I didn’t expect to get laid off. It was scary, but it taught me to bet on myself
After 12 years spent climbing the corporate ladder, losing her job in 2023 opened Ms Cassandra Ong's eyes to how flimsy that ladder has become in these volatile times. Here's how the 37-year-old set out to create a new path for herself.

For Ms Cassandra Ong (pictured), her retrenchment in March 2023 made her re-evaluate what she was working for. (Photo: CNA/Ooi Boon Keong)
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The news came in March 2023, on a normal day like any other.
A team member who reported to me reached out to confide that she had just been let go. My initial reaction was disbelief: “Are you joking?”
When she replied, “No, Cass, I wouldn’t joke about this”, I knew I was next in line. Sure enough, one short video call later, I was jobless.
It was the most significant career setback of my life by far – and I was only 35.
When I first started working in the early 2010s, my approach to building my career was simple: Work hard, get promoted, switch jobs for better pay and perks, and eventually settle into a role that would offer stability until retirement.
It sounds idealistic, but it mirrored the tried-and-true formula that had worked for my parents' generation – a steady path that promised security and a solid foundation for the future.
But times change.
ON SWALLOWING HARD PILLS
Throughout 2024, each new report of layoffs at big-name companies such as Dyson and Samsung felt eerily familiar, reminding me of my own retrenchment the year before.
I had built a strong track record, led efficient teams and even weathered three rounds of layoffs in previous roles. Yet, none of that shielded me when my turn came.
In hindsight, the signs were there: A company struggling with product-market fit and an inevitable downsizing of marketing teams.
Still, nothing prepared me for its suddenness. Right up until two weeks before the layoffs, management assured us that jobs were safe. That lack of transparency was the hardest pill to swallow.
I’ve always been pretty pragmatic, usually believing that I can handle anything thrown at me, but this was completely unfamiliar territory. I grappled with a whirlwind of emotions – shock, loss and a gnawing sense of rejection.
Self-doubt crept in. “Maybe I didn’t do enough,” I thought. “Maybe I wasn’t good enough.”

At the time, I didn’t know many other people who had undergone retrenchment. I had no road map, no one I could take cues from or ask for advice.
So I sought out a career coach. For the first time, I let my guard down, tearing up in front of someone who wasn’t a close friend or family member.
Once I got a handle on my emotions, I was able to think more clearly.
There was a lot to consider: How would I take care of my family? How long could my savings last me? What do I do next, head right back to corporate life? Or look for ways to upskill or reskill?
Then, increasingly, I found myself mulling over a third option, one I’d never really had the guts to pursue: Should I start a new venture, something entirely my own?
DO I STILL WANT TO CLIMB THE CORPORATE LADDER?
Like many others, I had considered branching out on my own several times before, especially when corporate frustrations peaked.
These thoughts of seeking more fulfilment and gaining more control of my own time and schedule were fleeting fantasies though, easily dismissed during the good times when everything seemed to be going well. I was afraid to rock the boat when it always seemed to be sailing smoothly.
During the COVID-19 pandemic, I realised these “good times” were not always guaranteed. I survived multiple layoffs but saw colleagues who were accomplished and well-respected in their fields lose their livelihoods in an instant, due to a simple cost-cutting exercise.
That once-reliable corporate ladder? It now felt flimsy, with rungs that could snap without warning.
Getting retrenched was a wake-up call.
I could no longer ignore the growing frustrations I felt with corporate structures: Office politics, rigid hierarchies and the reality that no matter how hard I worked each day, my job scope would always be defined by someone else higher up on the ladder and my earnings would always be capped by a monthly salary.
In 12 years of working non-stop, I had never been fully free to maximise my skill sets and engage in work that really meant something to me beyond the bottom line.
I needed to re-evaluate what I truly wanted in my career.
I took the leap and set out to build something entirely my own.
NEW JOURNEY WITH NEW GOALS
In April 2023, I teamed up with two trusted former colleagues to create OtterHalf, a fractional marketing agency that gives businesses access to experienced marketing professionals on a part-time basis at a fraction of the cost.
Starting a business was a crash course in resilience. Those first few months tested me in ways I hadn’t anticipated.
I was juggling financials, managing operations and wearing every hat imaginable, all while trying to build an entirely new work-life balance from scratch, especially while parenting my two young daughters.
Honestly, it was rough, but for the first time in years, it all felt right.
I learnt more in that first year-and-a-half of OtterHalf than in four years of doing a business degree.
Most importantly, I wasn’t working towards arbitrary goals set by others. I was working for myself, for what mattered to me.

In March 2024, OtterHalf closed off our first year with a six-figure revenue – a milestone that, to me, reaffirmed I was on the right path.
To be completely honest, I haven’t seen huge monetary rewards yet and there’s still a sizeable chance that my business won’t succeed in the long run.
But my goals have shifted beyond these conventional metrics.
Now, instead of climbing the corporate ladder, I want to build something meaningful for myself, for businesses seeking to make a difference and for my team members who have stood by me through thick and thin.
I want to focus on my personal growth, work on my own terms, provide for my family and strive towards achieving financial freedom before I’m too old to enjoy it properly.
Being my own boss also means that I’ve been able to spend much more time with my kids. I can drop them off at their schools and be there for my girls when they return home. This is something I treasure immensely.
Work never ends, but they’re only young once, right?

LEARNING TO BET ON MYSELF
I used to believe that if I worked hard and played by the rules, the corporate world would automatically reward me with stability, fulfilment and even more control of my time.
But there are no guarantees – not in this world or in this life.
I’ve realised I can’t leave my future to chance or let others define what I want or what I’m worth. Instead, I need to take control of my own career and my life. It’s up to me to engage in work that allows me to put my values into action.
Yes, there are no guarantees. It’s all a gamble.
But if I have to bet on something, I’d rather bet on myself.
Cassandra Ong is the founder of OtterHalf, a fractional marketing agency.
If you have an experience to share or know someone who wishes to contribute to this series, write to voices [at] mediacorp.com.sg with your full name, address and phone number.