Starting something new—whether it’s launching a business, switching careers, or choosing the road less travelled—comes with excitement, vision, and hope. But behind every bold move are moments of doubt, fear, and unexpected challenges no one really prepares you for.
In this episode, we sit down to unpack the things we wish we knew before we began. The hard truths. The silent struggles. The stuff that doesn’t make it to the highlight reel. We talk about:
Why no one warns you how hard it will actually feel
The mental health dip that comes with leaving stability
How lonely and misunderstood the journey can be
Learning to ride the emotional rollercoaster of slow seasons and burnout
Why passion isn’t enough—and what actually keeps you going
Whether you’re just starting out or deep in the middle of figuring it all out, this episode is your reminder that you’re not alone—and you’re not doing it wrong. Building something real is messy. But it’s also brave. And it’s worth it.
Dateline NBC
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Are You A Charlotte?
In 1997, actress Kristin Davis’ life was forever changed when she took on the role of Charlotte York in Sex and the City. As we watched Carrie, Samantha, Miranda and Charlotte navigate relationships in NYC, the show helped push once unacceptable conversation topics out of the shadows and altered the narrative around women and sex. We all saw ourselves in them as they searched for fulfillment in life, sex and friendships. Now, Kristin Davis wants to connect with you, the fans, and share untold stories and all the behind the scenes. Together, with Kristin and special guests, what will begin with Sex and the City will evolve into talks about themes that are still so relevant today. "Are you a Charlotte?" is much more than just rewatching this beloved show, it brings the past and the present together as we talk with heart, humor and of course some optimism.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.