Most success isn’t built in your comfort zone—it’s forged in the moments you’d rather avoid. In this episode, Darren Kittleson joins Bridget Stuart to explore why the path to success often runs straight through discomfort. Darren shares how resilience, accountability, and facing inconvenient challenges head-on have shaped his decades-long career in real estate, training, coaching, and agribusiness. From leading multiple brokerages to teaching thousands of sales professionals across North America, Darren reveals the mindset shifts and daily habits that keep top performers consistent—especially when the market or life throws curveballs.

Episode Highlights

• Why leaning into discomfort is the fastest path to growth
• The numbers every real estate professional should be tracking
• How to use coaching for clarity, consistency, and results
• Darren’s hard-earned lessons from rebuilding after major setbacks
• How coaching brings clarity, accountability, and measurable growth
• Financial practices that protect your business in any market
• Why social media can distort reality and how to keep perspective

Guest: Darren Kittleson

Darren Kittleson is a multiple real estate brokerage owner and Operating Principal of several Keller Williams market centers in Wisconsin. He serves as a Leadership & Production Coach with The Coaching Nexus, a role that reflects his real estate expertise, lead-generation insights, and decades of training experience. Darren is a past President of the Council of Real Estate Brokerage Managers (CRB), certified CRB, Real Estate Negotiations Expert (RENE), and Seller Representative Specialist (SRS) trainer. He’s a Keller Williams International Master Faculty member, MAPS coach, and founding member of the Siebold Success Network.

Connect with Darren:

Website: www.darrenkittleson.com

Phone: 608-212-3126

Instagram: @coachkittleson

Facebook: @DRKittleson

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 in the business, she’s known for her deep commitment to personal development, business mindset, and helping real estate professionals grow with purpose. 

Connect with Bridget:

Website: therealbridgetstuart.com

Instagram: @therealbridgetstuart

Facebook: @TheRealBridgetStuart

Interested in being a guest on The Inner Estate?

I would love to hear your story. You can view available dates and request to join the show here: calendly.com/bridgetstuart67/theinnerestatepodcast