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313: What’s the pebble in your shoe? Pivoting from Wall Street to RadReads with Khe Hy

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Is change whispering to you? For Khe Hy, a former investment banker on the fast track of keeping up with the corporate Joneses, the discomfort from following the status quo first started feeling like a pebble in his shoe. “Psst! There’s more out there for you,” it whispered. 

Once that pebble became unignorable, Khe made his move—even with a wife and two young kids to support—which is what made it feel all the more urgent that he live and work in alignment with his spirit.

In this conversation, we talk about his decision to leave Black Rock, how he follows his instincts when building his new content and education business, and how sneaky “shoulds” and insecurity often stem from unmet needs we had growing up.

Be sure also to check out Khe’s episodes on Free Time: 163: Leveraging Idea Kernels to Create Compelling Content with Khe Hy, and 129: The $10K Work Framework with Khe Hy.

More About Khe: Khe Hy is the founder and CEO of RadReads, an online education company that helps professionals lead productive, examined, and joyful lives. Khe is creator of the $10K Work productivity method and teaches the popular cohort-based course Supercharge Your Productivity. RadReads provides guides, trainings, and coaching for over 36,000 professionals to help them gain back free time, scale their impact and make their little dent in the universe.

Before founding RadReads, Khe spent 15 years working on Wall Street and was one of the youngest Managing Directors at BlackRock. He's been called Oprah for Millennials by CNN, and the Wall Street Guru by Bloomberg and his work has been featured in the Wall Street Journal, TedX, Barrons, Time Magazine, and Quartz.

🌟 3 Key Takeaways:

  • Make an angel investment in yourself: Designate (and save) an amount of money you can afford to lose, that would give you enough time to pursue your ideas and experiment to see what sticks. 

  • The 5 Whys Concept can help you identify the real feelings and motivations for your decisions. Ask yourself why you did something. Then ask why the answer is important to you. Then why that answer is important to you. After 5 “whys” you will almost always be at the root of what you want or feel.

  • Manage your energy instead of your time. Email, for example, can usually be done when feeling low-energy rather than using your best and highest energy on it. Techniques like RIZE (Reach Inbox Zero Everywhere) can help you do it quickly, efficiently, and in appropriate amounts. 

✅ Try This Next: Twice a week, take a piece of paper and a pen, go somewhere quiet, and reflect on a question about your life or business. Ask yourself, "What is the pebble in my shoe?” or, “If everything went great, what would my life look like in ten years?” This is less about having precise answers, and more about creating the space for reflection.

📘Books: 


🔗Resources:


🎧Related Podcast Episodes:

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