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From AI to healthcare: what’s on at Singapore’s biggest skills and careers festival this year

Discover over 140 ways to shape what’s next for your career, from planning to upskilling, at SkillsFuture Festival 2026

Time Out Singapore in partnership with Skills and Workforce Development Agency
SkillsFuture Festival
Photograph: Skills and Workforce Development Agency | SkillsFuture Festival
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There’s always room to learn something new – whether picking up new skills for an AI-driven world, exploring a different industry or simply figuring out what’s next for your career. From September 16 to October 28, Singapore’s annual SkillsFuture Festival returns with more than 140 events and activities islandwide, giving you plenty of ways to upskill, connect and get inspired.

With roadshows, workshops, career fairs, expert talks, skills and career advisory sessions and even walk-in job interviews on the agenda, this year’s programme covers everything from new technology and AI to finance and healthcare, aviation and media. Here’s where to start, depending on where you want your career to go next.

SkillsFuture Festival
Photograph: Skills and Workforce Development Agency

Want to explore your options? Start at PLQ Plaza 

The SkillsFuture Roadshow at PLQ Plaza from September 16 to 19 is a good all-rounder. Browse jobs and training opportunities, speak to careers and skills advisers for free and explore courses with training partners. There are even walk-in job interviews if you’re ready to make a move.

SkillsFuture Festival
Photograph: Skills and Workforce Development Agency

Curious about AI? 

AI is changing the way we work, and you can get better acquainted with what that means for you at the Work Reimagined: AI and Digital Roadshow from October 8 to 11 at VivoCity Central Court. Expect insights into how AI and digital technologies are transforming work, alongside tech-sector career opportunities, free workshops and activities, and on-site career advice. Don't miss Microsoft’s AI on Autopilot: Meta-Prompting and Workflows session and learn how 10 Ways Copilot Chat Can Save Your Time Every Day on October 8.

And that’s not all – there’s more AI action at SkillsFuture Festival @ Central at HDB Hub from October 2 to 3, with learning sessions focused on using AI at work and in everyday life.

SkillsFuture Festival
Photograph: Skills and Workforce Development Agency

Looking to level up in media or finance? 

Working professionals can head to one-north from September 21 to 24 for a closer look at career and training opportunities in the media sector, with free workshops and career advice on offer. Explore how The Smart Local has built beloved brands over the past decade with TSL Media Group x GenAI in Content Creation on September 21, or learn how AI tools can help you take content from script to screen with The One-Person AI Production Team: Script, Present, Edit and Publish on September 23.

Meanwhile, the UOB Plaza roadshow from September 28 to October 1 puts the spotlight on finance, including how AI is reshaping roles across the industry. Take a closer look with AI-Ready Financial Services: Building Skills for the Future on September 29, or find out How AI Agents are Changing Finance Work on October 1. You can also learn about Building Your Professional Brand with AI and LinkedIn on the same day.

SkillsFuture Festival
Photograph: Skills and Workforce Development Agency

Considering a career in healthcare? 

The Healthcare Jobs and Skills Fair at Century Square Main Atrium from October 22 to 25 is worth adding to your calendar. Alongside healthcare jobs and training opportunities, you’ll find walk-in interviews, career advice and course sign-ups. 

And that’s not all. Regional events at SingPost Centre, Northpoint City and Our Tampines Hub will bring opportunities in areas including aviation, connectivity, digital and care closer to communities across Singapore. So whether you’re starting out, considering a career switch or simply keen to keep learning, there’s likely something at the festival to help you take that next step. Find out more here.

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