Lessons from an honest conversation with Anita Kapoor over thosai in Little India

By Khalil Adis

Anita Kapoor has interviewed international celebrities and some of Singapore's most powerful people.

A former journalist turned TV host, Anita radiates authenticity and that shines through every time she tells someone else's story in front of a camera.

But sitting across from me at Bangalore Cafe in Little India over thosai and masala tea, she had her own story to tell.

Twenty over years of friendship made it easy to skip the pleasantries and go straight to what really mattered - housing anxiety, especially as a freelancer in Singapore.

"Tara Barker gave me my very first opportunity to write for Women's Weekly. I was writing about interior decoration because I knew a little bit about it and I just kind of had a feel for it. And then one thing led to another and I started working in the industry," she said, on how she transitioned from print to on-camera work. (See the full interview in Part 1 here.)

From hosting acclaimed shows on Discovery, TLC and Channel NewsAsia, Anita became one of the region's most recognised faces.

For someone who knew her back in our writing days, attending the same press conferences together, she became, at least in my eyes, larger than life.

She built an incredible career as a freelancer, travelling the region and becoming one of Asia's most beloved TV hosts.

But despite that illustrious career, Anita was surprisingly candid about her struggles as a freelancer and her own home buying journey.

"In the good times, no," she said, when asked if she'd ever thought about getting a full-time job. "But when you're having bad times, or when you don't know where your next pay cheque is coming from — or, for example, when my mum got ill and I had to become a caregiver and think about somebody more than just myself, those are the times I thought, oh my god, I'm going to go get a regular job." 

Anita's story echoes what a significant number of Singaporean freelancers such as content creators, independent consultants and gig workers can identify with.

What followed over the next two hours was one of the most candid conversations we've had so far.

Here are ten things Anita wants every Singaporean freelancer to know.

1. Housing anxiety is real  but freelancers feel it differently (Part 2)

"My housing anxiety only started in the last five to six years. Prior to that I co-owned my mum's home. Before that, I'd been renting for the last 20 years," she said.

But unlike salaried employees, the anxiety hit Anita on three fronts at once - what she calls a "triple whammy": single, a freelancer and in her 50s.

"The anxiety was that I had sold my mum's flat. There's a certain amount of money that comes back, and I was thinking, should I buy a flat? Really only in my 50s, which is a very different situation. Single, 50 and wanting to buy a flat."

That anxiety only sharpens when it comes to applying for an HDB Flat Eligibility (HFE) letter, a system generally built around couples and families.

If you're single and freelance and reading this: the first thing Anita wants you to know is that you are not alone in feeling it.

See the full interview in Part 2 here.

2. Keep really good records of your invoices (Part 3)

If there's one piece of practical advice from this entire conversation that every Singaporean freelancer should act on today, it is this.

"Keep really good records of your invoices. It's really a good idea to get the client to sign the invoice, or have a 'paid' stamp on it," said Anita.

Why does this matter?

Because your invoice records are the closest thing a freelancer has to a payslip.

When a bank or HDB assesses your income, they need to see that money came in consistently over a sustained period.

For a salaried employee, that evidence exists automatically through CPF statements and employer records.

For a freelancer, it only exists if you've created and maintained it yourself.

That means issuing proper invoices for every piece of work.

Keeping copies of every payment received.

Building a paper trail that tells the story of your income in a language financial institutions can actually read.

Most freelancers only find out how important this is when they're already in the middle of a loan application, scrambling to reconstruct records they should have been keeping for years.

Build your own system.

Start now, not when you're ready to buy.

Now.

See the full interview in Part 3 here.

3. "The hardest part was discovering how resistant I was to owning something" (Part 4)

That's Anita's confession after renting for more than 20 years and the line that stopped our conversation completely.

Why would someone be resistant to home ownership, especially in Singapore, where tenants are largely at the mercy of their landlords?

"When you have conversations with people, they're like, huh, you're resistant to owning it? I'm like, yeah, because I've rented for 20 years, and the freedom to just pick up and go was always there," she said.

Freelancers are wired for mobility.

The ability to pivot, to take the next project, to move toward the next opportunity without institutional constraint is part of what makes independent work sustainable and meaningful in the first place.

Home ownership can feel like the opposite of that.

"Home ownership in Singapore is a very big deal, because there are a lot of ways to live here. You can either live in an HDB or in private property, and the difference is several hundred thousand dollars. It just became a very practical thing. Okay, I've rented for many, many years. Is it time?" she asked.

What she wasn't prepared for was the psychological resistance to commitment, especially in a life built around professional flexibility and personal freedom.

With some money already sitting in her CPF Ordinary Account (OA) from the sale of the flat she had co-owned with her late mother and with rental rates climbing, Anita felt the time had finally come.

See the full interview in Part 4 here.

4. Applying for the HFE as a freelancer? OMG (Part 5)

The frustration that Anita, and so many other freelancers, feel when applying for the HDB Flat Eligibility (HFE) letter is real.

"The terminology, figuring out that this site isn't really set up for my set of circumstances, and then trying to find out how to navigate it. What documents are needed. It's very different because you have to prove how your income came into being," said Anita.

For anyone thinking of buying an HDB flat, the HFE letter is the gateway document, whether you're going for a Built-To-Order (BTO) or resale flat.

For many, it's their very first rung on Singapore's property ladder.

For salaried employees, the application is relatively straightforward: payslips, automated CPF contributions pulled through Singpass and an employer letter.

The system is built around conventional employment.

Anita had to figure the whole process out on her own, which made it arduous.

She had to build a system from scratch, assemble documentation that doesn't exist automatically, and present her income in a format the system could actually assess.

Nobody had explained any of this to her beforehand.

She has since gotten her HFE approved.

But she still wishes someone had told her what to expect before she started.

See the full interview in Part 5 here.

5. Reserve your CPF before 55 (Part 6)

"The surprise was that I could actually reserve my CPF," said Anita.

Most Singaporeans know CPF can be used toward housing.

Fewer know you can proactively reserve your CPF OA savings before age 55, specifically for your housing payment.

This is a step that's rarely explained proactively. Many buyers only discover it too late - after their OA savings have already been transferred to their Retirement Account.

At that point, they're paying in cash.

If you're under 55, planning to buy a home and intending to use your CPF OA, do your CPF reservation [at least two weeks before your 55th birthday here] .

The CPF system has more flexibility than most people realise.

See the full interview in Part 6 here.

6. Clean up your credit history at least three months before applying (Part 7)

"You need to clean up your credit if it's not doing well. The most important document is the Credit Bureau Report, which, by the way, you can apply for online and get within five minutes. It's all automatic," she said.

Your credit rating determines whether HDB or the banks will lend you money for your home.

If you've got outstanding credit card bills or other instalments, it's worth cleaning up your credit history at least three months before applying for your HFE.

"If you've taken up a lot of loans before, if your credit card has a balance, you're going to see all of that, and it does affect your credibility," said Anita.

See the full interview in Part 7 here.

7. Show proof that you got paid (Part 8)

"I got paid."

Three words that summarise the entire freelancer home loan application.

Not a payslip. Not an employer letter. Not a neat monthly CPF contribution.

Just proof that is self-assembled, self-organised, clearly presented.

One that showed that money came in and came in consistently enough to service a mortgage.

Anita's approach was to build her own financial system.

"If you issue invoices, and I know not everybody does, some people just get receipts depending on the type of freelance work, you need something that says, 'I got paid,'" said Anita.

It is a way of organising and presenting your income that tells its own story, in a format HDB and the banks can follow.

None of this is complicated.

But it requires an intentionality and discipline that most freelancers do not apply to their finances until they actually need to.

See the full interview in Part 8 here.

8. The HDB system is in desperate need of a redesign (Part 9)

"The HDB system is also in desperate need of a redesign."

This is Anita's most significant observation and the one that goes beyond personal experience into something bigger.

Singapore's public housing system is one of the most celebrated in the world.

But let's face it, Singapore's workforce is changing.

The gig economy isn't a fringe phenomenon.

According to government data, more than one million Singaporeans are engaged in some form of freelance, self-employed or gig work.

The one-size-fits-all approach needs refining.

"We could increase the cap. The $7,000 could go up for basic BTOs, because there are many people who are self-employed or freelance and there are also many employed people whose first jobs pay them very, very well, but they're still living at home with their parents. So they can't get a basic HDB. They have to go straight to Prime or Plus, which is a lot to start with in your 20s or 30s," said Anita.

A system designed for the Singapore of 1980 is being navigated by the Singapore of 2026.

That gap is where housing anxiety lives for an entire generation of Singaporean freelancers.

See the full interview in Part 9 here.

9. Stop low-balling us (Part 10)

"Stop low-balling us."

That was Anita's answer to a question about whether covering other people's stories of struggle and resilience had shaped how she approaches her own financial and life decisions.

It wasn't the answer I expected.

But it was exactly right.

Two decades of interviewing people across the full spectrum of Singapore society, from the powerful and the vulnerable alike, had taught Anita something specific about her own worth: the market will pay you what you accept.

Your negotiation starts from wherever you position yourself.

Freelancers who undercharge aren't being humble.

They are being complicit in a systemic undervaluation of independent creative and professional work that compounds across an entire career.

Know what you're worth and charge accordingly.

Stop accepting less because the system makes you feel like you should be grateful for whatever you get.

"We've got the goods. We know what we're doing. Pay us better, so we don't have to struggle through life," she said.

See the full interview in Part 10 here.

10. Don't rely on your credit card (Part 11)

"Not rely on my credit card."

That was Anita's answer to the final question of our conversation - what would she tell her younger self, just starting out as a freelancer with no guaranteed income, about buying a home in Singapore?

"The things I would have done better? Keep way better records. Not rely on my credit card, because that was so destroying. And think about what I actually really want for my life. Do I want to own a home? If you don't want to own a home, then you've got to make sure you have the savings to cover your rental. If I want to own a home, then these are the steps I need to take as a freelancer," she said.

Anita's answer echoes what many of us navigated during our own financial uncertainties in our twenties and thirties.

Build your savings instead.

See the full interview in Part 11 here.