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I told her I would do what I could. I had visions of going to the Eiffel Tower or stepping behind one of those kiosks on the Rive Gauche, trying to fulfill her dying wish, only to be arrested by a gendarme for littering. It took a while but I delivered. I found a beautiful forest in Provence, overlooking ancient villages and vineyards. I planted some of the ashes at the base of a cedar, took a picture, and reflected on her life. She will be in France forever.

We never had the ultimate deathbed conversation—the final good-bye, the reckoning of a life, the lessons passed along. We didn’t do the thank-you-love-you-what-has-it-all-meant-see-you-on-the-other-side discussion. That wasn’t her style. I don’t think she wanted to face it and I didn’t want to force it. In retrospect, that was my mistake. We should have had that conversation. It didn’t need to be forced.

What are you proudest of in life?

What’s one story you’d like me to tell my grandchildren about you?

How strange that the journalist son failed to string together a few simple questions just to get us started. I think I know what she would have said, but I’ll never know for sure. I wish I could have heard her answers in her voice. I just needed to ask.

Seeking Context

I call these legacy questions. They ask what we’ve accomplished or changed and inquire about the lives we’ve touched. They are questions about meaning, spirituality, lessons learned, gratitude, regrets, people and purpose. Most of us think about questions like these as we move through life—especially toward the end, when we take stock, look back, and think about what it all meant and what difference we made. But legacy questions also ground us along the way. They add meaning to the present and context to the future. By asking them early and often, we take stock of our lives and check our bearings and seek balance.

What have I accomplished?

How do I want people to remember me?

Throughout this book, drawing from my experience as a journalist and the kinds of questions I’ve asked people over the years, I’ve examined how to seek answers, chart a course, or pry information out of people who would rather not give it. I’ve looked at how questions set the stage for creativity and unlock the mysteries of people and the natural world. Legacy questions are different. Whether you ask them of yourself or others, these questions open the door for reflection and resolution. They seek context. They can be existential or spiritual. Whether you are ready to think about a legacy in the literal sense or are merely pondering the meaning of life, legacy questions ask about meaning and gratitude, mistakes and adversity.

You gain perspective from these questions by starting at the end.

Why Didn’t I Ask?

My mother was a survivor—as were so many Depression-era kids. Her family lost pretty much everything in the market crash of 1929. Through the early years of the Depression, just as Mom was coming into adolescence, her family was forced to move from place to place. They split up for a time when she and her mother had to move in with relatives in Philadelphia while her father stayed in New York to find work. He finally succeeded, and they reunited, but money remained tight. The jobs were not secure. Her mother went to work too, in a settlement house, but died soon after—of acute appendicitis, most likely—when Mom was just sixteen.

Still, my mother finished public high school in New York City and, egged on by her outspoken aunt, went to college. That was not something a lot of young women did in 1938. College was no escape, however. She was a student when Pearl Harbor shook the planet and pulled America into world war. Shortly after her graduation, her beloved fiancé, an army doctor, diagnosed his own brain tumor. He died before they were to be married. I’m convinced Mom never quite recovered. That Paris trip was a rare escape.

Mom got a job as a social worker, earning $35 a week. That’s when she met my dad. They married but were from different worlds. Mom’s family had been in America for generations and was educated and established. Dad’s family was first generation, poor, and barely literate. She grew up with role models. He grew up on his own. She was outspoken. He had not yet found himself.

Mom bore the second of her three children in a taxicab as they raced across Manhattan to Lenox Hill Hospital. Lora, born premature, brought something else to the family, Down syndrome. Over the years, her disability became another flashpoint between them. My parents’ marriage ended badly, bitterly.

Life was seldom serene and never settled. Mom, always a fighter, battled what she called the “system” to gain education and independent life for Lora. Though she clearly was proud of her kids, she always found something to criticize. But as difficult as she was at times, my mother also was smart and quick and could be wickedly funny. Mom judged everybody with a profane blast that made us wince. “Asshole!” she would shout if the driver ahead of her was turning too slowly. “Idiot,” she’d comment if the pharmacist failed to fill the prescription properly.

Mom and I had our own rip-roaring fights. But we could also sit and talk about the world or human nature for hours on end. She had opinions about everything. My youngest sister, Julie, and I were with her at the end. At about 2:30 in the morning, the hospice nurse came in and turned her a bit. Mom opened her eyes and said, “Peace.” It was the last word she spoke.

When I went back a couple of days later to thank the hospice staff, I asked the social worker how many people have a meaningful conversation where they come to terms with one another and what they’ve done in their lives. Do they ask about their lessons learned, resolve some regret, or celebrate their life story?

“Not many,” she told me. “Not many.”

The Rabbi

Not long after Mom died, and purely coincidentally, the Hospice Foundation of America asked me to host a video for a continuing education course for end-of-life professionals. I didn’t hesitate. The course involved interviewing clinicians, hospice workers, physicians, social workers, and spiritual care providers, asking them about research and best practices. They shared their experiences and their stories.

While interviewing these experts, I discovered a common theme. These remarkably caring people, who so clearly see life as a journey and death as an inevitable destination, were uncommonly good listeners and superb questioners. They told of conversations, sometimes with difficult patients or fractured families, that helped people come to terms and grieve, but also to appreciate life and find a narrative—a legacy. Questions served as part of the therapeutic toolkit. Asking people about their fears and concerns, about their quality of life and their accomplishments invited intensely personal and revealing reflection.

One of the most memorable people I met, Rabbi Gary Fink, dealt with the big what and the why questions every day. As the spiritual care adviser for hospice in Montgomery County, Maryland, this soft-spoken man with the gray beard works with people who occupy all parts of the religious spectrum, from those who find comfort in faith to those who reject religion altogether. Still others, he told me, create their own spirituality or approach mortality in a fatalistic way.

Gary Fink never judges. He never rebukes or asks if a patient believes in God. Instead he asks:

What is meaningful to you?

The answers reflect the range of human experience, he explained. Faith. Family. What I did for my school. The work I did with the blind.