Sometimes, the most meaningful conversations aren’t the longest ones. Our conversation with Sherman lasted just 12 minutes, tucked between a busy schedule, yet those few minutes were filled with thoughtful reflections and genuine wisdom. While this feature is shorter than our usual interviews, the depth of what Sherman shared made every minute count, leaving us with perspectives that stayed with us long after the conversation ended.
Who is Sherman Ho?
Sherman Ho is the co-founder of Happiness Initiative, a member of A Good Space Co-operative (AGS), and a social entrepreneur committed to making well-being skills accessible to everyone. Through the Happiness Initiative, he leads one of Singapore’s largest evidence-based community well-being programmes, the Well-being Circles.
Relationships First
When we think about what motivates someone, we often expect to hear about ambitious career goals, personal milestones, or long term plans. So I was surprised that our conversation kept returning to one simple idea: relationships.
When I asked what values mattered most to him beyond his work, he didn’t hesitate.
Relationships, he said, are his anchor. Every major decision he makes eventually comes back to the people who matter most in his life. Career opportunities, work commitments, and even personal aspirations are all weighed against one question: How will this affect the relationships I care about? It was a simple answer, but one that challenged how I think about success.
We’re often taught to chase achievements, promotions, and productivity. In a fast-paced society like Singapore, it’s easy to fall into the habit of comparing ourselves to others and measuring success through material possessions. Yet hearing someone deliberately place relationships above all else made me wonder whether we sometimes pursue the wrong milestones. Sherman also shared that as people grow older, their priorities naturally evolve. Many of us spend our younger years focused on building careers and chasing personal goals. But as we grow older, we often come to realise that our greatest sense of fulfilment doesn’t come from what we’ve achieved, but from the relationships we’ve built along the way.
The Reality of Leadership
Despite leading an organisation, one of Sherman’s biggest lessons wasn’t about strategy or management. It was about people. Leadership, he admitted, is far more difficult than he ever imagined. Every individual brings different perspectives, personalities, and challenges. Navigating those differences while helping people work towards a common purpose is rarely straightforward. His honesty was refreshing. His perspective made me reflect more deeply on what it truly means to be a leader. Leadership isn’t simply about making decisions or setting direction. More often, it’s about understanding people, building trust, and learning how to work through differences.
A Community Built on Trust
One story Sherman shared stayed with me long after our conversation ended: Before COVID, many social impact organisations shared a modest co-working space managed by Social Collider.
Sherman shared that the working space was not particularly impressive as the building was old and run down. Yet, what it lacked in appearance, it more than made up for in the community it fostered. People did not just know one another professionally. They built genuine friendships and deep trust.
Sherman recalled attending a gathering where someone mentioned struggling to secure an HDB office space. Almost without hesitation, another organisation offered to let them apply under their organisation’s name first, trusting that the administrative details could be sorted out later. That level of trust really struck me. It was not built overnight, nor was it something that could be created through formal networking events. Instead, it grew through countless conversations, shared experiences, and people consistently showing up for one another.
Listening to that story made me realise that community is not created by a physical space alone. A building or room can bring people together, but it is the relationships formed within it that give the space its meaning. They were not simply neighbours sharing an office. They were people connected by genuine trust, care, and a shared sense of purpose.
Living In the Present
As our conversation drew to a close, I asked Sherman whether he had a five-year plan. He laughed. The truth was that he didn’t. Entrepreneurship often means figuring things out one step at a time, and even planning a year ahead can feel uncertain. Rather than pretending to have every step mapped out, he has learnt to embrace that uncertainty. There was something reassuring about that honesty. In a culture that constantly encourages us to plan every stage of our future, it was refreshing to hear someone acknowledge that it’s okay not to have all the answers.
Final Reflection
Sherman’s final piece of advice was simple: enjoy this season of life.
When we’re young, we have the freedom to experiment, make mistakes, and step outside our comfort zones. There is no need to have everything figured out just yet. Instead, embrace the opportunities that come your way, stay curious, and allow yourself to grow through every experience.
I went into this conversation expecting to learn the secret to happiness. Instead, I left with more questions than answers. As I reflected on everything Sherman shared, I realised there was one thread that connected every part of our conversation: relationships.
Achievements matter. Good grades, career milestones, promotions, and personal successes are all worth celebrating. But they were never meant to be the foundation of our happiness. Those moments are fleeting. The relationships we nurture, however, are what sustain us through both our highest highs and our lowest lows. If there is one lesson I am taking away from this conversation, it is this: treasure the people already in your life, and remain open to meeting new people, embracing new opportunities, and building meaningful connections. At the end of the day, happiness is not something we achieve. It is something we cultivate through the people we choose to love, and who choose to love us in return. Perhaps, that is the true meaning of happiness.
If you’d like to follow Sherman’s work, you can connect with him on LinkedIn or find him on Instagram at @lordofdonkeys. To learn more about the work of the Happiness Initiative, visit their Linktree, Instagram @happinessinitiative.sg or website for resources, programmes, and updates.
This is part of a series called People Behind Purpose, where we sit down with changemakers in A Good Space to discover more about their work, build deeper connections, and gain fresh perspectives on creating social impact.
Through these conversations, we hope to share our experiences, reflections, and key takeaways so that others can be inspired by the journeys and insights of those driving change in our community.
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Written by Ye Weixuan – [Programmes and Community Engagement Intern]
