Regaining our Humor and Humanity | Ray Ortlund

Regaining our Humor and Humanity | Ray Ortlund

Why are so many young leaders burning out, exhausted, and frankly, a little miserable? In this episode, Grant sits down with pastor, mentor, and author Ray Ortlund to uncover why next-gen Christians so easily fall into the trap of a grim, transactional "pay-as-you-go" faith.

Ray breaks down why living with gusto and having a saintly blast isn't a compromise on holiness, but biblical wisdom from Ecclesiastes designed for longevity and resilience. If you've been slogging through ministry under the heavy weight of performance, this conversation is the perspective shift you need to find true rest in the finished work of Christ.

In this episode, they talk about:

  • Breaking free from the grim moralistic trap that makes some Christians miserable.
  • Why Jesus' call to "Come to me and rest" is a radical, punk-rock declaration.
  • Handling over-scheduling and learning when to say no to protect your family and health.
  • What it means to budget for sin when you are physically and spiritually depleted.
  • Ray's personal life goals for maintaining deep, 50-year friendships.
  • Letting go of your own self-importance and letting God make your life count.

👉 Get Ray's Book, Eat Drink and Be Merry: https://www.crossway.org/books/eat-drink-and-be-merry-tpb/

👉 Check out Renewal Ministries: https://renewalministries.com/

👉 Follow Ray on Instagram: https://www.instagram.com/rayortlund/


MORE RESOURCES:

➡︎ Watch Grant's THINQ talks here: https://thinqmedia.com/speakers/grant-skeldon

➡︎ Create a free THINQ Account and download the THINQ Media app on your smart TV to access more trusted content like this on topics from all channels of culture at: https://thinqmedia.com/

➡︎ Take our assessment to see how you apply the THINQ Framework to your everyday life: https://thinqmedia.com/assessment/

➡︎ Attend THINQ events where you can gather with like-minded leaders, ask better questions and have conversations that lead to wisdom: https://events.thinqmedia.com/

➡︎ Lead a THINQ-guided conversation with your family or small group: https://thinqmedia.com/engage/


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➡︎ Join us at THINQ Summit 2026 in the heart of Nashville, Tennessee: https://events.thinqmedia.com/summit26

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More from the THINQ Podcast Network:

➡︎ Rhythms for Life with Rebekah and Gabe Lyons: https://www.youtube.com/@rebekah_lyons/

➡︎ The InFormed Parent with Suzanne Phillips: https://www.youtube.com/@InFormedParent/

➡︎ UnderCurrent with Gabe Lyons: https://www.youtube.com/@gabe_lyons/

➡︎ NeuroFaith with Curt Thompson: https://podcasts.apple.com/us/podcast/neurofaith-with-curt-thompson-md/id1613240148/

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The Beautiful Battle of Sanctification | Matt Chandler

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In this episode, Grant sits down with pastor and author Matt Chandler to unpack a massive shift happening in youth culture and what it really looks like to lead with prophetic clarity today. Fresh of...

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Navigating Play, Pain and Prayer | Tyler Staton

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19 Maj 1h 3min

Forging Ride-or-Die Friends in a Flaky World | Jennie Allen

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The Blueprint for Fighting Fair in Marriage | Dr. Emerson Eggerichs

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In this week's episode, Grant sits down with legendary author and marriage expert Dr. Emerson Eggerichs (author of Love and Respect) to dive into the messy, but necessary work of resolving conflict in...

5 Maj 59min

Intentional Singleness | Riley Kehoe

Intentional Singleness | Riley Kehoe

In this conversation, Grant Skeldon sits down with author and speaker Riley Kehoe to discuss a topic that often feels like a four-letter word in Christian dating culture: waiting. For many in the nex...

29 Apr 52min

How To Do The Dating Challenge | JJ & Kait Tomlin | Part 2

How To Do The Dating Challenge | JJ & Kait Tomlin | Part 2

In this second installment of the Dating Challenge 2-part series, Grant is joined by friends JJ and Kait Tomlin, the powerhouse couple behind the Heart of Dating ministry. Kait, a dating coach and aut...

24 Apr 33min

How To Do The Dating Challenge | Alec & Maddie Bevere | Part 1

How To Do The Dating Challenge | Alec & Maddie Bevere | Part 1

In the first half of a 2-part series on Dr. Henry Cloud's Dating Challenge, Grant sits down with Alec and Maddie Bevere for a raw, funny, and deeply practical look at what it means to steward your dat...

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