Get Comfortable Being Uncomfortable | Darren Kittleson on The Inner Estate

Success doesn’t happen in your comfort zone—it’s built when you face the moments you’d rather avoid.

In this episode of The Inner Estate Podcast, host Bridget Ann Stuart sits down with Darren Kittleson—real estate leader, master coach, and founder of Generations Beef—to talk about resilience, accountability, and thriving in both business and life.

From leading multiple Keller Williams brokerages in Wisconsin to serving as a Leadership & Production Coach with The Coaching Nexus, Darren has spent decades training and coaching thousands of real estate professionals across North America. His insights reveal how leaning into discomfort can transform your results, protect your business, and help you stay consistent—even when the market gets tough.

If you’re ready to grow your business, strengthen your mindset, and get comfortable being uncomfortable, this conversation is a must-watch.

Episode Highlights:
Why discomfort fuels personal and business growth
The key numbers every real estate professional should track
How coaching creates clarity, accountability, and results
Darren’s lessons from rebuilding after major setbacks
Financial strategies that protect your business in any market
Why social media can distort reality—and how to stay grounded

About Darren Kittleson:
Darren is an Operating Principal of multiple Keller Williams market centers in Wisconsin, a past President of the Council of Real Estate Brokerage Managers (CRB), a certified CRB, RENE, and SRS trainer, and a Keller Williams International Master Faculty member. He’s coached and trained thousands of top performers, and as founder of Generations Beef, he’s passionate about regenerative agriculture and sustainable food production.

Connect with Darren:
Website: https://www.darrenkittleson.com/
Phone: 608-212-3126
Instagram: @coachkittleson
Facebook: Darren Kittleson

Host: Bridget Ann Stuart
Bridget Ann Stuart is an executive strategic performance real estate coach and host of The Inner Estate podcast. With 27 years of experience, she is known for helping real estate professionals align mindset, strategy, and personal growth to achieve lasting success.

Connect with Bridget Ann Stuart:
Website: therealbridgetstuart.com
Instagram: @therealbridgetstuart
Facebook: The Real Bridget Stuart

🎙 The Inner Estate Podcast — conversations that inspire clarity, action, and success from the inside out.

Timestamps:
00:00 The Transformative Power of Inconvenience
03:47 Embracing Discomfort for Growth
07:28 Controlling Your Business Amid Market Changes
11:24 Building Consistency in Revenue
15:03 Learning from Failure and Embracing Risk
18:59 The Importance of Continuous Improvement and Coaching
28:48 The Journey of Coaching and Personal Growth
30:19 Rebuilding After the Recession
32:31 Lessons Learned from Financial Struggles
34:24 Facing Legal Challenges and Accountability
37:11 From Adversity to Success
37:49 The Importance of Sharing Experiences
41:35 The Pressure of Perfection in Social Media
46:39 Inconvenient Advice for Financial Awareness
49:14 The Impact of Sleep on Productivity
52:57 Final Thoughts on Coaching and Growth