In an era where the internet and creator economy are reshaping careers, a traditional 9 to 5 is no longer the only way to make a living. This podcast explores the stories of people who’ve chosen unconventional career paths—be it entrepreneurship, freelancing, or content creation. Join us as we invite guests from diverse backgrounds to share their journeys, insights, and advice on building fulfilling, nontraditional careers.
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
Inside the Private Network World: Christine Song on Reputation, Founders & the Courage to Start Over
Christine Song, founder of Five to Nine Society, discusses transitioning from a corporate HR career to entrepreneurship, building a private network, and navigating the challenges of startup life in an interview with Maggie, offering insights into founder dynamics and personal fulfillment.
5 Nov 2025
Choosing to Build: Jia Chen on Risk, Hackathons, and Founding Early
Founder Jia Chen discusses with host Maggie her journey of foregoing traditional software engineering roles to establish her own company, offering insights into entrepreneurship and creative pursuits in an interview.
28 Oct 2025
What Happens After You ‘Make It’ with Zach Wilson
Zach Wilson, data engineer and founder, explores the challenges of finding purpose and meaning after achieving conventional success, discussing burnout, identity, and redefining achievement in an interview.
21 Oct 2025
Unlearning Success: Rachel's Journey from Tech Layoffs to Food Media Founder
Rachel describes her transition from tech layoffs to founding a food media company, highlighting the process of redefining success; this is an interview.
14 Oct 2025
In Conversation with Maddy Zhang: Breaking into Big Tech and Beyond — Google, Airbnb & More
Maggie interviews Maddy Zhang, a software engineer, who recounts her experiences at major tech companies like Google and Airbnb, discussing career navigation and creative expression.
7 Oct 2025
Do Bold Sh*t: Robb Gilbear on Coaching, Identity & The Future Beyond 9 to 5
Robb Gilbear discusses his unconventional journey from music and corporate HR to founding a coaching business, Growth Habit, exploring themes of identity, entrepreneurship, and creating meaningful work in this interview.
23 Sept 2025
From Wall Street 9-to-5 to Wellness Startup: Selina Li on Building Gymii
Selina Li discusses transitioning from Wall Street to founding Gymii, an AI-powered nutrition app, after leaving finance to pursue her entrepreneurial passion in this interview with Maggie Mae.
13 Jun 2025
‘I don’t regret skipping 9-5 to build AI Agents’ with Chatforce CEO Robert Ciborowski
Chatforce CEO Robert Ciborowski discusses his journey from university to founding an AI automation startup, highlighting the challenges and strategies that led to early investor interest in this interview episode.
6 Jun 2025
How to Know When It's Time to Leave Your Job (7 Research-Backed Signs)
Host MAGGIE INDATA shares research-backed signs and actionable frameworks, including Jeff Bezos' regret minimization framework, to help listeners decide when to leave their jobs in this solo episode.
20 May 2025
C-Suite to Serenity: Letting Go of Prestigious Titles with Jenn Bieri
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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
12 Apr 2025
Why Discipline Doesn’t Work: Janis Ozolins on the Process of Elimination and Experimentation
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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
4 Apr 2025
'I Left Private Equity to Start a Yogurt Company': Kiki Couchman on Building in Public
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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
28 Mar 2025
"I Turned Down Job Offers Post Layoff": Ashna Mankotia’s Tech to Apparel Leap
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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
21 Mar 2025
Burnout to Breakthrough: Megan Lieu on Building an Authentic Personal Brand
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/ (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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
13 Mar 2025
Crafting a Business You Love by Doubling Down on Your Strengths with Nick Singh
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/ (https://www.linkedin.com/in/nick-singh-tech/)
DataLemur: https://datalemur.com (https://datalemur.com/)
Ace the Data Science Interview: https://amzn.to/4iNfYZZ (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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
7 Mar 2025
How to Discover Your Startup Idea and Scale From 0 to 1 Million with Julius Founder Rahul Sonwalkar
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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
28 Feb 2025
The Time I Left My 9 to 5 Trailer: The Truth Behind Dream Jobs with Maggie Ma
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
Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.
Who has been a guest on The Time I Left My 9 to 5
Names identified in recent episode analyses. Showing up to five guests.
Christine Song
Jia Chen
Zach Wilson
Rachel
Maddy Zhang
Reach and audience
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Apple Podcasts (US)
5.0 / 5
1 ratings
Podcast Authority Score: 6 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
13
Social presence
0
YouTube
0
Engagement
0
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Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about The Time I Left My 9 to 5
Who hosts The Time I Left My 9 to 5?
Maggie host the show. Published by Maggie Ma.
How often do new episodes come out?
The show publishes weekly, based on its RSS feed.
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The show does not typically feature guests, based on episode analyses.
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