On Crafting a Legacy — Conversations with Curious Souls at Singapore’s First Meetup
In the heart of Singapore, a group of curious souls came together for a unique gathering — a curiosity café designed to spark meaningful conversations and connections. This casual yet thought-provoking event took place on January 6, 2025, to explore life’s big questions and foster human connection.
This was the first time such a meeting was facilitated in Southeast Asia, following previous events in Hong Kong and Taipei. The diverse group included welcoming individuals from all walks of life from Singapore, creating a rich tapestry of perspectives and experiences.
Round One: Initial Thoughts and Feelings
As with other typical Curious Souls Cafe events, this meetup was primarily structured as two rounds of discussions: the first used question cards for structured dialogue, while the second encouraged participants to generate their own topics. This balance of structure and spontaneity allowed for both deep reflections and free-flowing exchanges.
The first round revealed cultural nuances specific to Singapore. Despite the deep discussion, it turned out to be joyful and light-hearted thanks to the harmonious atmosphere from Singaporeans. The questions chosen by them were:
1. Pet Peeves: The Boundaries of Tolerance
“What is one of your pet peeves?”
The discussion from the first-comer began with a simple yet revealing question: “What is one of your pet peeves?” The responses ranged from light-hearted irritations to profound reflections on social values.
Entitlement and Lack of Empathy: Some participants expressed frustration with entitlement or a lack of empathy in social interactions, particularly in the workplace. This sparked a broader conversation about fairness and mutual respect as essential components of human connection.
“Tissue-Chopping” in Singapore: A uniquely local practice — using tissues or personal items to reserve tables (“chope”) at hawker centers — ignited a passionate debate. While common, it was criticized by one participant as inconsiderate, depriving others (and hawkers) of opportunities. This example illustrated how small, everyday actions can reflect larger issues of entitlement and awareness.
Acceptance Over Annoyance: Not everyone had strong pet peeves. Some participants shared their efforts to cultivate acceptance, recognizing that behaviors stem from diverse thoughts, emotions, and circumstances. This perspective highlighted a spectrum: from irritation to compassion, with some viewing pet peeves as opportunities for self-reflection and growth.
The discussion revealed that even minor irritations can uncover deeper values, such as empathy, fairness, and self-awareness, and encouraged participants to consider the impact of their actions on the wider community.
2. What’s Missing in Life? Aspirations and Insecurities
“What do you feel is currently missing from your life?”
The second question, “What do you feel is currently missing from your life?” prompted deeply personal reflections, uncovering shared desires for growth, stability, and connection.
Self-Realization: Some participants spoke of untapped potential, framing it as an inner journey rather than external achievements. They expressed a yearning to push past personal limitations and explore their true capabilities.
Career and Stability: The stress of finding job security and navigating career transitions was a recurring theme. For some, like a young participant studying cybersecurity, uncertainty about the future weighed heavily.
Creative Expression: A desire to engage in artistic pursuits like writing or painting emerged as an aspiration for one participant. This also demonstrates a desire for a balance between practical work and personal passion.
Travel and Relationships: Longing for travel and deeper connections with loved ones highlighted the human need for both adventure and belonging.
Consistency and Self-Improvement: One participant shared their struggle with self-discipline, aiming to align their actions with personal goals — a reminder of the ongoing challenge of self-mastery.
Belonging and Community: The search for a “tribe” resonated with one participant and a facilitator, underscoring the importance of finding like-minded individuals who share values and interests.
This discussion demonstrated that participants were not solely seeking external achievements but were also yearning for internal fulfillment, creativity, and meaningful connections.
Round Two: Personal Reflections and Legacy
The second round, driven by participant-generated questions, invited even deeper introspection. Let’s see which questions received the most votes and were discussed first.
1. Writing Your Own Obituary: Crafting a Legacy
“If you are able to write your own obituary, what would it be?”
This deep question from one of our facilitators opened a profound dialogue about mortality, values, and the legacy we leave behind.
Transformation and Growth: The Singaporean spoke of his life as a journey of self-discovery, recounting how a transformative experience in his early thirties shaped his outlook.
Joy and Fleeting Moments: Another envisioned a tombstone with a QR code linking to joyful life moments, paired with a quote from William Blake’s The Fly. This choice reflected an appreciation for life’s fleeting beauty and a desire to celebrate happiness.
The Dash: A participant referenced the poem The Dash, which reflects on how one lives and loves between the dates on their tombstone. This highlighted a focus on the small, meaningful moments that define a life well-lived.
Positive Impact and Relationships: Echoing The Dash, many hoped to be remembered for their kindness and contributions to others, emphasizing the importance of relationships and shared values over material achievements.
Encouraged by one participant, our other facilitator also shared his afterthoughts on this discussion later in our regional WhatsApp group, where participants collaboratively share resources. He pointed out how the peak-end rule might have an impact on people’s perception of the obituary.
This conversation revealed diverse perspectives on life’s meaning, from the transformative power of love to the impact of small, everyday moments.
2. Coping with Uncertainty: “Waiting Out”
“What do you do to wait out? / How do you wait out?”
The final question, “How do you wait out uncertainty?” explored strategies for navigating the ambiguous, in-between moments of life, hoping to inspire the asker on how to approach the current uncertain period she was experiencing.
Acceptance and Patience: One facilitator emphasized the value of passivity with a Chinese saying, accepting what is beyond one’s control, trusting that time and life experiences will lead to resolution. This idea reminds another facilitator of Taoism, and one participant of flow.
Active Engagement: In contrast, some participants preferred action over passivity, believing in taking steps to shape their future rather than waiting for things to happen — there is no need to “wait it out” because the experiences gained during this period can prepare them for what is to come. A facilitator added that passion can also be cultivated. These perspectives framed the waiting period as a valuable time for growth and learning.
Acts of Kindness: One participant pointed out that the suicide rate in Singapore is one of the highest in the world. The remedy can be simple yet profound — witnessing or offering small acts of kindness can provide hope and meaning, reminding everyone of the power of human connection.
This discussion emphasized that waiting is not merely passive — it can be an active process. The waiting period can be an opportunity to look inward — times of uncertainty can be opportunities for self-reflection and personal growth. Practices like meditation, mindfulness, and self-reflection were seen as essential tools for maintaining inner peace during such times.
Reflections and Connections
The evening concluded with a “moment of truth,” where participants shared their key takeaways and feedback. One participant expressed gratitude for the opportunity to engage deeply with others, learning from diverse perspectives. She noted that by the end of the session, the faces around the room (which she had met before in other, less thought-provoking events) felt more “real,” reflecting the transformative power of authentic conversation.
Other meaningful events like Playback Theater were also shared, offering creative ways to deepen these discussions beyond the Curious Souls Cafe. Overall, the participants appreciated the café as a rare and meaningful space for introspection and casual philosophical discussion, emphasizing the need for such community gatherings.
Conclusion
This first Singapore gathering of the Curious Souls Café demonstrated the power of thoughtful conversations in fostering connection, self-reflection, and community. Through honest dialogue, participants explored their values, aspirations, and perspectives on life, leaving with a renewed sense of purpose and belonging.
As the evening drew to a close, one sentiment echoed throughout the group: the world could always use more spaces like this — where curious souls come together to ask questions, share stories, and find meaning in life’s journey.