All Episodes

July 24, 2025 35 mins
What if the “dream job” you worked so hard to earn… wasn’t your dream anymore? In this episode, Natalie sits down with Lindsay MacMillan - a former VP at Goldman Sachs who walked away from a prestigious Wall Street career to follow a lifelong dream of becoming a published author. Since leaving Wall Street, Lindsay has signed major book deals with Penguin Random House, taken the TEDx stage four times, and created a multi-faceted creative business aligned with her values. Together, they unpack what it really takes to leave a good job, why the “Plan B” trap keeps so many women stuck, and how to navigate the financial, emotional, and identity shifts that come with choosing the creative path.  This conversation is an honest, vulnerable, and deeply empowering look at what happens when you stop settling for a life that looks good on paper, and start creating one that actually feels good. TIMESTAMPS 00:00 - Why Natalie cut her trip short + the power of honoring your season 01:03 - From Wall Street to writing: How Lindsay made the leap from VP to published author 02:32 - The real reason people are quitting corporate (hint: it’s not burnout) 04:47 - Walking away from a “good on paper” job to follow your dream 06:58 - How Lindsay earned a VP promotion, and still knew it was time to go 09:05 - The simple shift that helped her unlock work-life balance (and still get promoted) 10:32 - Why prioritizing creativity made her better at her corporate job 12:31 - A realistic financial game plan for leaving a high-paying job 17:00 - How to build a portfolio career that funds your creativity and freedom 21:00 - The mindset shift that helped Lindsay stop working like she was still in corporate 23:01 - How to say no to misaligned money (and trust you’ll be okay) 26:17 - Why “pretty good” is the most dangerous place to be 29:21 - What it really looks like to build a creative career on your own terms RESOURCES + LINKS Get Lindsay’s New Novel: Summer On Lilac Island Build Your Freedom-Based Business Operating System™ This Summer At Our First-Ever Freedom High Summer School: A Live Challenge Designed To Help You Grow Your Audience, Make More Sales + Use AI Without Losing Your Voice. Save Your Seat Here. Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).
Mark as Played

Advertise With Us

Popular Podcasts

24/7 News: The Latest
Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

The Clay Travis and Buck Sexton Show

The Clay Travis and Buck Sexton Show

The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.