The year has been a big wake-up call, a memento mori (“remember you must die” in Latin) for Cara Chiang.

Dubbed as the one who might take over the tailoring business that made shirts for Singapore’s founding Prime Minister Lee Kuan Yew, that career trajectory has now hit a snag.

Sharing how she recently left CYC, the iconic brand her great-grandfather, Chiang Yick Ching, founded in 1935, Cara was further shaken by two major events this year.

In June, she lost her father suddenly to a heart attack. Six weeks later, her Ah Nia (Shanghainese for grandmother) also passed away.

“Everything that I was very comfortable with has been removed this year,” she told

“I might die tomorrow. So am I cool with what I am doing today?”


Ironically, Cara plays a Happiness Agent in the newly released Tiong Bahru Social Club, a local dystopian comedy that explores the deeper theme of how happiness can be an illusion.

In the film, the job of Happiness Agents is to make their assigned residents happy, even while their own happiness level is being measured and manipulated by artificial intelligence. 

Following the story of a young guy who is searching for the meaning of life, he later comes to learn that a controlled environment where everything is perfect isn’t necessarily going to make one happy.

Cara plays a Happiness Agent in the new local satirical comedy, Tiong Bahru Social Club, which looks at how happiness can be an illusion. Image source: Tiong Bahru Social Club

“It is not real happy but fake happy,” says Cara, who has a role as an extra.

“I took it up because it looked like fun. Of course, upon further thought, I realised that it’s so fitting,” she recounts.

“I feel like Singapore’s and society’s expectation of me to be a certain way can be so stifling. And I tried to fit into that mould for a while, but I just couldn’t.”

Opening up about her dark years as a teen, Cara reveals that she struggled with coming to terms with her identity while growing up. 

All this led to self-harm, where she punished herself “for being incapable of being ‘normal’”. 

Cara shares: “I was going through family, friendship and relationship difficulties. At age 14, I started cutting myself. I felt everything very deeply, and I didn’t know how to deal with it.

“My classmates didn’t appear to have similar struggles, which made me feel like something was wrong with me.”

During her school’s Be Yourself Day, 15-year-old Cara dressed as her hero, Gerard Way, who was the lead vocalist of rock band My Chemical Romance.

An incident where she was touched without consent by someone she considered a friend also left her shrouded in shame. 

Cutting brought some temporary relief, but Cara admits she often felt “even more alone after that”. 

Eventually, it was the love from concerned church friends that helped her to feel better, and she stopped harming herself.

“I soon realised that telling them about my internal struggles did more to alleviate the hard feelings than harming myself in private did,” she says.


It’s a lesson that Cara would learn again much later.

Sharing about how unbottling her emotions has benefited her in recent months, Cara says that going for counselling has been a great help.

In early 2019, a breakup led her to see a counsellor in a church. This became her first step in turning her life around.

Cara started going back to church regularly, where she reconnected with old friends who have become a source of prayer support and encouragement.

Confessing that she had spent many years of living her own way – instead of God’s way – she says: “I would still talk to God and pray. But He wasn’t my steering wheel. He was my spare tyre.”

However, as Cara started to make God her priority, she began drawing closer to Him, finding peace like no other.

“Speaking to God and allowing Him to speak to me through verses is a thousand times better than trying to deal with it on my own,” she says.

Psalm 139:7-24, in particular, brought encouragement.

“For someone who once didn’t like herself, it is very comforting to know that God knows even the parts of me that I dislike. As much as I try to hide them from people, He knows them already,” explains Cara.

Disclosing how she had felt like she was “made a bit broken”, she now knows God did not make a mistake when creating her.

“God already knew what he created me for. I don’t have to figure it out on my own,” she says.

Over the years, Cara has also noticed: “Sometimes I slip, sometimes I fall, but God always brings me back to Him.

“I tell Him: ‘God, you’re my GPS.'”


Reflecting on all that has happened this year, Cara says: “I had high hopes that when I came back to God, good things would happen. But I was very naïve to think that just because you are a Christian or believe in God, you will only draw good things in your life.”

“God also brings us through difficult times for a reason,” she adds, though she may not be able to see the reason yet.

Shortly after losing two family members whom she was close to, Cara left the tailoring business.

Cara with her brother and mother at the Singapore Stories 2020 premiere (left). It was the last project she had with CYC before leaving, and she was among the five finalists for the design competition. A departure from the formality that CYC is known for, the prints for Cara’s streetwear capsule collection (right) were inspired by the uncertainty and darkness, as well as the joys and hopes her great-grandparents must have felt on their boat journey to Singapore in 1935.

Formerly the product development and marketing manager at CYC, she had been shaking up the brand with her millennial’s sensibilities. But a few months ago, Cara left CYC because of differing opinions on how to take the business forward.

She shares: “It was – and still is – a difficult time. However, I am very grateful for my time at CYC.

“Some people go to MBA school, I went to CYC and got my training there. I learned so much.

“At CYC, I learnt about creativity and commerce, and the constant balancing act between the two factors. It was truly a life-changing experience.”

While waiting for her what-next, Cara has been taking time to rest, read, catch up with friends and family, and reconnect with herself. She also goes for long hikes in nature.

During this season, Cara has also been making time to “sit in the woods”, while contemplating the next path to take.

“I was so invested in the brand legacy of CYC. It was tied to who I am. I am still learning to detach my identity from my work – that I am not my work,” she admits.

It was on one of these walks that Cara also felt prompted to remove the proverbial mask – the metaphor of the façade she hid behind – on her experiences as a teen “to help others feel less alone in their pain”.

In this season, Isaiah 40:31 is one of the verses that she is holding on to, as well as Jeremiah 29:11.

“Waiting is really difficult for me because I like to have a goal to work towards,” she says. “But I will continue to have faith in God’s plan for me.”

“There are days when I feel uncertain and anxious about the road ahead, but I trust God to lead me into a new chapter.”

In the meantime, Cara is helping out with the e-commerce platforms of two social enterprises, using her marketing skills to drive more interest to their websites. She is also involved in styling and directing photo shoots, copywriting and proofreading.   

One of these initiatives is ACTS Market, started by her mum, Cheryl Lee, which retails products made by disadvantaged people, such as women who used to be trafficked and people with disabilities. 

The other is Flourish, which was started 10 years ago by a group of Christian women to create jobs for women in Cambodia living in challenging circumstances. Cara is also designing crochet backpacks and handbags – made from easily accessible material like garbage bags – that the women can learn to make for sale.

The third is “a secret project” that she plans to announce at a later date.


In the face of the losses Cara been through this year, one can’t help but think of the Bible characters of Job and Joseph who continued to trust in God and eventually saw His plans for them.

“All of us go through weird, unexpected challenges. So this is my unique struggle,” she says.

One of the blessings of this post-CYC season for Cara is getting to spend more quality time with the people she loves. She is pictured here with her goddaughter, Alyx.

Encouraged by the lyrics of Desert Song, Cara affirms: “In every season, You are still God, I have a reason to sing.”

She says: “During the good season, I won’t feel so egotistical. And during the bad season, similarly, I won’t be pulled down. God is in the middle ground. That is what I’m holding fast to.

“There are days when I feel uncertain and anxious about the road ahead, but I trust God to lead me into a new chapter.”

All photos courtesy of Cara Chiang unless otherwise stated. The featured image is a film photo by Cara’s close friend Charlotte Hand. It was taken one month after Cara saw her first counsellor in 2019.

  1. Do you find it difficult to love yourself? What comfort can you draw from God, your Creator? 
  2. Are you wearing a mask? Is there any part of yourself that you’re hiding from others?
  3. God has a purpose for your life. Have you discovered it yet?