Make It Work

There's a moment in early motherhood that most never admit out loud. The moment you look at your baby and think — I didn't sign up for this. When the career you spent a decade building feels like it's slipping away. When you wonder if choosing to have children was a mistake.

Professor Winnie Jiang went there. And she came out the other side with the science to explain why — and what to do about it. I first reached out to Professor Winnie 2 years ago and it’s a conversation that was definitely worth the wait!

Winnie is an organizational behavior professor at INSEAD Singapore, a Yale PhD, and one of the world's most influential management thinkers (Thinkers50 Radar Class). But in this conversation, she shows up first as a young mom of two under five — still in the trenches, still figuring it out, just like the rest of us.

From Singapore's unique pressures on working mothers to navigating a dual-career marriage without letting resentment quietly build, we go deep on the things working moms in Asia rarely say out loud.

What we get into: 
😶 The shame of not wanting to call yourself a mother — and why it makes complete sense 
💔 Why the "back to work after three months" fantasy falls apart, and what the timeline actually looks like
 ⚖️ The invisible power struggle happening in dual-career marriages — and the conversation that can fix it 
🧭 The six anchors of meaning that explain why your job can feel empty even when it looks great on paper 
🤖 Why AI might give working moms something no one else has — time
If you've ever felt like a worse professional for becoming a mother — or a worse mother for caring about your career — this episode was made for you.

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Chapters:
00:00 When Motherhood Feels Like a Career Killer 
01:12 Introduction
02:59 Finding Your Spring After the Hardest Winter 
04:05 Why Your Village Changes Everything 
09:58 How to Find Meaning When You're Running on Empty 
26:28 Why Work Feels Like a Relief (And That's Okay) 
27:03 The 6 Anchors That Make Work Feel Worthwhile 
31:21 The Resentment No One Talks About in Marriage 
43:02 What Workplaces Get Wrong About Working Moms 
49:30 Could AI Actually Give Moms Their Time Back?
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Connect with Winnie: 
👋 LinkedIn: https://www.linkedin.com/in/winnie-jiang-363ab745/
👋 Instagram: https://www.instagram.com/winnieeeyunn/

Follow Make It Work! ⁠https://linktr.ee/makeitwork.podcast⁠
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📥 Email: [email protected]
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#WorkingMoms #CareerSeasons #ModernMotherhood #Resilience #WomenInLeadership #MakeItWorkPodcast

In this special Mother's Day episode, I sit down with the OG of Make It Work: the woman who shaped me to uncover stories we’ve never actually talked about and how she ‘made it work’ as a working mom for our family of 5 back in the 90s. We dive into the hilarious, honest clash between Gen X and millennial "gentle parenting," where she shares her unfiltered take on my modern motherhood choices. We also unpack emotional childhood moments—including a surprising memory I had completely forgotten and remembered very differently!

In a very personal and heartwarming conversation, we explored: 
🕰️ How she navigated intense workdays and early motherhood (and why she refuses to use the word "burnout") 
🤯 The hilarious generational divide over how millennial parents approach things—from assessing danger to baby-led weaning 
💡 How we remembered the exact same core childhood memory entirely differently 
🤝 The secret to our strong relationship today 
🌟 How she survived the darkest tunnels of marriage and motherhood 
🙋🏻‍♀️ Her answers to questions that listeners sent through!

Whether you are navigating generational differences with your own parents (or children!) or just trying to survive the daily juggle, I think this episode will hit home for many of us.
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Chapters:
00:00 - Is It Burnout or Just Motherhood?
01:28 - OG of Make It Work
03:51 - When Ambition Meets Early Motherhood
07:49 - The Quiet Hard Parts of Marriage
19:14 - Two Generations, Two Very Different Approaches
23:57 - Growing Into Ourselves
24:51 - CCAs, Tuition, Pressure & Trying to Fit In
27:29 - What Gen X Really Thinks About Gentle Parenting 
31:38 - The Memory We Remembered Completely Differently
38:37 - What Makes Us Work
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Watch more:
From $2K Salary to Financial Independence: A Working Mom’s Playbook ft. SG Budget Babe: https://youtu.be/dJTtBomK9_s
When You Show Up Anyway: A Mother’s Story of Loss and Leadership - Maria Li: https://youtu.be/Pwv8XfGJp9A
Navigating Life's Transitions With Belief - Sarah Wong | On The Soft Power Project: https://youtu.be/H2Lb05Awnm8
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Follow and connect with Sarah & Make It Work! ⁠https://linktr.ee/makeitwork.podcast⁠

📷 ⁠Instagram:⁠ https://www.instagram.com/makeitwork.asia/
💼⁠LinkedIn⁠: https://www.linkedin.com/company/make-it-work-asia-podcast/
🎵 ⁠Facebook⁠: https://www.facebook.com/people/Make-It-Work/61566472637714/
🍏Apple: https://podcasts.apple.com/us/podcast/make-it-work/id1701442085
🎵Spotify: https://open.spotify.com/show/78ulY0B27nYxGB6jPCABPI?si=abfc48d037d943be
📥⁠Email⁠: [email protected]
Join our free ⁠Mommas Making It Work whatsapp community⁠ to find a group of like-minded mommas: 
https://bit.ly/MIWcommunity
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#WorkingMoms #MillennialMotherhood #Gentleparenting #MotherhoodUnplugged #HappyMothersDay #MakeItWorkPodcast

What happens when the traditional career ladder meets the reality of motherhood?
In this episode, I am joined by Huda R (founder of The Mum Collective and host of Mum Interrupted podcast) to unpack the reality of navigating ambition and motherhood in Singapore.
Huda and I started on very similar tracks, climbing the corporate ranks before motherhood brought an unexpected forcing function to our lives. Today, we sit down to discuss how those parallel tracks diverged into different—but equally ambitious—destinations. We dive into how we are intentionally channeling our drive today: from my journey of building a portfolio career that protects my flexibility, to Huda’s path of homeschooling her kids and fostering deep connections through her Mum Circles.
If you’ve ever felt torn between the career you built and the mother you want to be, this episode is your reminder that you can write your own script.

In this episode which felt like two friends trading stories and comparing notes, we talked about:
- The concept of "downshifting" — and why navigating a career pause is harder, not easier
- Owning your decisions (and why it's okay to change your mind)
- The very real tension of raising kids outside the mainstream in Singapore — enrichment classes, primary school pressure, and swimming against the tide
- What "matrescence" is and why no one warned us about the internal shifts of becoming a mum
- My journey from a borrowed microphone to nearly 40 episodes
- Mum guilt and the mental load — what equity really looks like when both parents are working
- Why community outside your usual circles can be the thing that saves you in a season of uncertainty
- What a portfolio career actually looks like, and how the "wilderness period" can be reframed as an investment
- Raising kids outside the structured preschool system in Singapore — what a typical day looks like for Huda
- The "Singapore script" — how cultural expectations shape the way we judge ourselves and each other as mothers
- How faith has deepened and shifted through the journey of becoming a mum
- Finding your way back to ambition without losing the flexibility you fought hard for
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Connect with Huda:
Instagram: @themumcollective.sg
Substack: https://themumcollectivesg.substack.com

Resources:
-The Power Pause by Neha Ruch
-Two Truths newsletter
-Portfolio Careers Asia
-Remarkable Women group
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1:31 – How our podcasting journeys began
3:52 – Origins of the 'Make It Work' podcast
7:42 – Standout truths from interviewing dozens of mums
8:19 – "Downshifting" — reframing career pauses
11:56 – Owning your decisions (and changing your mind)
16:46 – How 'Mum, Interrupted' came about
18:07 – Mum guilt & the mental load
18:41 – What still feels unresolved after all these conversations
19:30 – The enrichment class pressure & primary school anxiety
23:42 – What does a "homeschool" day actually look like?
25:56 – "I'm hesitant to call it homeschooling..."
28:38 – Resources & books that helped
35:31 – The Singapore script — and questioning it
52:09 – Sarah reflects: the ambition piece
55:11 – Faith and becoming a mum
55:11 – Can we have it all?
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Follow and connect with Sarah & Make It Work! ⁠https://linktr.ee/makeitwork.podcast⁠
📷 ⁠Instagram:⁠ https://www.instagram.com/makeitwork.asia/
💼⁠LinkedIn⁠: https://www.linkedin.com/company/make-it-work-asia-podcast/
🎵 ⁠Facebook⁠: https://www.facebook.com/people/Make-It-Work/61566472637714/
🍏Apple: https://podcasts.apple.com/us/podcast/make-it-work/id1701442085
🎵Spotify: https://open.spotify.com/show/78ulY0B27nYxGB6jPCABPI?si=abfc48d037d943be
📥⁠Email⁠: [email protected]
Join our free ⁠Mommas Making It Work whatsapp community⁠ to find a group of like-minded mommas: 
https://bit.ly/MIWcommunity

#MakeItWorkPodcast #WorkingMothers #CareerAndMotherhood #CareerTransition #PodcastForMoms

From saving $20,000 on a $2,000 salary to making work optional while raising two young boys, Dawn Fiona Cher—better known online as SG Budget Babe—has spent the last decade helping others take back control of their money and mindset. A mom, author, Director of Government Affairs , and financial educator, Dawn continues to work in both corporate and content creation—not because she has to, but because it fuels her purpose.

In this episode, I sit down with Dawn to talk about what it really takes to grow your wealth while juggling motherhood, ambition, and a life you actually want to live. She shares the turning point that made her chase financial freedom harder than ever (hint: it happened mid-breastfeeding), the unglamorous truth of building a side hustle, and how she successfully negotiated for flexibility at work after proving her worth.

Dawn opens up about how her own childhood struggles with money shaped her, why time-blocking (not 5AM routines) keeps her grounded, and the life lessons she’s deliberately modeling for her kids. Her practical, no-nonsense wisdom is a refreshing reminder that success isn’t about balance—it’s about clarity, discipline, and alignment.

In this energizing conversation, we explored:
📈 How Dawn reached financial independence in slightly over a decade (and still works by choice)
👶 The raw truth about managing work while mothering two young kids
🧠 Why “imposter syndrome” is actually a signpost—not a dead end
🗂️ How she schedules her chaotic week using time-blocking, not rigidity
💡 What it means to be visible, credible, and irreplaceable at work
✍️ Her journey from corporate employee to trusted voice in finance—and what’s next

Checkout:
💻 Dawn’s 7-Day Investing Challenge (Discount code: MIW) →https://nas.io/budgetbabe/challenges/investing-101-crash-course?discountCode=MIW

📘 Take Back Control of Your Money by Dawn Fiona Cher → https://www.amazon.sg/Take-Back-Control-Your-Money/dp/9815323075

🎤Sarah’s interview with Dawn on The Financial Coconut: I Left My Job to Care for My Family - Was It Worth It? [W&S 144]
https://www.youtube.com/watch?v=v6p3G4lZjBk&list=PLpo30qPT9yc6yAyrtqz7506sfiYaorR8Z&index=6

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Chapters:
00:00 Intro
01:07 Meet SG Budget Babe: PI, Mom, Finfluencer
02:08 From $2K Salary to Financial Freedom
05:39 How She Actually Juggles It All
13:26 The Call That Changed Everything
25:50 How She Earned Trust at Work
26:26 Are You Invisible at Work?
31:06 How She Negotiated Flexibility
34:09 The Rule Behind Her Side Hustle Growth
42:31 How She’s Raising Money-Smart Kids
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Connect with Dawn here:
👋 Website: https://sgbudgetbabe.com/
👋 LinkedIn: https://www.linkedin.com/in/fionacher/
👋 Instagram: https://www.instagram.com/sgbudgetbabe/

Follow and connect with Sarah & Make It Work! ⁠https://linktr.ee/makeitwork.podcast⁠

📷 ⁠Instagram:⁠ https://www.instagram.com/makeitwork.asia/
💼⁠LinkedIn⁠: https://www.linkedin.com/company/make-it-work-asia-podcast/
🎵 ⁠Facebook⁠: https://www.facebook.com/people/Make-It-Work/61566472637714/
🍏Apple: https://podcasts.apple.com/us/podcast/make-it-work/id1701442085
🎵Spotify: https://open.spotify.com/show/78ulY0B27nYxGB6jPCABPI?si=abfc48d037d943be
📥⁠Email⁠: [email protected]

Join our free ⁠Mommas Making It Work whatsapp community⁠ to find a group of like-minded mommas: 
https://bit.ly/MIWcommunity
—-------------------------------

#WorkingMom #FinancialFreedom #SGbudgetbabe #CareerTips #InvestingForBeginners #ProductivityForMoms #MakeItWorkPodcast #WomenWhoLead #SideHustleSuccess

From a 15-year career at Procter & Gamble to taking a 4 year career pause to be a stay-home-mom to building ConnectOne, a company that helps high-growth startups find and develop their teams — Elena Chow has spent decades helping others build meaningful careers, all while raising four children and navigating her own seasons of work and motherhood.

In this episode, I sit down with Elena, who shares her rare honesty about the paradox of being around but not present, what “balance” really looks like in different seasons of life, and why sometimes, the bravest thing a woman can do is pause.

Elena opens up about stepping away from corporate life, starting over as an entrepreneur in her 40s, and how faith, community, and purpose guided her through each transition. As a recruiter and pioneer member of the Portfolio Careers Asia group, she also shares her candid advice for mothers today — whether you’re taking a break, returning to work, or exploring a more flexible, fractional path.

As a mother, founder, and mentor to many, Elena reminds us that having it all doesn’t mean doing it all — it means understanding the season you’re in, and choosing what matters most in it.

In this heartfelt conversation, we explored:
💼 How Elena pivoted from corporate to entrepreneurship — and built Connect One from scratch
🧭 What it means to “fake it till you make it” with courage and humility
👩‍👧‍👧 The hardest lesson about being present as a working mom
💬 Why there’s no such thing as perfect work-life balance — only shifting seasons
✨ How women can thrive in today’s world of fractional work, portfolio careers, and flexible opportunities

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Chapters:
00:00 Debunking Work-Life Balance Myths
01:01 Introduction
03:14 How She Knew It Was Time to Leave Corporate
07:56 The Hardest Part of Being a Mom-Entrepreneur
16:08 What She Wishes She Knew Earlier
24:52 The Unexpected Way Her Kids Learned
26:25 Why Volunteering Changed Everything
27:16 The Trips That Shifted Her Family’s Worldview
31:06 The Truth About Career Pivots for Moms
42:21 The One Thing Moms Returning to Work Must Hear
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Connect with Elena here:
👋 ConnectOne: https://www.connectone.com.sg/
👋 LinkedIn: https://www.linkedin.com/in/elenachow/
👋 Join Portfolio Careers Asia group: https://www.linkedin.com/groups/14287306

Watch more:
When You Show Up Anyway: A Mother’s Story of Loss and Leadership - Maria Li: https://youtu.be/Pwv8XfGJp9A
Navigating Life's Transitions With Belief - Sarah Wong | On The Soft Power Project: https://youtu.be/H2Lb05Awnm8
Parenthood Across 10 Countries: The Village Every Parent  Needs - Marina Lopes: https://youtu.be/hDMbVn725uA
29 Weeks Too Soon: Motherhood, Identity, and Building Something Radically New: https://youtu.be/Yau2wLUNS5U?si=srWjlnBhnBKuqZ9o

Follow and connect with Sarah & Make It Work! ⁠https://linktr.ee/makeitwork.podcast⁠
📷 ⁠Instagram:⁠ https://www.instagram.com/makeitwork.asia/
💼⁠LinkedIn⁠: https://www.linkedin.com/company/make-it-work-asia-podcast/
🎵 ⁠Facebook⁠: https://www.facebook.com/people/Make-It-Work/61566472637714/
🍏Apple: https://podcasts.apple.com/us/podcast/make-it-work/id1701442085
🎵Spotify: https://open.spotify.com/show/78ulY0B27nYxGB6jPCABPI?si=abfc48d037d943be
📥⁠Email⁠: [email protected]

Join our free ⁠Mommas Making It Work whatsapp community⁠ to find a group of like-minded mommas: 
https://bit.ly/MIWcommunity
—-------------------------------

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#WorkingMoms #CareerTransitions #FractionalCareers #WomenInLeadership #MakeItWorkPodcast #WorkingMom #FutureOfWork