Podcast · Episode 084

People Pleasing Makes You Numb to Anger, Desire & Life

August 6, 2025 · With Oliver Cowlishaw

People pleasing seems like it comes from a good place. You’re just trying to make sure everyone’s all right and that people like you. But the deeper you dig, the darker it gets. Oliver and I both used to be terrible people pleasers and have done our own work to get past it. In this conversation we talk about what it costs you, including self-abandonment and losing touch with your own anger and desire, and what helped us change.

My guest is Oliver Cowlishaw. He works with men to overcome nice guy tendencies, insecurities and other behaviors that keep them stuck, through retreats and personal coaching. He’s been on the channel before, and we worked together for a while. You can find him on his YouTube channel or work with him.

In this episode

  • Oliver’s recent men’s retreat in Ireland, the sacred combat, and how many grown men had never sparred before.
  • Bottom-up confidence: how trusting your body, from fighting to balancing on ledges, may carry into the rest of your life.
  • Fighting side by side builds bonds: the respect Oliver noticed after his fights, and my old LARP shield walls and bouncer training.
  • Why physical challenge needs emotional safety, how Oliver runs play fighting with check-ins and feedback, and why everyone’s edge is in a different place.
  • Our most cringeworthy people pleasing: I couldn’t ask anyone to pass the salt, and Oliver played hour-long DJ sets of music he despised.
  • Self-abandonment means changing yourself to fit what you assume others want, like Oliver apologizing for being upset when his girlfriend turned up 30 minutes late.
  • Rejecting yourself before anyone else can, friend-zoning yourself by hiding desire, and my themed journal for noticing and expressing it.
  • Being able to take a no, and sitting in the fire of rejection or urges without having to act on them.