How to Connect with Millennials Without Sounding Outdated

[This article was generated by ChatGPT and has been edited by the Surer team for clarity, readability and context.]

Newsflash: Millennials aren’t the fresh-faced graduates they used to be.
In 2025, the youngest Millennial in Singapore is pushing 30. The oldest? Closer to 44, likely juggling a career, a mortgage, a toddler, and the aching realisation that bubble tea now causes heartburn.

If you want to connect with Millennials as a general insurance intermediary, it’s time to update your playbook.

Here’s what works — and what absolutely doesn’t.

👩‍💼 1. Respect Their Hustle

Millennials are the side-hustle generation.
According to LinkedIn (2024), 81% of Millennials in Singapore have some form of secondary income — from freelance design work to selling home-baked goods on Carousell.

💬 When selling insurance:
Acknowledge their multiple income streams. Offer solutions like personal accident insurance for gig workers, equipment insurance, or professional indemnity cover for freelancers.

🔑 Key phrase:
“Protect your passion project and your day job.”

🏠 2. Talk About Real Adult Stuff

Forget the avocado toast memes. Millennials in Singapore are focused on building real financial security.
Over 65% own property, and a growing number are caring for ageing parents while raising young children — the classic “sandwich generation.”

💬 When pitching:
Talk about family protection, property coverage, critical illness riders — topics that feel relevant to their current stage in life.

🔑 Key phrase:
“Let’s safeguard everything you’ve worked so hard for.”

📲 3. Blend Digital Ease With Human Expertise

Millennials were raised with ICQ, MSN Messenger, and now live on WhatsApp and Slack. They expect fast digital service — but also value authentic human advice when making big decisions.

💬 When engaging:

• Offer digital-first interactions (like e-policies, WhatsApp consults)

• But don’t shy away from setting up a call or coffee chat for serious conversations.

🔑 Key phrase:
“Get expert advice with just a few taps — and a friendly voice when you need it.”

❌ What NOT to Do

🚫 Overuse slang like “YOLO” or “lit” — it’s cringey.
🚫 Assume they’re reckless spenders — they’re actually cautious value seekers.
🚫 Talk down to them — treat them like capable adults making smart decisions.

Bottom Line:
If you approach Millennials with respect, relevance, and convenience, they’ll become some of your most loyal, long-term clients.
Plus, they’ll probably recommend you to their entire condo group chat.