I have known Ruth since junior college, when we were schoolmates at VJC. Even back then she had a certain je ne sais quoi that magically drew people to her. She did not follow a predictable path, and she has never seemed to want to. She is a free spirit in the truest sense, and somehow that has always made the people around her want to be a little braver too.

Over the years I have moved in and out of her orbit. I cheered her on when she started her first floral business, and again when she started Blessed Blooms, the brand she runs now, built around an idea she calls making love visible through flowers. What strikes me most about Ruth, though, is how much of her life is organised around kindness. She wrote a book to raise money for charity, as did her husband. She sits on the board of Child at Street 11, brings her son along to volunteer in the community, and hands flowers to the elderly in the rental flats near her home. She and her husband do not just talk about these things to their son. They live and model these principles, every day.

There is a poem I’ve associated with Ruth for a long time (she’s told me she has always loved it), and I think it comes close to a life philosophy. It is William Blake’s Auguries of Innocence:

To see a world in a grain of sand

And a heaven in a wild flower,

Hold infinity in the palm of your hand

And eternity in an hour.

It is a very Ruth thing, to build a life around finding the whole world in something small and meaningful. When I read her answers, I kept seeing the poem behind them.

I’ll let you read the rest of the conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Ruth, founder of Blessed Blooms, a floral brand in Singapore built around the idea of making love visible through flowers. Before this, I was a teacher but I left the profession to pursue entrepreneurship and create a life that allowed me to be more present for my family while building something meaningful.

Today, my work goes beyond just selling flowers. Through Blessed Blooms, we create everyday floral experiences for gifting, gratitude, grief, celebration and connection. I also work with corporate teams, schools and community groups through workshops and community initiatives. A big part of what drives me is the belief that small acts of care can have a real impact on people’s lives.

On the family side, I’m a mum to an 11 year old son who’s a national diver, and family remains at the centre of many of my decisions. I’m also involved in community work as a board member of Child at Street 11 and through various ground up initiatives.

Right now, I think I’m at a season where both work and family are becoming more intentional. I’m learning how to build a business that is sustainable and purpose driven, while also being fully present for the people and moments that matter most.

How old are your children, and who is the primary caregiver at home?

I’m the primary caregiver. My son is 11, foster daughter is 3 but she has just been reunited with her biological mom and they have since moved back to Malaysia.

How you think

Was there one thing that made you change after becoming a parent?

Becoming a parent changed the way I see both time and responsibility.

When my son was born, I remember looking at this tiny newborn and feeling the weight of it all. Newborns are so precious and completely dependent on the people around them. It made me realise that as parents, we are shaping someone’s world, not just keeping them alive, but shaping how safe, loved and seen they feel.

It also gave me a much deeper appreciation for my own parents. You suddenly understand the quiet sacrifices, worries and invisible labour that parents carry every single day.

More than anything, becoming a mum changed my perspective on life itself. Parenthood made me realise how fleeting time really is. The days can feel very long sometimes, especially in the exhausting seasons, but the years pass incredibly quickly. Children grow while we’re busy living ordinary days, and one day you realise those moments are gone forever.

That awareness has made me more intentional about how I spend my time and what I want to build my life around. It’s also part of why I started my business and why the idea of “making love visible” matters so much to me now. At the end of the day, achievements come and go, but the love, memories and presence we give to people are the things that truly stay.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Yes I feel that my time is so limited and whenever I’m at work I’ll be missing my son’s milestones. They grow so fast and we can’t buy back time. So I decided to focus on him and left teaching. I never looked back since and don’t regret my decision at all. He’s 11 now and I still feel I don’t have enough time with him.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

I still remember feeling very guilty once when my son was 3 and I had to leave work early to attend his kindergarten concert.

At that time, I was running the flower studio during one of our busiest periods. The concert happened to fall right during crunch time, just before we closed the day’s orders and the drivers arrived to collect the flowers. I remember standing there debating whether I should stay back to help because the team was overwhelmed. But deep down, I knew I couldn’t miss the concert for the world, so I left at the very last minute and rushed down so I wouldn’t be late.

That tension between work and being present still follows me today.

Last year, during a family trip to Japan, we were having dinner beside a beautiful waterfall in the mountains. It should have been one of those peaceful family moments. Instead, I was glued to my phone trying to firefight an emergency delivery issue back in Singapore.

I still remember my husband looking at me in frustration, almost wanting to grab my phone and throw it into the running water.

I think moments like these stay with me because they remind me how easy it is for work to quietly take over the very life we’re working so hard for in the first place.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

When my son was a newborn, my husband and I used to joke that our main parenting philosophy was simply to make sure he doesn’t die 🤣 We were exhausted first time parents trying to survive the sleepless nights, endless diaper changes and breastfeeding schedules. Looking back, that mindset actually helped us put things into perspective. In those early days, small problems can feel enormous because you’re so tired and overwhelmed, but we kept reminding ourselves that if the baby was safe, fed and loved, the rest could be figured out.

As he grew older, our parenting philosophy evolved beyond just keeping him alive and happy. We became much more intentional about character building and the kind of person we hope he grows up to be.

More than achievements or grades, we care deeply about him having a good heart. We want him to be kind, generous and aware of people around him. One thing we often tell him is to look at other people’s plates and see how you can help fill theirs too.

At the same time, we encourage him to do hard things and to keep showing up consistently, even when he doesn’t feel like it. Whether it’s training, school, relationships or life in general, we want him to understand that growth often comes from learning to stay through discomfort instead of avoiding it. And to just keep showing up, no matter what.

I think parenthood has also made us realise that children learn far more from what we model than what we say. So a big part of parenting for us is trying to live out the values we hope he carries forward one day.

What is the one generational pattern you are consciously trying to undo?

I think our parents did the best they could with what they knew, and a lot of it came from love, survival and wanting to raise resilient children. I’ve realised that while authority can create obedience, it doesn’t always create connection or trust. With Jude, I’m trying to parent with more conversation and explanation instead of just control. Of course there are still boundaries and consequences, but I want him to feel safe expressing himself, asking questions and even disagreeing respectfully.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

I built a flower business, but more than that I think I built a way of helping people express love, care and connection through everyday moments. Before this I was a teacher and while I loved working with children, I realised I also wanted to create something of my own and build a life with more flexibility and meaning for my family.

Honestly, I didn’t enter floristry because I grew up dreaming about flowers. I was drawn to the business first, but along the way I discovered how powerful flowers can be in people’s lives. They appear in moments where words often fall short, grief, celebration, apology, gratitude, love. Over time, it became less about flowers themselves and more about what they carry between people. That’s why the idea of “making love visible” became such a big part of my work and life.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

I think what I’m really building for my son is not just a business, but a way of living. I want him to grow up seeing that work can be meaningful, that success is not only about money or titles and that it’s possible to build something with heart. I hope he sees that kindness, relationships and integrity matter just as much as achievement.

At the same time, I also built this life because I wanted more presence. Leaving teaching and becoming an entrepreneur gave me the flexibility to be there for school events, competitions, ordinary afternoons and the little moments that would otherwise be missed. I’m not sure he fully understands it yet but I hope one day he’ll realise that many of the decisions I made were shaped around being able to have more life with him while still building something meaningful.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

We have the power and freedom to make our own choices. Don’t succumb to societal’s standards, we build the life we want and we put in the hard work and sacrifice to get there. Dont complain about our situation because we are where we are because of the choices we make, we are 100% responsible for both the good and bad. If we are unhappy with something, we take action to change it. If we choose not to do anything about it, then we can’t complain.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

Not to follow the crowd blindly, let Jude learn at his own pace. Sadly, we can’t run away from the PSLE system so as responsible parents, we still have to do our due diligence to make sure his studies are on track to meet the minimum standards to get to the next level. Sometimes I wish I don’t have to struggle to do 听写 with him 🤭

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

Love is unconditional. No matter what happens, kids don’t bear grudges and they will love us back no matter how much we scold them or “disappoint” them. They really mean what they say and their love is so pure. It’s something you have to experience yourself and it can’t be taught or learned.

What is one thing you do to teach your child or children to be kind?

We model kindness and talk about it. We will always point out situations when we can extend some kindness to others in our everyday - holding the lift door for others, greeting cleaners, guards along the way, thanking servers. When we’re overseas and meet the homeless along the streets we would talk about it and encourage him to give some money instead of pretending they don’t exist. He has since learned to notice them and always ask us for money to give them.

We also bring him along whenever we have charity events and always try to involve him, no matter how small. He joined the kids to wash cars 2 years back when the kindergarten had a fundraising event. He would also help to give out food and flowers to the elderly in rental houses near our area on occasions.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

Ignore what others say, everyone’s path is different and we would know our child the best so do what we feel is right for our child and doesn’t matter what others do or say

And finally

What do you cook when you want to show your child or children you love them? Recipes welcome.

(Soupy) Mac and cheese. It’s simple: just boil the pasta, melt whatever cheese we have in the fridge, add some milk (my son likes it soupy) and bake it to get a crispy top.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Wet wipes!

If you had one hour to yourself this week, what would you do with it?

Uninterrupted sleep with all my pillows and bolster on the whole bed to myself!

And finally, what is in your cup right now?

Pipping hot coffee and so much gratitude for what I have, who I am now and the people who are in my life.

What stays with me about this conversation is how much of Ruth is about kindness, and how deliberately she practises it.

She wants her son to have a good heart more than good grades. She tells him to look at other people’s plates and see how he can help fill theirs. She points out the cleaners and the guards and the people sleeping on the street so that he learns to notice them rather than walk past. Ruth and her husband model it daily: fundraising with their son for charity, in the books they each wrote to (also to raise money for charity), and in the flowers given to the elderly nearby. It is a life made of small acts of care, grain by grain.

This is the same Ruth I knew back then, the one who never followed the crowd and never seemed to mind. She said it plainly in her answers: don’t succumb to society’s standards, build the life you want, and take responsibility for all of it. She left teaching because she did not want to keep missing her son’s milestones, and she has never once regretted it. Ruth is a free spirit, but a deliberate one.

I think that is why Blake’s poem is so apt. Ruth has built a whole working life around the idea that a flower can hold something as large as love, and that a small act of care can change someone’s day. Making love visible is not a tagline for her. It is how she has always moved through the world.

She said her cup right now holds piping hot coffee and so much gratitude for what she has, who she is, and the people in her life. That sounds about right. Ruth has always been good at holding eternity in an hour, and a heaven in a wild flower.

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A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

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🍵 “More from A Cup With” ☕

I got to know Jillian through her husband Kin, who I have known for years. Jillian is a third culture kid, who grew up in Australia and Indonesia as a child, followed by nine years in New York. Then next up was Hong Kong, where she met her husband, who convinced her to move to Singapore.

Two years ago, she started her own batik kidswear brand, Dots and Dribble, which she created from scratch. From the brand work, the designs, the sourcing trips to Indonesia, she does it all while raising two young kids in Singapore. Jillian has mentioned that “starting this store was also a way for my kids to connect with their Indonesian and Malaysian heritage.”

(I should mention I’m a customer. I buy her batik for my kids, and her batik painting kits too, because I love her tasteful designs and my kids are happy to wear them as well!)

Third culture kids often have a complicated relationship with the question of where they are from. Their roots are made up of many places, none of them fully. After a life of moving, Jillian is doing the work of rooting, and I think many of us feel this more urgently with children. She is giving her two children a thread back to where she and Kin came from. She is also making something personal and beautiful for them.

I’ll let you read the rest of the conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Jillian. I always knew I wanted to do something creative. After art school in New York, I worked in digital agencies for a decade, but when I took a break to be more present with the kids, I realised I wanted to make something that was entirely mine. Two years ago, I started Dots and Dribble, an online store specialising in batik kidswear. It was a way to blend my design background with my kids’ heritage—and it’s been a whole learning process.

How old are your children, and who is the primary caregiver at home?

My kids are seven and four, and I’m the primary caregiver. My husband’s work involves quite a bit of travel and client dinners, so he pitches in when he can. We also have a wonderful helper who assists with cleaning, cooking, and childcare.

How you think

Was there one thing that made you change after becoming a parent?

You’re always split. In school, anything less than an A is a failure. As a parent, I’ve had to unlearn that getting C’s across everything like work, kids, myself beats an A in one thing and nothing else.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

I was one month into a new job when I found out I was pregnant. Hiding it while feeling sick at a job I hated was miserable. But it made me ask: why am I doing this to myself just so my employer doesn’t feel bad? I quit six months later. I was privileged to have options such as my partner’s support and the ability to freelance again. At that point the realization was clear: I couldn’t keep sacrificing my family for a job I didn’t love.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

Parenting made me examine my people-pleasing. My dream job at an ad agency came at ten months postpartum. Working until 1–2am, waking at 3am with a baby, then starting at 7am wasn’t sustainable. Nobody talks about this. I was up at 2am sweating, stressed and miserable, wondering why. Then I looked around: no mothers in core roles. During COVID, with everything falling apart and still pitching, it was clear I had no future there. I had to leave.

How has your parenting philosophy evolved, with age, with experience, or with each subsequent child if you have more than one?

I realised how neurotic I am as a parent. Before kids, I was a go-with-the-flow type of person, but parenting changed that completely. I am not a planner but having kids is 90% logistics and 10% the craziness that comes with it. A set schedule with an early bedtime allows both the children and me to thrive. With my second child, I had less time to be neurotic and just aimed to enjoy the chaos…to a certain extent!

What is the one generational pattern you are consciously trying to undo?

Emotional awareness. Being aware of your own emotions and naming them is such a powerful tool. After a long day, I catch myself scolding the kids for little things and have to consciously step back and ask: Is it because I’m tired? 99% of the time, the answer is yes.

What you built

Tell me about what you built. What made you choose this, and not something else?

I launched a modern batik shop for kids to blend my design background with my Southeast Asian roots. My kids don’t speak Bahasa or Malay, so this was a way to give them that connection. It felt like the right combination of everything I cared about.

Is there something in what you built that you made specifically for your children, whether they know it yet or not?

It started with my son’s preschool dress-up days. All the cultural outfits were cheap, fast fashion junk. I set up the shop to solve that problem for him. But then I discovered something unexpected: I loved building this. It showed me what fulfilling work could be manageable—spending as little as ten minutes a day or long hours over a weekend working on your project. But I’ve learned to be ruthless about what matters and prioritize. Over time, it compounds into something meaningful.

When your children are old enough to look back at the choices you made, what do you hope they take from it?

That your self-worth is not tied to your productivity or achievements. Being a good person is about building your confidence, nurturing relationships, finding meaning in your work and trying new things. Not everything in life has to have a measurable outcome.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

Let them be kids. The only results you should measure is: were they better than they were last year? That’s the only result that should matter but unfortunately that’s now how it works here. Raising kids in Singapore is different from how I was raised in Australia. We had no homework. I didn’t have exams until I was in grade 9 and I turned out ok (I hope). For this generation on social media it’s chaos. There’s too much literature out there. I get FOMO watching other kids hit milestones mine haven’t. But I’ve learned: just try things and see what works. You can always change your mind. And as much as I love them, honestly, my kids are extremely average. And that’s okay.

What you have learned

What has your child taught you that no colleague, mentor, or book ever did?

To love someone so unconditionally that it hurts. Before you become a parent, you’re the centre of your own universe. But the minute a child grows inside you, your life and choices become bigger than yourself. Your kids can be absolute sh*ts and you’ll still worship them. Parents, you understand this dilemma.

What is one thing you do to teach your child to be kind?

My son is seven and pushes boundaries at the playground. Boys have a lot of physical energy and use rough play to socialise. Nothing wrong with that. We just guide it, teaching acceptable behaviour and how to manage emotions when things get intense.

My daughter is the opposite. She’s extremely sensitive and shy. She doesn’t need reminding to be kind to others. She needs reminding to be kind to herself, to stand up for herself.

You can’t force kindness into kids. You can only model it and hope they see it. Slowly, they start taking your lessons into consideration when you least expect it.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

Oh, so many. I feel like there’s too much advice being thrown around. Sometimes the best thing you can do is just be. Just do. Then learn from it.

And finally

What do you cook when you want to show your child you love them? Recipes welcome.

Korean seaweed soup is the ultimate comfort food in our house.

What is one thing in your bag you never fail to have on hand when you bring your children out?

Water bottles and tissues! Singapore is so hot.

If you had one hour to yourself this week, what would you do with it?

A massage and a meal with my husband! One hour well spent to recharge and come out a better person.

And finally, what is in your cup right now?

A hot latte. Or three lattes. After becoming a parent I can have 3-4 coffees a day and I still conk out at night.

What stays with me about this conversation is that Jillian is doing two things at the same time.

She is giving her kids a way to reach back to where she and Kin came from, and she is also showing them what it looks like to build something of your own.

She said she hopes they learn that self-worth is not tied to productivity. I’ve been caught up in the 996 narrative working in startups for years, and I have to admit that as a parent now, it’s just not possible to sustain that. She also realised a very real and painful truth, no one doing the core work of that agency was a mother. You can replace “agency” with many other industries, and that’s the hard truth. And that’s what I admire about Jillian and other mums I’ve interviewed, after they came to that realisation, they’ve taken things into their own hands, literally.

People who grew up rooted in one place tend to inherit their heritage almost without noticing it (ie me). People who grew up between places have to choose theirs. Jillian is choosing batik. She wants it to be something her kids can hold, and something she can build with her own hands and turn her design eye to. She is making it between school runs and sourcing trips, in pieces. It’s growing because she kept showing up to the next ten orders, then the next fifty.

Jillian said she needs a hot latte to get through the day. Underneath that latte is something quieter, the conviction of a third culture kid who took the long way to Singapore and is using everything she gathered along the way to give her children, and herself, something beautiful to belong to.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

What does it take to have a full-time career as a founder and to raise 4 children?

I met Elena many years ago when she tried to hire me. There was an up-and-coming startup, a role being shaped, and a conversation about whether I would be the right fit. I wasn’t, in the end. But Elena made an impression on me. She ran that conversation with an attentiveness that lingers and also a keen hustle. She was one of the first recruiters I met that seemed to actually care about her candidates’ careers (not to mention the first who actually focused on recruiting for startups in those very early days).

Years later, I learnt that not only did Elena not come from a HR and Recruitment background, she was building her company while raising 4 children! It was a thread that I picked up, and I genuinely got curious. What does it take to do what Elena did?

The more I read her responses, the more it comes down to one instinct. Elena sees what’s in front of her, trusts her read, and acts. About ConnectOne, she writes almost in passing: “It was not intentional, I never thought I’d start a HR and Recruitment company but when you see a problem in front of you and you know the solution, you go plug that gap.” Fifteen years in corporate watching how great companies build great teams, and when she saw the gap nobody was filling for VC-backed startups in Singapore, she went and plugged it.

The same instinct showed up in how she raised her four. While her friends were sending their kids to Learning Lab to learn European history, Elena sent her daughter to art class and got chided by a friend for being a bad mum. On teaching kindness, she shrugs: “I never did intentionally. But if anything, I brought them with me on multiple overseas social mission trips from a young age, and I think that experience has inculcated a sense of empathy that no lecture or textbook can impart.” Elena was remarkably consistent: she sees what matters, chooses that, and ignores the consensus.

Elena is in a pivoting season now. The question she keeps asking has shifted from “How do I build more?” to “What is worth building next?” Like Sam, she’s further along the journey, with children mostly grown. Talking to Elena reminded me that the wisdom from this stage of parenting sounds different. It’s less hurried, more circumspect, and I appreciate seeing it from her angle.

Here is our conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I would say I’m in a pivoting season.

For many years, my focus was very much on building — building my family of 4 kids, building a HR and executive search practice, building networks within the startup ecosystem, and building teams for high-growth companies. That season was energising because everything felt like forward momentum.

But over the past year or two, I’ve started asking different questions. Instead of “How do I build more?”, the question has become “What is worth building next?”

That shift has led me to explore several new directions - supporting fractional leaders or portfolio careerists, rethinking the kinds of organisations and leaders I want to work with and venturing into a new space that I am currently in a discovery/research phase. In many ways, the pivot is less about abandoning the past and more about reframing how the past experience can be used in a different way.

How old are your child or children, and who is the primary caregiver at home?

My kids are between the ages of 28 to 18 haha. They don’t need a caregiver anymore.

How you think

Was there one thing that made you change after becoming a parent?

My ambition at work was no longer the same. Before that I was always gunning for the promotion, I remember crying as I was the 2nd fastest to be promoted in my cohort and not the fastest! After becoming a parent, my priority was to rush home as fast as I could from work.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

I was in a meeting and had more than 10 missed calls right after a one hour meeting. I remember that occasion (although there were many of the same before but this was one that as they say “ the bucket overflowed”) because it was one of the triggers that told me,” Hey, I think it’s about time that I spend more time with the kids, right?”

Also my second son who was super challenging to handle (he had ADD and was constantly distracted) was going to P1 and I knew I would have to be around more for him.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

That meeting as described above - while it was not anything dramatic but it was a build up that culminated in a seemingly innocent ordinary meeting triggering that thought.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

I was a lot more involved, even fanatic to the point of counting the hours I spend with my kid vs my helper at home - to one of “I have done my best to impart the best foundation for you and hence I trust that all decisions that you make are well thought through and values based”. Especially with 4 kids, you apply the way you raise consistently (principles, values etc) and let them base off that to grow.

What is the one generational pattern you are consciously trying to undo?

Some members of my husband’s family have severe anxiety and I am always on the look out for manifestation in my kids and pay special care to helping them with it. My family has a short temper and in the same way, I recognise them in my kids. Awareness is the foundation of the resolution.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

My first 15 years was in corporate and I did not build anything for myself other than the knowledge of how great companies approach building great teams. I took that knowledge and first hand experience to start ConnectOne, which I built to help tech startups build great teams. It was not intentional, I never thought I’d start a HR and Recruitment company but when you see a problem in front of you and you know the solution, you go plug that gap! Hence I am pretty proud of being (one of) the first HR company that specializes in helping VC backed startups. Many have jumped in since then but it is still nice to be recognized as the first.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

No none haha. But if any of them come up to me and say “Mum, let me take over your business and grow it”, I would definitely think hard!

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

From a career standpoint - start by working in corporate but always aim to build your own before you are 40! And if possible build for an exit :) which I did not of course.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

Can I answer it in the context of what I gave myself permission to do? :)

Not be FOMO and send them to enrichment classes and tuition after tuition! While my friends’ kids were going to the Learning Lab to learn about European History, I sent my daughter to art class (this is a true story as a friend chided me for being a bad mum for doing this). I also did not send them to music classes but they picked up guitar on their own and played beautifully :)

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

Boys can be mum’s best friends! Contrary to what most will say that have girls as they are your best companion. But I truly enjoy spending time with my boys and while they were so difficult to raise (naughty and disruptive!) but they are the sweetest now

What is one thing you do to teach your child or children to be kind?

Hmm, I never did intentionally. But if anything, I brought them with me on multiple overseas social mission trips from a young age and I think that experience has inculcated a sense of empathy that no lecture or textbook can impart.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

On parenthood? That raising 4 kids is very expensive and that I should have been wiser with investing my money when I was younger haha. Funny that no one ever told me that - they were concerned more about our capacity than money (or maybe they were too paiseh to articulate it).

And finally

What do you cook when you want to show your child or children you love them?

I am very fortunate that I never had to cook at home as my husband/helper does all the cooking. But what they appreciate is my making of Mum’s jelly cheese cake on their birthday!

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

My kids are grown but they still ask me for tissue paper haha.

If you had one hour to yourself this week, what would you do with it?

I have many more hours now that my kids have grown but if I had that extra hour, I would like to join this iphone photography thing that a friend has launched, finish my chinese landscape art and double down on some AI automation.

And finally, what is in your cup right now?

A cup full of joy and gratitude for the blessings of energy and optimism even as i stand at the verge of the next third of my life (I think of life in thirds)

In Elena’s responses, she carries a wonderful sense of energy and positivity that I admire. She has made many tough choices building her company while bringing up her children, and while many of them were not easy, I sense a strong conviction in her choices, where she knew what she wanted and went all out to get it.

That conviction reshaped her as a mum. In the early years she was, in her own words, fanatic, counting the hours she spent with her kids against the hours her helper did. Years later, with four kids 28 to 18, she trusts what she put down: “I have done my best to impart the best foundation for you and hence I trust that all decisions that you make are well thought through and values based.”

And you can see what they got. They picked up guitar on their own, and came home from her overseas mission trips with empathy no textbook would have given them. Elena raised them on principles and values rather than schedules, and the foundation has held.

And now, she’s pivoting to think about what’s worth building next.

It’s a question I wouldn’t have known to ask in my twenties, although it was something I already did start working on after I had my first child and got hit by the shock that was Covid. Elena is much further along her journey, and is sizing up the materials for the next play. But underneath it all, she doesn’t sound like someone in a hurry, and the joy in her voice is the part I really admire.

I would like to carry that gratitude in my cup too.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

I’ve known Cass for years. Singapore is small enough that paths cross more than once if you stay in the same orbit, and ours did, going back to her Foodpanda days. Later, when she was made redundant from a tech role in 2023 and started her own fractional marketing agency, I had the chance to work with her team on a few campaigns. That’s where I really saw it up close: her hustle, optimism, and the relentless energy that doesn’t seem to run out. If you ask me whether someone is hungry, Cass is.

But I’ve also seen the other side of her. The way she is with her two girls. The way she is actively thinking about the kind of environment they are growing up in, and the version of her they are watching. I’ve been a little curious about the person beneath all that drive, so I asked her to share more.

What follows is our conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Cassandra, founder of OtterHalf (www.otterhalf.co), an award-winning fractional marketing agency based in Singapore. We work with tech startups and SMEs as their part-time marketing team, jumping in, helping them grow, and sometimes making ourselves redundant in the best way possible. I have 14 years of experience across companies like foodpanda, Chope, and Tripadvisor before a tech layoff in 2023 became the unlikely catalyst for everything I’m building now.

At home, I’m a mum to two girls. I grew up in a fairly chaotic household, so peace at home isn’t something I take for granted. Right now in both work and family, I’d say I’m in a good place. Still building, still doing work that feels meaningful, and genuinely happy with where things are, stress and all.

How old are your children, and who is the primary caregiver at home?

My girls are 5 and 8. It really does take a village, and I’m lucky to have mine. My husband, our helper, and my in-laws all play a big part in keeping things running. That said, I’m very much in the thick of it too, and yes, I still co-sleep with both girls. One of the gifts of founding OtterHalf and going remote is that I get to be around for the ordinary moments. My daughters literally peel me away from my workstation to remind me to eat dinner or go bathe. Some days, that’s the most grounding part of my day.

How you think

Was there one thing that made you change after becoming a parent?

Before kids, I’ll admit I was pretty superficial about my career choices. I made decisions based on what I personally liked. I love food, so I told myself to join a food company. I joined an FMCG because it was THE company every marketer wanted on their CV, not because I was passionate about their products or what they stand for. I just went where people went.

After having my girls, I started thinking a lot more about what I actually wanted to contribute, and why. It made me ask harder questions, like what can I do that would positively influence the environment my daughters grow up in? That question affects a lot of what I do, from the clients I choose to work with, to the card game I built, to the workshops I now run for kids. It gave my work a reason beyond myself.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Yes, it was the layoff in 2023. I was Head of Marketing at a B2B SaaS company when almost the entire marketing function was made redundant. At that moment, I had two young daughters at home and no job. I could have spiralled.

But something in me went very still, the thought about starting my own venture. I thought: if not now, when? I called two trusted ex-colleagues, we put our heads together, and within a month we’d launched OtterHalf as the first fractional marketing agency in Singapore. We closed the year with six-figure revenue. But more than the numbers, I remember thinking: I don’t want my daughters to ever feel that a setback is the end of the story. So I decided to write a different one.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

The one that stays with me happened in the early days of building OtterHalf. We were out as a family on a weekend, but I had my phone out the whole time. Replying to messages, checking in on work, one eye on the girls and one eye on the screen. My husband turned to me at some point and said, “Going out with you is like going out with a teenager.”

To a certain extent, it was true. I was physically there and completely elsewhere. That comment has stuck with me and I start being more intentional about putting the phone down, especially on weekends. I’m still working on it, but I think about that line more than I’d like to admit.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

When my eldest was born, I was inexperienced and pretty anxious. Parenting to me was ensuring that she sleeps through the night, cries less, and is well fed. I would also google every little thing, and even send her to A&E at the slightest fall.

By the time my second came along, I’d loosened up quite a bit. I think she got a more relaxed version of me, and she probably benefited from that.

Then starting my own business made me rethink about how both my girls grow up. I want them to see that life doesn’t always go to plan, and that’s okay. That you can lose something and build something better from it. I want them to grow up with confidence that they can figure things out, having watched someone they love navigate the hard parts and keep going.

What is the one generational pattern you are consciously trying to undo?

Growing up, there was an unspoken rule that parents were the authority and you didn’t question them. You just complied. I understand why that generation parented that way, but I saw what it cost — in communication, in closeness, in the things left unsaid.

I’m consciously trying to undo that. I want my girls to feel like they can come to me with anything. The moment they’re afraid to tell me something is the moment I’ve lost the most important part of being their mum. I’d rather be the person they run towards than the one they hide things from.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

I started OtterHalf because the agencies I kept interacting with were focused on brand building — impressions, reach, awareness. But as someone who had spent years working at startups, I couldn’t justify marketing spend on brand impressions alone. The environment I was in was cutthroat enough that my team could have been asked to leave if I spent a lot of money driving impressions that led to little conversions. So at some point I thought: maybe I could just be the agency I had been searching for all along.

As I built the agency, one thing stayed consistent: the belief that businesses have the power to contribute to a better world. That shaped who we work with, why we created Ottie’s Fishy Business, a card game that teaches kids the fundamentals of marketing, and why I care so much about using the skills I have to better the environment my girls grow up in.

These days, my weeks look a little like this: running the agency from Monday to Friday, and on weekends, stepping into a room full of kids to teach them about marketing through play. Two very different rooms, but the same thread running through both. I’m building things I actually believe in, and that feels like the point.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

Ottie’s Fishy Business was made because of them and for them, and they know that. My daughters asked me one day: “Mama, what do you do at work?” I tried explaining marketing and quickly realised how abstract it all sounded. So I made a card game. It took eight months to develop and test. They were my harshest critics and my loudest cheerleaders. But beyond the game, I think everything I’ve built at OtterHalf is for them too. I want them to grow up knowing their mum built something from scratch, after a setback, and that it worked. That’s the version of female leadership I want them to grow up watching.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

That you can always forge your own path. That a closed door isn’t the end, sometimes it’s the thing that sends you in the right direction. I also hope they take from it that work doesn’t have to swallow you whole. That you can build something meaningful and still show up for dinner. I haven’t always gotten the balance right, but the intention has always been there. I hope that counts for something.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

What I wish I had given myself more permission to do was to be kinder to my younger self. To accept that failing is part of it, and that what matters most is whether you get back up and try again.

Singapore can make that hard. There’s a certain pressure to have it together, get good grades, get good careers, and look like you’re moving in the right direction and not let people see you stumble. I internalised that more than I realised. The layoff I experienced forced me to sit with the uncertainty, and then to get up anyway. And somewhere in that process, I stopped being so afraid of getting things wrong.

I wish I’d learned that earlier (so much wasted tears on bad grades), mostly for my girls to grow up watching a mum who isn’t afraid to fail, and who shows them what it looks like to keep going regardless.

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

That happiness is not about the things that you have but how present you are for the life that’s already in front of you. Kids have no interest in your achievements or your title. They just want you, fully, right now.

What is one thing you do to teach your child or children to be kind?

Every night when we wind down, we play a little game called “tell me three things you like about today.” It’s become our ritual. And whenever I can, I pull out a moment from the day when one of my girls was kind to someone, and I name it out loud.

Like the time my daughter gave up her scooter for another child who really wanted to scoot and was crying for it, even though she really wanted to scoot too. I made sure she knew I saw that. That it mattered.

I think kindness grows when it’s noticed. Kids do more of what gets reflected back to them. So I try to be the one who catches it, calls it out, and makes it feel like something worth repeating.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

Give yourself some grace. When I started OtterHalf, I was catastrophising constantly. What if this doesn’t work, what if I lose a client, what if I’m not enough. No one sat me down and said: you’re going to feel like you’re failing even when you’re not. The discomfort is part of the growth. I wish someone had told me that. I’d have spent a lot less energy on dread.

And finally

What do you cook when you want to show your child or children you love them? Recipes welcome.

My girls’ favourite is spaghetti bolognese baked pasta.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Wet tissues.

If you had one hour to yourself this week, what would you do with it?

Body massage.

And finally, what is in your cup right now?

Water.

What stays with me about Cass’s answers is how often the things that happen to her gain a new sense of purpose for her and for her daughters. The layoff became a company. The questions her girls asked about her work became a card game. Even her husband’s comment that going out with her was like going out with a teenager became a reason to put the phone down on weekends.

Underneath all of that is something Cass names plainly: the belief that businesses have the power to contribute to a better world. That belief is what shapes the clients she takes on, the card game she spent eight months building, and the environment she’s actively trying to set for her girls.

She told me she doesn’t want her daughters to feel that a setback is the end of the story. So she decided to write a different one. That takes a whole lot of courage.

And at this q&a’s heart is her answer to the question about teaching kindness. This question tends to shine a light on a softer side of a person, the part of them that sits closer to who they are at their core. When Cass described how kids do more of what gets reflected back to them, and how that kindness needs to be caught and named out loud to take root, I get it.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

I met Sam in 2019, when I was a new mum still finding my feet. I had reached out to her looking for a coach, without being fully sure what I was actually looking for. I just knew I felt off. The work self I used to recognise had got wrapped around a very small person, and I couldn’t work out who I was inside the new shape.

What I remember from those early sessions is how little she needed me to perform. She asked questions, listened, asked more. She was in no hurry. Coming out of my big tech role, where every conversation had an agenda, the pace took getting used to.

We worked together over the next few years. Somewhere along the way the professional relationship softened into something warmer. I have since graduated from coaching, as these things go, but Sam has stayed. She is a friend whose perspective I still reach for on the days that need it.

Reading her answers for this interview, I kept coming back to her response about control. About realising she needed to heal herself in order to parent differently. About still undoing and doing. Most of us could recognise some version of that in ourselves if we sat with it long enough. What stayed with me was how patient she is with her own language. She doesn’t claim to be finished with any of it. She is in the middle of the work, and says so.

A Cup With is a series where I sit down (usually over text, sometimes over coffee, always between an errand or two) with mothers who are building lives and work that look nothing like what they left behind. Sam’s children are in their twenties, so her picture is further along than some of the women I am speaking to. Reading her responses from where I am, with a toddler and a seven-year-old, feels like encouragement.

I’ll let her tell you the rest.

Who she is

Tell us a little about yourself: your work, your family, and where you are right now in both.

I am an executive coach. I had 2 career transitions from pharmacist to a regional sales executive and then to becoming a professional coach. My kids are between 19-27 and they are all on their way into the world. I am enjoying this stage of life with more freedom and space for myself.

How old are your children, and who is the primary caregiver at home?

My kids are mostly grown and need little physical care. My role as a primary caregiver has shifted to more of a mentor and advisor.

How she thinks

Was there one thing that made you change after becoming a parent?

The great responsibility of looking after my babies made me think deeper and further about who I am. As they are now older, I am thinking about my new roles and adjusting to new boundaries with them.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Interestingly, I was a pioneer in working from home. 3 months after giving birth to my eldest, the Singapore branch office went fully virtual. That went on for a long time and I lived in a way that was a dream for many of my friends at that time. As the kids grew, I realised I needed to as well. So once my office moved back into being in person, I relished the personal contact with others. I grew a lot in that middle stage of my career.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

The moment I felt the tension was many years after. I was in a much more senior role. Large country size client accounts, long hours and the increased complexity of the workplace started to wear me down. I was completing a large tender response at 3am and that tension was clanging in my head and heart. I was not present for my family and everyday was just a big rush. I hear myself say I can’t do this for too long more. There must be something else.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

With age, with experience, and as my family has grown, our relationships and roles changed. It moved from being a caregiver to a coach to a mentor and now as a supporter.

What is the one generational pattern you are consciously trying to undo?

Control. I grew up in an extremely strict household with parents who had their own generational trauma. Luckily working in a more westernised environment helped me to see another way of parenting. I struggled with control as a child and as a parent. With experience I learn to parent differently. It was late in my life that I realised I do not need to live like this. As the kids grew, I also realised I needed to heal myself to have better relationships with them. So I sought therapy and made great strides in finding a better way to be a parent and a person. I am still undoing and doing.

What she built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

My top value has always been service to others. You can see it in the roles I excel in. It became clearer working with a coach and I was able to move towards a profession that is even more aligned with my values, my natural gift of intuition and a lifestyle that I desired. Thus, being an independent coach was the best way for me. For the last 10 years, I worked hard and now I have a thriving coaching practice and a life that is filled with meaning and freedom.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

Rather than build something, I wanted my children to see that there are many ways to live a life. I am the example of how they can design their lives if they are convinced in what they want and to be willing to do the hard work of building it. I want them to be free.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

I hope they never limit themselves and their imagination of what they can do for themselves and others. That they know they can choose how they are, their attitudes, their values even in the worst circumstances that are beyond their control. To learn to trust God and trust themselves.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

I wished I was less influenced by the environment and be more present with my children. I wished I had given myself the permission to have grace for myself, to enjoy the moment and to truly feel the joy of having kids.

What she has learned

What has your child or children taught you that no colleague, mentor, or book ever did?

That children are unique and they come knowing what they want. They possessed their own unique set of features. That I am privileged to be chosen to be their caretakers. That my role is to love, support and help them become who they really are. That I too, can be who I really am.

What is one thing you do to teach your child or children to be kind?

I demonstrate kindness to others. There is nothing more powerful as a lesson to see your own parents do it.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

In the end you only have your children for a season. Cherish the time you have, be present and let go of the rest.

And finally

What do you cook when you want to show your child or children you love them?

I love to cook so I cook based on their preferences. The challenge is that they all like different foods! So they push my creativity in cooking to my limits. I make them up based on what I have in the fridge and what they like to eat.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Money, tissue paper and a power bank 😅

If you had one hour to yourself this week, what would you do with it?

I will draw, paint, write, walk or read.

And finally, what is in your cup right now?

There is a lot of space in my cup right now. I am designing and working on the next stage of life. I have been thinking about what I would want to do given the space, time and resources I have now; things I can pursue now that I could not have when my kids were young. So I have applied to do the Executive Masters of Change with INSEAD, specially designed for coaches and leaders who want to develop themselves to the next level. Interestingly, this desire to go for further education is inspired by my kids going for theirs. Other than the program, in the next 5-6 years, I want to get my MCC credential, the highest level for ICF Certified coaches, explore being a coach supervisor to help other coaches, grow my practice and travel the world as far as my curiosity takes me. I am currently learning Korean and am eager to be able to speak like a native. Then, I will eagerly await my next role - becoming a grandmother!

One of Sam’s answers stuck with me. The one where she wrote that children come knowing what they want, and that a parent’s role is to love and support them into who they really are. And then, almost as an aside, she wrote that she too can be who she really is. It’s a good reminder that this runs in both directions.

I will always be grateful for the role Sam played in my life when I was at a loss. She was the person I sat with when I was new to being a mother and couldn’t quite find the shape of who I was turning into. On difficult days, her voice is still somewhere in the background of how I think. Reading her answers, I see more of the life that shaped that voice. The three-month-old at home while the office went virtual. The 3am tender response when something in her said enough. The therapy she sought later, first for herself and then for her children. The years of building quietly towards this. A cup, eventually, with space in it.

A mother whose children are nearly grown sees the season differently. She has the softness of hindsight, and a clearer sense of which of her own worries turned out to matter and which did not. When Sam writes that you only have your children for a season, she is writing from the other side of it. This line settles differently when someone has traveled the path.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

In our conversation, the lamp came across as a record. A way of saying: you arrived, and you changed how we see light. Their studio is a way to keep their hands moving, and to stay connected to the part of themselves that needs to bring concepts to life.

Xinnie calls herself a recovering workaholic. When the kids came, saying no to projects got easier. She still has the late-night calls sometimes, and she still feels guilty when her daughter walks up and asks if she can help so they can play. But the direction of travel is clear: she is showing up for family.

What follows is our conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Xinnie and I’m an illustrative designer. I come from a big family, have my own little family now and it’s been a journey of rediscovering myself as both a human and a parent.

How old are your child or children, and who is the primary caregiver at home?

They are 4 and 2, my husband and I both care for them while they aren’t in infant care. We’re also grateful for grandparents and our siblings who help us create a loving environment for them when we have our hands full.

How you think

Was there one thing that made you change after becoming a parent?

Learning to regulate my own emotional needs.

Alot of parenting now runs on what’s out there, the latest parenting hack, advice, pedagogy. These are great but when you’re parenting your kid, you’re actually re-connecting with your inner child and unresolved issues as well.

It’s not easy to face but being honest with myself on certain issues has helped me to confront them and show up as a more whole and authentic person to my kids.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Yes, I am a recovering workaholic! My brain is always thinking about something life or work-related and when my kids came along, suddenly it was easier to say no to things, turn down projects that I knew would be draining my time away from them. I am still learning how to prioritise things, but balancing career/work with kids means something’s gotta give, and I’d rather give up certain aspects of my career in order to show up for them more.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

I was having a late night call and my daughter came up to ask if she could help me at work so I can play with her.

Those meetings don’t happen very often but still I felt really bad.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

I don’t think it’s been that long enough to evolve but my husband and I often discuss how to better meet our kids’ needs and be present with them.

What is the one generational pattern you are consciously trying to undo?

Using shame or taking away of privileges as a form of getting them to comply.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

My husband and I run a design studio of sorts together, as a way to still carve out time for our passion projects and doing what we love which is to create and bring our concepts to life.

We both come from an Industrial Design background, so it’s a natural course to still want to build something and explore different mediums.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

We didn’t build anything specifically for them, but we did make a lamp inspired by my son when he was born.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

I hope they learn how to take chances, but also have wisdom to seek advice from those from different walks of life.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

That’s a tough one (only choosing one thing). I wish I had stood my ground in my wish to go abroad to live and study in my formative years. I’m too much of a scaredy-cat now!

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

To “just do it lah.” They’re just so unabashed and go with the flow. Mistake, what mistake?

What is one thing you do to teach your child or children to be kind?

To do unto others what you’d wish was done to you. Gentle hands and words reflect a gentle heart for others as well.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

That life is going to be hard but it’s going to be ok too.

And finally

What do you cook when you want to show your child or children you love them? Recipes welcome.

Cheese toast.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Myself! And of course my phone (to navigate, pay for meals, show them photos of past memories).

If you had one hour to yourself this week, what would you do with it?

Go to a very quiet cafe, drink good coffee and read/sketch.

And finally, what is in your cup right now?

Thinking how to fill their cup.

What I love about Xinnie's answers is how unvarnished they are.

“That life is going to be hard but it’s going to be ok too.”

“Just do it lah.”

“Gentle hands and words reflect a gentle heart for others as well.”

She made a lamp inspired by her son. Not for him, inspired by him. I wonder if more of parenting is like that than we admit. Not just building things for our kids, but letting their arrival rearrange the things we were already making.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

Entering Wei Ting’s home, you’d spot a coffee corner. For someone like me, whose utilitarian tastes meant that coffee was just at best a Nespresso machine (it still is!), her coffee corner was a revelation, a proper espresso machine with nice glasses and cups, all neatly arranged. Of course, we all wanted to have a nice cuppa.

Wei Ting was on my team at Entrepreneurs First, where we worked on scaling our growth during COVID. During the Covid period of 8-person meeting limits, our team would assemble at each other’s homes while dialing into Zoom. Wei Ting generously opened her doors a few times and I would recall how her eyes lit up as she walked us through her kitchen, pointing things out the way someone does when the space is genuinely theirs and they have thought about every part of it. The living room was spacious in a way that felt deliberate, a home designed to be lived in by every member of the family. I remember thinking that the care she put into that space said something about how she sees the world.

When Wei Ting later told me she was thinking of striking out on her own, building a business around children’s products, I felt excited for her. It felt like a courageous and natural next step, one that spoke directly to her strengths and also her stage in life. I’d like to believe that as a mother myself, I acutely felt her own tension of balancing career and motherhood.

Reading her responses to these questions, what stayed with me was her answer about the weight of words. She wrote about growing up with labels that stuck quietly and shaped how she saw herself. And when she describes the work she is doing now, with her own children, to focus on guiding behaviour rather than defining who they are, it is a slow, deliberate redirection, and I think that is harder than a clean rupture. You have to keep choosing it, day after day, in the small moments when the old words are right there.

This is the first conversation in a series called A Cup With, where I sit down (usually over text, sometimes over coffee, always between someone’s school run and someone else’s nap window) with mothers who are building lives and work that look nothing like what they left behind. Wei Ting is the right person to begin with. She builds from what is real and in front of her, from her children’s enthusiasms, from the materials of her actual life.

I will let her tell you the rest.

Who she is

Tell us a little about yourself: your work, your family, and where you are right now in both.

I run a small kids’ e-commerce store where I curate and design products for children and families. Alongside that, I’m also a content creator, sharing snippets of family life, kids’ meals, and little things that make everyday life easier.

I’m a mum of two young kids, 7 and 3. I’m the primary caregiver, but my husband is very involved too. Right now I’m focusing more on them, with one transitioning into primary school and the other still very little, while juggling work that I genuinely enjoy and that also brings in some side income.

How she thinks

Was there one thing that made you change after becoming a parent?

My priorities shifted. I no longer dwell on trivial things or unnecessary concerns. My kids’ wellbeing comes first.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

I realised I didn’t want a career that constantly pulled me away from my kids or made me feel like I had to choose between the two.

That was what pushed me to build something of my own. I wanted flexibility, and also something I enjoy and find meaningful.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

I remember during the COVID lockdown, I was working from home while my one-year-old was playing nearby. At one point, he pulled on the wooden playpen and it fell on him. He was okay, but I felt a deep sense of guilt.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

With my first child, I did a lot of research, reading books, joining parenting groups, and trying to follow what I thought was the “right” way, from sleep training to BLW.

With my second, I’m much more relaxed. I’ve learned there isn’t just one way to raise a child, and it’s more important to tune in and respond to their cues.

What is the one generational pattern you are consciously trying to undo?

The pattern I’m consciously trying to undo is the way words were used to define me. Comments about my body, my character, my worth, often without realising the weight they carried.

Children absorb everything. Those words became the voice in my own head, shaping how I saw myself for years.

So with my child, I want to be intentional. I want them to feel valued for who they are, not how they look or what they achieve. When a child knows their worth isn’t conditional, they carry that confidence for life.

What she built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

I built a kids’ retail brand that really came from my own life as a mum. I was already searching for more sustainable options for my kids, and realised there was space to curate products that are fun, thoughtfully designed, and eco-friendly.

Along the way, I also built an online community. It started from creating content for my brand, and I realised I genuinely enjoyed it. I began sharing things that work for me, as well as things I personally find comforting or inspiring. I didn’t expect it, but people started to resonate with it and follow along.

I didn’t set out choosing this over something else. It was more of it’s what I genuinely enjoyed and kept coming back to.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

My online store is actually named after my son, Big Head haha. So in a way, it already started with him.

A lot of what I bring into the store or create is influenced by my kids: what they enjoy, what keeps them engaged, and what makes play more meaningful. We even developed our own bubble toys because he loved them so much, and it eventually became something we sold in the store.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

That it’s okay to try different things and not be afraid of failing. I hope they see that you don’t always have to follow the usual path, it’s okay to do something different, and to figure things out along the way.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

To slow down and not feel like I have to optimise everything, enrichment, milestones, schedules. Kids don’t need a perfectly planned childhood.

What she has learned

What has your child or children taught you that no colleague, mentor, or book ever did?

Finding joy in small ordinary moments.

What is one thing you do to teach your child or children to be kind?

I try to model it, in how I speak to them, to others, and in small everyday situations.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

To prioritise my own wellbeing. You can only truly pour into others when your own cup is full.

And finally

What do you cook when you want to show your child or children you love them?

ABC soup. It’s something my mum always made for us when we were kids, and her soups are unforgettable. I hope my kids will remember my soups the same way. It’s easy to put together, colourful, comforting, and nourishing.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Snacks!

If you had one hour to yourself this week, what would you do with it?

I would go to a cafe to enjoy some pastries and a good cup of coffee.

And finally, what is in your cup right now?

Iced Matcha Latte.

I asked Wei Ting about generational patterns because I wanted to understand what she carries from her own childhood into the one she is building for her kids. Her answer is one I keep coming back to. The idea that words can stay with you and quietly shape how you see yourself is something most parents would recognise, if they sat with it long enough. What I find remarkable is the precision of her redirect. She is choosing, with her own kids, to guide behaviour rather than define who they are. That distinction sounds simple when you read it. Living it, in the tired hours when patience is thinnest, is another thing entirely.

The store, Big Head, is named after her son. The bubble toys that exist because he loved bubbles. Her home has a spacious living room. There is a consistency to how Wei Ting builds, and it starts with paying attention to what the people around her actually need.

I think that is what I keep finding in these conversations. Building and caring are not separate activities. They grow from the same place, and they look like each other if you know where to look.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you'd like to follow along, subscribe below.

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