1장
Facing Your Fears: The Question That Changed Everything
"What would you do if you weren't afraid?" This simple question, emblazoned on Facebook's walls, struck Michal Oshman like lightning on her first day at the tech giant. Despite her impressive resume-military service as a commanding officer, multiple degrees, leadership positions at prestigious companies-she had been living with crippling anxiety that manifested in constant catastrophic thoughts and physical symptoms. This powerful question would become the catalyst for her transformation and the foundation of this book, which has become a favorite among Silicon Valley executives and mindfulness practitioners alike. Since its publication, the book has been translated into 12 languages and featured on numerous bestseller lists, with celebrities like Arianna Huffington and Adam Grant praising its unique blend of ancient wisdom and modern application. What makes Oshman's approach so compelling is how she draws from 3,000-year-old Jewish teachings to address very contemporary issues of anxiety, purpose, and belonging-proving that sometimes the oldest wisdom offers the freshest perspective on our modern struggles.
2장
The Soul's Eternal Flame
For years, I sought relief from my anxiety through conventional therapy and medication. Therapists focused on my childhood-my father's work as Israel's top forensic pathologist exposing me to death, my Holocaust survivor grandparents' trauma. While this helped normalize my feelings, it became a limiting cycle of reopening wounds without healing them. Despite years of therapy, my anxiety only worsened.
My breakthrough came from an unexpected source: Jewish wisdom. Around Passover, I discovered that the Hebrew word for Egypt, "mitzrayim," means "boundaries" or "narrow straits"-symbolizing our internal chains and self-imposed limitations. This revelation coincided with hearing Facebook VP Nicola Mendelsohn speak about balancing her executive role with family and religious observance. Inspired, I reached out to Professor Kate Miriam Loewenthal, who directed me to Hasidic teachings.
There I encountered the Tanya, which describes the soul as "comparable to the flame of a candle which continually flickers upwards." This powerful metaphor helped me see my anxiety not as a disease but as part of the human condition-the beautiful struggle of a soul yearning to grow beyond its current state.
The Hebrew concept of "neshama" (soul), related to the word for "breath," suggests that every human has both a body and a soul-a divine flame that needs nurturing. According to Genesis 2:7, the human soul is essentially God's breath, injected into Adam's body to bring it to life. This understanding helped me realize that my essence wasn't just shaped by my upbringing but contained something deeper and untouchable that existed before my experiences.
Why do we struggle to connect with our souls despite believing in them? Jewish mysticism introduces the concept of "kelipa" (shell)-a metaphysical barrier obscuring the soul. This shell represents mundane distractions like money, work, success, and beauty that become our focus and source of fear. Unlike the body and ego, the soul is eternal and immune to fears of failure or rejection, seeking instead meaningful experiences like growth and fulfillment.
When God found Adam hiding after eating the forbidden fruit, His first question was "Ayeka?" (Where are you?). Rather than asking "What have you done?" God invited self-reflection. This taught me to move beyond blame and look inward, asking not what happened to me, but who I am and where I am on my journey.
Jewish wisdom showed me that struggle isn't a bug in the system-it is the system. These principles transformed how I manage anxiety, helping me breathe, sleep, and smile again. By finding and growing our neshama beneath its fearful shell, we can control fear rather than letting it control us.
3장
Finding Purpose Beyond Self-Focus
Viktor Frankl's experiences in concentration camps taught him that finding meaning comes not from what we expect from life, but what life expects from us. Similarly, Rabbi Shneur Zalman asked a struggling businessman to consider what he was "needed for" rather than what he needed. This shift in perspective-from self-focus to purpose beyond ourselves-holds the key to overcoming fear and anxiety.
Jewish wisdom teaches that feeding the ego starves the soul. The concept of "bittul"-self-nullification or nothingness-involves emptying yourself of self-focus to make space for something greater. Rather than suggesting you don't matter, bittul proposes that being full of yourself blocks purposeful living. The solution isn't adding more personal satisfaction but shifting focus from "I am everything" to "I am not everything."
I discovered this truth while volunteering as a "big sister" to a girl from a women's shelter. Despite my busy schedule and initial reluctance, the experience of focusing on someone else's needs rather than my own anxieties brought unexpected fulfillment. When we utilize our talents and experiences for others' benefit rather than obsessing over ourselves, we find the purpose that dispels fear.
The Hebrew word for "me" (ani) contains the same letters as "nothingness" (ain), revealing a paradox: we are simultaneously everything and nothing. Rabbi Simcha Bunim advised keeping two notes-one saying "The world was created for me" and another reading "I am but dust and ashes." This duality helps balance self-importance with humility.
I found practical value in this approach during career disappointments, using the "dust and ashes" note to gain perspective and let go of ego-centered thinking. Conversely, when doubting my ability to write this book, I used the "world was created for me" note to recognize my unique mission to share Jewish wisdom.
Discovering your purpose begins with identifying your strengths-activities that make you feel strong and in flow. Using Marcus Buckingham's definition, strengths are activities that make you feel naturally strong, whether or not you excel at them. My strengths include helping others grow and building company cultures, which led me to join TikTok as Europe's culture lead despite loving my Facebook position.
Purpose isn't one dramatic life mission but evolves through different phases of life. Sometimes we discover our purpose by first learning what it isn't, through disappointments that ultimately redirect us. Accepting that we can't control everything in life-relationships, career, health-helps manage fear. According to the Baal Shem Tov, perhaps a soul comes to Earth for decades just to perform one meaningful favor for another person. Whatever your purpose, finding it replaces despair and anxiety with meaning.
4장
Crossing Life's Narrow Bridges
My grandmother Chana's harrowing escape from a train bound for Auschwitz-squeezing through a crack and jumping despite gunfire-was shared to prepare me for life's hardships. These stories instilled both admiration and fear, causing Nazi-themed nightmares throughout my childhood and developing intense anxiety about suffering worldwide. As an adult, this manifested as paralyzing panic attacks, even during what should have been happy moments like a Paris vacation with my new husband.
Walking home one Friday evening in London, feeling the absence of Israel's Shabbat energy, I heard young men singing "Gesher Tzar Me'od"-a familiar Jewish song whose meaning suddenly struck me profoundly. The lyrics declare "The whole world is a very narrow bridge, and the main thing is to have no fear at all."
This song, inspired by Rebbe Nachman of Breslov's words from the 1700s, resonated deeply with me. Despite living in difficult times of physical suffering and leading a community facing poverty and anti-Semitism, Rebbe Nachman realized that while he couldn't change life's realities, he could transform himself and help his community do the same. He turned Torah principles into daily practices, teaching that even in difficult situations, one should face fear and move forward without hesitation.
Jewish wisdom promotes action over excessive analysis. When receiving the Torah, the Israelites declared "Na'ase v'nishma"-"We will do, and we will hear," promising action before understanding. This principle contrasts with our generation's tendency to over-analyze rather than act.
I began lighting Shabbat candles despite initially having no desire to observe Shabbat. After three weeks of this simple action, I felt a connection to myself and my heritage. Sometimes just doing without overthinking is the only way to move past fear and toward fulfillment.
Trust represents another narrow bridge many find difficult to cross. Despite its inherent uncertainty, trust forms the foundation of effective teamwork. When coaching a "dysfunctional" leadership team where members avoided sharing information or making decisions together, I discovered trust was the missing element. Building trust is challenging-it takes time to establish yet can be destroyed instantly. The first step is choosing to believe in your team's ability to build trust together.
The author emphasizes that crossing bridges makes us more resilient and stronger. I've learned to accept my anxieties as part of myself and use action as my antidote to fear. Instead of living in constant fear of failure, disappointment, and death, I choose life-a far better lifestyle.
5장
The Wholeness of Broken Hearts
At twenty-three, I experienced devastating heartbreak when my boyfriend unexpectedly ended our relationship, leaving me feeling like a complete failure. After two years of healing, I discovered a transformative principle: "There is nothing more complete than a broken heart."
This Jewish wisdom from Rabbi Menachem Mendel Morgenstern suggests that true growth happens in the cracks between broken pieces, where wisdom and strength develop into beautiful imperfection. I realized I wasn't meant to mend my brokenness back to my previous state, but rather to incorporate it as part of my more complete self. My heartbreak ultimately led me to meet my husband and become who I am today-the complete yet broken version of myself.
While heartbreak is painful, our souls remain intact through suffering. Viktor Frankl found meaning in Auschwitz through his love for his wife Tilly. After learning of Tilly's death post-war, Frankl experienced profound grief yet discovered new purpose by sharing his psychological insights with the world. His equation "Despair equals suffering without meaning" became his guiding principle. Despite devastating loss, Frankl chose to move forward rather than remain in grief, ultimately helping millions through his book "Man's Search for Meaning."
We also experience self-inflicted brokenness-the pain from our own actions. During Yom Kippur, I found myself envying a seemingly "perfect" former classmate at synagogue, observing her grace and apparent effortlessness before catching myself in this comparison. This jealousy triggered shame and self-criticism. Later, I learned from Hasidic teachings that these "strange thoughts" surface during quiet moments because our soul wants us to self-correct. Rather than feeling ashamed, these negative thoughts should be viewed as opportunities for growth.
Jewish wisdom recognizes the perpetual conflict between our good inclination (yetzer tov) and bad inclination (yetzer hara), teaching that this internal struggle is what makes us human and helps us grow.
I once discarded broken objects and tried to "fix" emotional scars to achieve perfection. Now I value brokenness, keeping chipped nails and repairing torn blankets as reminders of imperfection. When Moses broke the Ten Commandments tablets upon seeing the golden calf idol, the broken pieces were kept alongside the new tablets in the Ark of the Covenant-symbolizing that brokenness and wholeness exist together.
Similarly, at Jewish weddings, the groom breaks a glass as a reminder that even in happy marriages, things break, and these moments strengthen relationships. Brokenness isn't something to discard but to honor as part of our completeness.
Throughout life, our hearts will break in multiple ways, but we're designed to both break and continue living fully despite brokenness. The most prideful moments come from overcoming difficulties and emerging stronger. The Zohar teaches that "Weeping is lodged in one side of my heart, and joy is lodged in the other"-we carry both sadness and joy, failure and forgiveness, simultaneously within us.
6장
Creating Space for Others to Flourish
We often dominate conversations and spaces due to fear and ego attachment. When we impose ourselves by talking over others, offering unsolicited solutions, or failing to listen, we're taking up too much space out of fear of appearing ignorant or losing control. This tendency limits diversity of opinions and stunts growth in relationships, teams, and families.
The Hebrew concept of "tzimtzum," meaning "contraction" or "concealment," offers a profound model for human relationships. According to Rabbi Isaac Luria's 16th-century teaching, before creation, only God's infinite light (Ohr Ein Sof) existed, filling all space. For creation to occur, God contracted part of His light to make room for the world and its inhabitants. This divine act of self-limitation teaches us that when we contract ourselves-limiting our dominance, advice, or control-we create space for others to grow.
Our evidence-based world values constant display of knowledge and experience, but concealing can be more impactful than revealing. As leaders, parents, or friends, we don't need to showcase all our wisdom. Instead, we should consider what others truly need from us, sharing only what's appropriate for their current capacity and circumstances.
Early in my marriage, I would constantly ask my husband "Where are you?" whenever we spoke on the phone, which irritated him as he felt untrusted and confined. Once I stopped asking and gave him space, he naturally began sharing his whereabouts. After twenty years together, we've learned to practice tzimtzum by contracting ourselves when needed to create space for our unique "togetherness."
Though it seems counterintuitive, making space for others actually makes us more impactful and brings greater personal fulfillment through humility and contentment. This principle applies beyond personal relationships to professional settings, where creating space for team members to contribute leads to better outcomes and stronger engagement.
The practice of tzimtzum requires self-awareness and empathy rather than ego. It means recognizing when our presence is helpful and when it becomes overwhelming. It means understanding that sometimes our absence creates more value than our presence. By contracting ourselves appropriately, we allow others to expand into their full potential while paradoxically becoming more complete ourselves.
7장
Building Cultures of Belonging
I've experienced workplace discrimination and exclusion throughout my career-being told to straighten my curly hair to appear "professional," having my Jewish identity mocked, and being penalized for showing emotion. These experiences taught me that success often required hiding my true self. I eventually quit a toxic workplace that was "contaminating my soul," realizing no paycheck was worth the inner suffering.
During a networking meeting, a colleague commented on my "Jewish nose," causing me to instinctively cover it with my hand. This experience highlighted how my Jewish identity was perceived negatively in the workplace, adding to my growing sense that my authentic self wasn't acceptable in professional settings.
The concept of "culture" extends beyond workplaces to include any group where people connect-families, friendships, schools, and communities. Culture defines how people share values and belong, and we should consider the atmosphere we create around us.
My first Facebook interview differed dramatically from previous experiences when my manager asked how to pronounce my name correctly and inquired about what mattered to me personally. When I mentioned being Jewish, he began sending "Shabbat Shalom" texts every Friday for five years-a simple act that made me feel fully welcomed. As Sheryl Sandberg emphasizes, showing empathy is crucial, and Satya Nadella believes "the C in CEO stands for Culture"-and I would add, it also stands for Care.
Honest conversations are crucial for building trust, despite discomfort or potential conflict. When conversations are avoided, issues remain unresolved and relationships suffer. I value being known as the "Elephant Caller" who addresses uncomfortable truths to improve relationships and company culture-part of my commitment to "tikkun" (repair).
For giving feedback, I use a framework called the "one percent tool," adapted from Japanese philosophy. The premise is that we're doing things right 99% of the time, with just 1% needing improvement. This approach frames feedback positively while minimizing defensive responses. In my family, we regularly ask "What one percent can you give me?" and preface constructive criticism with "Do you want to hear the one percent?"
Facebook's motto "Fail harder" transformed my relationship with failure, neutralizing fear by framing it as necessary for growth. Being praised for underachieving changed my perspective-failure became valuable for learning. Discussing failure openly isn't meant to diminish confidence but to normalize vulnerability.
Creating an inclusive, warm culture means showing people they can be authentic without fear of judgment-flawed, quirky, emotional, quiet, passionate-helping them remove their masks. Mistakes and failure should be accepted. Caring for others, giving constructive feedback compassionately, and speaking honestly from the heart encourages others to do the same.
8장
Leadership with Heart and Humility
Leadership isn't about commanding through fear but through care, empathy, and humility. My journey from an authoritarian military commander to understanding true leadership taught me this essential lesson. Initially drunk on power and focused on discipline over people, I later realized my mistake when confronted with how my former soldiers remembered me-as someone to fear rather than respect.
A "mensch," a Yiddish term meaning "a decent person," represents someone who acts with care, integrity, fairness, and humility. While not every mensch is a leader, ideally every leader would be a mensch. Such leaders focus equally on tasks and people, remaining attentive to others' needs. They lead by example, doing more than they ask of others.
One of leadership's greatest obstacles is ego. During Passover, Jews avoid "chametz" (leavened foods) and eat only "matzah" (unleavened bread). This practice symbolizes the struggle against ego: chametz represents our inflated self-importance that rises like bread with yeast, while matzah remains flat and humble. By removing chametz, we're reminded to deflate our egos to achieve freedom and growth.
According to Jewish wisdom, everyone is called to lead in some capacity. The Lubavitcher Rebbe famously said "everyone must be a leader"-not necessarily as a company executive or prime minister, but by believing you have something meaningful to contribute. Parents lead families, teachers shape children's futures, and in every role we have potential to influence others.
Many leaders create a gap between their authentic selves and their professional personas. There's no reason to maintain two versions of yourself-you should be one person wherever you are. As Jacinda Ardern demonstrated, vulnerability and strength can coexist; compassion doesn't equal weakness. Brene Brown calls this "taking off our armor," explaining that innovation requires vulnerability since it inherently involves failure.
Jewish wisdom teaches that humans weren't created for isolation but for connection. We're meant to feel valuable as members of communities and families. As a leader and mensch, your role includes creating spaces where people genuinely belong-welcoming environments without judgment where no one needs to wear a persona to fit in.
One profound way to make people feel they belong is simply being present with them. People instantly know if you're truly engaged or merely pretending to care while distracted. Meaningful leaders connect deeply, remaining involved despite life's overwhelming "too muchness."
Leading like a mensch means doing right by others and the world. Unlike the Latin "caritas" (charity as optional kindness), the Hebrew "tzedakah" comes from "tzedek" meaning justice or righteousness. Giving isn't just nice-it's the right thing to do, correcting societal imbalances. As a leader, let tzedakah be your north star, thinking about what you're needed for rather than what you need.
9장
Parenting with Soul-Centered Wisdom
My most meaningful leadership role has been as a parent. Until having my own family, I measured my worth through my parents' eyes, making decisions to please them rather than following my own passions. When I became pregnant, I was consumed by anxiety, believing I needed complete control over who my child would become.
During my first pregnancy, I suffered from dual anxieties: fear something would go wrong with the birth and overwhelming responsibility about raising a happy, strong child. I believed I needed complete control, convinced by my psychoanalysis studies that children were blank canvases entirely shaped by parental conditioning. When my water broke unexpectedly, my carefully planned cesarean was denied, teaching me my first lesson about the impossibility of perfect control in parenting.
My inability to breastfeed my firstborn became one of my most traumatic experiences. While other mothers produced milk easily, my baby screamed from hunger, making me feel like an immediate failure. In this dark moment, my typically reserved father provided unexpected comfort, calling her "another miracle" and assuring me she needed a happy mother above all. This experience taught me about Winnicott's concept of the "Good Enough Mother"-that children benefit when parents aren't perfect but remain loving and supportive.
Seven years and three children later, I still believed my role was to tell my children who they should become. Seeking parenting wisdom, I discovered King Solomon's advice: "Teach a child according to his way; even when he grows old, he will not turn away from it." This ancient guidance suggested parents should nurture children's inherent nature rather than imposing our vision of who they should be.
The Hebrew word "chinuch," commonly translated as "education," actually means "initiation" or "inauguration"-dedicating something to its particular purpose. As parents, our role isn't to fix our children or define their exact path, but to help them discover their own journeys. I realized my children weren't blank canvases but unique souls with their own neshama, each carrying a distinct purpose.
After raising three children as an anxious mom, I approached my fourth child differently, having learned that parenting wasn't all about me. I practiced tzimtzum-contracting myself to make space for my child to discover their own path. This doesn't mean creating an empty void of uncertainty, but rather a safe space with clear boundaries for growth and discovery.
Making space for children doesn't mean passive parenting. As family leaders, we create the culture, values, and belief system that make our children feel safe. Children grow confident with positive structure and clear expectations. Being by their side means guiding them without living life for them.
Judaism perceives life as a journey of the soul. My husband and I decided that developing our children's souls, personalities, and humanity would always take priority over academic or professional achievements. We structured our family values on principles like respect, kindness, and honesty, praising these behaviors and addressing their absence. As Adam Grant says, "The real test of parenting is not what children achieve, but who they become-and how they treat others."
10장
The Journey Back to Your Essence
At forty-one, I decided to have a fourth child despite strong objections from everyone around me. Years before, such comments would have unsettled me, but Jewish wisdom had transformed me-fear was now living beside me, not inside me. This wisdom also helped heal my relationship with my mother, who I invited to be with me during delivery. At my daughter's birth, I felt I had given birth to two beings: my baby girl and a new version of myself.
A parable tells of a man seeking the shortest path to Jerusalem's Temple, only to find it blocked by thorns and obstacles. When he returns to the boy who gave him directions, the boy explains: "The shortest way is often the longest way and the longest way is often the shortest." Like this man, we often seek quick fixes in our self-improvement, but Jewish wisdom teaches that what seems like the shortest path often yields no results.
Every descent is necessary for ascent-the further we fall, the higher we may rise when we work to right ourselves. Rather than taking shortcuts, we must embrace the longer, more meaningful journey to discover our true purpose.
"Teshuva," often translated as "repentance," actually means "return"-returning to your true essence, to who you were created to become. Unlike traditional repentance with its connotations of guilt, teshuva is about rediscovering your eternally good and pure essence. This return requires both connection with God and participation of others through forgiveness and understanding.
Every morning when we wake, Jewish wisdom teaches that our souls have been restored to us-a renewed vote of confidence from God. This daily spiritual awakening reminds us that we can do a little teshuva every day, assessing where we are versus where we ought to be, and moving forward with purpose.
The journey of teshuva invites us to reflect: Where am I on my journey? What bridge am I planning to cross? What actions do I need to take? What is my soul telling me about my purpose? What needs tikkun (repair) in my life? What are my mitzrayim (narrow straits)? Who do I need to make more space for? How far am I from the person I'm designed to be? What makes me whole despite my brokenness? And perhaps most importantly, what first step will I take to move forward?
The question that began this journey-"What would you do if you weren't afraid?"-isn't just about eliminating fear but about living fully despite it. By reconnecting with our soul's essence, finding purpose beyond ourselves, crossing the narrow bridges of life, embracing our brokenness, making space for others, building cultures of belonging, leading with heart, and parenting with wisdom, we can transform our relationship with fear from one of paralysis to one of partnership in our journey toward becoming who we were meant to be.
