A Cup With Elaine

Of choosing flexibility across three cities, parenting a 21-year-old, and what the other side of the school gate years looks like.

Elaine is my cousin, and also the person who gave me my first internship and my first taste of marcomms when I was 19. I had some free time, wanted to feel helpful, so I thought why not? I learnt very quickly that behind glamorous events and press launches was a dedicated and hardworking team making it happen. I learnt how to pick up the phone to speak to strangers, arranged for press kits to be sent to the media, practiced my pitch, and learnt that disappointment was part and parcel. But that internship taught me something I’ve carried into every job since: there is no ceiling when it comes to hard work. If you’re willing to do it, there are always opportunities.

In the years after, Elaine became something of a compass for me. Her career has crossed Singapore, Hong Kong, and now Auckland, from hotel PR to founding her own agency to building a personal branding consultancy. Through all of it, she has been a testament that a good voice of reason paired with common sense always wins. And as a mum to her daughter Alexis, now 21, she has been a role model for what balancing a career and a daughter can actually look like, not in theory but across two decades of real choices.

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

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Who you are

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

I’m Singaporean at heart, but Auckland has been home for the past nine years. Before that, I spent a wonderful decade living in Hong Kong.

I’m the mum of a newly minted 21-year-old university student who now has a wonderfully full life of study, work and friends. Watching her step confidently into adulthood has been one of the greatest privileges of my life.

Professionally, I’m a personal brand strategist specialising in LinkedIn content strategy, ghostwriting and community outreach. I help founders, consultants and business owners turn their expertise into stories that build credibility, trust and authority.

What sets me apart is my background in PR and FMCG marketing. I don’t just write posts - I develop a strategic content narrative that positions each client in a way that feels authentic to them. Beyond the writing, I help grow an engaged LinkedIn community that becomes a supportive audience and, ultimately, a source of meaningful business opportunities.

My career has taken a few interesting turns. I started in hotel PR at Mandarin Oriental Singapore before moving into agency life, managing lifestyle campaigns at Directions Marketing & Communications and later founding my own agency, Firefly Marketing & Communications.

A move to Hong Kong opened another unexpected chapter. I started a lifestyle blog called Simply Fabulicious, back when blogging was the social platform of the day and long before newsletters and Substack existed. That little blog introduced me to incredible brands and opportunities, including the Langham Hospitality Group. When I later moved to New Zealand, they invited me to help lead the rebranding of Auckland’s Langham Hotel into the Cordis - a project I’ll always remember fondly and proudly.

After Covid, I worked across several Auckland PR agencies before joining The Attention Seeker, where I led the personal branding team. Eventually, I left to build my own consultancy, bringing together everything I’d learnt over two decades in communications. Looking back, my career has evolved from telling company stories through the media to helping leaders build platforms and voices of their own.

These days I love the flexibility that running my own business brings. It allows me to do meaningful work while designing a life that gives me freedom and space.

Where am I right now? In many ways, I’m in the season they call the “sandwich generation”, caring for ageing parents in Singapore while cheering on a daughter who is now on her way to graduating and building her own independent life in Auckland. It can be emotionally stretching, but I don’t take for granted that I still get to do life with both my mum and my daughter. That feels like a real gift.

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

Alexis has just turned 21.

These days, we joke that we look after each other. She’s “Boo” to me, I’m “Moo” to her, although I’ve recently been promoted to “Momster” which, apparently, comes with the territory. I do miss the days of being called “Mummy.”

Our relationship has changed completely. I’ve gone from telling her what I think and will do to genuinely asking for her opinion. For many years I was her primary companion, but now I happily compete with university, her internship work, a wonderful boyfriend and a very busy social life. That’s exactly how it should be.

How you think

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

Motherhood shifted my perspective from making decisions that were best for me to making decisions that were best for someone else.

Every choice - where to live, what jobs to take, how much to work, even how I spent my weekends - was no longer just about my own ambitions or enjoyment. It became about creating emotional security, financial stability and opportunities for my daughter. You begin to think much further ahead because your decisions ripple into someone else’s future.

Elaine with Alexis, aged 4

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

Working full-time no longer felt like the right fit for me.

For many years I’d built my career around flexible, work-from-home roles - running my own agency in Singapore and later blogging and freelancing in Hong Kong which meant I was present throughout my daughter’s early years.

That changed after we moved to New Zealand. Although my role was officially part-time, it regularly stretched into full-time hours. As my daughter navigated the challenges of settling into a new country at age 11, I realised she needed more than an empty house after school.

I chose to leave that role rather than move into full-time work. It meant I could be there when she came home, welcome her friends into our house, quietly observe the friendships she was forming and create space for those everyday conversations that often reveal far more than direct questions ever do.

Looking back, I believe the pre-teen years are some of the most important. Children may look grown up on the outside, but inside they’re still figuring out who they are.

Tell me about a moment when you felt the tension between work and being present most acutely.

There wasn’t one defining moment - instead it was a series of ordinary moments that slowly became impossible to ignore.

I remember being in the office, desperately looking through school holiday programmes that ran from 9am to 5pm, simply so that I could get through another working day. And I remember asking myself a much bigger question: Why did we move here in the first place?

The answer was obvious.

We hadn’t left Hong Kong simply for another job. We moved because I wanted my daughter to experience a different kind of childhood - one with less pressure, less tuition, less chasing the next exam and more room to discover who she was. I wanted her to grow up with an Asian foundation but within the openness of a Western education.

If I wasn’t actually present for that journey, then I realised I was asking her to navigate it largely on her own.

That was the turning point. I left the role and returned to remote, flexible work. Financially it wasn’t always the easier choice, but it was the right one. Looking back now, I wouldn’t change it.

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

With a 21-year-old young adult, it’s a completely different season of parenting.

I try to tell less and listen more because I’ve learnt that adulting advice isn’t always welcome. Sometimes the greatest act of love is allowing your child to make mistakes instead of trying to prevent every disappointment.

I no longer live with a child who depends on me for everything. I live with a young adult. It’s less like parenting a child and more like sharing a home with a roommate who is finding her own way in the world and in many moments, I am grateful that I still get to be there to see things unfold.

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

The idea that love is measured by achievement.

Growing up in Singapore, many of us were taught to work hard, perform well and keep striving for the next milestone. Those values have served me well, but they can also quietly become the measure of our worth.

I’ve tried to raise my daughter knowing that who she is matters more than what she achieves. All I want is that she truly knows that with everything she attempts - she has genuinely put in her best effort. Things will not always go her way, but once she knows what her best looks like, I hope she will know that she has been true to herself, and that already is a success metric.

What you built

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

If I could have chosen any career, I think I would have been a bartender because I genuinely love listening to people’s stories - especially over a good drink. Or a DJ, because music is about an era of collective memories, and I used to spin a set or two growing up so I like the idea of bringing people together to celebrate a moment. Or perhaps I would have been an interior designer, because beautiful spaces and the aesthetic are important to me and have a remarkable way of shaping how I feel.

But life doesn’t always unfold according to the plans we make.

What I realised early on was that I could write. So I combined my curiosity about people, my love of storytelling and my interest in strategy, and found my way into PR.

Today I help founders and business owners tell stories that build trust and open doors. Looking back, I think every version of my dream career had one thing in common: helping people feel seen.

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

I built a career around flexibility.

It may not always have been the fastest-growing or highest-paying path, but it allowed me to be there for school pickups, sports days, after-school conversations and the ordinary moments that often become the important ones.

One day I hope she’ll realise that many of my career decisions weren’t simply about work - and that they were about being present for her.

When your child is old enough to look back at the choices you made, what do you hope she takes from it?

I hope she sees that careers evolve. Titles change. But the people who matter most will always remember whether you were there.

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 actually raised my daughter in both Hong Kong and New Zealand and looking back, one of the greatest gifts was stepping outside the Singapore system.

Having more time and less academic pressure gave her space to discover who she was, pursue her own interests and make thoughtful decisions about her future.

Singapore offers incredible opportunities, but I’m grateful she also experienced a childhood where life wasn’t always about keeping up with everyone else.

What you have learned

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

That people need to be loved differently at different stages of life.

The way a five-year-old needs you isn’t the way an eleven-year-old does, and it’s certainly not the way a twenty-one-year-old does. Parenting has taught me that relationships only thrive when we’re willing to keep adapting.

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

I try to model kindness rather than lecture about it.

Whether it’s remembering someone’s birthday, helping a neighbour, going out of my way for a friend or simply listening well, I hope she’s seen that kindness is found in ordinary moments, not grand gestures.

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

You don’t have to solve every problem.

Sometimes your child isn’t looking for advice - they’re simply looking for someone safe enough to tell the story to (minus the judgement).

And finally

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

Babi Tau Yew, without question.

It somehow is comfort food for her and a reminder of home and her childhood all on one plate.

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

These days it’s the house keys. We live in an apartment with two security keys that can’t be easily replicated and there have been occasions when either of us has thought that the other person had the keys on them and closed the door behind us.

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

I have lots of hours to myself these days.

And finally, what is in your cup right now?

Coffee. Always coffee, and NZ coffee is really the best in terms of a lovely aroma and a full bodied rich flavour.

Preferably a really good Americano, enjoyed while it’s still hot if it’s in winter or on ice when it’s in summer - which, as any parent knows, is always something of a stolen luxury.

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I’ve balanced this series with mothers wrangling toddlers and school runs, and those on the other side with articulate, self-aware and loving adult children, such as Elaine. When I asked what she’d do with one hour to herself this week, she said she has lots of hours to herself these days. To me, knees deep in the trenches of parenting, it’s what the school gate years eventually turn into, and it arrives sooner than any of us in the thick of it can imagine.

What she did with the years before those hours is the part I keep returning to. She built a career around flexibility, not as a compromise but as a design choice, and she made that choice again and again across three cities. Leaving a role in Auckland when Alexis was eleven so there wouldn’t be an empty house after school. Choosing to be around for the everyday conversations that reveal more than direct questions ever do. Careers evolve, titles change, but the people who matter most will always remember whether you were there.

I saw the early chapters of this up close. The cousin who put a phone in my hand and had me cold calling for press kits is the same person who spent two decades proving that hard work has no ceiling, and that common sense, applied consistently, outlasts every clever strategy. Now she’s in the sandwich years, caring for her mum in Singapore while sharing a home in Auckland with a young adult who calls her Momster.

Somewhere in between, there’s a really good Americano, still hot, finally drunk in peace.

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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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