Overthinking About Dream Jobs

Overthinking About Dream Jobs

September 2, 2026 · 47 min

About this episode

The episode explores the realities of achieving dream jobs and the complexities of ambition and career satisfaction.

What if you actually get your dream job... and then realize you're not living the dream you thought you would? This week, Amanda is joined by Cherie Brooke (@cherie.brooke) and Jean (@_jeanluo), hosts of the Tiger Sisters podcast (@tigersisterspodcast), who both left impressive corporate careers after discovering that the jobs their younger selves would have killed for no longer fit the lives they wanted. Together, they overthink golden handcuffs, the privilege built into pursuing passion, and why a job doesn’t have to provide purpose, identity, money, joy, and self-actualization all at once. They talk about taking sabbaticals, experimenting before making a giant career leap, letting yourself “fade in and out” of ambition, and why a perfectly good job that pays the bills might actually be part of your dream life.  A thoughtful spiral about ambition, career pivots, and building a dream life instead of obsessing over one perfect job.Further Listening: Tiger Sisters Podcast - Join the "Magical Overthinkers Club" by following the pod on Instagram @magicaloverthinkers. - To access early, ad-free episodes and more, subscribe…

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