#10: Leroy Milton: Pedestals, Breaking Cycles and Dancing with Fear

Full Show Notes Available At: http://www.olivermanalese.com/10

Today on the show we get an inside look at the journey of Leroy Milton, a badass coach, and co-founder of self-help comedy brand, 2HelpfulGuys. Hear about the intense amounts of physical pain that manifested from putting people on pedestals, the breakdown that led to breaking through his old fear-based cycles, and how he's learned to be with fear instead of getting rid of it. There is so much to relate to in Leroy's story and I know you will walk away with a fresh perspective on fear, change, and looking up to people in your own life. His honesty, bluntness, and depth is incredibly refreshing. Enjoy!

You Can Also Subscribe To The Show on iTunes Here: http://itunes.apple.com/ca/podcast/the-o…d1200840535?mt=2

Ways to Listen:

  1. Listen on iTunes
  2. Listen on Stitcher
  3. Listen on Google Play
  4. Listen on Soundcloud
  5. Download as MP3

Meet Leroy Milton:

Leroy Milton is a badass coach and cofounder of 2HelpfulGuys, the comedy self-help brand. Leroy guides his clients toward connecting with their dark stories and using it to propel their lives forward. Leroy believes through vulnerability, we can truly discover who we are and what we’re capable of. When Leroy isn’t coaching or making hilarious sketch comedy, he’s found cooking, hiking, or practicing yoga.

What You'll Learn:

  • The consequences of putting people on a pedestal
  • The value of experiencing intense amounts of physical pain
  • The conversation with the man in the mirror
  • Noticing repeating fear-based cycles
  • Having impossibly high standards set by parents
  • Why you should "feel it" instead of "fighting it"
  • The importance of allowing the "I'm not good enough" to just be there
  • The power of sharing your pain and fear and making it real


"I created the story in my head that unless I am that famous, I am that rich, I am that powerful, I am nothing. It’s all this unless. And all this 'unless' mentality made me feel not good enough in the eyes of anybody."

“You might have idols, you might look up to people but don’t put them on pedestals because everyone has the exact same shit going on."

“I never hit the finish line, the finish line always just gets pushed a little out of my reach."

“Everyone has a different process."

“If the pain is too intense, something is going on."

"The pain of staying the same has to outweigh the pain of change."

"The fear is there to keep you in this safe comfortable position that is oddly enough, very uncomfortable."

On Fear: “It’ll never go away, it’ll just get quieter."

“I’m not good enough will forever live inside of me, it will forever be there. I just want to make it quieter."

“Dance with the fear.” Seth Godin

Defining Success: “Being comfortable in the process that you are in right now, knowing that there is more ahead of you and you’ll get there as long as you stay true to yourself."

"In order to change you have to feel that pain and when that pain becomes unbearable that’s when change really happens."


2HelpfulGuys - Self Help Comedy:

Follow Leroy on Facebook:

Oliver's Picks Newsletter

Breakthrough Coaching with Oliver

Follow Oliver on Facebook

E-mail Oliver

Posted in Personal Growth, podcast and tagged , , , , , , , , .

Leave a Reply