The Black Sheep Leadership Podcast

How to Retire from People Pleasing (Without Becoming Cold or Cruel)

Black Sheep Guru

People pleasing isn’t kindness — it’s a survival strategy that’s outlived its purpose.

In this powerful episode of Black Sheep Leadership, the Black Sheep Guru breaks down why Black Sheep are especially vulnerable to people pleasing, the two dangerous forms it takes, and how to retire from it without becoming bitter, cold, or cruel.

Blending insights from The Subtle Art of Not Giving a F and 100 Days of Rejection, this episode prepares you for the emotional discomfort, social backlash, and internal rewiring that comes with reclaiming your self-respect.

If you’re tired of being the “Nice” Guy or Girl especially to people that don't deserve it and ready to be free, this episode is your permission slip.