Intro
Cassandra Ong is a Singaporean marketer and founder who rebuilt her career after an unexpected layoff shook her confidence and sense of identity. From leading teams at FoodPanda, Chope, and TripAdvisor to launching her own agency, OtterHalf, her story is about starting again when you’re unsure, overwhelmed, and not convinced you’re ready.
In this episode, we talk about what really happens after a layoff, how confidence breaks and slowly returns, and the long process of figuring out how to build something of your own. Cassandra shares how she used “grief in motion” to turn fear into forward momentum, why her first four months in business weren’t actually “real business” at all, and how a simple card game she created with her daughter opened unexpected doors.
From retrenchment shock to her first non-friend sale, this is a conversation about rebuilding from the inside out — one small step at a time.
Story Highlights
- Discovering the emotional aftermath of a layoff and the identity shock that followed
- Using grief as fuel to start OtterHalf
- Realizing her early work was “social credit,” not real business traction
- Losing money for consecutive months and having to rethink her business model
- Pivoting toward retainers and more predictable income
- Creating a marketing card game with her seven-year-old daughter
- Learning sales for the first time after a decade in marketing
- Balancing motherhood, ambition, and rebuilding self-belief
Quote
“Nothing prepares you for a layoff. Even when I expected it, when it finally happened I just thought… oh my God, why is it me?”
About Cassandra Ong
Cassandra Ong is the founder of OtterHalf, a fractional marketing agency supporting startups and SMEs in Singapore. Before starting her own business, she held marketing roles at FoodPanda, Chope, and TripAdvisor. After being laid off in 2023, she used the setback as a turning point, launching OtterHalf and later creating Ottie’s Fishy Business, a card game designed to make marketing fun and accessible. Today, she runs workshops for kids, students, and communities, blending creativity, education, and practical marketing know-how.
Why This Conversation Matters
Cassandra’s story is one many people recognise: the quiet pain of a layoff, the slow erosion of confidence, and the messy process of rebuilding a career when your belief in yourself feels shaky. This conversation dives into the emotional side of reinvention and the internal questions that surface when everything familiar falls away. It is about fear, identity, motherhood, and the small wins that eventually rebuild confidence. It is a reminder that progress is rarely clean, but it is always possible.
Turning Points
After her layoff, Cassandra faced a sudden shock to her identity and confidence. She tested three directions at once — job hunting, upskilling, and starting her own business — while realising her early clients were relying on social credit rather than true traction. Her first non-friend sale became the moment she finally felt real validation, but a year in she hit her lowest financial point, forcing a pivot toward a more sustainable retainer model. Around the same time, a small project with her daughter grew into Ottie’s Fishy Business, opening an unexpected creative path and giving new meaning to the work she was building.
Key Lessons
- Rebuilding confidence takes time and action, not just intention
- Early wins do not always equal real traction
- Fear and uncertainty are natural parts of reinvention
- Career change is rarely linear
- Self-belief grows through small steps and real-world feedback
- Creativity can emerge from unexpected moments
- You find out what works only by trying
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