Charting a Course Towards a Life Well-Lived | Congregation Beth Am

Charting a Course Towards a Life Well-Lived

By Rabbi Heath Watenmaker on
September 9, 2018

Earlier this summer, over the July 4th holiday, my family and I gathered in Los Angeles to celebrate my grandmother Dorothy’s 99th birthday. Surrounded by friends and family, there were four generations of Watenmakers present celebrating our family’s matriarch. My paternal grandmother, Dorothy, was born in July of 1919 in Chicago - she began her life as a preemie, born two months early. Her father died when she was only three years old, and so she and her sister, Ida, and mother, Flora, all moved in with her Uncle Sol (who she called “Unc”), Aunt Lena (Flora’s sister), and their two children, Eli and Seeme, to the apartment above the family’s grocery store on the North Side of Chicago. From the time they moved in together, my grandmother told me that her cousins became siblings - in my life, they were always my great aunt and uncle. Unc was like a father to her, and she had two moms. Her life was simple and at times difficult, with so many mouths to feed in the middle of the Depression.

After studying art at the University of Chicago, she met a smart, handsome young man named Herm - who eventually became a doctor. Not long after meeting, they got married, moved from Chicago to Los Angeles, and had two children, my dad and my Aunt Carol. As Herm’s practice grew, they enjoyed a good life, eventually moving into a great house in Bel Air, and then, he died from a rare disease at far too young an age. She had spent three years caring for him, by his side night and day. It was a devastating blow, and upended her life - in her late 50s, she had to move out of her home, and moved through a series of apartments in the first couple of years after Herm’s death. Within a couple of years, she decided to go to work to better support herself. For those first few years  after my grandfather’s death, my parents tell me that she seemed to exist in a fog, a shadow of herself, which she finally stepped out of a few years later when my parents told her they were pregnant with me, her first grandchild. To this day, she still wears her wedding ring, even though my grandfather has been gone for over forty years, and she has told me on many occasions that Herm was and is the love of her life.

When she was 93, she lost her daughter, my aunt, who died at far too young an age after a short and difficult battle with cancer. At 92, she became a great grandmother when my son Ilan was born, and to this day, she is still an important part of her two great-grandchildren’s lives. They know her, they talk about her often, and I think that even at seven and four, they recognize how remarkable she is, and how fortunate they are to have such a real relationship with their great grandmother. I am truly in awe of what a strong, resilient person she is, and it’s such a joy to see her tender interactions with my kids.

Like so many lives, my grandmother’s has been one of ups and downs, of sweetness and sorrow, of celebration and struggle. When I asked her recently if she would say she’s had a successful life, if she’s had a life well-lived, she was quick to answer with a resounding “Yes, absolutely.” She told me that she has learned in her life that family is the most important thing (and also really crispy french fries). 

As we gather tonight on this eve of Rosh Hashanah, we begin the work of reflecting on our actions over this past year, of retrospection, of taking account of ourselves and our souls, which we are called to over the next Ten Days of Teshuvah, the Ten Days of Repentance. Tomorrow morning, we will recite Un’taneh Tokef - a declaration of the power of this day of Rosh Hashanah on which our tradition calls us to consider our mortality. It asks mi yashkit u’mi y’toraf - who will be tranquil and who will be troubled? -- forcing us to ask ourselves how tranquil and how troubled we are.  This is our annual opportunity to evaluate the choices we have made, and to consider the ways in which we might make adjustments to our lives.

In the 5th century of the common era, the rabbis of the Talmud grappled with the question of what a successful life, a life well-lived, might look like. Rabbis, as you know, typically answer a question with another question. So our Sages responded to the question “What is a successful life?” by posing five questions they said we’ll all be asked when we leave this world and come before God, to be held accountable for the life we have lived.

You may or may not believe in an afterlife, or a God who will judge us when our life has ended. But regardless of your beliefs, the questions remain powerful ones -- and I believe they still speak to us today. These questions, asked by our Sages nearly two thousand years ago, can help us to measure our own lives, and offer some guidance on how we might want to change.

The first question: Nasata v’natata b’emunah - Did you conduct your business faithfully? At first glance, this is a surprising choice for question number one. It seems so pedestrian, practical and down-to-earth -- not particularly personal or “spiritual.” But it is just the opposite -- deeply personal and deeply spiritual. This is not a question about whether you were dedicated to your work. It asks, instead, did you conduct yourself with honesty and integrity?  As Rabbi Ed Feinstein of Valley Beth Shalom in Los Angeles explains:

Nasata B'emunah: were you a mensch, even in the competitive world of business? Were you honest with your customers, fair with your clients, and gracious to competitors? Nasaata b'emunah, God asks: were you faithful to yourself, to your own principles? What does business do to us? How many human beings must earn their livelihood at the expense of their own humanity? How much of us must die in order to make a living? Our self-respect? our dignity? our morality? our principles? our ideals? our dreams?[1]

This aspect of our lives will not be evaluated based on our earnings or outpacing others, but on whether we live out our deepest values. It’s a deeply personal question - were you honest and honorable, even when no one was looking? Did you cut corners or fudge things or cheat -- a little or a lot -- when you thought you could get away with it? Being truthful and decent in our dealings with others is the first pillar of a successful life. 

The second question: Kavata itim laTorah - Did you designate times for Torah study? It’s not exactly shocking that the rabbis of the Talmud imagine a question relating to Torah study, but the way in which they ask the question is telling. Rabbi Shlomo Yitzchaki, better known as Rashi, the 11th century French commentator, explains this question by pointing out that, “one needs to set specific times for Torah study because a person also needs to be sure to deal with regular pursuits, like work, for without regular pursuits, there is no Torah. Therefore, one needs to set specific times for Torah study lest he be pulled into regular pursuits for the whole day.”[2] Rashi’s concern is one of balance: if all we do is sit and study Torah all day every day, then we’ll never tend to the realities of this world -- earning a living, spending time with family, eating, and sleeping -- but conversely, if we focus only on those real-world concerns, they can easily overwhelm us, and we’ll never make time for Jewish learning. Therefore, our Sages say, we shouldn’t leave it to chance. We should set a regular, fixed time for higher pursuits, carving out a space for cultivating our minds and nurturing our souls.

Even back in the 11th century, it seems, people were -- or felt -- incredibly busy. How much more so in our own day. Ron Wolfson shares this story in his book The Seven Questions You’re Asked in Heaven:

“I once asked a friend if he makes time for study. ‘Study?’ [he responded] Who has time to study? I barely have time to breathe between commuting to my job, working, coming home, grabbing some dinner, and then plopping in front of a TV or a computer before flopping into bed. And the next morning I get up and do it all over again.’”[3]

Sound familiar? We live in a time and place where it is easy to get caught up and swept away by the myriad forces pulling our lives in different directions. This question is not just about making time for studying Torah; it’s about setting priorities, finding something that grounds us, that provides a foundation and a framework for how we engage with the world around us.

Many of us make it a priority to build Jewish learning into our children’s lives. But Torah study may matter even more for adults.  It puts us in touch with how Jews have thought about the fundamental issues of life. Put a different way, when we make time for Torah study, we step into an ongoing conversation. As Reform liturgist and philosopher, Dr. Larry Hoffman explains, “Judaism is a rolling conversation through time that anyone can enter into at any time. This conversation is both internal AND can happen with other people. It is a conversation that...has been happening throughout history.”[4] Studying Torah is not just about taking out a book or reading from a scroll in the ark. Torah is a process; it’s interactive; it promotes intellectual, emotional and spiritual growth.  When we make time to study Torah, as many Beth Am members do every Shabbat morning, or in their Sh’ma Groups, we join the process, we enter into the conversation, we begin our own dialogue with Jewish wisdom .

The third question: Asakta b’priya u’reviah - Did you engage in procreation? Or, to understand this question more broadly: Were you engaged with your family? Did you make time for your loved ones - - whether family you’re related to or the family you choose? Were you truly present for them -- not just physically there but mentally and emotionally with them? Did you give your best energies to caring for them?

Here’s Rabbi Feinstein again:

We leave ourselves in our children. But not just genetically. This holiday we talk about a Book of Life; a book in which all our deeds and thoughts, in public and in secret, are recorded and described. The Book is not in Heaven. And the Book is not a metaphor. The Book exists in the hearts and minds and memories of our children. They watch us. They know us. They remember: Every act of charity, of kindness, of love. Every moment of cruelty, indifference, of selfishness. They watch, they know, they remember.

"I can't be home, I have a meeting...

"I won't be able to make it, I have an appointment...

"This is really important, I hope you understand..."

…[There is a] myth that we can have it all, without making choices: we can pursue our careers, and have all our dreams, our personal development, our professional fulfillment, our happiness, and at the same time, raise happy, well-adjusted children. Without ever facing a conflict, or bumping against the limits on our time, or our energy.[5]

Every choice we make has a consequence, a cost, says Rabbi Feinstein. But our perception of those costs is often dictated by the context of the culture surrounding us. What if family became our starting point, and everything else was beholden to that?

A few weeks ago, I listened to an interview with Retired Astronaut Commander Frank Borman. In December 1968, Borman, along with Jim Lovell and Bill Anders, aboard NASA’s Apollo 8, became the first humans to leave Earth’s orbit, orbit the moon, and return safely to Earth. In a recent interview on This American Life, Borman, who is now 90, spoke about his experience, which was particularly intriguing, because he was largely unimpressed by the whole thing. Towards the end of the interview, the producer shifted away from Borman’s journey, to what happened shortly after: Just seven months after Borman’s mission, Buzz Aldrin and Neil Armstrong set foot on the moon and the Soviet Union halted their space program, which for Borman had been the point of the whole thing. So he did something that today seems kind of amazing. He quit. He left the job so many kids dream about. In the interview he was asked:

If you had stayed, could you have walked on the moon?

[To which he replies:] Oh, yeah. I could have. Probably. I probably could have walked on the moon.

The producer asks: Did you want to?

Borman says: No. Why? Look, the answer to your question -- I would have not accepted the risk involved to go pick up rocks. It doesn't mean that much to me. Somebody else wanted to do it. Let them take my place. I love my family more than anything in the world.  I would have never subjected them to the dangers simply for me to be an explorer.[6]

Here’s a man who had sailed through stars, traveled around the moon, watched the Earthrise, who decided that the risks outweighed the potential cost to his family. And so he chose his family.

The fourth question: Tzipita l’yeshua - Did you await salvation? As Reform Jews, we don’t often talk about the messianic age; and the early Reformers, stressing reason above all, denied belief in a personal messiah who would bring about our salvation. But what this question is really asking is “Did you have hope?” Despite the brokenness and the ugliness that surrounds us in our world and perhaps even in our personal lives, are we able to maintain hope in our hearts for the world as we know it ought to be, rather than being resigned to the world as it is? Are we hopeful that the best days of our lives are ahead of us?

Ron Wolfson explains,

It is remarkable, when you think about it - the stories of hope and goodness that emerge out of darkness. Viktor Frankl, a psychologist and a survivor of Auschwitz, writes in his masterpiece Man’s Search for Meaning: “The last and greatest human freedom is the freedom to choose your attitude.”[7]

The medieval philosopher Maimonides, in his 13 Principles of Faith, included this fundamental Jewish belief: “Ani ma’amin b’emunah sh’leimah b’viat ha-Moshiach, I believe with complete faith in the coming of the messiah, and, though he may be delayed, I will wait daily for his coming.” Maimonides was teaching the Jewish people resilience and persistence -- a lesson that has served us well. Even when the results are not right in front of us, when the reward or positive outcome is delayed, Judaism reminds us that we can always choose to hope.

And finally, question number five: Pilpalta b’chochmah, Havanta davar mitoch davar? The fifth question has two parts: Pilpalta b’chochmah, Did you ask questions about your life experiences that led you to wisdom? and Havanta davar mitoch davar? Did your analysis lead you to understanding?[8] Essentially, did you find time to really reflect on your life, to review the decisions you made. Did you recognize the moments when you may have missed the mark?

This act of introspection is the major work of the High Holy Days. This is a time when, each year, we are able to pause, to reflect, to engage in cheshbon hanefesh, an accounting of our actions and our choices from the past year. After careful reflection, we must own up to the moments when we weren’t our best, when we hurt those whom we love.

This last question reminds us of the importance of careful discernment. We achieve wisdom not only when he have studied or earned degrees, but when we can be truly honest with ourselves, own our mistakes, and make amends when necessary.

I was recently reminded by my son’s second grade Jewish studies teacher at Gideon Hausner Jewish Day School that in Hebrew, the word for “to improve oneself” is L’hiSHtaPeR. The Hebrew root of this word - Shin, Pey, Resh --  is directly connected to Shofar, suggesting that the call of the Shofar on Rosh Hashanah and Yom Kippur is a call to wake up and to engage in the work of improving ourselves.

This kind of healthy self-reflection also helps us to develop a sense of resilience: our tradition recognizes that as humans, we inevitably make mistakes. It’s part of our DNA. But what really matters is this: How do we respond when we have missed the mark? How do we take responsibility for our missteps and misdeeds? And, most important, once we have acknowledged what we have done, how do we return to the right path? How do we learn from the experience to insure that we do not engage in that behavior again? How do we foster within ourselves a sense that we are living a good life, a successful life, a life well-lived?

A little over a week ago, at Aretha Franklin’s funeral, one speaker shared:

“[Aretha] lived with courage. Not without fear, but overcoming her fears. She lived with faith. Not without failure, but overcoming her failures. She lived with power. Not without weakness but overcoming her weakness...I think that the secret of her greatness was that she took this massive talent and this perfect culture that raised her and decided to be the composer of her own life song. And what a song it turned out to be.”[9]

At the end of our life, when we stand in judgment, accountable for our lives, the Talmud teaches that we will be asked: Did you conduct business with integrity? Did you designate times for Torah study? Were you engaged with your family? Did you live with hope in your heart? Did you ask questions about your life experiences that led you to wisdom and did you gain understanding?

As we begin a new year tonight, what are our answers to these five questions? Where do we need to make changes? How can we strive to become our best selves, and look back, at the end, on a life well-lived?

Avinu Malkeinu, kotveinu b’sefer chayim tovim, Avinu Malkeinu, enter our names in the Book of Lives Well-Lived.

Shanah tovah u’metukah. May this be a good and sweet year for all of us, with plenty of crispy fries.


[1] Rabbi Ed Feinstein, “God’s Four Questions,” Yom Kippur 1993. See

[2] Rashi commentary on Babylonian Talmud, Shabbat 31a

[3] Ron Wolfson, The Seven Questions You’re Asked in Heaven: Reviewing & Renewing Your Life on Earth

[4] Lawrence Hoffman, 100 Great Jewish Books: Three Millennia of Jewish Conversation.

[5] Rabbi Ed Feinstein, “God’s Four Questions,” Yom Kippur 1993. See

[7] Wolfson, The Seven Questions You’re Asked in Heaven

[8] This translation is based on Wolfson’s reading.

Congregation Beth Am
  • 26790 Arastradero Rd., Los Altos Hills, CA 94022
  • (650) 493-4661 Contact Us

We strive to live as a holy community whose study and practice of Judaism inspires and challenges us to "do justice, to love kindness and to walk humbly with our God" (Micah 6:8).