In this TayTalks episode, Taymeyah and Greg Wasserman explore what it really means to build a career (and a life) that aligns with who you are. Greg reflects on early career experiences that shaped his leadership style, including retail “character development”, managing teams across multiple offices, and navigating constant change during his years at Yahoo.

The conversation moves into startups versus big corporations, unpacking the myth of stability, the impact of silos, and why understanding how decisions affect people on the ground actually matters. Greg also shares openly about reaching a mental health breaking point in late 2022, what it took to ask for help, and how that moment reframed his perspective on time, relationships, and purpose.

This episode is a reminder that you don’t have to have it all figured out, but you do have to listen to yourself, stay curious, and let people show up for you.

Why Listen:

• Your gut often knows before you can explain why something feels off
• Stability is a myth; both startups and big companies change
• Leadership is about communication, listening, and understanding motivation
• Silos exist everywhere and knowing when to break down or embrace them, is a skill
• Asking for help isn’t a weakness; it’s a form of self-awareness and a gift to those around you
• Life is ultimately, as Greg beautifully puts it, about time and relationships

Send this to anyone you think would enjoy. Then tag @taytalks_pod with your takeaway so we can repost it.

✅ Subscribe on Apple Podcasts, Spotify, or your favorite app—so you never miss a TayTalks deep-dive on nonlinear paths and full-circle moments.

🎙️ Come for the science and storytelling. Stay for the reminder that purpose often begins where certainty ends.

🤍 If this episode resonated:

Share it with one friend who needs to hear it.

Tag @taytalks_pod with your takeaway so we can repost you.

Leave a quick rating on Apple or Spotify, your words help more ambitious humans find the show.