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Are You Settling for “Less Than”? (Greg Holder ep. 294)

Lead pastor of St. Louis’ The Crossing joins John O’Leary on the Live Inspired Podcast to share how to never settle for “less than” life.

Twenty years ago, Greg Holder left corporate America because of an unyielding ache to make a difference.

Since then, Greg has been lead pastor of The Crossing, a non-denominational church in St. Louis, passionately calling tens of thousands of people from diverse spiritual backgrounds to consider what it means to follow Jesus in today’s world.

Today, Greg shares how many slowly, over-time begin to lead less satisfying, less fulfilling, less hopeful lives and how to break that cycle.

This conversation will remind you that your life has significance and you have the potential to change the world through your life’s impact.

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  • Over 20 years ago, Greg left corporate after being called to be a pastor because of a longing desire to make a difference.
  • We’re living in a VUCA – volatile, uncertain, complex and ambiguious – world.
  • “People are longing for a world view that gives us a way out of a VUCA world, while acknowledging we’re in it.”
  • Here I stand, I can do no other. Greg leans on his trusted community to collaborate when he’s being called into something more.
  • Faith is not living in denial.
  • Desire to flourish yet accept settling: We play it safe and surround ourselves with people exactly like us and attempt to blend in by being ghosts of ourselves because we forget we were made to make a difference.
  • It’s not doubt that’s toxic to faith. It’s silence. By getting permission to ask hard questions, particularly in faith, Greg has been able to explore the answers, even when their may not be “answers”.
  • “My dad left a legacy that I don’t think he fully appreciated. He set off so many chain reactions of love and goodness.”
  • Spend less, give more. As part of Advent Conspiracy movement, thousands of people have chosen to celebrate Christmas in a counter-cultural way.
    • Greg shares the story of a son who gifted his dad coffee beans with a note requesting they only drink the coffee together while having meaningful conversations.
  • The open-handed generosity + hospitality Greg recieved while doing mission work around the globe has been life-changing for him. “I’ve been on the receiving end of meals that I know cost more than any meal I’ve served to a guest. That’s as humbling as it gets.”
  • Cultivate a culture of listening. In these particular days, Greg seeks to continue to learn by having conversations where truth can be spoken and where we listen to each other.
  • Learn more about Greg Holder here.
  • Get a copy of Greg Holder’s book Never Settle.


About our sponsor: Keeley Companies wholeheartedly believes that if you get the people right -the results will follow. They set themselves apart with a forward-thinking culture that empowers their people and fosters loyal partnerships. Keeley Companies are a proud sponsor, partner, and super fan of the Live Inspired Podcast. Learn more about Keeley Companies.


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  1. Q. What is the best book you’ve ever read?
    A. A Failure of Nerve by Edwin Friedman and the Bible. [John asked Greg what book of the Bible he recommends for listeners. If you’re looking to get familiar with the voice of Jesus, Greg recommends Matthew, Mark, Luke or John of the New Testament, or the Book of Philippians.]
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Be less self-conscious + be freer.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. Two journals I kept from my daughters first year away at college.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. C.S. Lewis  and I'd ask him to tell me about his writing process.
  5. Q. What is the best advice you’ve ever received?
    A. Lean into the gifts you have and stop trying to be someone you’re not.
  6. Q. What advice would you give your 20-year-old self?
    A. Trust Him sooner. Jump into the story with both feet
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. He followed Jesus fully and loved his friends with all his heart.