Some journeys to financial security and self-discovery are anything but straightforward. Edward Choy’s story is losing it all – and finding himself again.
After graduating with a Master’s degree in Theatre from NUS, Edward was bedazzled by the high-flying world of banking. Lured by the promise of quick success, he soon found himself chasing commissions and fast money.
Addicted to the highs of big trading profits, he plunged into high-risk investments. This led to the wipe out of nearly $100,000 from his grandfather’s inheritance and own life savings, shortly after getting married. That was all of the money he had at the time, surviving with just $40 in his bank accounts.
At his lowest, Edward wrestled with depression and found himself staring into oblivion on a balcony on the 20th storey. What pulled him back was the support of those around him – and a return to his first love: theatre.
Today, Edward is a successful actor, host, voice artist, lecturer, and corporate trainer. Alongside his wife, acclaimed actress and playwright Jo Tan, he has starred in major productions such as The LKY Musical and Late Company, and co-hosted a CNA climate change documentary with his wife.

The LKY Musical
Edward Choy, second from left (playing Dr Goh Keng Swee), Adrian Pang, centre, playing LKY, Sharon Au, second from right, (playing) Kwa Geok Choo
Now, he is working towards his next goal: a milestone $1 million investment portfolio that will give him and his wife the creative freedom to pursue their projects without financial worries.
I’ve crossed paths with Edward many times over the years, from personal finance events to a friend’s wedding where he was the emcee. This time, I sat down with him to talk about the ups and downs he has faced, and how he is redefining what success looks like.
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Dinesh: What first drew you into banking?
Edward: It was like the wild west before the Global Financial Crisis (GFC) in 2008. Bankers used to hang around behind the tellers waiting for retirees who’d just collected their CPF or sold their property! My ex-girlfriend at the time was in retail banking and she earned more than 8 times what I was earning as a freelance performer, so I thought, “hey maybe I could do this”.
Funnily enough, I managed to get an interview despite not having any financial background, because I acted in an event for the bank. I just asked the client if they were also hiring for banking roles. Ask and you shall receive, right?
Dinesh: You mentioned that you sometimes sold financial products you didn’t fully believe was the best. How did that affect your sense of purpose?
Edward: It tore me. On the one hand, we had to act in our clients’ best interests, but on the other hand, our commissions depended on getting our clients into different products.
None of it was illegal, but I couldn’t live with it. One morning, I was brushing my teeth before going to work, and I looked at myself in the mirror and asked “what am I doing with my life?”.
I put in my resignation the same week.
Dinesh: How did you end up losing a $100,000 of inheritance and your life savings? What kind of risk were you taking on?
Edward: Derivatives, really. I got addicted to the feeling of being up a few thousand dollars in the two or three hours it took for me to teach a class at NUS.
When my trades went south, I made bigger and riskier bets to try to make back what I had lost. I was treating the stock market like a casino – and eventually lost everything.
Dinesh: How did you recover from that?
Edward: It broke me. I’d just gotten married and promised to give my parents the best life possible, they’re going to live on private property and have two cars, and my wife will have whatever she wants.
Less than a year after that, I was down to $40 in my bank accounts. I genuinely credit to my faith for talking me off making the worst possible decision on that 20th storey balcony.
It took me just under 7 years of aggressive saving and disciplined investing to make that money back, and I’ve been blessed to grow my portfolio very nicely since.
Dinesh: What made you return to the performing arts?
Edward: Honestly, I just felt physically ill whenever my clients lost money off the products I recommended and sold them.
I remember the first time I stepped in a rehearsal room after quitting my job I felt so secure – and I knew I was home. And then my future wife walked in, and that was the confirmation. Yes, I met my wife on the first play I did after I quit, it was really serendipity. We’ve been married 13 years now.
Dinesh: You’ve starred in popular productions like The LKY Musical, Late Company, and Por Por’s Big Fat Surprise Wedding, which also starred your wife, Jo Tan.
But, performing arts is notorious for not paying well. What keeps you going?
Edward: That’s the reality of the economics of the performing arts in Singapore, and pretty much the world. What I earn from acting in advertisements, voiceovers, hosting events, teaching, delivering corporate education programmes – all of those multiple income streams – allow me to do theatre.

Late Company
(from left) Edward Choy, Adrian Pang, Janice Koh, and Karen Tan
The magic of storytelling and sharing that space with the audience and other talented actors is irresistible. I’ve loved it since my first role in the Drama Club at Serangoon Junior College. I’ve always been deeply introverted but when I step on stage, I get to be truly alive.
I still get quite star-struck around some of the big stars in the shows I’ve been in. I have fond memories of getting to try Jeanette Aw’s tiramisu before she started her bakery business (she’s genuinely a good chef), but my fondest and probably most embarrassing memory is standing beside Kit Chan on stage at the Esplanade Theatre while we were doing Forbidden City. It was National Day, and the theatre company had decided to get her to lead the audience in singing “Home” at the end of the show. So, the crew handed out lyric sheets, and I helpfully offered to share my sheet with Kit. Who then calmly and kindly whispered to me:
“Edward, I know the lyrics to Home.”
Wah piang! I wanted to just dive into a hole and disappear.
Dinesh: You and Jo often work closely together, whether it’s in theatre productions or when you travel to support her solo show Forked. What’s it like managing the behind-the-scenes aspects of her career, and how do you balance that with your own professional work?
Edward: I actually had to turn down a role I was offered this year because I had committed to following Jo to Australia to help her with her award-winning solo show “King”.
I’ve become quite sanguine about it – if it’s meant to be, then it is. Whenever we travel, I bring along my recording gear, and I’ve become very good at finding ways to buffer the sound in the places we stay in overseas. It’s quite fun to be recording ads that are going on air in Singapore while staying in an apartment in Edinburgh or a hotel room in Sydney. I’ve also become quite a decent mobile phone photographer because of her – during COVID, we shot four music videos featuring her singing parody songs, I had to learn to shoot and edit videos because of that.
Honestly, it’s a lot of fun getting to follow my incredibly talented wife around the world, and even better when she does all the talking in social situations and I get to fade into the background.
Dinesh: You’ve shared that you’re building towards a $1 million portfolio. What does that number mean to you personally?
Edward: I come from a lower middle-class background – my dad was a driving instructor; my mom was a beautician. We’ve never been rich, but my parents worked hard to make sure I never felt poor.
Getting to $1 million is on the one hand a symbolic achievement: I think my parents would be very proud of me if I get there. But on the other hand, it’s a big enough amount of money that it compounds spectacularly and will give Jo and I the freedom to pursue projects we believe in without always worrying about the next gig and paycheck.
I also have very little CPF, as a freelancer so I’m not obliged to contribute to anything other than MediSave – so it’s my responsibility to create a safety net of investments and insurance that lets my wife create the shows she wants to without having to worry so much about the money, while making sure we’re provided for when we’re older.
My portfolio is roughly:
- S-REITs: 20%
- Other Singapore stocks: 10%
- US stocks: 15%
- China stocks: 20%
- Money Market Fund: 5%
- Crypto: 30%, (mostly BTC, ETH, and SOL).
I have a simple rule, when money comes in, I invest it straight away. I don’t get to spend it because it’s already gone. It’s my personal finance hack against overspending. If everything goes to plan, I will hit my target between 2030-2035.
Building From Scratch: Difficult, But Not Impossible
From losing every dollar he had to rebuilding both his finances and sense of purpose, Edward’s journey is a reminder that redemption is possible after financial ruin.
For him, money is not as much about status or show, but more to do with freedom and diving deeper into his passions.
Edward ended our chat saying, “Sure, I could make more as a banker, but I’d hate it every day of my life. I’d rather have less and love every day of my life.”
And, it made me realise that perhaps that’s the truest kind of wealth there is, the kind that lets you live, not just survive.
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