Ditching the Rules: Build Confidence and Community

Send us Fan MailIf you’ve ever wondered what it really looks like to step off the traditional career path and actually thrive, this episode is for you. I sit down with Sara O’Connor—once a high-powered attorney, now a renowned artist and rising force in the poker world—to trace her extraordinary journey of reinvention. We unpack how Sara went from billing in six-minute increments at an international law firm to creating vibrant, tactile art and launching a nonprofit in the poker community.Sara shares the raw moments behind her pivots, including the courage it took to walk away from a “safe” six-figure job and the two-year mental reckoning of untangling her identity from her career. You’ll hear how she built creative and entrepreneurial success on her own terms, the unique lessons poker taught her about confidence and self-worth, and her hard-earned advice for anyone feeling like their “secure” job is draining them dry.Ready to challenge the rules you’ve been taught about “success”? Sara’s story is packed with inspiration and actionable insights—plus, she drops some wisdom on finding the right support system and playing the long game with your dreams. Want to connect with Sara? Check out her art at https://www.saraoconnorfineart.com/,  find her on Instagram (@sarahoconnorfineart), or follow her poker journey on Twitter (@SarahSmartist) and TikTok (@pokerwithsara). If you're ready to take the next step and get unstuck and unstoppable, you can find time on Ken's calendar at https://unstuckcareer.com/unstuck