Episode 37: From Imposter Syndrome to Earned Authority with Anya Cheng

Anya Cheng didn’t build her career by waiting to feel ready. She built it by acting in moments when nothing felt certain.

After immigrating from Taiwan and graduating into the 2008 financial crisis, she couldn’t get a single interview. So she created her own access, waiting outside buildings in Chicago winters, knocking on doors, and cold-calling publishers until someone said yes. What looks like persistence was actually precision. She was using what she already knew how to do. As a former reporter, she knew how to approach strangers, ask questions, and follow leads, and she used those strengths to move forward.

That same pattern carried her through 15 years at Target, McDonald’s, eBay, and Meta, and eventually into founding Taelor, an AI-powered men’s clothing subscription service. But what stands out is not just how she kept going, it’s how her relationship to confidence evolved. Anya doesn’t see confidence as something you wait to feel. She built it through action, by trusting her own thinking before anyone else validated it. She shares what it looked like to lose opportunities when she stopped trusting herself, and what changed when she began to stand in her own point of view. She also speaks candidly about imposter syndrome, not as something that disappears, but something you learn to recognize and manage early.

This episode is about what it really means to earn your authority, through repeated moments of showing up, learning, and choosing to trust your voice when it matters most.

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Where to find Anya: 
LinkedIn: https://linkedin.com/in/anyacheng
Email: [email protected]

Connect with Kristiana: 
Website: https://www.worthytolead.co/ 
LinkedIn: https://linkedin.com/in/kristianacorona 
Instagram: https://www.instagram.com/worthytolead/ 
Substack: https://worthytolead.substack.com/