ABOUT CAI CHENGYING
Cai Chengying is the current Deputy Chief Executive Officer of Pro Bono SG. She oversees efforts in fundraising, grants administration, supporter engagement, communications and legal support for the non-profit sector.
Prior to joining Pro Bono SG in February 2020, Chengying was a litigator in private practice. She volunteered with Pro Bono SG’s various legal aid programmes after getting called to the Bar and was seconded to the Criminal Legal Aid Scheme to do full-time pro bono criminal defence work as a pioneer CLAS Fellow in 2015.
ABOUT PRO BONO SG
Pro Bono SG is a Singapore registered charity which helps the vulnerable and disadvantaged through legal awareness, guidance and representation, so that they may have access to justice in Singapore.
What began as a department within the Law Society of Singapore has grown into a national charity whose initiatives now span family and immigration matters, as well as capacity building for the non-profit sector — supporting over 150,000 individuals and organisations to date.
Can you share your journey as a changemaker – and what has kept you motivated to continue?
My journey started in 2015 with a nine-month secondment to the Criminal Legal Aid Scheme (CLAS). At the time, I was working at a large law firm, and my then-boss supported my decision to go.
While it was a sacrifice for my firm, I felt it aligned with the volunteer work I was already doing. The experience was eye opening and challenging. I went from having my own secretary at a large firm to handling 30 to 40 cases at a time without any paralegal support. I realised the need for criminal legal aid was staggering.
After my secondment, I was so invested that I brought 6 or 7 of the open cases back to my private practice to see them through. Each case showed me a different struggle in Singapore, and I honestly felt that I learnt more from these cases than I gave. When a charge was withdrawn for a client who had a mild intellectual disability, I remember turning around to see his entire family crying with relief. It was in that moment that I realised the work we do impacts a much wider community. This realisation keeps me going.
“That was my first insight into how the work we do doesn’t just impact one person, but a much wider community.”—Chengying
What kind of change are you trying to create, and who does it impact the most?
I am trying to create a more holistic, person-centric approach to legal support by working with a much bigger ecosystem of helping hands.
My work has evolved to focus on providing multidisciplinary support and integrating services to avoid duplication. This involves setting up new initiatives, such as our community-based offices in locations like a Taoist temple and a TCM clinic. This approach, which we call community lawyering, brings legal services directly to where people are.
The impact of this work is widespread. It helps individuals who need legal help and their families and communities. It also supports non-profits by providing them with legal and compliance services, as well as advisory work. We even have pilot programs to assist with things like contracts and governance. Ultimately, the goal is to create a more effective system of support for vulnerable communities by fostering partnerships and working collaboratively.
Chengying conducting a learning journey at Tian De Temple, where Pro Bono SG operates a Community Law Centre
What challenges have you faced in your changemaking journey, and how did you overcome them?
The biggest challenge I have faced is balancing my work with my personal life. When I first started at Pro Bono SG, I had one child, and now I have two.
It’s a constant effort to do my best at work without bringing my stress home to my family. I have realised that to sustain this work in the long run, I have to prioritise my own well-being to avoid burnout, which is a common problem in the social service and legal sectors.
Another challenge is staying relevant and adapting to the evolving needs of the community. Pro Bono SG’s role in the ecosystem changes depending on government policy, and we need to be ready to shift our focus and resources to fill new gaps. To overcome this, I believe in continuously having my finger on the pulse of the community and being willing to innovate. This requires building partnerships and being a resource for other organizations.
Chengying at a community outreach to the charities sector
Who or what has made your changemaking journey possible?
My journey has been possible because of a few key enablers. The first is opportunity. My CEO at Pro Bono SG gave me a chance to take on a new role in 2020 that combined governance, fundraising, and communications.
I told him I had “zero experience” in any of these areas but he had a strange faith in me. He offered me the flexibility to work from home, and even suggested I shadow him to see if I liked the role. This willingness to invest in me was a game-changer. Every role I have taken in the past five and a half years has been a new position that required a leap of faith from the organisation.
Secondly, it’s about having strong support systems and mentors. I have learnt from people within Pro Bono SG, the private sector, and other non-profits. The organisation also invests in sending staff to conferences to learn best practices from other jurisdictions. I believe the professionalisation of the entire non-profit sector will enable iron to sharpen iron. When we work with other professional non-profits, they raise our standards.
“I feel that a lot of my successes or achievements at work are really because of the opportunities I’ve been given.”—Chengying
How has this journey changed you personally, and what are your hopes for the future?
My journey has been a profound personal transformation. For the first time in my career, I became a “curious lawyer”.
Before this, my career decisions were based on what was convenient or what would open doors. Now I’m driven by a desire to understand and address different societal struggles. I’ve learnt that the work is bigger than any one person and that it requires a collective effort from many helping hands.
Looking ahead, my hope for the future is to continue to find ways to grow and scale our impact. This means continuously assessing where the need lies and where Pro Bono SG can have the most acute impact. I believe the key is to strengthen partnerships and become the first port of call for other social service partners. My hope is that we can continue to work together to provide comprehensive support and ensure help is available where and when it’s needed most.
“I came across so many different cases and each made me a little bit more curious about the different issues in society.”—Chengying
SG60 Series: Stories of Giving and Community Spirit
The SG60 Series is a storytelling and research initiative that reimagines philanthropy by spotlighting how everyday individuals, including those from disadvantaged backgrounds, are powerful changemakers in their own right.
We examine the challenges they face, the enablers that support them, and the impact they create. These insights offer ecosystem enablers a valuable opportunity to explore how they can better empower changemakers and catalyse grassroots action. Above all, the stories affirm that anyone can be a changemaker in their own way.
We are deeply grateful to all the changemakers who generously shared their journeys with us.
