The Time I Left My 9 to 5

Inside the Private Network World: Christine Song on Reputation, Founders & the Courage to Start Over

Wed, 26 Nov 2025 14:00:00 GMT

Christine Song spent ten years moving from corporate HR into high-growth startups, serving as Head of People and CPO across multiple companies, hiring executives, supporting founders, and navigating the speed and pressure of early-stage environments. Eventually, she walked away from the C-suite to build something of her own. Today, she’s the founder of Five to Nine Society, an invite-only network for operators, founders, and investors.

In this episode of The Time I Left My 9 to 5, Christine Song shares why she outgrew the startup people-ops path, how she knew she was in the “danger zone” of boredom, and what shifted as she stepped into entrepreneurship. We talk about founder dynamics, performance, backdoor references, building a reputation you can stand behind, the realities of burnout, finding grounding outside of work, and how she grew an audience by saying what most people in HR won’t.

📲 Stay Up to Date with the Show:

Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

Podcast YouTube: @thetimeileftmy9to5.podcast

00:00 Introduction

01:57 Christine’s Career Journey

03:24 Transition to Entrepreneurship: Building Five to Nine Society

04:18 Inside the Role of a Chief People Officer

06:22 Startups vs. Corporate: Challenges, Rewards, and Key Differences

08:15 Taking the Leap into Entrepreneurship

11:25 Support Systems, Runway, and Assessing Risk

15:10 What Five to Nine Society Is and Why It’s Invite-Only

25:36 Why Founders Need to Diversify

26:20 Building a Network Through Social Media: The Good and the Bad

31:06 Balancing Work and Personal Life

35:00 The Realities and Challenges of Startup Life

37:42 Making the Leap (Again) into Entrepreneurship

42:14 Christine’s Vision and Advice for Aspiring Entrepreneurs

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Choosing to Build: Jia Chen on Risk, Hackathons, and Founding Early

Wed, 05 Nov 2025 20:31:00 GMT

In this episode of The Time I Left My 9 to 5, Maggie sits down with Jia Chen, a 21-year-old founder, indie musician, and content creator who turned down software engineering offers from Disney and Intuit to build her own company.

Jia shares her journey from studying finance to switching into computer engineering, winning 23 hackathons, and raising six figures in funding after a viral pitch video. Jia opens up about navigating parental expectations, building Sprint.dev to 20,000 users and $48K profit, and balancing creativity across music, tech, and social media.

Whether you’re a student, early-career creative, or aspiring founder, Jia’s story is a masterclass in following curiosity, betting on yourself, and building in public.

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What Happens After You ‘Make It’ with Zach Wilson

Tue, 28 Oct 2025 18:27:25 GMT

This isn’t just a story about quitting a job — it’s about rediscovering meaning after you’ve already “made it.” 

Zach Wilson, data engineer turned creator and founder, walked away from a high-paying career in big tech to build something of his own. What started as a leap toward freedom became a deeper journey into burnout, identity, and what success really means once you already have it. 

In this conversation, we unpack what it really takes to build a meaningful life after success — systems over ambition, investing and learning from a new form of education, integrity over hype, and the long game of finding purpose in your work. 

If you’ve ever wondered what comes after achievement, this episode will hit close to home.

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Unlearning Success: Rachel's Journey from Tech Layoffs to Food Media Founder

Tue, 21 Oct 2025 20:30:00 GMT

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In Conversation with Maddy Zhang: Breaking into Big Tech and Beyond — Google, Airbnb & More

Tue, 14 Oct 2025 18:00:00 GMT

In this episode of The Time I Left My 9 to 5, Maggie sits down in San Francisco with Maddy Zhang, a senior software engineer and content creator with over 100,000 followers online.

Maddy opens up about her journey from studying computer science at MIT to landing roles at Amazon, Microsoft, Google, and Airbnb. She shares how she navigated rejections, defined impact in her work, and built a creative outlet through social media.

From the realities of Big Tech to handling online criticism and finding meaning beyond work, Maddy’s story is full of insight and inspiration for anyone pursuing a career in tech—or looking to express themselves outside of it.

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Do Bold Sh*t: Robb Gilbear on Coaching, Identity & The Future Beyond 9 to 5

Tue, 07 Oct 2025 18:00:00 GMT

Robb Gilbear’s journey has been anything but linear, from dropping out of high school, building record labels, and DJing internationally to climbing the corporate HR ladder before founding Growth Habit, a coaching business built on boldness and authenticity.

In this conversation, Robb shares why leaving the 9–5 was a “20 out of 10” decision, the hidden costs of job security, and why entrepreneurship is both the biggest challenge and greatest self-development journey. We dive into identity, ego death, money mindsets, and how to give yourself permission to create meaningful work in a changing world.

If you’ve ever wondered what it really takes to leave the corporate path and build your own, this episode is for you.

📲 Stay Up to Date with the Show:

Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

Podcast Youtube: ⁨@thetimeileftmy9to5.podcast⁩

Chapters

- 0:00 Intro

- 2:40 Returning to Entrepreneurship: The Old Market is Gone

- 6:06 The Trade of Entrepreneurship: Choosing Passion Over Stability

- 12:54 Is Entrepreneurship Really for Everyone?

- 15:46 Finding My Path Early: Dropping Out of High School

- 17:30 Entrepreneurship in the Blood: Ice Cream Bikes, Hustles & Military Discipline

- 19:21 Giving Myself Permission: Outsider Energy, DIY Flyers & Sharing a Bill with Daft Punk

- 22:29 Parenting & Struggle: Redefining Success While Raising Kids in Debt

- 25:49 The Corporate Pivot: From High School Dropout to HR

- 32:27 Realizing Music Was Avoidance & Coaching Was the Path

- 34:24 Going All-In on Growth Habit

- 38:06 From Golden Handcuffs to First Clients: Advice for Sarah & Marcus

- 47:33 Reframing Sales: Why Coaches Struggle to Sell & How to Shift

- 52:45 The Common Denominator in Every Thriving Practice

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From Wall Street 9-to-5 to Wellness Startup: Selina Li on Building Gymii

Tue, 23 Sep 2025 16:47:58 GMT

Selina Li grew up in Hong Kong playing competitive golf for 16 years, even representing the national team, before heading to Penn to study economics. That path led her into a quant role at JP Morgan — but the 9-to-5 left her searching for more. Selina left finance to pursue computer science at Cornell Tech, where she started building Gymii, an AI-powered nutrition tracking app inspired by her athletic background.

*Use promo code "MAGGIE" to get 15% off Gymii!*

In this episode, Selina shares her journey from sports to finance to startups, the identity shift she faced leaving golf, the reactions she encountered when walking away from a prestigious job, and how she grew Gymii from an idea rooted in a personal challenge into a fully launched app.

📲 Stay Up to Date with the Show:

Host Instagram: / @maggieindata

Podcast Instagram: / thetimeileftmy9to5.podcast

Podcast YouTube: / @thetimeileftmy9to5.podcast

Chapters

00:00 – Introduction

01:51 – Selina Li’s Story in Brief

02:51 – Starting Gymii: The First Steps

05:27 – What is Gymii?

06:30 – Leaving Competitive Golf After 16 Years

08:43 – Life at JP Morgan: Lessons from the 9–5

13:30 – Quitting Finance: Reflections and Reactions

18:23 – The Cornell Tech Experience

23:40 – Finding the Right Co-Founder

26:32 – Future Plans & Advice for Aspiring Entrepreneurs

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‘I don’t regret skipping 9-5 to build AI Agents’ with Chatforce CEO Robert Ciborowski

Fri, 13 Jun 2025 17:18:27 GMT

In this episode of The Time I Left My 9 to 5, we dive into the inspiring journey of Robert Ciborowski, CEO and co-founder of Chatforce. Skipping the traditional route, Robert transitioned directly from graduating from the University of Toronto to building his own startup. He shares his background, the challenges of founding a company, and the dynamic of working with three co-founders.

Robert discusses Charforce's innovative approach to AI automation, their unique features, and the successful strategy that garnered early investor interest. He provides valuable advice for aspiring entrepreneurs on ambition, building the right team, and the importance of lifelong learning. This episode is a deep dive into the life of a young founder making waves in the AI-driven startup landscape.

📲 Stay Up to Date with the Show:

Host Instagram: https://www.instagram.com/maggieindata

Podcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcast

Podcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast

Chapters

00:00 Highlight Overview

01:20 Robert's Journey from University to Startup

04:35 Early Coding and Game Development

08:10 Building the Capstone Team

12:39 Family Influence and Support

17:13 The Six-Month Gray Area

21:13 The Birth of Chatforce

22:48 The Three Co-Founder Dynamic Revisited

25:14 Empowering Knowledge Workers with AI Agents

28:15 The Philosophy Behind Chatforce

31:33 Getting Noticed by Investors

39:50 Advice for Aspiring Entrepreneurs

41:56 The Importance of Independent Learning

43:59 Leveraging AI Tools and Resources

53:09 Balancing Building and Learning

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How to Know When It's Time to Leave Your Job (7 Research-Backed Signs)

Fri, 06 Jun 2025 18:02:47 GMT

Welcome to the very first solo episode in the history of The Time I Left My 9 to 5 podcast! I asked on my Instagram what questions you had when it comes to considering leaving your 9 to 5, and I am answering all of them in this episode. I intentionally designed this episode to be research and statistics driven so that you can walk away with actionable frameworks that you can use to apply to your specific situation~

What You'll Learn:

✅ The Regret Minimization Framework - Jeff Bezos' decision-making tool for major life changes

✅ Why 82% of businesses fail (and how to avoid becoming a statistic)

✅ The exact amount you should save before quitting (hint: it's more than 6 months)

✅ The "If-Then Planning" method that increases goal achievement by 300%

✅ How to stay accountable when you're your own boss

✅ The 10-10-10 Rule for making tough decisions

✅ Why your nonprofit/teaching skills are actually gold in the corporate world

📲 Stay Up to Date with the Show:

Host Instagram: https://www.instagram.com/maggieindata

Podcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcast

Podcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast

00:00 - Introduction

02:15 - "How do you report to yourself?"

03:35 - If-Then Planning Method

05:45 - "How did you know it was time?"

06:10 - Regret Minimization Framework

07:30 - The 10-10-10 Rule

10:25 - "How much money should I save?"

12:00 - Ramen Profitability Calculation

12:40 - "How to test a career pivot?"

13:50 - 4 Ways to Test Drive

15:25 - "Pivoting from nonprofit?"

17:20 - "Leaving a permanent teaching job?"

18:20 - Loss Aversion Psychology

19:25 - Get your answers answered

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C-Suite to Serenity: Letting Go of Prestigious Titles with Jenn Bieri

Tue, 20 May 2025 15:45:35 GMT

In this episode, Jenn, a former global head of business operations, discusses her challenging transition to becoming a yoga teacher and later a professional coach. She opens up about the identity shift, financial concerns, and personal growth she experienced during this transformative period. Jen shares insights into how she balanced multiple ambitions, navigated significant life changes, and ultimately found a fulfilling career in coaching and leadership development. Her journey underlines the importance of self-discovery, support systems, and continuous learning in achieving career fulfillment.

📲 Stay Up to Date with the Show:

Host Instagram: https://www.instagram.com/maggieindata

Podcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcast

Podcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast

00:00 Introduction and Identity Shift

02:14 Journey from Accounting to Tech

03:18 Starting a YouTube Channel

04:01 Transition to Full-Time Yoga and Coaching

12:24 Navigating Financial Stability

17:30 Coping with Identity Shift

21:14 Building a Coaching Business

30:14 Future Plans and Advice

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Why Discipline Doesn’t Work: Janis Ozolins on the Process of Elimination and Experimentation

Sat, 12 Apr 2025 12:00:00 GMT

Ever felt stuck in a job that doesn’t excite you? Or maybe you’ve spent months—even years—chasing a side hustle with no results? Janis Ozolins knows exactly how that feels. For four years, he tried everything—YouTube, blogging, podcasting—with zero measurable success. No audience. No money. Just relentless trial and error.

But he never gave up.

In this episode The Time I Left My 9 to 5 podcast, we dive into:

How he stayed motivated when nothing was working (hint: it wasn’t just discipline).
The exact moment he realized he was living in a bubble—and how a single book shattered his limiting beliefs.
Why his first "successful" business model wasn’t sustainable—and how he finally found the sweet spot between passion and profit.
The financial rollercoaster of entrepreneurship—how he planned his escape from the 9-5 (with a pregnant wife and a mortgage).
The biggest mistake he made while building his side hustle (spoiler: it involves switching jobs at the worst possible time).

If you’ve ever doubted whether you’re cut out for entrepreneurship, or if you’re tired of grinding with no results, this episode is for you.

📲 Connect with Janis:

Instagram: https://www.instagram.com/jaozolins

📲 Stay Up to Date with the Show:

Host Instagram: https://www.instagram.com/maggieindata

Podcast Instagram: https://www.instagram.com/thetimeileftmy9to5.podcast

Podcast YouTube: https://www.youtube.com/@thetimeileftmy9to5.podcast

00:00 Intro

01:29 The Journey Begins: From Corporate to Creative

04:37 The Struggles and Persistence

10:01 Discovering the Visuals Niche

18:45 Making the Leap: Quitting the 9 to 5

22:58 Financial Realities and Creative Freedom

26:43 Staying Relevant in Content Creation

31:32 Advice for Aspiring Entrepreneurs

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'I Left Private Equity to Start a Yogurt Company': Kiki Couchman on Building in Public

Fri, 04 Apr 2025 21:49:36 GMT

In this episode of The Time I Left My 9 to 5, Kiki Couchman is a Stanford grad who left her job in private equity to build a yogurt company with her best friend. Kiki is the cofounder of Beny Yogurt, and I have to say, she's probably one of the coolest founders I've ever interviewed in the history of this podcast. Kiki's story is one of calculated risk-taking and determination, as she left behind a successful career in private equity to build a consumer product from scratch with no investment funding.

What I love about Kiki's story is her unique approach to building a business. Kiki and her co-founder Elan chose to build their brand in public, sharing behind-the-scenes moments on social media, and has already gathered over 12,000 loyal customers before the brand has even launched. Her always-on launch strategy, combined with the fact that the company is 100% bootstrapped, has forced her and her cofounder to think carefully about each step and every decision. With her forward-thinking mindset, bias towards action, and bravery, Kiki’s commitment is driven by creating a product that truly makes a difference in people’s everyday lives.

Without a doubt, Kiki is an inspiration to anyone looking to make a change.

I’m super excited to share this conversation with you, what made Kiki decide to leave her 9 to 5 behind, and how she has navigated the challenges and opportunities of building a business from scratch. But before we jump in, I’d love if you could subscribe to the channel if you’re watching on YouTube or rate the podcast if you’re listening everywhere else. You have no idea how such a small action can help me to continue bringing you more unfiltered, real conversations just like this one.

📲 Connect with Kiki:

Instagram: @couchwoman

📲 Stay Up to Date with the Show:

Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

Podcast YouTube: @thetimeileftmy9to5.podcast

00:00 Introduction

02:53 Kiki's Journey from Private Equity to Entrepreneurship

04:21 Building Beny Yogurt: Challenges and Strategies 1

0:49 The Role of Social Media in Business Growth

17:58 Partnership Dynamics and Personal Growth

24:07 Financial Decisions and Bootstrapping

29:06 Advice for Aspiring Entrepreneurs

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"I Turned Down Job Offers Post Layoff": Ashna Mankotia’s Tech to Apparel Leap

Fri, 28 Mar 2025 19:04:00 GMT

In this podcast episode, Ashna Mankotia, a former product manager and current content creator, delves into her transition from working in tech to establishing her apparel brand, Bazaar Customs. Laid off just before her 30th birthday, Ashana took it as an opportunity to pursue her entrepreneurial dreams.

During the conversation, she talks about her community-building endeavor, Saffron, which she opted not to scale into a million-dollar business to maintain its true communal essence. Ashana candidly shares her experiences of the identity shift from a corporate role to an entrepreneur, the financial preparation involved, and the challenges she faced while starting a clothing brand. She also reflects on her self-discovery journey in India, a country she left as a child, and the nuanced feelings of what her life might have been like had she grown up there. The podcast aims to provide insights into the realities of leaving a stable job to build something independently and advises on balancing one's passion with practical considerations.

📲 Connect with Ashna:

TikTok: @ohmygoshna

Instagram: @ohmygoshna

📲 Stay Up to Date with the Show:

Host Instagram: @maggieindata

Podcast Instagram: @thetimeileftmy9to5.podcast

Podcast YouTube: @thetimeileftmy9to5.podcast

00:00 Introduction

01:14 Identity Crisis and Entrepreneurial Guilt

02:36 The Reality of Content Creation

06:54 The Layoff Experience

09:31 Financial Preparedness and Taking the Leap

12:58 The Struggle of Self-Identification

14:45 The Saffron Community: Passion vs. Business

18:31 Scaling to a Million Dollar Business

19:10 The Value of True Community

22:42 Launching a Clothing Brand: Bazaar

24:46 Self-Discovery and Cultural Reflection

28:24 Challenges of Starting a Physical Product Business

32:00 Advice for Aspiring Entrepreneurs

36:53 Redefining Success and Flexibility

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Burnout to Breakthrough: Megan Lieu on Building an Authentic Personal Brand

Fri, 21 Mar 2025 12:25:00 GMT

Megan Lieu is a former data scientist who transitioned to a full-time content creator with over a quarter-million followers on LinkedIn and Instagram. In this episode of The Time I Left My 9 to 5 Podcast, Megan shares her journey from relying on traditional job roles for identity and stability to betting on herself and building a successful side business that surpassed her tech salary. She discusses the instability of the 9-to-5 job market, navigating burnout, and the identity loss associated with leaving a corporate job. Megan also provides insights on building and monetizing a personal brand, the importance of relatability, and staying authentic while catering to a large audience. The episode highlights the empowering aspects of taking control of one's career and finding fulfillment beyond conventional paths.

📲 Connect with Megan:

LinkedIn: https://www.linkedin.com/in/meganlieu/

Instagram: @meglovesdata

📲 Stay Up to Date with the Show:

Host Maggie Ma: @maggieindata

Podcast: @thetimeileftmy9to5.podcast

00:00 Introduction

01:03 Meet Megan Lieu: From Data Scientist to Content Creator

02:27 The Decision to Leave the 9-to-5

04:22 Navigating Burnout and Identity Loss

09:15 Building a Personal Brand on LinkedIn

21:58 Monetizing Social Media and Future Plans

30:15 Advice for Aspiring Content Creators

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Crafting a Business You Love by Doubling Down on Your Strengths with Nick Singh

Thu, 13 Mar 2025 13:45:42 GMT

If you have been thinking about starting a side project for a while but unsure how to take that first step, Nick offers some invaluable advice in this episode!

Nick Singh is a LinkedIn top voice, best selling author, and founder of DataLemur, a platform that has helped over 200,000 people prepare for SQL and data science coding interviews.

Nick’s story isn’t just about leaving a 9-5. It’s about realizing he wasn’t using his full potential at big tech. In this conversation, Nick got extremely real about feeling below average at his software engineering job at Meta. This is a story of how he eventually decided to carve out his own niche instead of following the traditional career playbook. While many of Nick’s peers chased promotions or VC funding, Nick chose to write a book and build his own path, even when people doubted him.

We talked about the real side of leaving a 9-to-5—the struggles, the uncertainty, and the myth of overnight success. Nick opened up about questioning his career, tuning out outside noise, and staying action-biased instead of overthinking every move.

📲 Connect with Nick:

LinkedIn: https://www.linkedin.com/in/nick-singh-tech/

DataLemur: https://datalemur.com

Ace the Data Science Interview: https://amzn.to/4iNfYZZ

00:00 Introduction

00:32 Nick's Early Career and Realizations

01:15 The Decision to Leave Big Tech

02:36 Life After Quitting the 9 to 5

05:31 Finding and Validating New Ideas

13:05 The Importance of Commitment Over Ideas

18:58 Creating a Unique Niche

23:08 Balancing Work and Passion Projects

24:50 The Barbell Strategy Explained

28:35 Validating Ideas on LinkedIn

31:35 Overcoming Doubts and Criticism

35:02 Building DataLemur: Sacrifices and Lessons

40:46 Advice for Aspiring Entrepreneurs

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How to Discover Your Startup Idea and Scale From 0 to 1 Million with Julius Founder Rahul Sonwalkar

Fri, 07 Mar 2025 15:40:42 GMT

Rahul SonWalkar, an ex-software engineer at Meta and Uber, has scaled his tech startup, Julius AI, from 0 to 1 million users within the first year. His work has been so impactful that Harvard Business School now teaches analysis to their MBA students using Julius—an incredible achievement for a company that started from scratch.It’s impressive to see what he’s built in such a short time, especially considering that, at just 24 years old, Rahul walked away from a high-paying job in big tech with great career outlook to pursue his own vision.

If you’re thinking about starting your own business, trying to figure out which idea to put your efforts behind, this episode is a must-listen.

We discussed the complexities and uncertainties of leaving a stable job to pursue personal ideas and the process of validating those ideas. Rahul shared insights on building a user-focused product, scaling the business, and finding the right team members. More importantly, we touched on the challenges and sacrifices of being a founder, including maintaining personal relationships and managing work-life balance.

00:00 Introduction

01:23 The Leap from Corporate to Startup

04:18 Challenges and Realizations in the Early Days

11:35 Building and Scaling Julius AI

24:38 The Future of Julius AI and Data Science

31:56 Reflections and Advice for Aspiring Entrepreneurs

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The Time I Left My 9 to 5 Trailer: The Truth Behind Dream Jobs with Maggie Ma

Fri, 28 Feb 2025 22:43:33 GMT

In the debut episode of The Time I Left My 9 to 5, host Maggie Ma introduces the podcast, aiming to explore the stories and lessons from those who have moved away from traditional career paths. This podcast isn't about quitting for quitting's sake but rather about discussing career choices and redefining success on personal terms. Maggie shares her own journey from a data scientist in tech to an entrepreneur, highlighting the doubts, challenges, and insights gained along the way. Through candid conversations with various guests, listeners will get a deep dive into the emotional histories, wins, and failures of their career transitions. The show promises to challenge conventional thinking and open up discussions about the evolving landscape of fulfilling work in the modern era.

Time Stamp

00:00 Introduction to The Time I Left My 9 to 5

01:00 The Changing Landscape of Career Success

02:03 Maggie's Personal Journey

03:04 Inspiration Behind the Podcast

05:06 Sneak Peek of Upcoming Episodes

08:26 Final Thoughts

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