The Truth About Leadership Pain | Ep 21

How much pain can you take? In this episode of The Shift Podcast, Matt and Evan unpack the brutal truth behind personal and professional growth: it always comes with pain. You’ll learn why leadership pain is unavoidable, how avoidance becomes your cap, and why disruption and discomfort are actually the fuel for your next level. From skydiving and 75 Hard to Maxwell, Goggins, and Hormozi—this episode is loaded with real-world wisdom. If you're trying to grow your business, your leadership, or yourself… this conversation will stretch you.

Chapters:
0:00 Introduction – Growth Hurts. Here’s Why.
0:56 The Formula: Growth = Pain
2:30 Change Always Involves Loss
4:05 Leadership Pain: What Most People Never See
5:50 Avoidance is the Real Limiter of Growth
7:15 Stagnation, Decline, and the Myth of “Easy”
9:35 If You Won’t Embrace Pain, You’re Not Ready to Lead
10:55 From $1,000 Problems to $100,000 Problems
13:20 Leaders Don’t Just Face Pain—They Create It
15:00 Why Vision Is Disruptive by Nature
17:00 Skydiving, 75 Hard, and Building Pain Tolerance
20:55 You Only Grow to the Threshold of Your Pain
22:40 Leaders Choose the Hard That Leads to Growth
25:10 3 Leadership Questions to Ask Yourself This Week
26:00 Final Thoughts + Maxwell’s Lesson on Lifelong Pain

Contact:
theshiftpodcast.co

Matt Ware:
https://themattware.com

Evan Weiland:
https://evanweiland.com

Recommended Books:
Leadership Pain by Dr. Sam Chand
The Infinite Game by Simon Sinek