are gone.
What Is a Good Person?
What does it mean to be a good person?
“At the moment of conception,” says the Talmud, “an angel takes the drop of semen from which the child will be formed and brings it before God. ‘Master of the Universe, what shall be the fate of this drop?’ asks the angel. ‘Will it develop into a strong person or a weak one? A wise person or a fool? A wealthy person or a poor one?’ Whether the person will be wicked or righteous, this he does not ask.”
Why not? Why doesn’t the angel ask God if the soon-to-be-formed person will be wicked or righteous? Because the sages believed we—not our genetic makeup, not our environment, not even God—are responsible for our moral choices. The genetic fix might be in when it comes to how tall or how strong we will be, perhaps even how intelligent we might be, but not how decent we might be. Our decency is up to us.
What Is Love?
What is love?
Ideal love is growing the heart to encompass another without possessing them, to accept and tolerate their foibles without controlling them, to listen with care, to make allowances for differences, to share intimacies with respect and appreciate each other.
A crucial difference between our human and animal loved ones is that our animals don’t care why we love them, and we couldn’t tell them if they did. Whether seldom or often, people say “I love you” to each other, but they almost never say why. The crucial question is: Why not?
Now is the time to let the people you love know why. Pour out your gratitude for their sacrifices and yours over the years that have nurtured your love for each other. Tell them how they make you laugh. Tell them what they mean to you and tell them why. Then your love for each other will abide not only for today and tomorrow, but long after you are gone.
Have You Ever Cut Someone Out of Your Life?
Did you ever have to cut someone out of your life? What lesson is there within that decision to guide your loved ones in their relationships?
Hopefully, when we make a mistake, we can accept responsibility for it, apologize, and make amends. In doing so, we hopefully attract the same type of person in our relationships. But sometimes we will have those in our life that are not kind, that use us or betray us. When someone shows you that they are that person, let them go.
We each have a line that once crossed by another creates damage that cannot be undone or excused. Physical abuse; a breach of trust by telling an embarrassing, painful secret to others; an outright lie to or about us; always taking, never giving; ghosting; gossiping—whatever your line is, at some point someone close to you will likely cross it and you will have to make a decision. There is a lot for your loved ones to learn from those moments. Tell them your “when I had to cut someone out of my life to stand up for myself” story. Because as much as we all want to be respected by others, it’s self-respect that matters most.
How Do You Want to Be Remembered?
When your loved ones want to envision you after you die, what do you want them to see? Where are you? How old are you? Who are you with? What are you wearing? What are you doing?
There is yet another blessing given to human beings. We not only have the ability to remember, but we also have the ability to consciously create memories for others to hold.
You can decide while you are alive which memories and moments you want to create for your loved ones to hold; what beauty for them to embrace when the sadness of loss creeps into their hearts. Help them see you as you yourself want to be seen, to remember you as you wish to be remembered, to feel your love for them when only memory and love remain.
What Is Good Advice?
What are your top five sayings that encapsulate the accrued wisdom of your life experience?
“Your task is not to seek for love, but merely to seek and find all the barriers within yourself that have built against it.” —Rumi
“Don’t go to the hardware store for milk.” —Author unknown
“Everyone you meet is fighting a battle you know nothing about. Be kind. Always.” —Robin Williams
“Pick your battles. You don’t have to show up to every argument you’re invited to.” —Mandy Hale
“What is it you plan to do with your one wild and precious life?” —Mary Oliver
What Will Your Epitaph Say?
What will your epitaph say? A headstone has room for fifteen characters per line and four lines total. What would you want it to say and why?
This is one of those questions that make your ethical will not only something that will be cherished by those you love after your death. It is also an opportunity to ask yourself if you are living up to your own ideals. Tell your loved ones what you want your epitaph to say about your life. Then ask yourself if you are living the truth of those words or just pretending. If you don’t like the answer, it’s never too late to change.
What Will Your Final Blessing Be?
If you could speak to your family at the end of your own funeral, what would you say? What would your final blessing to them be?
This final question about imagined last words is predicated on the impossible. None of us will ever get to speak to the people we love who gather at our funeral. If there is a subtext to this entire book, a single lesson amid its many questions and answers, it is simply this: Don’t wait. Don’t withhold your final blessing until you can no longer bestow it. Don’t wait to tell your story.
Make it a love letter to the people you love most. Let them wrap themselves in your values, your faith, your hard-earned wisdom and steadfast love. Tell them your truth. Tell them your story so they hold you in their hearts as you have held them in yours; now, and when you are gone.