Shoulda, woulda, coulda: A sermon for Vayeitze

Shoulda, Woulda, Coulda

When I was growing up and would suffer a disappointment, losing a soccer game because an opposing player found the back of the net despite my efforts as goalie, not being cast in a role I wanted in a school performance or the solo for the upcoming choir concert, or not getting an invitation to a party of one kind or another, I can recall my mom of blessed memory saying to me, “shoulda, woulda, coulda.” Honestly, if I remember correctly this response from my mom infuriated me. In the moment of disappointment, I wanted company at my pity party and was not always ready to move onto the “what can I do better next time” conversation. However, as per usual with the gift of hindsight, my mom was teaching me an important lesson; disappointments will happen, it’s what we do with those setbacks or losses to guide us going forward where we grow. Even if I wasn’t ready to move on from the pity party, her urging always pushed me.

Shoulda, woulda, coulda, perhaps a mantra for those who know disappointment. A framing for growth mindset, in our current educational scholarship. In all the Hebrew Bible, there is no greater exemplar of this than Leah who we meet in this week’s Torah portion. We learn of Leah in Genesis 29:16 and 17: “Now Laban had two daughters; the elder was named Leah, and the younger was named Rachel. Leah’s eyes were weak, but Rachel was beautiful of form and of face.” The portion continues with the deception of Jacob as Leah becomes his wife in the place of Rachel and in the morning as Jacob awakens surprised to find her as his wife. Leah is a pawn in her father’s schemes and, we can only imagine her disappointment as the text reveals that Jacob “loved Rachel … so much more than Leah.”[i] The truth is that we don’t have all that much information about Leah when we first meet her. We know she is not the favored wife, and the text intimates that she was loved, just not as much as her sister. Rabbi Shai Held asks us to:

imagine Leah’s predicament, and her humiliation. She is older and less physically attractive than her sister. While Rachel presumably has suitors, Leah remains alone, with no sense that this situation is likely to end happily, or soon. Perhaps her father thinks he is doing his elder daughter a favor, protecting her honor by deceiving Jacob into marrying her. Perhaps Leah herself harbors the fantasy that Jacob will learn to love and appreciate her. Imagine her feeling, when, on the morning after her wedding, her husband’s only response to discovering that she, rather than her sister, is his wife is an excruciating mix of outrage and disappointment.[ii]

Leah’s pain does not go unnoticed though. God sees that she is not favored and opens her womb.[iii] And it is in the naming of her sons that we begin to see Leah’s acceptance of the “shoulda, woulda, coulda” in her own life as she bares children in rapid succession. Her first son is named Reuven, Leah names him thus because “God has seen my plight, yes, now my husband will love me.” [iv] Shimon is born next, and Leah grants his name noting that “God heard that I am despised and has given me this one too.”[v] Without giving up hope, Leah’s third son is named Levi for she prays, “my husband will be attached to me.”[vi] But then something inexplicable happens. The text provides us with no hints, however, when Leah’s fourth son is born, she names him Judah, Yehudah, because “this time I give thanks to God,” she explains.[vii] Leah managed to move through her frustration to a place of gratitude. It is not that a magic wand of gladness was moved over her, something fundamentally changed about her perspective in the midst of pregnancies and child rearing. We can imagine a thousand reasons for this change, yet the Torah does not provide us with the reasoning. We can only know that Leah knew disappointment and through her pain she found the capacity to feel grateful even amid her sorrows.

It is taught in the Talmud about Leah that “she was the first person in the history of the world who ever expressed gratitude to God.”[viii] Leah teaches us that disappointment does not impede gratitude, nor does gratitude prevent the possibility for disappointment. As Rabbi Held teaches, “Judaism does not ask us to choose one feeling or the other but rather makes space—indeed seeks to teach us to make space—for the sheer complexity and contradictoriness of human experience. Who better than Leah to teach us that a broken heart can also have moments of profound fullness.”[ix]

On the Shabbat of Thanksgiving weekend, a weekend unlike any that we’ve experienced before, there can be no better message. We have known disappointment this week because our plans needed modification in the interest of health as this pandemic rages. How can we take our disappointment and feel all the feelings while also making space for gratitude and blessing? My colleague Michelle Shapiro-Abraham penned a poem for Rosh Hashanah that also fits perfectly for this weekend. She wrote:

Shards of Glass: A Poem for the New Year

A friend once told me
that we smash a glass at a wedding
to bring a bit of sadness into a joyous moment; so that
we know how to bring a bit of joy into the sad ones
I come from sturdy stock who know how to keep our sorrow on our fingertips
So our feet are free to dance
My people have celebrated New Years when the food is old and stale
And Freedom when none is in sight
My people leave the house of mourning to celebrate the Sabbath
And my people find a 100 blessings a day even
when the days are thick with smoke
And you can barely find yourself in the darkness

Remind my tired soul, I beg You
My kitchen is far too clean and the china is still in the basement
Remind me how to stop the mourning
for tables that don’t need extensions
quiet synagogues with no children to be shushed
For lives lost along the way
Help me to shake the sadness to my fingertips
and free my feet to dance across the family room floor
Let me embrace my blessings
Let me drink deep of gratitude for all I have
Let me shake off this foolish melancholy
and help me find the broom so I can sweep away
the tiny shards of glass left alone under the wedding canopy[x]

Shoulda, woulda, coulda, my Jewish mother’s attempt at finding the space for the disappointment and the blessing. May there be space for these and all of the other emotions this Shabbat and even in their complexity, may we find the blessing. Ken y’hi ratzon.


[i] Gen. 29:30

[ii] Held, S. (2017). The heart of Torah, volume 1. Philadelphia: Jewish publication society. P. 60,

[iii] Gen. 29:31

[iv] Gen. 29:32

[v] Gen. 29:33.

[vi] Gen. 29:34

[vii] Gen. 29:35.

[viii] Held, p. 63 citing BT Berakhot 7b.

[ix] Held, p. 63.

[x] https://reformjudaism.org/blog/shards-glass-poem-new-year?fbclid=IwAR116OAHNI8ovYGFosQKtmnM-Z4dqMQyVthi9LBzNHnw4GwCsebrUAX50zs

About rabbisteinman

I am a rabbi living in North America. I was ordained from HUC-JIR. This is my blog.
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