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Recalibrating Our Ambition (Yom Kippur 5784)

Recently, a friend shared a comic with me that really hit home. 

The comic has four boxes; the top two are labeled “Young Me”, and the bottom two are “Adult Me”. 

In the top two boxes, young me exclaims “I want to achieve great things! An astounding career! An amazing house! World peace!”

In the bottom two boxes, adult me, looking a bit more seasoned by the world, looks at a tiny potted plant and wistfully exclaims “I want to grow a basil plant.”

The comic is as funny as it is poignant: I would imagine that many of us can relate to the sense that as we age, our ambitions change.  

Sometimes, to pass the time, or change up the energy when my kids are bored or bickering, I’ll ask them a round of rapid fire questions— What’s your favorite color? What’s your favorite food? If you could go anywhere in the world right now, where would you go? And the perennial favorite: what do you want to be when you grow up? 

Over the years, their answers have ranged from “a babysitter” to “an engineer” to “a scientist” to “a mom” to “gymnastics instructor” to “rockstar”. 

We played this little game again recently and my younger daughter said “What about you mom? What do you want to be when you grow up?”

Before I could even answer, the older one chimed in “She’s already a grown up. She’s a mom!”

With just a touch of mischief, the younger one retorts “She’s a RABBI mom!” 

I can’t help but play along and tell them it’s not fair— I should still get to say what I want to be when I grow up. What if I want to be a Broadway star, or an author when I grow up? They laugh. The idea that I could still be something else seems outlandish to them: but the truth is, I am already “what” I want to be when I grow up, even as I continue to work on the “why and how” of I want to be, as I keep growing up. 


My friend and teacher, Rabbi Larry Hoffman recounts a story in his book “The Journey Home.” about a spirituality workshop he once led. 

He asked people to draw a line corresponding to the shape of their life’s course. He instructed participants to draw a heavy line to correspond to their life lived so far, and a dotted one to portray the way they expected their lives to continue. Most people’s drawings looked like a hill with a long upward incline, then a peak, then a short downward slope. Rabbi Hoffman describes how older people ended the first part of the exercise around the crest of the line or slightly on the downhill slope of the other side; while younger people, “who saw their lives in ascendancy, had stopped their heavy line before reaching the top, but then continued the hill-like pattern in dotted anticipation of what was sure to come. Both ages assumed the point of life is to rise to the top.“

Of course, there were a few outliers: a woman who drew a line that looked like a double hump on a camel— representing the two pinnacles of raising her own children, and then being a part of her grandkids’ lives. Others drew spiral shapes that moved across the page without any discernible rise or fall. 

Yom Kippur beckons us to stand here each year, and consider the big picture of our lives: to imagine the dotted lines, and to see our lives in the wider horizon of human experience, to consider what we want to be as we continue to grow into each new moment of our being. 

An entire machzor filled with liturgy that calls out to us to examine how we are living: how do we speak to those whom we love? How do we care for the vulnerable? How do we work to repair what’s broken around us? 

Not a single page in the entirety of that machzor that asks us: did you get into the “right” college”? Get the promotion? Did you land the bigger job— buy the big house, the new car? 

And yet: when I think about the meaning behind the lines people drew in Rabbi Hoffman’s spirituality workshop, it feels hard to ignore the role that ambition plays in how we draw the maps of our own lives. I’ve been thinking a lot about ambition this past year, and the role it plays in influencing our choices in the world. 

An article caught my eye earlier this summer about the airline industry, and how they are having a terrible time filling captains jobs. A Reuters article describes the impact: 

At United Airlines, bids for roughly half of the captain vacancies have gone unfilled, meaning United can’t find enough first officers who want to become captains. Meanwhile, at American Airlines, more than 7,000 pilots have chosen not to take the captain upgrade, and the number of people declining the upgrade has at least doubled in the past seven years. 

One of the pilots interviewed for the article explains: 

"Taking a captain's job would have boosted [my] pay by 40%, but it would have been costly. If I did that, I would've ended up divorced and seeing my kids every other weekend"

Stories like this can be found in nearly every sector of American industry— the headlines are all a variation on the theme.  One particular headline from the Guardian shouts in bold font: “‘A bigger paycheck? I’d rather watch the sunset!’: is this the end of ambition?” 


For the good part of this summer, I carried a book with me everywhere I went called “All the Gold Stars” by Rainesford Stauffer. A book all about ambition— the title a nod to the achievement culture that so many of us grew up with: a shiny gold star sticker meant to say “good job”.  The irony of this particular book is that every time I thought about opening it– I just didn’t. Perhaps lacking the ambition to dive into an analysis of ambition itself.  

What I found once I finally dived in, was a thoughtful, sociological analysis of how ambition works in American culture: sturdily sitting on a foundation of capitalism that tells us that if we have more, we will be more. On that foundation of capitalism, we encounter an understanding of ambition that tells us that someone must always be ahead, and therefore, others must be behind. This version of ambition tells us that the best way forward is up, up, up, grind, grind, grind. That all the gold stars, the good report cards, the awards, the promotions— that those things are what life is really about. 

The word itself is rooted in Roman politics: ambitio, from the Latin verb ambire, which referred to political candidates going around to solicit votes. Or, we can trace our more modern understandings of the word to not one, but three separate Greek words, including “philotimia”-- -love of honor, “eritheia”--- rivalry or strife, and “philodoxia”--- love of acclaim. 

Later understandings of the word have biblical connotations as well. The Geneva Bible includes the following margin note: “Adam ate the forbidden fruit not so much to please his wife, as moved by ambition at her persuasion”. In his book “Ambition: A History from Virtue to Vice”, author William Casey King notes “ambition, therefore, is at the core of original sin.”

Ambition could be neutral; and it enjoys mostly positive regard in our culture; but it is impossible to ignore the contexts of social, racial and gender privilege that have turned it into something with the potential to slowly poison other parts of our lives.  Ambition is no longer neutral when we consider the ways in which it has been rewarded in some and punished in others. 

And still: I can’t help but think that we can go deeper still. That encoded in our humanity, there is something more for us to wrestle with when we consider our strivings. 

In an interview  with Stauffer, she reflects on the audience for her book—- who is this 263 page book on reimagining ambition for? 

She answers simply: “anyone whose self-worth is under strain”. 

If we go looking for stories and wisdom around ambition in Jewish sources, we find there a wider range of possibility for how we aspire, not just what we aspire to. 

Our tradition loves the number three— threes are easy to remember. 

And so I offer two very different “threes”: 

Our first “three”:  in Pirke Avot, we learn ““Jealousy, lust, and ambition, take a man out of the world.” 

הַקִּנְאָה וְהַתַּאֲוָה וְהַכָּבוֹד, מוֹצִיאִין אֶת הָאָדָם מִן הָעוֹלָם

Jealousy, lust— ambition, defined here as a quest for honor, literally take us out of the world as it is: they turn our hearts in the wrong direction; away from the lives we have in the here and now, maddening us with a quest for more. 

I am reminded too of the teaching, just verses earlier in Pirke Avot that asks:

 אֵיזֶהוּ עָשִׁיר, הַשָּׂמֵחַ בְּחֶלְקוֹ

Who is rich? 

He who is happy with his portion. 

And our second “threes”, also from Pirke Avot— from the very first chapter: 

עַל שְׁלשָׁה דְבָרִים הָעוֹלָם עוֹמֵד, עַל הַתּוֹרָה וְעַל הָעֲבוֹדָה וְעַל גְּמִילוּת חֲסָדִים:

Shimon the Righteous used to say: the world stands upon three things: Torah, being of service, and the practice of acts of loving kindness.

Three things– three impulses, that could take us out of the world, distracting us from the real work of being human. Jealousy, lust, ambition. 

And three things that build up this world, giving it a sturdy foundation: learning, being of service, and acts of love and kindness. 

What I love about these two texts is that they direct us to see ourselves as part of the world— on the one hand, a version of ambition that is so personally motivated that it takes us away from the world. And on the other, a vision of a life guided by curiosity, giving, and love which gives our world a sturdy foundation. 


Today, on this day of searching honesty and self-reflection, I wonder most about the spiritual dynamics of ambition.  

How might our striving be for good? 

How might we be gracious to ourselves—- and to those around us, by honoring ourselves as we are, without feeling compelled to keep drawing that heavy line upward? 

I recently asked a group of friends and community members to talk to me about their relationship with ambition.  Stories of what they thought life would be like as young people, fresh out of college or grad school poured out of them— stories that reflected a belief that ambition was a straight line up, with markers and milestones assumed. 

One friend, who over the last year decided to step away from a successful career in PR shared with me the messaging she felt she had learned earlier in her adult life— that  the higher paying the job, the less transactional it  would be. This idea felt reinforced by the way that people talked about professional ambition–  

“As we climb the proverbial ladder and talk about a company as a family and career challenges as opportunities, and pay as bonuses. But any job, even if you enjoy your work, and being a part of a great organization, even if you work for yourself, can be primarily a means to an end. A paycheck. What you do for a living isn't what you live for.”

What you do for a living isn't what you live for.

If what you do for a living (which so often is the wellspring for ambition)  isn’t what you live for; then what is? 

I think part of what we live for is connection to something bigger. 

Sounds cliche but I mean it. 

I believe that humans are hardwired to want to feel connected to a bigger picture. 

My life is a speck of a speck of a speck in human history. 

What are we all here to do, if not to be a part of the human story. 

The human story has to be about more than drawing a straight line uphill— ticking off milestones and accomplishments. 

As this new year comes into full view, I want to think more intentionally about the how and why of my ambitions and aspirations; not just the what

I think that’s why we’re here today. 

Not because any of this is new or novel. 

Not because we don’t know what we should strive for and how we should live. 

But because it’s hard to do, and easy to forget. 

Because sifting through our values and our goals and our intentions while sitting in this beautiful space together is one thing— but it’s so counter-cultural. 

Out there, the world will tell us that other things matter. The house, the promotion. The new car. 

But here, in this space,  we are reminded that it’s Torah, Avodah and Gemilut Chasadim; learning, service, and acts of love and kindness. 

There’s a passage in our Shabbat prayerbook, Mishkan T’fillah, offered as a study text on Shabbat morning that I love, written by Lily Montagu, an early 20th century leader in the British movement for Liberal Judaism. 

She wrote: 

Let us consider well, in the light of religion, what are the things worth bothering about. Perhaps we shall find ourselves bothering about mere trivialities—indulging in fears which have no foundation now and never will have any reality. Perhaps we are wasting our opportunities altogether or using them in a futile way. Let us pray for guidance, and let us remember that when all the rubbish is pushed to one side, there are many things which we shall have to bother about, which concern us immensely because they concern the wellbeing of the community as a whole… In spite of our absurd inadequacy, in spite of all our weaknesses, we can affect by our lives, the life of humanity in its progress toward God.[2] 

When all the rubbish is pushed to the side, where will our ambitions have taken us? Will they lead us to work for our own benefit, or to bother about things that concern the wellbeing of the community, and the world as a whole? 

Who will be tranquil and who will be troubled? 

Who will be able to connect the dotted lines of their future lives, and make out a picture that reflects their souls’ ambition? 

Who will reach what they thought was the peak, and look around dissatisfied by how they feel on the inside? 

For me, these are the questions that animate my curiosity about ambition, and its impact in our lives. 

My curiosity about ambition comes, in part, from a sense that my own ambitions have evolved and distilled into something different than they might have been 20 years ago.  

Evolving ambitions are at the heart of what we are here to do today. In our self-examination— looking back over the heavy lines already carved in the timeline of our lives, how will we begin to draw the dotted line ahead? 

Today, more than ever, I see our tradition as the guidebook for the deep, soul ambitions that will never earn paychecks, but may very well sustain and heal our world.

In thinking about ambition, and it’s potential— it would be all too easy to make ambition the strawman, and paint it as a net-negative force in our lives. And certainly, we could hold up the effects of our country’s toxic achievement culture, which we thrust on children as early as that first “elite pre-school application”, and say— what good is ambition? Is it worth the anxiety, ill effects on our mental health, and deepened social disparities that see it create?But that would be to dismiss the best aspects of ambition: the motivating force of aspiration, our human capacity to create, dream and imagine. 

I think about that question I keep asking my daughters, “what do you want to be when you grow up?” and how instead, I might model for them a life dedicated to thinking about how they want to be in the world, rather than just what

Ambition is powerful.

If ambition tells us that we will be successful if we keep grinding away and stay busy, then ambition can also remind us that rest and restoration are Jewish values worth elevating. 

If ambition can build towers to the sky and faster cars and new computers, then ambition can also create a more just world. 

If ambition can push us to ascend to greater professional heights, then ambition can also motivate us to be better friends and community members.

May our ambitions in this year ahead make us curious, and open to ever-evolving aspirations. May our ambitions lead us to build a world on a sturdy foundation of learning, service to others, and acts of love and kindness. 


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