Op-ed: A Journey of Family, Work, and Starting Over

Entrepreneurship, for me, has never meant just building a business. It has meant building a life – one that keeps changing with every stage.

I write this piece as I spend two weeks at my parents’ home in Bengaluru, a trip I had to make overnight for a family emergency.

From being newly married, to becoming a mother 19 years ago in Dubai, to now managing a home with growing children in Singapore and ageing parents in India – every year has been different. And that’s what entrepreneurship gave me: the freedom and flexibility to adapt, to rise again, and most importantly, to not be afraid of failure- something I’ve always hoped my children would learn from watching me.

In Dubai, building my firm with a dear friend was an intensely personal journey. We were younger and definitely more foolish – saying yes to almost everything and figuring it out later.

Every decision, every win, every setback – it was all shared between the two of us. Even today, decades later, he’s still the person I call when I’m stuck – and somehow, we end up laughing more than solving the problem.

In my second phase, and now wiser being the mother of two girls, when I first walked into APRW, what stayed with me was something very simple.

There were many women around me – leaders who are entrepreneurs, each on her own journey. No one was making a big deal about it. It wasn’t a “diversity effort” or a headline. It was just normal.

It also marked a new phase in my journey, where I found a different kind of strength. Being part of a larger group of partners brought new energy, new perspectives, and a sense of collective support.

It also meant learning that your idea may not always be the best one in the room – and that’s a good thing. My husband would certainly agree.

In an industry where we often talk about women in leadership as something we are still working towards, here was a place that had quietly been doing it for years. No noise, no spotlight – just good work, mutual support, and a lot of empathy.

And I truly believe empathy is something we need much more of in today’s workplace.

As an Indian who has spent more than half her working life in Singapore, I’ve also come to realise that home doesn’t have to be just one place. It can be two countries, two cultures, both equally yours.

Singapore made this possible for me and the family. Though it took a while, it’s a place that truly accepts people from different backgrounds – not just in words, but in the opportunities it gives.

It allowed me to grow, start again, and take on new challenges.

I still remember being 40 and wondering if I was starting too late. But instead of holding back, I chose to take that step forward – trusting my instinct rather than overthinking it.

Looking back now, that decision changed everything. It wasn’t too late – it was exactly the right time.

This experience gave me the confidence to step into new markets like Indonesia. It wasn’t easy – I failed many times – but each time, I got back up and kept going. That’s been a big part of my journey.

As the firm where I am completes 30 years – no small milestone in Singapore – my own decade long journey here feels special not just because of work achievements, but because of everything around it.

For me, the biggest successes are personal – a happy home, children who are now on their own journeys, being there for my parents, and the friendships I’ve built along the way.

It gave me the freedom and flexibility to work when I need to, and from where I can. But you also carry the worries over weekends, some sleepless nights, but you let the highs rule over the lows.

Work took me to many places, and through that, I found not just colleagues, but lifelong connections around the world.

And in the end, that’s what entrepreneurship has really given me – a full, meaningful life, both at work and beyond… and plenty of stories along the way.

Anu Gupta, is owner-director of Singapore-based communications firm APRW.