We've been noticing a trend 📈

Some of our members have been sharing their interest in starting a business - be it a consultancy, coaching, products, social biz, or other forms of services. But before they get started, many of them want first to validate their business idea 💡

Common questions to be answered: "What is my USP (unique selling point), who is my specific target audience, is there real paid demand for what I am offering?"

The Courage Chapter team is running a business validation clinic (online) session this Saturday 15 August, from 8:30am - 10:30am to help aspiring business owners work on their business ideas. We will use Claude as the predominant AI tool to run the "market validation skill" in our clinic, but you can feel free to use another AI tool that you’re comfortable with. No prior AI knowledge required; we can all learn together🪴

Sign up here: https://luma.com/rju0lcar

Why this, why now? We believe that the future is filled with multiple pathways. No longer are people looking at "full-time employment" as the only viable option for a meaningful career. Some others are also looking to supplement their income, and build a portfolio career.

Many people are exploring being a fractional solopreneur, starting side hustles, running "One-Person-Companies" (OPC). However, it’s tough and lonely being a solo founder. We want to grow a community where people can build their future together and help each other to thrive.

Join us 😊 This is our first time doing this format - let's learn and grow together.

Register for Free

We hope July has been going well for you ^-^ In recent days, we’ve seen more bustling activity on our Courage Community WhatsApp group - where members have been sharing about their new business ventures, role opportunities, general resources/news, and just simple words of encouragement. It’s heartening to watch the community grow closer together!

🚀 AI Native Circle - The Courage Entrepreneurs Edition

We are back with our 4th season! This time round, we are working with community members with 15+ years of deep expertise who are ready to turn their experience (or a validated new idea) into a new stream of income that creates impact.

In one focused day, you’ll use Claude to build four working AI agents — not four ideas, BUT four tools you keep using after the programme:

• A website builder agent that turns your expertise into a clear, credible offer

• An AI council and advisory board that pressure-tests your thinking

• A content marketing agent that writes in your voice, consistently

• A lead generation agent that finds prospects and personalises your outreach

Info session: 3 August (Mon), 7:30pm (online) — come sharpen your idea before you apply. We will run through a Market Validation exercise together.
The Actual Bootcamp Day: 22 August (Sat), 10am–5pm.

This one’s application-only, and kept deliberately small — maximum 8 participants per class — so everyone gets real, hands-on support.

Your expertise took 15 years to build. It’s time it started generating an additional stream of income.

Apply for the AI Native Circle Info Session here → https://luma.com/8ycp5nor
Sign up for the Bootcamp here → https://courageboss.netlify.app/

Check out what our past graduates built: https://ainativebootcamp.netlify.app/builds

P.S. Pic from prev cohort :)

💖 In other news, Social Service Reternship: Cohort 3 Wrapped!

Our Cohort 3 corporate professionals just wrapped up their Social Sector Appreciation & Immersion Day — and wow, what a journey!

Over the past week, we had the privilege of journeying with our Reternship Participants - sitting down with practitioners who’ve actually made the leap (shoutout to our panelists from NCSS, Lions Befrienders, Care Catalyst Collective, World Vision and Yong-en Care Centre!), reflecting deeply about what a transition really costs, what fulfillment means, and walking away with a personal “Northstar Statement” + tangible next steps. We also visited 2 SSAs - New Hope (tackling homelessness) & St. Andrew’s Autism Centre (for persons with autism).

We are happy to have received a satisfaction rate of 4.7/5 ⭐ Likelihood to recommend: 9/10 ⭐ But honestly, what was more amazing is that unprompted, almost everyone told us what they’re doing next. Signing up to volunteer. Networking with SSA leaders, or taking the bold step to just try a project.

Is passion enough to make the leap? What does culture shock actually feel like once you’re in? Turns out these are exactly the right questions to be asking before you jump. That’s the whole point of this programme — not to sell anyone on the social sector, but to help them (and the agencies!) date before they marry 😄

A career spent solving problems and leading teams has so much transferability in ones’ 50s or 60s! We just need to find possibilities to activate these latent skills. Cohort 4 details coming soon — stay tuned!

☕August Courage Kopi Meet

Warmly organised by the Courage Community Engagement team - with Siew Yean leading the efforts!

As you look ahead to your next chapter, the traditional standard re-employment options might feel a bit too restrictive or challenging due to factors beyond your control. What if, instead of looking for your next role, you created it?

The best way to predict your future is to create it. Let’s hear real stories from fellow senior professionals who successfully transitioned from the corporate ladder to absolute autonomy in our coming Courage Kopi Meet Session:

Date & Time: 6 Aug 2026, 2:30pm - 4:30pm
Venue: Staytion Lifestyle Centre@ Dhoby Ghaut MRT (NSL) 11, Orchard Rd, B1-13 Dhoby Ghaut, Singapore 238826

Register to meet like-minded folks & gain inspiration from our fellow community members: https://forms.gle/1wsFMPHmj4aXLYLh7

Best regards,
The Courage Chapter Team

Happy July 🥳

We’d like to welcome new members, and also refresh our familiarity with old members 👋

Who is The Courage Chapter?

The Courage Chapter is a community for senior professionals navigating their next chapter of work and contribution. We journey with them through reternships, fractional roles, mentoring, and community programmes, helping them turn experience into meaningful, flexible ways to keep contributing.

What We Stand For

We want to expand the ways people can contribute throughout life, no matter their age. Traditional thinking assumes that contribution declines once a role or title ends. We believe the opposite. People don’t lose their value as they grow older, however what often disappears are the pathways to keep contributing value, and the autonomy to choose various types of work.

Our belief shapes how we work. We believe that upskilling and certificates alone don’t open doors. A referral beats a cold application every time, and the way to earn one is to be visible and credible: build something, share the journey, help someone else first. Get through the door and prove your value :) Everything stacks. That’s the philosophy behind the programmes we run.

The 4C Reinvention Model

Our framework for reinvention in transitions is the 4Cs: Clarity, Capacity, Creation, and Care. Clarity is knowing who you are now and what you want to contribute. Capacity is building the skills, confidence, and networks to act on it. Creation is where it gets real, short-term projects, volunteering, building in public, proving your value instead of just listing it, like our Social Service Reternship or AI Native Circle. Care is the community that supports you through your journey, and where you support someone else, too.

Join our Recent Partnerships!

🚀 Inter Poly Forum (by Ngee Ann Poly)

We are pleased to be partnering with Ngee Ann Poly on their Interpoly Forum 2026, inviting our community to share their life stories with 500 high-potential poly students across Singapore.

Sign up if you’re keen to speak about any of these themes:

1. Who am I Beyond My Job?

2. What Really Matters in Life?

3. When the World Changes, Who Do We Become?

4. How much is enough?

More details about themes here.

Date of event: 16 Sept 2026, 1pm - 4pm
Format: Human Library - you will speak in a roundtable format, where students rotate to your theme in groups of 8-10. You will share your story, and they will ask you their curious questions!
A token Honorarium will be given for your time & energy!

Register your interest and share your story here: https://forms.gle/aqCXV33YqqfvXnXbA

Email reternship@thecouragechapter.com if you have enquiries.

💖 Social Service Reternship Programme

We are running a final Q&A for the Social Service Reternship Programme this Thursday 2 July, 11am! (for those who missed our info session panels)

The Social Service Reternship is a structured pathway helping experienced professionals transition into meaningful work in the social service sector. It's part of Courage's “Clarity & Creation” pillars in the 4Cs, contextualising corporate skills and turning learning into real, hands-on contribution.

Cohort 3 dates: 11, 12, 18 July (appreciation course), 24 July (charity immersion day)

Please save the invite for the Q&A call here: https://calendar.app.google/jrdMgvAiiUiodKxt6 (if you’re unable to join us but still keen to have a chat, please PM The Courage Chapter team at +65 8176 8278)

🤩 Available Roles

• Fractional HR (3-4 days) - leadership coaching skills & operational rigour preferred : Apply here

• Compliance Manager & Board Secretary - ideally with Finance background: Apply here

• Special Projects Manager - ideally with consulting background (similar to Chief of Staff role): Apply here

• People & Operations Manager (full-time or fractional possible, shld be strong in people ops): Apply here

• Finance Manager - should have CA and Charity Finance exp incl. restricted & unrestricted funding: Apply here

🌱Pilot: Courageous Conversations

Finding Clarity, One Walk at a Time.

Our amazing community member and HR leader, Alan Lee, has offered to run “Courageous Conversations” for our Courage members. During our other events, some members had asked whether he would be willing to journey alongside those navigating career or life transitions. After discussing with Alan, we are happy to introduce Courageous Conversations - Finding Clarity, One Walk at a Time.

Why: Career and life transitions can be exciting, but they can also feel uncertain and challenging. Having a fellow traveller who listens without judgment—someone who has experienced similar transitions and accompanied others on theirs—can sometimes make the journey a little less lonely and a little clearer.

What: You will take a leisurely 90-minute walk along quiet paths, enjoying nature while having a one-to-one conversation. Alan’s aim would be first to understand where you are on your journey, and second, to explore how you feel about the progress you’ve made so far. His role is not to provide answers or tell you what to do, but to listen deeply, ask thoughtful questions, and create a safe space for you to discover your own next steps. You’ll end the walk over a good cup of coffee or tea. No fee or payment is expected.

When: Walks will be arranged at mutually convenient times, with the frequency determined by each person’s needs and availability.

Feel free to PM Alan at +65 9635 0101 to arrange a meet up! Let us know how things go as well, would love your feedback along the way :)

👥Event Updates

AI Native Circle Cohort 3

Best vibes ever! We expected stress, frustration, and binge snacking. Instead, AI Native Circle Cohort 3 finished early. Every participant left with a working AI agent, and the energy to keep going!

1 working AI agent, 1 published website (using Anthropic's Claude Design, no less), discussion about SEO optimization... And we closed the day by building an AI advisory council together.

Cohort after cohort. Participants assume the AI will be the hard part. It never is (except for maxing out tokens). Technical feasibility is almost a given now. The constraint isn't the technology. It's the imagination. What would you build next?

CourageActive Monthly Walk

We had a lovely community walk starting from Stadium > Marina Bay Sands, followed by a good breakfast catch up last Saturday! As usual, sun was blazing, folks were chatty, hearts were full! Come join our WhatsApp group chat if you want to participate in our next walk: https://chat.whatsapp.com/HY6qTiZPq9p7EpmhD88iwD

Many thanks to Jen for organising this wonderful route and leading us through this walk!

Courage Kopi Meet: Movie & Reflection

We had a great time watching snippets of the movie “The Intern” followed by some heartfelt reflections on transitions, relearning & growing at every stage of life. Our heartfelt thanks to Siew Siew for facilitating this session!

Sharing Your Story

We were also delighted to have Ngee Ann Poly invite our community members George & Sally to share about their transition to their second wind with their internal staff 🥰 Thanks both for sharing your stories and inspiring others, one step at a time :)

Final Request (for Semi-con industry folks)

If you or your friends are from the Semiconductor industry, this one is for you! The AMTA (Advanced Manufacturing Training Academy) would like to engage some of our community members experienced in semiconductor industry to identify AI training & adoption needs for the industry.

For starters, a first meeting will be scheduled to identify some folks as industry partners, to help AMTA with industry outreach 😊 if you’re selected, you have the opportunity to be engaged on a paid project basis.

Please PM Ser Yong +65 9845 0099 if you’re keen 🌟

Cheers and here’s to a fruitful July ahead for everyone!

Best,
The Courage Chapter Team

We’re happy to share a couple of good roles/projects!

• Finance Manager (6 months, full-time) - JD here

  • Criteria: To be a chartered accountant, and have experience with restricted & non-restricted funding

• Partnerships & Fundraising Manager (4 months, full-time/4 days per wk) - JD here

  • Criteria: to be attuned to the women-empowerment cause, and have experience with fundraising, independent

• People & Operations Manager (Permanent, full-time/fractional) - JD here

  • Criteria: To have good understanding of HR ops, and preferably some experience in non-profit space (compliance, grants), and comfortable with systems, balancing figure in the team (warm, grounded)

• Special Projects/Chief of Staff (Permanent, full-time) - JD here

  • Criteria: To ideally be an ex-Project Leader level in consulting firms, preferably with experience in impact funding space

• Compliance Manager & Board Secretary (Permanent, fractional/full-time) - JD here

  • Criteria: Preferable to have some finance background

• Fractional HR lead (Permanent, fractional 3-4 days/wk) - JD here

  • Criteria: Strategic, able to coach senior leaders, and operationally strong (this is a small charity and the HR lead does end-to-end HR)

Some of our folks got featured in media & panels! 👏

Poh Wah & rYo were interviewed by MoneyFM 89.3 on their take about Meaningful Work in their 50s. So cool!

Listen here: https://audio.sph.com.sg/podcast-ep/01ktp0cd3g3rfyne77qsza0fdt/

Our members Sangeeta and Sharon spoke on a career panel with University of the Arts students on how fresh grads can thrive in the Arts/Media industries.

We really see the value of meaningful engagements like these, with media, schools, corporates - as they help with portfolio building, new experiences, and act as visibility/credibility markers as you pave your next chapter! Hope to bring more of such opportunities to our community members.

Courage AI Native Showcase & Cohort 3 Launch

It has been a blast running the AI Native Circle over the past few months, where we’ve run 2 classes for 25 professionals thus far. Our participants built their own AI Agents for their consultancies/businesses, job search, grant applications for non-profits, or personal finance 🧡 They showcased their AI Agents + learnings during our demo day, where members of the public could learn from them.

We believe that this is the future economy - our professionals have to not only learn new skills, but build products (move from theory to practical), and then showcase them online and offline. This helps them stand out from the crowd - this not only helps with repositioning, but is also a fundamental mindset shift of being an #AINative and the ability to learn anything! Check out our participants’ cool videos here: AI Native Playlist

Our goal is to empower >100 Courage Chapter members in 2026 in becoming AI Natives.

Sign Up for the AI Native Circle Cohort 3 here: https://ainativebootcamp.netlify.app/

Watch the info session here:

Social Service Reternship Programme - Cohort 3 Launch

We are also happy to launch our 3rd cohort of Social Service Reternship, supported by Institute for Employment and Employability (e2i)! 🎉 If you’re considering the social services as a next career option, join our info session!

💭 Is passion enough — or is that what trips people up? What does culture shock actually feel like? Who thrives, and who struggles? What does success even mean beyond career progression?

On 15 June 2026 (8.00pm–9.30pm, Zoom), we are sitting down with Wendy & Poh Wah for a candid, deep conversation about what it really takes to make the move. Moderated by none other than our co-founder Jesslyn Yim 😎

Wendy is Head of Talent & Transformation at YWCA, Founder of Incite Insights, and our wonderful trainer behind our Social Service Reternship Programme. Poh Wah is the Learning & Organisation Development Lead at St. Andrew’s Autism Centre, previously a technology leader for the past 3 decades and made a brave leap into the social sector through our Social Service Reternship Programme!

Register here: https://us06web.zoom.us/meeting/register/CQeqMnJuTYKs_sjXxafM6Q

Courage Kopi Meets + CourageActive Walk

Our wonderful volunteer team - Jen, Siew Yean, Siew Siew, Malik, Lin have been hard at work planning great community gatherings for us!

Courage Kopi Meets: an in-person gathering for Courage members and friends to connect, share, and grow together. Life transitions can bring uncertainty, questions, and unexpected possibilities.

Join us on 25 June for a reflective and interactive session where we’ll explore how we can navigate change with greater awareness, confidence, and purpose.

Together, we will:

• Reflect on where we are in our current season of life

• Discover strengths and perspectives that can support us moving forward

• Explore possibilities for the next chapter ahead

Expect thoughtful conversations, personal reflection, and meaningful connections with fellow members of The Courage Chapter.

📝25 June, 3:30pm – 5:00pm
📍 Singapore Sustainability Academy @ City Square Mall (180 Kitchener Rd, #06-10, Singapore 208539)

👉🏻 To register, click here: https://forms.gle/szAHdAFu9mddQWE17

CourageActive Walk

Join our morning walk from Sports Hub to Gardens by the Bay on 27 June 2026!
Meet up location: Stadium MRT (control station)@ 7.45 a.m.

Route: Stadium MRT -> Tanjong Rhu -> Founders’ Memorial Park -> Marina Barrage -> Gardens by the Bay (~2hrs)

Sweat-O-Meter: 💧💧paved
Getting there: MRT: Circle line Stadium station

Hit the registration link: https://forms.gle/4Ae4bJL2PU1VYDpY6

Not yet on our WhatsApp Group Chat? Join us!

Join our WhatsApp group to get timely updates about roles/programme. We send newsletters 1-2 times per month, but send messages more frequently on WhatsApp for quick updates.

Join WhatsApp Group

Lastly, I (Kai Ning) was reflecting about my learnings about the “future of job search” - wrote a piece on LinkedIn: Creation, Contribution, Proximity, Visibility. Hope it resonates with you, and do share your thoughts with me as well! LinkedIn Post here.

Have a wonderful week ahead!

Best,
The Courage Chapter Team

We are pleased to share that we have signed a Terms of Reference (TOR) with the Association of Small and Medium Enterprises (ASME) to support their SME members in engaging experienced professionals for fractional roles and projects!

Many SMEs face challenges that require expertise but may not necessarily need a full-time hire. A huge thank you to Ryo Leong for representing The Courage Chapter Community and sharing his fractional journey as a marketer at the ASME panel! Stories like these help companies better understand the value that experienced professionals can bring to today’s evolving needs.

We will continue sharing project and role opportunities as they emerge through this partnership.

Launch of Cohort 3 of the Social Service Reternship

Applications are now open for Cohort 3 of our Social Service Reternship!

The programme was created to make it easier for experienced professionals and social service agencies to explore working together.

For social service agencies, hiring is often a risky decision. They may need talent, but may be unsure whether a candidate from a corporate setting will thrive in their environment.

For experienced professionals, many are curious about the sector, but may not know whether it is the right next chapter for them.

Through the programme, we act as a bridge. We help agencies engage professionals at lower risk and lower cost way before a long-term commitment, while helping our professionals quickly understand the mindsets & skillsets to thrive in that environment.

Dates for Cohort 3:

• Social Sector Appreciation: 11, 12, 18 July

• Immersion Day: 24 July

Register for Cohort 3 and find out more about the social service:

Sign up here!

Watch our recent info session recording featuring alumni Edmund Tang, peppered with “date before you marry” analogies:

AI Native Circle: Building Your First Agent (and Beyond!)

Last week, we hosted Cohort 2’s AI Native Circle Showcase, where participants shared the AI Agents and workflows they have been building and refining after the bootcamp.

Projects included:

• Jobs to be done AI agent

• Grants and funding AI agent

• Pipeline and go-to-market AI agent

• Personalised daily AI News agent

• Chief of Staff AI agent

We were also delighted to have alumni from Cohort 1 return to share how they have continued to apply AI in their projects. (This was unplanned, but in true Courage Chapter fashion, we are proud to see their growth and let our alumni speak for themselves!)

A personal reflection as we continue to organise more AI Native Circles is that AI is a powerful tool, but it is ultimately a means to an end.

Participants who found it the most effective did not necessarily build the most sophisticated agents. We observed that it is those with a strong understanding of their challenges, priorities and goals tend to get the most out of it! In many ways, becoming AI Native is also a process of gaining clarity. Just that you have tools now, helping augment your time and expertise!

Quoting Stephen Covey’s The 7 Habits of Highly Effective People, a classic habit to begin with the end in mind. What is the business outcome you are trying to solve for, and how can AI help get you there? These are the questions we can explore and build together!

Our next AI Native Circle info session is happening this week (4th June, SGT 7:30 PM), we would love to have you join us!

Register for Info Session

New Courage Community Calendar Now Available

We have launched the community calendar to make it easier for members and friends to see upcoming programmes and gatherings at a glance.

Some upcoming highlights include:

• Movie reflection Session: The Intern

• Courage Active Walk at Kallang

We encourage you to bookmark the calendar and join us whenever something resonates with you and where you are in your journey.

Bookmark Courage Calendar

Warmly,
Kai Ning & Jess
The Courage Chapter

We are happy to announce that the Social Service Reternship Cohort 3 is now open, back by popular demand 🥳☀️

Many of our senior professionals are exploring meaningful ways to contribute to society in their next wind. Our Reternship Programme provides them with a structured, supportive pathway to transition into the social service sector 💪🏼

We spoke to multiple charity leaders to find out exactly why some succeed, while others fail in their transition into this unique sector. We built these insights into a deeply reflective and experiential Reternship programme, where participants get firsthand experience learning from sector leaders, leverage their past experience & skills, and understand the mindsets and skillsets to thrive in the social sector.

This isn’t just a course, it’s a stepping stone into meaningful, purpose-led work. We’re working closely with charities to co-create project opportunities that are impactful, low-risk, and mutually beneficial. While projects are still in development, this is the perfect time to be part of shaping what’s to come.

If you’ve been thinking about exploring a second wind in the Social Sector - Join our Info Session to hear directly from sector leaders & industry experts in an unfiltered Ask-Me-Anything format.

📆 27 May, 9:30am–11:00am
🔗 Zoom Webinar (Sign Up: https://tinyurl.com/SSReternship-Participants1)

Our Panelists for info sess:

Bernard Chew, CEO at St. Andrew’s Autism Centre, one of our best charity partners over the past two years, who has hired and worked closely with our experienced professionals transitioning from the corporate world.

Edmund Tang, Manager, Special Projects at St. Andrew’s Autism Centre. Edmund was a corporate leader who made the switch through our Social Service Reternship Programme — and went on to work with SAAC in various capacities.

The session is moderated by the wonderful Wendy Yeo, Founder of Incite Insights & Head of Talent & Transformation at Young Women Christian Association (YWCA). Wendy has extensive experience in both the social service sector (previously as a Psychologist) and corporate HR leadership.

Sign Up for Info Sess

Social Service Reternship Cohort 3 dates:

📅 11 July (Sat), 12 July (Sun), 18 July (Sat) — Social Sector Appreciation
🏢 24 July (Fri) — Immersion Day at Various Charities

Programme fee: S$800 (U.P. S$1,300, Co-funded by e2i)

More info about The Social Service Reternship here: https://www.thecouragechapter.com/social-service-reternship

If you have any questions before the Info Session, please write to reternship@thecouragechapter.com. Look forward to seeing you!

Warmly,
Kai Ning & Jesslyn
The Courage Chapter

Happy month of May!

PRUPrime (Prudential) Updates

We are happy to share that 20+ of our Courage community members have successfully landed retainer projects with Prudential, under their flagship PRUPrime Programme! ✨

Functions include: Product Marketing, Customer Resolution, HR (Competency, Benefits, Culture & Org), Policy Services, Due Diligence, Risk & Quality Assurance, Data Governance, Partnerships, Project Coordination, Claims Servicing, etc)

Huge congrats to those starting their new journey with Prudential, and we hope to bring more of such opportunities to our community in time to come.

Other Success Stories this year

We’ve also been hard at work with other opportunities - and are proud to share that a couple of Couragers have been offered some opportunities including - Head of Talent & Transformation, Head of Comms/Branding (fractional), Senior Manager Volunteer Management, Deputy Director Corporate Sales, and Partnerships Manager (fractional).

Other members have moved from short term projects, to longer-term contracts with companies/charities, including Special Projects, Head of Facilities, Learning & OD. Some have started short-term projects in IT, Procurement, etc.

Warm congratulations to our Courage members for embarking on their new chapters and we look forward to hearing about their journey ahead!

AI Native Circle Cohort 2 - Last Call

After a fabulous first run, we’re really excited to launch our 2nd cohort of AI Native Circle on 16 May 9am - 6pm (Sat) 🚀 - 4 slots remaining

Our goal: to build a safe space for our community to move beyond using AI like a search engine, to building AI Agents & systems for better professional & personal lives 🌱

We believe that experienced professionals who learn how to work with AI early will likely have a huge advantage. Domain expertise x AI = Competitive moat.

Our AI training partner: we chose to work with Wan Wei, founder of ANCHR AI Labs as she teaches in a friendly, highly guided & personalised way as a non-technical founder, to ensure that everybody sets up their system right and walks away with minimally two AI Agents by the end of the class.

If you’d like to join Cohort 2, register here: https://ainativebootcamp.netlify.app/

Watch the info session recording here:

Our AI Native graduates will also showcase the AI Agents they’ve built on Claude Cowork on 26 May 630pm - 9pm SGT. Join us - seats are limited (waitlisted): https://luma.com/e9qp5vsv

Previous cohort presentations - watch their professional videos here: https://www.youtube.com/playlist?list=PLH3JN6YFczfahgwTj9YoyMmAxHTsCYkRt

Sign Up for AI Native Circle

Our Next CourageActive Walk is happening next Monday (18 May)

Join our morning walk + Breakfast at Coney Island next Monday 18 May 2026, 8am-10am!

Meet up location: Punggol Coast MRT (control station)

Route: Punggol Coast MRT > Coney Island (loop inside) --> Punggol Coast MRT (~2hrs 30mins walk loop back to starting point)

Hit the registration link below:

https://forms.gle/MDk2nMYxW31ynjX29

Special thanks to Siew Yean & Malik for organising the upcoming CourageActive Walk!

Register for Walk

Some Reflections

We’ve increasingly observed an expansion in “what could be possible” for many of our community members - in this longevity journey, some have started fractional roles while building their own impact organisations (shout-out to Victor and KH!), others have built AI agents and are working on monetising them (shout out to Damien), others have embarked on higher education (shout-out to Jen & Ryo for your Masters & Doctorade journey) - some have even gotten interviewed by Straits Times about their AI-journey (wow! Kudos to Grace :)), some are running their own trainings to help others on their entrepreneurship path (shout-out to Siew Siew)! And all this is just at the top of our heads… We are sure there are many many more!

Want to get updated more frequently? Join our Courage WhatsApp Group!

Join WhatsApp Announcement

Look forward to catching up soon!

Warmly,
Kai Ning & Jess
The Courage Chapter

We recently had the opportunity to speak at the World Ageing Festival 2026 - Embracing Longevity.

We’re noticing that much of today's longevity conversation focuses on healthcare, medicine, and extending lifespan. But that’s only half the story.

The harder question is: What do you do with those extra years?

Because having more time doesn’t automatically mean having more purpose. Many in the community have gained decades of experience, built deep expertise, and developed real wisdom. Yet in this next chapter, they often find themselves wondering:

• Identity: Who am I if my career changes or ends?

• Contribution: How do I use what I know to matter?

• Transitions: How do I navigate this shift with confidence?

💡 The Ageing Narrative Shapes The Experience

In Singapore, ageing is framed as a phase of decline, something to worry about and withdraw from, people disengage from the planning and conversation.

How we see ageing shapes how we experience it.

When it’s framed as a new chapter, a space to explore what’s possible, people stay curious. They experiment. They stay willing to try things they’ve never tried before. They stay in the game.

🤖 AI Native Circle — Building Confidence For What Comes Next

This is exactly what we’ve been exploring through our AI Native Circle.

We recently ran our pilot as a safe space for experienced professionals to explore new tools and unlock possibilities.

A space where experienced professionals could:

• Try new tools with confidence

• Build AI agents in ways relevant to their actual situation

• Ask questions without judgment

What surprised us was what happened once they permitted themselves to experiment.

They saw where AI could amplify their thinking, support their “work”, and extend their impact. One person built an AI coach for leaders. Another automated her entire operations workflow. A parent created a PSLE personalized tutor for her child. Someone rebuilt their sales pipeline for their budding consultancy.

Shout out to our Cohort 1 and their AI agents ✨

🚪 AI Native Circle — Info Session

We’re opening up the next run of AI Native Circle for experienced professionals ready to explore what’s possible in this chapter of their life.

If you’ve been wondering:

• “Am I too late to this?”

• “Is this even for someone like me?”

• “Where do I even begin?”

• “How do I stay relevant and impactful?”

Come for the info session. Hear from Wan Wei, who built AI products as a non-technical founder. Get clarity on whether this is for you. Come with your questions, your curiosity, and an open mind.

See you virtually on Wednesday, 29 April 2026, 7:30 PM SGT (recorded)

Register Now!

🌿 Things Are Progressing

Our Courage Onboarding sessions have also found a steady rhythm. Whether you’re new or have been quietly observing, it’s a simple space to reconnect, meet people navigating similar transitions, and find your footing again. It happens at noon, on the last Friday of every month.

Register for May 2026’s session

And somewhere along the way, this newsletter has grown to ~2,000 of you. Thank you for being here.

If you’d like to stay connected with the community, join the Courage Events WhatsApp group to stay in the loop and join our community-initiated events.

Warmly,
Kai Ning & Jess
The Courage Chapter

Wishing you a joyous Hari Raya weekend!

This newsletter’s theme is about designing your next chapter with intention - to stay ahead of the curve! We all have some inkling of what would make life fulfilling, and sometimes we need just the right environment to build the relevant skills to THRIVE, and not just “survive” 💪

AI Native Circle: A safe space to learn, build, and showcase what you create

We welcomed 90+ of you during our recent AI Native Circle Info Session (watch here), where our partner ANCHR AI Labs (Wan Wei) shared key concerns from professionals in their 40s, 50s and 60s:

These aren’t just individual concerns — they reflect a broader shift many people are trying to make sense of. Rather than feeling left behind, we should feel right on time.

3 key points

1. You’re not behind - nobody has a real headstart. You’re right on time if you start now! Most popular tools are merely a few months old (e.g. Claude Cowork), and even developers are figuring it out in real time.

2. Your experience isn’t obsolete, value = experience augmented with AI. AI doesn’t replace experience. It amplifies it.

3. The real risk is not AI — it’s waiting too long to engage. This is not a slow trend you can observe from the sidelines. Adoption is compounding quickly, and the gap between users and non-users is already forming.

The people who start now build workflows, gain confidence, and create proof. And 12–24 months later, that gap becomes very hard to catch up.

As mentioned in our previous newsletter, we are running our AI Native Circle Intensive on 29 March, from 9am to 6pm SGT.

👉 You can find more details here: https://ainativecircle.netlify.app/

Due date to sign up: 21 March 2026.

Why AI Native Circle?

We designed this as the kind of environment we wish existed earlier:

1. A safe space for non-technical builders
No jargon, no judgement. Just practical, guided learning alongside others with similar interests figuring it out together.

2. Learn by doing, not just consuming
You won’t just attend “lessons” — you’ll build.
From workflows to small tools, we focus on real application in your work and life.

3. Turn learning into visible proof
On 16 April (evening), you’ll get to showcase what you’ve built, supported by Singapore Global Network.
Not just for confidence — but to start building a portfolio of relevance in the AI era.

Sign Up - AI Native Circle Intensive

Social Service Appreciation Course - Cohort 3 Now Open!

After 2 successful cohorts in 2025, we are launching our 3rd edition of Social Service Appreciation Course, for corporate professionals keen to transition into the social sector! [April/May 2026 - indicate your interest so we may contact you for more info!]

As people live longer, healthier lives, the idea of a single linear career in one industry is slowly fading. More professionals today are exploring what we call purposeful longevity — using the next chapter of their careers to contribute meaningfully to society.

For many, the social service sector feels like a natural place to do that.

Yet we have also observed something important.

While many corporate professionals have valuable skills in strategy, business development, finance, HR, marketing, technology, and operations, transitioning into the social sector is not always straightforward.

The sector operates differently. Different constraints. Different stakeholders. Different ways of measuring impact.

And often, professionals who want to contribute don’t know how to translate their experience into this new context, while charities remain skeptical if corporate professionals truly understand the sector well enough to contribute effectively.

This is why we created the Social Service Appreciation Course.

The course is designed as a thoughtful entry point for professionals who are curious about contributing to the social sector.

Over three days, participants will:

• Gain a deeper understanding of how Singapore’s social service ecosystem works
• Learn how charities operate and the realities they face on the ground
• Reflect on their own skills, values, and motivations for their next chapter
• Explore how their professional experience can be applied meaningfully in the sector

The course is facilitated by experienced social service practitioners who themselves have crossed between the corporate and social sectors, helping participants bridge that gap with honesty and practical insight.

But more importantly, this is also a space for reflection.

Many participants tell us that beyond understanding the sector, the programme helped them think about deeper questions:

• What kind of contribution do I want to make in the next chapter of my life?

• What values do I want my work to reflect?

• What does meaningful work look like for me now, and how may I build my capabilities towards my goals?

Following the course, participants will also be invited into a growing community where they can:

• Join immersion visits to social service agencies
• Meet leaders and practitioners in the sector
• Explore collaboration and project opportunities through our Social Service Returnship initiatives

If you are someone who has spent years building experience in the corporate world, and you are curious about how that experience might be applied toward social impact, this course may be a meaningful starting point.

Indicate Interest for Cohort 3

Lastly….

We are happy to partner up with City Sprouts, to organise an Impact Visit to their campus!

Join us on 30 March to learn more about City Sprouts, meet the amazing team, and explore how you might meaningfully contribute to their growing social enterprise 🌱

I'm sure most people have heard of City Sprouts, but here goes anyway: they are a social enterprise that transforms underutilised urban spaces into vibrant green hubs for #community, #education, and #sustainability. Through their spaces, workshops, community programmes, and events, they reconnect people with nature while supporting social and environmental impact initiatives across Singapore.

During this visit, you will get a behind-the-scenes look at how their space operates, the communities they work with, and the ways their programmes bring together sustainability, education, and social impact.

They are excited to meet individuals who may be interested in joining their Programmes and Events team (full-time roles + volunteering opportunities available)! Would highly recommend you to visit if you're exploring work in sustainability & social impact 😊

Date: March 30, 2026
Time: 9:30 AM – 11:45 AM

Sign up for the impact visit here by 27 March:

Sign Up - City Sprouts Impact Visit

We look forward to meeting you soon!

With love,
Kai Ning & Jesslyn
The Courage Chapter

Happy March! :) the year of the Fire Horse has certainly galloped quickly along.

Many of our community members are rethinking what the next chapter of work and contribution looks like, while the world of work has been changing rapidly in recent times. At The Courage Chapter, our mission has always been to support experienced professionals in building lives of purposeful longevity centred around fulfilment, flexibility, fitness, and finances.

We’ve increasingly realised that building future-of-work capabilities such as AI literacy can be a massive game changer for our community. Many professionals shared that they feel uncertain about how quickly AI has developed, and wonder how to stay relevant in the workforce. Personally, I think we should turn the question around.

Instead of asking “How do I keep up?”
What if we asked: “How can I use this moment to turn my experience into something even more powerful?”

I truly believe that experienced professionals who learn how to work with AI early will likely have a huge advantage. We’re at the very start! The infographic below shows that 84% of the world hasn’t had their first AI conversation yet.

We want our Courage Community to stand out as top contributors to society in their next chapter - Imagine a Singapore society where our senior professionals dish out their wisdom & experience, efficiently leveraging AI! What a gamechanger😎

Introducing AI Native Circles - a collab between The Courage Chapter & ANCHR AI Labs

We are happy to share that we’re piloting the AI Native Circle - a collaboration between The Courage Chapter & ANCHR AI Labs. We are building a safe and practical space for professionals in their 40s, 50s and 60s to explore AI in a hands-on way and gain the confidence to apply it meaningfully in their work.

When we did a soft launch, we were floored that >100 experienced professionals reached out wanting to learn more.

That is why we are hosting an #AINativeCircle Info Session next week:

📅 18 March, 7:30pm – 8:30pm SGT

During the session, our AI partner Wan Wei will share her journey building AI products as a non-technical founder, and share about the AI Native Circle Intensive Pilot Workshop on 29 March.

If you are curious about learning how to build your own AI agent for real work tasks, and more importantly gain confidence working with AI tools, we would love to have you join us.

Register here: https://tinyurl.com/AINativeCircleInfo

Prudential PRUPrime Programme Updates

We’ve also been hard at work with one of the biggest programmes we’ve had - with our partner Prudential.

We’ve received >300 applications for the PRUPrime Programme, and have nearly finished the selection process. More than 20 professionals have been offered and onboarded to PRUPrime (and a few more to go!), and we can’t wait to hear from their experience in the year ahead.

Surbana Jurong - Career Transitions Workshop Collab

We recently had the opportunity to work with Surbana Jurong to facilitate a workshop on career transitions for their employees. The session focused on helping participants reflect on their strengths, identify transferable skills, and think more intentionally about what their next chapter of work might look like.

Through guided discussions and practical exercises, participants explored how to articulate their experience more clearly and consider new ways their expertise could continue contributing in a changing world of work.

It was encouraging to see many thoughtful conversations emerge around purpose, relevance, and how professionals can continue growing and adapting across different stages of their careers.

Many thanks to Sally Sng, who conducted the workshop, and Ryo Leong, who shared his 2nd chapter story with our audience!

We have many other exciting things lined up, and we’d be sharing them with you really soon!

Till then, have a wonderful week ahead <3

Warmly,
Kai Ning & Jess
The Courage Chapter

Happy 2026! We blinked and it’s now February 🤯

We’ve welcomed new members to The Courage Chapter, and would like to share the various ways you can gain access to roles/projects:

1. Job Board: Access it here

2. WhatsApp Announcements: Access it here

3. LinkedIn: Access it here

4. Newsletters like this one!

Speaking of roles…

Are you (or know of anyone) keen & suitable for these roles or projects? (click into each link to access the JD)

1. [Non-Profit] Curriculum & Programmes (fractional - 2.5 days/week)

2. [Non-Profit] Programme Executive (full time)

3. [Non-Profit] Quality Surveyor (2 year contract)

4. [Non-Profit] HR Project Manager (HRMS Implementation) (2-3 years contract)

5. [Non-Profit] Curriculum & Programmes (fractional)

6. [Non-Profit] Head of Finance

7. [Non-Profit] Student Care Teacher

8. [Training] Freelance Trainer (Evergreen) - for various charities/orgs

9. [Ed Platform] Director, Corporate Sales (full time)

10. [Ed Platform] Deputy Director, Business Development (full time)

11. [Medtech] Business Development Lead

12. [Medtech] Customer Communications Specialist (fractional)

13. [Expert Advisor] Logistics and Supply Chain: Cross-Border & Customs (3 hours/week)

14. [Expert Advisor] Logistics and Supply Chain: Regulatory and Compliance (3 hours/week)

Signed an MOU with United Nations Global Compact Singapore!

We are happy to announce we signed an MOU with United Nations Global Compact Singapore to kickstart our Sustainability Reternship Programme - aimed at upskilling & certifying our professionals in carbon accounting, and providing real-life project opportunities with SMEs, with the eventual goal of empowering them to run their own sustainability projects with other clients. While we’ve already kicked off our first run, we may be running others this year, depending on the demand from both our community & SMEs.

Updates on Unilever Value In Value Up & Prudential PRUPrime Programme

For those who applied for the Unilever Value-In-Value-Up and Prudential’s PRUPrime Programme, we warmly thank you for your application!

Updates on Unilever Value In Value Up:
Due to some leadership and business direction changes, work was paused temporarily. However, we received news recently that the programme is slated to continue! We will be in touch shortly with more updates (some of you have already been approached for interviews🎉)

Updates on Prudential’s PRUPrime:
Selections are ongoing, and some interviews have been scheduled. Look forward to hearing the results real soon! We hope to have your understanding - we may not be able to do individual updates via email/WhatsApp due to the quantity of applications received. You will be informed on a rolling basis of your application results, so stay tuned! 😊

How you can contribute: Courage Projects - Our Personal Appeal!

Having run for >2 years, The Courage Chapter team has been happy to work with 30+ company partners, and >1,200 professionals in our growing community. Over the years, our small team has met many of you, and we were heartened by your encouragement, advice & support.

We recognise that we are sitting on a “Goldmine” - our community of corporate professionals, deep in experience, know-how, and network. We have always wondered: with all the brains in this group, what can we not achieve? (Simplistically, if everyone could refer 1 role to someone else in the group, would the community not be self-sustaining? If we could collectively use our voices to advocate for productive longevity, doing what we do best - marketing, project management, recruitment, leadership, etc - would we not move the needle together?)

As a small core team, we are conscious that our capacity can sometimes limit the pace and scale of impact we hope to create. We’ve taken your feedback seriously and are opening up a small number of focused projects where community members can contribute their skills and experience.

We envisage this initial phase to run for approximately three months (“Phase 1”), with the possibility of extending into a second phase depending on how the projects evolve.

For a start, we are launching three projects, which you can read more about here: COURAGE PROJECTS

We have organised a briefing call on 6 Feb, 230pm - 330pm to share more details. If you’d like to find out how you can contribute, do join us for this call!

Calendar invite: https://calendar.app.google/QNx57M7ycSJivLga7

Courage Projects

Enjoying our Get-togethers :-)

We kickstarted Jan 2026 with a lovely walk at Botanic Gardens! >40 of you joined us (we even had to apply for an NEA license for this walk, haha!) We had an enjoyable, vibrant Saturday morning spent with everyone.

Join our “Courage Events” WhatsApp group chat to gain access to more member gatherings like these!

Join Courage Events

Informal Kopi Chat - Let’s meet & Chat!

We’d like to organise an informal get-together on 10 Feb 3pm @ YWCA Cafe Lodge (dhoby ghaut). If you’d like to join, save the calendar invite and see you:

https://calendar.app.google/mYSbt2vbhKE2u78g6

The topic will be loosely around “Fractional Work”, cross-learning from our members on their fractional journeys: what has worked, what hasn’t, opportunities etc. Happy to discuss other relevant topics as well.

An “Ageing Well” article from our Ageing Consultant Volunteer, Kang

Kang, who has extensive research and practical background on “longevity”, has launched a public education service on ageing well through a monthly newsletter. Each month’s issue will discuss how a specific contributor aids or impedes ageing well. Check it out: Ageing Well - Inaugural issue - Kang Kok Hua

Ageing Well Article

As usual, we are very happy to take feedback from our community, and are open to new ideas to develop the #ProductiveLongevity space in Singapore. We are contactable at hello@thecouragechapter.com.

Have a wonderful week ahead!

Warmly,
The Courage Chapter Team

We’re proud to share a meaningful milestone! Our programmes are now backed by SNEF’s Alliance for Action on Empowering Multi-Stage Careers for Mature Workers (AFA-EMW).

This is a big one for us. It brings together organisations that are ready to experiment with new ways of working, such as fractional roles, mid-career traineeships, and training built specifically for senior professionals.

More importantly, it strengthens our vision of a future where experienced workers have dignified, flexible, and purposeful pathways to stay engaged, contribute meaningfully, and grow in their next chapter.

And with this momentum, we’re excited to share…

Announcement: Introducing PRUPrime Programme

A new opportunity created in partnership with Prudential Singapore.

Many of you have told us you’re seeking work that allows you to contribute deeply without returning to a rigid full-time structure. PRUPrime was built with this exact intention in mind.

Join a community of skilled professionals who contribute to critical business needs – seasonal peaks, strategic projects, or bridging capability gaps. Work on projects that align with your expertise and lifestyle.

Examples may include:

• Business analytics

• Change management

• Claims assessment and support

• Customer support and engagement

• Data analytics

• Digital enablement

• Finance operations

• Process improvement and workflow design

• Product launch and initiatives

• Project management

• Recruitment operations

• Risk & Compliance

• Underwriting

🔥 What PRUPrime Offers:

A 12-month structured programme combining stability, purpose, and flexibility:

✅ Monthly Retainer + Medical Benefits
Receive a monthly retainer with medical benefits, even during non-deployment months.

✅ Flexible Deployment (minimum 6 months of work)
Be deployed full-time or fractionally for at least 6 months within a year, depending on business needs, with attractive pay during deployment months.

✅ Hybrid, Fractional, or Seasonal Work Options
Designed to fit your lifestyle and current life stage while offering meaningful career contribution.

✅ Continued Learning & Engagement
Access learning modules, engagement activities, and support from a dedicated programme coordinator.

✅ Meaningful Placements across Functions
Opportunities may span across areas such as Operations, Claims, Customer, Finance, Digital Enablement, and more, based on your strengths and organisational needs.

👥 Who We’re Looking For:

If you are a mature professional who’s excited to contribute to a dynamic organisation while enjoying the flexibility modern careers offer, we’d love to meet you!

🚀 Join us at our PRUPrime Info Sessions!

Physical Info Session (Highly Recommended!)
📅 4 Dec 2025, Thursday, 9:30am - 12pm (morning bites @ 9:30am)
📍 Prudential Singapore Office @ Labrador Tower, 1 Pasir Panjang Road #09-01, Singapore 118479
🤝 Hear from the Prudential team, enjoy a guided office tour

Virtual Info Session (if you can’t join us in person)
📅 10 Dec 2025, Wednesday, 10am - 11am
📍 Online via Zoom

🔗 Registration link

In Case You Missed It: Unilever’s Value in Value Up Programme

Last month, we shared about Unilever International’s Value-In Value-Up Programme, one of the pioneering initiatives under SNEF’s Alliance for Action on Empowering Multi-Stage Careers for Mature Workers (AFA-EMW).

If you weren’t able to attend the info session, you can catch up via:

• Replay link

• FAQ + Project Briefs

These resources will give you clarity on the types of projects being piloted and how organisations are rethinking roles to make better use of experienced talent. Sign up closes soon on 30 Nov 2025.

No Kopi Meet This Month, But Plenty of Ways to Stay Connected

And while there’s no Courage Kopi Meet this month (we’re knee-deep in these programmes 🫣☕️), you’re always welcome to hang out through our member-initiated community events.

👉 Join the Courage Chapter WhatsApp Community to stay in the loop.

With courage and gratitude,

Jesslyn & Kai Ning

It’s been a heart-full month for us. 💛

The Courage Chapter was recognised as one of 25 recipients of Stewardship Asia Centre’s SL25 Award, which celebrates solutions for social and environmental good across Asia Pacific.

Our winning project: The Reternship Programme, empowers experienced professionals like you to transition into sectors such as social service. Whether through short-term projects, part-time roles, skilled volunteering, or full-time opportunities, we’re building more pathways for meaningful contribution.

📰 Read the full feature in The Straits Times →

💼 New Reternship Collaboration with Unilever International in 2026

We’re also thrilled to share an exciting partnership with Unilever International, reimagining the Future of Work through:
Value-In, Value-Up: A New Way to Work, Learn, and Grow.

This progressive fractional work programme opens doors for experienced professionals who want to reignite their careers, strengthen their digital mindset, and co-create impact within one of the world’s most dynamic organisations.

Who is it for:
🌟 Strong curiosity to learn
🌟 Deep functional experience
🌟 Strong digital mindset
🌟 Desire to shape the future of work
🌟 Aged 40 and above

If this sounds like you, come join our Info Sessions next week to learn more about the 2026 cohort:
🗓️ Info Sess 1: 20 Oct (Mon), 8:30–9:30pm SGT
🗓️ Info Sess 2: 21 Oct (Tue), 4–5pm SGT
👉 Sign up here via Linktree

We’re co-creating this journey with Larissa Murmann, Digital CHRO of Unilever International, and her team. This is another meaningful step towards redefining what the Future of Work looks like for experienced professionals in Singapore and beyond.

🌍 Launching the Sustainability Accounting Reternship

We’ve also partnered with UN Global Compact Network Singapore (UNGCNS) to launch the Sustainability Accounting Reternship Programme.

Perfect if you’ve been curious about sustainability and want to build hands-on experience. Through this programme, you’ll:

💡 Receive subsidised training on Carbon Accounting from UNGCNS
🤝 Work on real sustainability reporting projects with local SMEs
📈 Build a tangible sustainability portfolio and make a real impact

We can’t wait to explore the green sector with you 🌱
👉 Express your interest here

☕ October’s Courage Kopi Meet: Design Your Next Chapter – Inroads and Possibilities

Our monthly Courage Kopi Chat is meant for Courage members and friends who are curious about us, our activities, how you can contribute to Courage projects, and grow with a like-minded community.

In this month’s Courage Kopi Chat, you’ll experiment with the Design Your Life approach — seeing your journey as a creative process where curiosity and reframing open new doors.

Through hands-on, reflective exercises, you’ll:
✨ Sketch out your Six-Point Persona and explore what energises you
✨ Learn how to turn problems into opportunities
✨ Prototype three possible life paths — and even use Gen AI to spark new ideas
✨ Shape your Personal Brand with guided prompts

Facilitated by Abhi Patwardhan, a former tech executive and founder of Alt-Lyf, who blends design thinking, storytelling, and lived experience to guide people through meaningful transitions.

💰 Pay-as-you-wish model: if you contribute $50 or more, you’ll receive a copy of Abhi’s book “Painting Your Retirement Canvas: The Art of Purposeful Longevity” — a small investment in yourself, your growth, and the conversations that could spark your next chapter.

📅 Date & Time: 29 Oct (Wed), 9am–12pm
📍 Singapore Sustainability Academy, City Square Mall
👉 Sign up here

💫 Looking Ahead

As we head toward 2026, we’re gearing up for more Reternship opportunities, deeper partnerships, and community conversations that keep our mission alive - to redefine the narrative of aging in Singapore.

With courage and gratitude,
Jesslyn & Kai Ning

🚀 A Practical Pathway for Senior Professionals Exploring the Social Service Sector

This month, the 2H 2025 Social Service Reternship Programme officially launched.

27 participants signed up to gain exposure, insights, and connections, while opening their minds, possibilities, and hearts to serving in various capacities.

At the launch, sector leaders shared perspectives on what it really takes to bridge into meaningful work:

• On contentment and calling
  “Pay is often a hygiene factor. What truly sustains people is the sense of purpose: “What does calling feel like to you? It’s something you are willing to suffer and push through for.”

• On evolving, not just changing
  “Once you come in, focus on evolving forward. Your growth is in the direction you choose.”

• On transferable skills and curiosity
  “We want to see your curiosity, that you care enough to understand stories, culture, and team dynamics. In any next chapter, your ability to adapt and learn is just as valuable as your experience.”

Hear from the participants, the one word that captures their experience.

“Clarity.” “Insightful.” “Reassured.”

☕ Where Are You Now? – Exploring the Currency of Courage

If you joined last month’s vision-boarding sessions, you might still be in that “messy middle”, excited about possibilities, but figuring out how it all works in real life.

Together, we’ll explore the balance between:

• The Practical Currency – Assess your financial needs, lifestyle priorities, and long-term sustainability. Through guided exercises, you’ll reflect on your non-negotiable expenses and how they shape your next steps.

• The Personal Currency – Revisit your motivations and vision. Does what drives you today truly support your long-term goals? Align your inner purpose with your practical reality.

📅 Date & Time: 23 Sep 2025, 2:00 – 5:00 PM

📍 Location: Singapore Sustainability Academy @ 180 Kitchener Rd #06-10, City Square Mall, Singapore 208539

💰 Pay-as-you-wish: Accessible to all while honoring your commitment

👥 Facilitator: Gordon YH Tan

Gordon is a seasoned leadership and career coach with a 32-year background in investment advisory, including leadership roles at HSBC, Coutts, JPMorgan, and Julius Baer. Since 2017, he has focused full-time on counselling and strength-motivation coaching, helping individuals and teams align their careers, finances, and personal purpose.

👉 Sign up here: Courage Kopi Meet - Sep 2025

💼 Opportunities for Your Next Chapter

If you’re ready to take action, here are two open roles you might explore (or forward to a friend):

• Head of Strategy (Insurance, 1 year) → https://app.loxo.co/job/MzI3NjktNXBoYzJqdzltZWUwejJoMA==

• Corporate Strategy Manager (Insurance, Full Time) → https://app.loxo.co/job/MzI3NjktZWQ2MDF1emdnazh0b2tuaA==

With courage,
Kai Ning & Jesslyn

It was wonderful hosting >100 community members across 2 Social Service Info Sessions, with our dear panellists & moderator.

They shared stories, candid opinions & did not mince their words about sector realities. We caught a glimpse of what makes a successful transition and the passion that goes behind the work they do every day. Glad that many could join us, and we look forward to seeing some of you at our #ReternshipProgramme.

📺 Missed the info session? Catch the replay:

🌱 Social Service Reternship Programme

The SSA Reternship is more than just theory. It’s about learning from the people who live and breathe this work every day. This year, we’re bringing together a powerful mix of practitioners and sector leaders:

Practitioner Sharing

• Soo Hong Ling & Yeo Ying Jie – Senior Social Workers, SHINE

• Eric Hu – Programme Head, SG Cares Volunteer Centre

• Joanna Tan – Former Executive Director, Children’s Wishing Well

• Shirley Lee – Executive Director, Catholic Family Life

Leadership Panel

• Bernard Chew – CEO, St Andrew’s Autism Centre

• Tim Oei – CEO, Mindfull Community Limited

• Seah Chin Siong – Board Chairman, Singapore Children’s Society, iShine Cloud, NVPC

• Wendy Yeo – HR & Talent Business Partner, and our very own Reternee

What you’ll get

• Real-life insights shared alongside the modules

• Honest perspectives on what the work is truly like

• Connections with practitioners and leaders passionate about impact
  

This is where learning meets lived experience, and where your next chapter can start to take shape!

🗓 Registrations close 31 August 2025
👉 Sign up now: https://www.thecouragechapter.com/ss-reternship-programme

📢 Hiring News

Meanwhile, our charity partners are looking for passionate people to join their teams:

Boys’ Town
Assistant HR Manager ($3.8K – $4.5K)
🔗 https://app.loxo.co/job/MzI3Njktem94d3Q1cnd2NnRqbmFzag==

HR Executive ($2.3K – $2.8K)
🔗 https://app.loxo.co/job/MzI3NjktNjhzbDkyZzY5ZHFlOTFtbg==

Daughters of Tomorrow
Bridging & Engagement Manager ($4.8K – $5.4K)
🔗 https://app.loxo.co/job/MzI3NjktNXloMTd3ZGVmNTBzczQ0MA==

☕ Next Courage Kopi Meet: Navigating Life Transitions with Purpose

With change comes uncertainty. With uncertainty comes the call for courage. And we believe courage grows strongest in 𝐜𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲.

We recently held a wonderful workshop on “𝐍𝐚𝐯𝐢𝐠𝐚𝐭𝐢𝐧𝐠 𝐋𝐢𝐟𝐞 𝐓𝐫𝐚𝐧𝐬𝐢𝐭𝐢𝐨𝐧𝐬 𝐰𝐢𝐭𝐡 𝐏𝐮𝐫𝐩𝐨𝐬𝐞”, grounded in practical, research-backed frameworks - William Bridges’ Transition Model and Positive Psychology. Our community walked away with deeper reflections on self-identity and visualized their “ideal future” through a creative (Points of You) vision board.

It was a privilege to hold space for such honest and meaningful reflections, and to gently guide our community toward clarity in their next chapter.

We’ve been encouraged to run these workshops more frequently and would love for you to join us next!

📅 Date: 28 Aug 2025, 2-5 pm
📍 Where: Online (Zoom)
👥 Limited to 20 pax 💰 Pay-as-you-wish: We want to make this accessible while honouring your commitment.

👉 Register here: https://forms.gle/7c5A2Yx9yhNALJGRA

With Courage and Gratitude,

Kai Ning & Jesslyn

Happy July :-)

We’ve been drumming up loads of activities for the community in the recent few months, and can’t wait to share what’s in the pipeline for everyone.

For starters, we did a review of the past 1.5 years, and we’ve:

🍀 Connected 45 professionals to various projects/roles across 20+ companies & charities (Check out our Job Board on www.thecouragechapter.com, where some of the projects/roles are listed)
☀️ Run ~20 workshops and panel sessions on various transition & skills topics attended by >600 community members
💎 Created a flagship #Reternship Programme for growth sectors

We are honoured to have received the Company of Good 3 Hearts 💗 Award by the National Volunteer & Philanthropy Centre (NVPC) earlier this month.

We are happy to announce that the long-awaited Social Sector Reternship Programme is now OPEN for applications!

More Details & Apply Here: https://www.thecouragechapter.com/ss-reternship-programme (limited to 25 slots)

The social services industry is a growing sector in need of good talent, while senior professionals are seeking out meaningful roles in their next chapter. What if we could help both charities & our professionals find a good fit in a low-risk, experiential and mutually beneficial way?

Together with Singapore Polytechnic, we are organising our 2nd round of the Social Sector appreciation course from 10-12 Sept 2025, with a chance to experience what it is like working with a charity.

There will be various projects to dip your toes in the sector, on an ongoing basis. Apply here! (limited to 25 slots)

Have questions? Join our Info Session about the Social Sector + Reternship with Industry Experts

Join us for an engaging, no-holds-barred Ask-Me-Anything (AMA) session featuring experts & industry practitioners from the sector!

Moderator:
Bruce Liew - Capability Implementation & People Strategy Director, NCSS

Panelists:
Karen Wee - Executive Director, Lions Befrienders
Jerome Yuen - Resources Development & Acquisition Director, World Vision
Geoffrey Teo - Finance Director, Allkin Singapore (Option 1)
Genevieve Chua - Board Chairperson, RSVP Singapore - The Organisation of Senior Volunteers (Option 2)

Option 1: 12 Aug 2:00pm-3:30pm (Sign up HERE)
Option 2: 12 Aug 8:00pm-9:30pm (Sign up HERE)

Back by popular demand… “Navigating Transitions with Courage” Workshop (online version)

We had an amazing #CourageKopi session earlier this month, on "Navigating Transitions with Courage" 🍀 Now back by popular demand, we are hosting an online version on 19th Aug 2025, led by Sally Sng, Systemic Team Coach & Founder of Axentiva Human Capital Practice. SIGN UP HERE

What we will cover:
🔹 William Bridges’ Transition Model – which explains why change is hard, and why managing the inner shift (not just the external one) is the real key to moving forward

🔹 Positive Psychology – a strength-based approach to help you reconnect with your purpose, values, and identity, especially at life’s turning points

🔹Leveraging the “Points of You” Leadership Tool

📅 Date: 19 August (Tuesday)
🕒 Time: 2:00 – 5:00 PM
📍 Zoom Session (Sign up here)
💰 Pay-as-you-wish: We want to make this accessible while honouring your commitment

Sharing a snippet from a participant's feedback from our previous run: "The stories shared by fellow participants were rich, heartfelt, and courageous. Each one reminded me that we are never truly alone in our journey. I left the workshop deeply grateful for the openness of the community."

💬 Join Our WhatsApp Community

Want to hear about upcoming events, jobs, and updates more casually?
Join our Courage Chapter WhatsApp Community:
🔗 Click to join

Till next time! Drop us a DM if you’ve any questions and we look forward to seeing you at our events.

Best regards,
Kai Ning & Jesslyn
Co-founders, The Courage Chapter

🎧 Hello to Our New Friends — And a Warm Welcome!

We’ve had a bunch of new folks join our community recently, especially after Kai Ning’s recent feature on CNA’s Work It podcast:

🎙️ Forget retirement – your most meaningful work can start in your 50s

The episode explores the gap between what people over 50 want to contribute and what’s currently available in the workplace, and how we might bridge that better.

If you haven’t had a chance to tune in, you can listen here. Welcome again to those of you who found us through the episode; we’re glad you’re here.

☕ What Happened at Our First Courage Kopi Meet

We kicked off our very first Courage Kopi Meet last month, and it was heartening to see so many of you show up with honesty, curiosity, and openness.

Snippets from the first Courage Kopi Meet

We’ve heard strong interest in the Social Sector Reternship Program, and many of you shared deeply about your curiosity (and uncertainty) around your next chapter. The energy in the room was hopeful, but also reflective.

That’s why our next Courage Kopi Meet is designed to meet you exactly where you are.

🗓️ Next Kopi Meet: Navigating Life Transitions with Purpose

This month, our Kopi Meet will be a special 3-hour workshop to help you pause, take stock, and reconnect with what matters to you.

More than just planning "what's next", more importantly is the inner journey of transition - what's happening inside us, as we navigate through change with clarity and courage.

What we’ll cover:

🔹 William Bridges’ Transition Model – which explains why change is hard, and why managing the inner shift (not just the external one) is the real key to moving forward

🔹 Positive Psychology – a strength-based approach to help you reconnect with your purpose, values, and identity, especially at life’s turning points

📅 Date: 22 July (Tuesday)
🕒 Time: 2:00 – 5:00 PM
📍 Location: Bettr Coffee @ The Foundry
💰 Pay-as-you-wish: We want to make this accessible while honouring your commitment. (Coffee available for purchase)

👥 Facilitator: Sally Sng, Advisor to The Courage Chapter
Sally is a seasoned senior consultant and team coach, with over 20 years of regional leadership experience in organisational transformation.

🔗 Sign up here

We’re co-creating this session with you because transitions are personal and not one-size-fits-all.

🌱 Sustainability Projects: Call for Interest

We’re also planting seeds for something new in the sustainability space. Much like the social service sector, this is a growth sector, and we’re currently exploring project opportunities with like-minded partners.

This is for those who have experience in the sustainability space or feel called to co-create something meaningful from the ground up.

If this resonates, we’d love to hear from you:
🔗 Share your interest here

💬 Join Our WhatsApp Community

Want to hear about upcoming events, jobs, and updates more casually?
Join our Courage Chapter WhatsApp Community:
🔗 Click to join

That’s it for now. Thanks for reading.
And thanks for believing that the next chapter can still be meaningful, connected, and courageous.

With warmth,
Kai Ning & Jesslyn
Co-founders, The Courage Chapter

It’s been a while since our last update (April!). Life’s been moving fast, and we finally carved out a moment to pause and share what’s been happening—and what’s coming up.

🎯 Where Our Reternees Are Now

Back in April, we kicked off our first Social Service Sector Reternship for community members curious about contributing to the social service sector. It’s been a power-packed few months, starting with an Appreciation Course, an Immersion Day with charities like St. Andrew’s Autism Centre, SHINE, SAMH, and then diving into real-life projects with charity partners. Our community members, turned Reternees took time to reflect on their motivations, transferable skills, and the mindsets that support meaningful transitions. Currently, our reternees are matched with charities working on real, on-the-ground projects—like fundraising strategy, partnerships, volunteer management, and HR Strategy.

It’s been humbling and energising. Our reternees are learning fast and contributing meaningfully. Coming from corporate experience, they are starting to see where their skills land well and where they need to adapt. And the charities? Many are seeing the value of experience brought in through a fresh lens —focused, hands-on and collaborative.

We’ll be announcing our second run very soon, so watch this space if you’re keen to explore the social sector as your next chapter (or recommend a friend who does!)

☕ Join Our Courage Kopi Chats! Meet Like-minded Community Members

We heard you —you want more chances to meet, connect, and grow together. So we’re kicking off Monthly Kopi Chats with our upcoming one on 24 June, 2-5pm SGT, in the beautiful Bettr Coffee @ Foundry! We are also honoured to have Six Seconds, global non-profit, run a workshop for us on an emotional intelligence topic “Authenticity”.

🔗 Sign Up Now (capped at 20 pax)

Alternatively, if you would prefer a one-on-one chat. Whether you're job-hunting, navigating a change, or just feeling stuck—book a call with us: 📅 Calendly link

💼 New Roles (Mostly Social Sector... For Now)

We’ve updated our Job Board!

Most roles are in the social sector at the moment. If you're open to using your experience in meaningful ways, take a look. You might find something that fits your rhythm now!

🌦️ A Quick Reflection on the Journey

Honestly? The hiring climate is still tricky. There are roles out there, especially in the social service sector, but they’re not always well-defined. Many organisations know they need experienced help, but don’t yet know how to leverage it well.

That’s why we believe experience is just the starting point. The real opportunity lies in learning how to translate that experience into today’s context—whether that’s through upskilling, adapting how you show up, or understanding how to thrive in leaner and more agile environments.

Overall, this season feels less like a job hunt and more like a journey of recalibration. The people we’ve seen make the most meaningful transitions aren’t waiting around for the perfect title—they show up with curiosity, clarity, and a mindset of contribution. That means asking thoughtful questions, getting to the heart of what organisations really need, and co-shaping what a role could look like—not just list what they’ve already done.

One of our Courage Chapter members put it beautifully:

"Being engaged with The Courage Chapter empowered me with new opportunities. It gave me a safe harbour to engage intellectually and helped me stay resilient during a challenging transition. I got to reapply latent skills, build new ones, and even found the confidence to start imagining my own advisory practice."

We think it’s not about having it all figured out. It’s about staying open, showing up, and trusting that the path forward can be built step by step—with others, and for good.

Thanks for reading.
Thanks for believing in what we’re building.
And thanks for being part of this with us.

With gratitude & courage,
Kai Ning & Jesslyn

How have you been? We hope that life has been good to you.

We have many exciting updates that we’d like to share!

Social Sector Reternship Programme - FINAL CALL

🤩Our first run of the Social Sector Reternship is happening from next Wed! We had many great sign ups, wanted to do a final reminder (limited slots left), please register within this week: https://www.thecouragechapter.com/ss-reternship-programme

The social services industry is a growing sector in need of good talent, while senior professionals are seeking out meaningful roles in their next chapter. What if we could help both charities & our professionals find a good fit in a low-risk, experiential and mutually beneficial way?

Together with Singapore Polytechnic, we have organised a social sector appreciation course (9-10 April) & a chance to experience what it is like working with a charity.

We have various projects available to dip your toes in the sector, from Fundraising/Comms/Partnerships, to Strategic HR, to Volunteer Management, and Programme Management. These projects will last 2 months, from June to July ‘25. More details in the link above. Email jeslynchua@thecouragechapter.com for queries.

Let’s Make Meaningful Change Together: Courage Cafe - MASTERMIND

All of our community members want to gain new opportunities to contribute to meaningful projects. However, the prelude to unlocking abundant opportunities for senior professionals is about designing new ways to work, advocate/changing mindsets, and growing together. Many things to be done.. 😁

Too often, we find ourselves waiting—for opportunities, for employers to change, for someone else to take action. But what if we became the change-makers? 🤔

We would like to invite you to our Mastermind Session - a collaborative problem-solving lab, where experienced professionals come together to tackle real employment barriers, develop solutions, and take ownership of driving change.

Instead of merely waiting for policy-changes or for companies to act, let’s in the meantime leverage our collective wisdom to build micro-projects, advocacy campaigns, and business solutions that make it easier for seniors to contribute meaningfully to the workforce.

Intrigued? Or know a friend who might benefit?

Sign Up for our Courage Mastermind on 23 April, 2pm - 5pm SGT, or sponsor a friend! More details here: https://tinyurl.com/ccmastermind1

Also… we are back at World Ageing Festival!

Last year, we had a blast at the World Ageing Festival. This year, we were invited back for #round2 from 8 - 9 April 2025! We would love to invite you to swing by to say hi (we are stationed at the SUSS booth). Register for free: https://www.worldageingfestival.com/waf2025

There are exciting topics this year: Women & Ageing, Policies on Ageing, Aging Care Products/tech, Cognitive Resilience, Affordability of Ageing, Care Economy, Building a Legacy with AI, and of course our favourite topic: EMPLOYMENT for second chapters! We will be speaking on 9 April, appx 930am on how you can build a fractional career… See you there!

Finally.. We also wanted to share updates on some success stories!

Over the past months, we’ve run the first batch of Unilever Reternship Programme, placing 10 SG-based senior professionals in various fractional (2 day/week) projects - Digital, Marketing, HR, Coaching etc. (one of them even did “ice cream scooping” in the Ben & Jerry’s cafe, haha! see pic below ;-))

Also, huge congrats to a couple more folks who landed roles in Financial Controllership, IT, admin, Fundraising, with clients in corporate & social sector :-)

We are excited for what’s to come in 2025, hang on tight and stay tuned! 🚀

In the meantime, hope to speak to more of you soon! We look forward to seeing you in various capacities and supporting you on this journey together.

Warm regards,
Kai Ning & Jesslyn
The Courage Chapter

In a blink of an eye, it is already mid-feb! Hope that you’ve had a lovely festive period. We’ve had quite some new community members join us recently - warm welcome to all 😊

We’ve been keeping busy, with new clients hiring for various roles (I’ll share our job board link at the bottom of this email), and organising the Unilever Reternship Programme for the 2nd year now! More on that later, but for now…

Having run The Courage Chapter for >1 year, we’ve spoken to hundreds of community members, and we found one consistent theme - in this life stage, you want meaningful ways to contribute your expertise, especially in the social sector.

However, some were unsure how to pivot into the sector, or whether they had the relevant skills. In the upcoming months, we’d be rolling out some initiatives to help you explore & transition into the social sector.

We’ve invited some esteemed speakers for an “Ask-Me-Anything” Session about the Social Sector [Limited Slots Available]

𝑫𝒂𝒕𝒆 & 𝑻𝒊𝒎𝒆: 15 March 2025, 930am - 12pm
𝑽𝒆𝒏𝒖𝒆: Yong-en Active Hub
𝑹𝒆𝒈𝒊𝒔𝒕𝒆𝒓 𝒉𝒆𝒓𝒆: Turning Success into Significance in the Social Sector

Panelists: Bruce Liew - NCSS Director of People Strategy, Genevieve Chua - Chairperson of RSVP, Tim Lee - Executive Director of Yong En Care Centre, Bernard Chew - CEO of St. Andrew’s Autism Centre

In this session, you'll discover:

• Why senior professionals are increasingly turning to the social sector and what keeps them inspired

• The emerging trends and the evolving landscape of social impact, high-demand skills & expertise

• Our panelists' personal experience working in the sector (incl. surprising lessons learned along the way!)

• Practical advice for senior professionals considering this transition

The Courage Chapter will also introduce unique project opportunities in the social sector on the day!

Still unsure what roles/projects you’d be keen to do? Join us for a sharing at National Library Board, on 4 March 2025 - 12pm

How may we ignite our next chapter and extend career longevity? Look forward to discussion topics like what is the new normal, hybrid retirement - portfolio careers, and hearing real-life stories on how others have made their transition!

𝑫𝒂𝒕𝒆 & 𝑻𝒊𝒎𝒆: 4 March 2025, 12pm - 1pm
𝑽𝒆𝒏𝒖𝒆: National Library - Launch Programme Room
𝑹𝒆𝒈𝒊𝒔𝒕𝒆𝒓 𝒉𝒆𝒓𝒆: Link

📢 We’ve now built a job board on The Courage Chapter Website! You can access it here: The Courage Chapter Job Board

Roles available:

• Finance Roles (Director/Controller/Executive)

• Fundraising Roles

• Communications & Marketing Roles (Manager/Executive)

• CEO of Social Sector Agencies (pls WA Kai Ning @ 96464458 if you’re keen to explore as we have some roles not listed on job board)

• Other social sector roles that care for elderly, at-risk youth

Please explore and put in your application through the job board.

Wishing you a wonderful week ahead. As usual, please don’t hesitate to drop us an email if you’ve any questions/feedback.

Best regards,
Kai Ning & Jesslyn
The Courage Chapter