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
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