High Holiday Toolkit for Men

Practicing accountability is profoundly beneficial for the soul and spiritual development because it fosters self-awareness, humility, and a genuine commitment to ethical living. By holding ourselves accountable, we acknowledge our imperfections and actively seek to align our actions with our values, leading to personal growth and a more meaningful life. In Judaism, the process of t’shuvah, which involves self-reflection, repentance, and making amends, is the embodiment of accountability. T’shuvah encourages individuals to confront their misdeeds, seek forgiveness, and commit to positive change, thus nurturing a deeper connection with oneself, others, and the Divine. This practice not only purifies the soul but also reinforces a lifelong journey of moral and spiritual improvement.

1. Personal Reflection and Journaling

• Daily Reflections: Set aside time each day during the month of Elul leading up to Rosh Hashanah to reflect on your actions, intentions, and behaviors. Write about moments where you acted with integrity and instances where you fell short. Consider what you can learn from each experience.
• Accountability Journal: Keep a journal specifically for noting your commitments to change and improve. Document your progress, challenges, and successes.

2. Cheshbon Hanefesh (Accounting of the Soul)

• Weekly Sessions: Dedicate time each week to review your actions and decisions. Evaluate them against your values and ethical standards. Ask yourself questions like, “Have I been honest in my dealings? Have I treated others with respect and kindness?”
• Monthly Reviews: Once a month, engage in a more extensive review of your actions and behavior. Use this time to identify patterns and areas for improvement.

 3. T’shuvah Meditation

• Guided Meditation: Practice a guided meditation focused on t’shuvah. Begin by finding a quiet space, close your eyes, and take deep breaths. Visualize yourself in moments where you have acted contrary to your values. Acknowledge these moments without judgment and visualize how you can act differently in the future.
• Breathwork and Visualization: Combine deep breathing exercises with visualization techniques. As you breathe in, imagine filling yourself with integrity, compassion, and accountability. How does it feel to be full of those character traits? Does it feel as if you actually have these traits or are just flirting with them at this moment? What do you want to do with these traits? As you exhale, release guilt, shame, and negative thoughts. How does this feel? Were you able to hold on to the positive emotions and traits? Do you see a change in yourself in some way from this reflection?

 4. Community Study and Discussion

• Study Groups: Form small study groups to explore texts related to t’shuvah, accountability, and integrity. Discuss the teachings and how they apply to your personal lives. This can include studying Maimonides’ Laws of Repentance or texts from the Talmud and Midrash.
• Sharing Circles: Create a safe space where participants can share their struggles and successes in practicing accountability and integrity. This communal support can foster a deeper commitment to personal growth.
  • One way to do this is by allowing people to share when they haven’t fulfilled their responsibilities without shame or judgment. But with an opportunity to explore why in a safe space, and get back in integrity by finding a way to take responsibility for whatever they brought up.

5. Acts of Tikkun Olam (Repairing the World)

• Community Service: Engage in acts of kindness and community service as a practical application of t’shuvah. Reflect on how these actions contribute to your personal integrity and accountability.
• Mentorship Programs: Participate in or create mentorship programs where older men mentor younger members of the community, sharing wisdom and guiding them in ethical and moral development.

 6. Prayer and Liturgical Reflection

• Selichot Prayers: Incorporate Selichot prayers into your routine during the month of Elul. These prayers focus on forgiveness and repentance and can deepen your reflective practice.
• Rosh Hashanah Services: Attend Rosh Hashanah services with a focus on the themes of t’shuvah. Reflect on the prayers and sermons, and consider how they apply to your journey of accountability and integrity.

 7. Ethical Will Writing

• Legacy Letters: Write an ethical will, a letter to your descendants articulating your values, ethical beliefs, and lessons learned. This practice can help clarify your own principles and reinforce your commitment to living with integrity.
• Annual Updates: Revisit and update your ethical will each year as part of your Rosh Hashanah preparations. Reflect on how your values and commitments have evolved over time.

By integrating these reflective and meditative practices into your life, you can use the powerful themes of t’shuvah and Rosh Hashanah to deepen your understanding of accountability and integrity. These exercises not only foster personal growth but also strengthen the bonds within your community, creating a supportive environment for collective spiritual development.

• Joseph Campbell and Jonah

Joseph Campbell’s “Hero’s Journey,” also known as the Monomyth, is a narrative framework detailed in his seminal work, “The Hero with a Thousand Faces.” This framework outlines a hero’s adventure and transformation through a series of stages. The story of Jonah in the Hebrew Bible aligns well with the hero’s journey narrative framework, as articulated by Campbell. This framework outlines a common pattern in storytelling, featuring stages such as: the call to adventure, the refusal of the call, the ordeal, and the return. Jonah’s story follows this pattern in several key ways:

1. Call to Adventure: Jonah is called by God to go to the city of Nineveh and warn its inhabitants of their impending destruction due to their wickedness. This divine command sets the stage for his journey and mission.
2. Refusal of the Call: Jonah initially refuses the call. Instead of heading to Nineveh, he boards a ship bound for Tarshish, attempting to flee from God’s presence and the daunting task ahead. But by boarding the ship and setting sail, Jonah crosses the threshold, leaving his familiar world and entering a realm of uncertainty and potential danger.
3. The Abyss/Ordeal – The Belly of the Whale: A great storm threatens the ship, and Jonah is thrown overboard by the sailors to calm the seas. He is then swallowed by a great fish, where he spends three days and nights. This period represents the abyss or the ordeal, a time of introspection, prayer, and transformation for Jonah. Within the belly of the whale, Jonah undergoes a profound spiritual transformation. He prays to God, acknowledges his mission, and repents for his initial refusal. This marks a significant internal change and acceptance of his role.
4. The Return: After three days, the fish spits Jonah onto dry land. Jonah is now prepared to fulfill his mission. He heads to Nineveh, thus crossing the return threshold, and delivers God’s message to the people. Even though his time in Nineveh is also faced with challenges, ultimately, Jonah carries with him a deeper understanding of God’s compassion and mercy, although his journey ends on a note of personal struggle with these revelations.

Jonah’s story encapsulates the essence of the hero’s journey, demonstrating themes of reluctance, transformation, acceptance, and the complexities of fulfilling one’s destiny. Continue below for prompts through your Hero’s journey, if you’re brave enough…

Stage 1: The Call to Adventure

Prompt: Reflect on Jonah’s initial call from God to go to Nineveh.

• Question: Have you ever felt a calling or a push towards a particular path or action in your life? Describe this moment.
• Reflection: Consider how Jonah reacted to his calling. How do you typically respond to your callings? Do you embrace them, avoid them, or something else?
• Action: Identify a personal calling or goal for the coming year. How can you take the first step towards it?

 Stage 2: Refusal of the Call

Prompt: Reflect on Jonah’s attempt to flee from his mission.

• Question: When have you found yourself avoiding or running away from a responsibility or challenge? What were the reasons behind your reluctance?
• Reflection: How did avoidance impact your life and those around you?
• Action: Identify one area where you are currently avoiding a challenge. What small step can you take towards addressing it?

Prompt: Reflect on the divine intervention that sent the storm and the whale.

• Question: Can you recall a time when unexpected help or a significant event redirected your path? How did it change you?
• Reflection: What do these interventions teach you about trust and surrender?
• Action: Think about a challenge you are facing now. How can you remain open to guidance and assistance, whether it comes from within or from others?

Stage 3: The Belly of the Whale

Prompt: Reflect on Jonah’s time in the belly of the whale.

• Question: Have you ever experienced a period of darkness or deep introspection? How did it affect you?
• Reflection: Jonah prayed and reflected during his time in the whale. What practices or rituals help you during difficult times?
• Action: Commit to a daily or weekly practice of reflection or meditation. How can this practice help you gain clarity for your journey?

Prompt: Reflect on Jonah’s journey to Nineveh after being released.

• Question: What challenges have you faced when trying to fulfill a difficult task? How did you overcome them?
• Reflection: How do you persevere in the face of adversity?
• Action: Set a specific goal related to your calling for the next few months. Break it down into manageable steps and identify potential obstacles. How will you address them?

Prompt: Reflect on Jonah’s confrontation with Nineveh and his message.

• Question: When have you had to face a major challenge or confrontation? What did you learn from that experience?
• Reflection: How does facing your fears or challenges shape your character and future actions?
• Action: Identify a major challenge you anticipate in the coming year. What resources or strategies can you use to prepare for and overcome it?

Stage 4: The Return

Prompt: Reflect on Jonah’s return and his continued learning.

• Question: How do you integrate the lessons learned from your experiences into your daily life?
• Reflection: Jonah’s journey didn’t end with Nineveh; he continued to learn. How can you remain open to growth and learning even after achieving a goal?
• Action: Plan a way to share your journey and its lessons with others, such as through mentoring, teaching, or writing. How can you inspire others through your experiences?

Culmination on Yom Kippur 2025

Prompt: Reflect on your entire hero’s journey over the past year.

• Question: How have you grown spiritually, emotionally, and mentally over the past year?
• Reflection: What have been the most significant lessons and moments of your journey?

Action: As you approach Yom Kippur, identify what you seek forgiveness for and what you are thankful for. How can you use these reflections to set intentions for the next year?

Instructions: A simple lesson can be created by taking four of these questions, posting them around the room, and assigning participants to each question at random. Break the group up evenly across questions. Have them spend 10-15 minutes responding to the question in group, and then rotate to the next question until all participants have engaged with each question. This is not a time for answers, but merely thought and reflection.

1. Imagine you have a few minutes left to live. What are you thinking about?
2. If you were to have one conversation with someone, a final conversation with them, who would it be and what would you want them to know and why?
3. The Talmud teaches that you will be asked 6 questions when you die. What questions do you think you will be asked when you die? What would your answers be today? Why did Judaism suggest these questions, of all questions, to be asked in heaven?

Here are the Talmud’s six questions. What are your answers?

The Talmud (Shabbat 31a)

• Did you do business with honesty and integrity?
• Did you fix set times for studying Torah?
• Did you participate in the commandment to be fruitful and multiply?
• Did you anxiously anticipate the redemption?
• Did you engage in the pursuit of wisdom?
• Did you have fear of Heaven?

4. Imagine that there is just enough time and energy to do one thing before you die. Just one thing. What would it be, and why?

5. In a 2014 TedTalk, David Brooks shared the following idea: I’ve been thinking about the difference between resume virtues and the eulogy virtues. The resume virtues are the ones you put on your resume, which are the skills you bring to the marketplace. The eulogy virtues are the ones that get mentioned in the eulogy, which are deeper: Who are you in your depth? What is the nature of your relationships? Are you bold, loving, dependable? Most of us, including me, would say that the eulogy virtues are the most important of the virtues. But at least in my case, are they the ones that I think about the most? No. So when it comes to resume virtues or eulogy virtues – on which ones do you spend your time?

6. Do you have a secret hunch about how you will die?

7. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

8. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet

Here are some reflective and meditative practices and exercises for Jewish men that use the imagery and symbolism of the sukkah, the lulav and etrog, and the time of year (Sukkot) to teach about vulnerability:

Sukkah Meditation and Reflection

1. Building the Sukkah:

• Purpose: Building the sukkah as a group activity fosters a sense of community and shared purpose. It also highlights the temporary and fragile nature of the structure, reflecting human vulnerability.
• Activity: Gather a group to build a sukkah together. As you work, discuss the themes of impermanence and reliance on others for support. Reflect on the effort required and the joy of creating something temporary but meaningful. Reflect on how the effort and cooperation required to build the sukkah demonstrate the strength found in community and collaboration. Share stories of times when vulnerability led to stronger relationships or personal growth.

2. Sitting in the Sukkah:

• Purpose: Spending time in the sukkah allows for contemplation of its symbolism and personal reflection on vulnerability.
• Activity: Sit alone or with others in the sukkah. Close your eyes and listen to the sounds around you. Feel the fragility of the sukkah walls and roof. Reflect on moments in your life when you felt vulnerable and how you responded to those situations. Think about how these experiences have made you stronger or more resilient. Share your reflections with the group if you feel comfortable, emphasizing the strength that came from these vulnerable moments.

Lulav and Etrog Meditation

3. Holding the Lulav and Etrog:

• Purpose: The lulav and etrog symbolize unity and diversity, as well as the balance of strength and gentleness.
• Activity: Hold the lulav in one hand and the etrog in the other. Meditate on the different parts of the lulav (palm, myrtle, willow) and what they represent. Think about the different aspects of yourself and your life that contribute to your overall strength and resilience. Consider how these elements come together to support you in times of vulnerability. Consider how acknowledging and embracing your vulnerabilities has made you stronger. Reflect on times when being open about your vulnerabilities has led to deeper connections or personal growth.

4. Waving the Lulav and Etrog:

• Purpose: The act of waving the lulav and etrog in all directions symbolizes reaching out to all corners of the world and acknowledging the presence of God everywhere.
• Activity: Stand in the sukkah or another quiet space. Wave the lulav and etrog in the six directions (north, south, east, west, up, and down). As you do, reflect on the areas of your life where you feel strong and those where you feel vulnerable. Consider how embracing your vulnerabilities has strengthened your faith, relationships, and personal growth. Pray or meditate on finding balance and strength in these areas, recognizing that vulnerability is part of your strength.

 Time of Year Reflection

5. Reflection on the Season:

• Purpose: The festival of Sukkot occurs in the fall, a time of harvest and transition. This can be a metaphor for the cycles of life and our own personal growth and vulnerability.
• Activity: Take a walk outside and observe the changes in nature. Reflect on the harvest season and what it represents in your life. Consider the things you have “harvested” this year—achievements, relationships, personal growth—and what you are ready to let go of. Write down your reflections and share them with the group if desired. Reflect on how moments of vulnerability have contributed to these harvests and strengthened you.

6. Gratitude and Vulnerability Journal:

• Purpose: Keeping a journal can help process feelings of vulnerability and cultivate a sense of gratitude.
• Activity: Each day of Sukkot, spend some time writing in a journal. Focus on moments when you felt vulnerable and how you dealt with those feelings. Also, write about things you are grateful for, especially those that emerged from moments of vulnerability. Reflect on how acknowledging your vulnerability has contributed to your personal growth and resilience.

Group Discussion and Sharing

7. Vulnerability Circle:

• Purpose: Sharing personal stories of vulnerability can create a sense of community and mutual support.
• Activity: Gather in a circle in the sukkah. Take turns sharing a story about a time when you felt vulnerable. Listen actively and offer support to each person who shares. Reflect on how these experiences have shaped you and what you have learned about yourself and others through them.

These practices can help Jewish men connect with the deeper meanings of Sukkot, using the sukkah, lulav, and etrog as tools for meditation, reflection, and personal growth.