Why Rejection Is the Fastest Path to Confidence with Klyn Elsbury | #55

Confidence isn't something you're born with. It's built one conversation, one courageous ask, and one uncomfortable moment at a time.In this episode of I Can Fit That In, Erin Coupe sits down with leadership sales trainer, speaker, and communication strategist Klyn Elsbury to explore how persuasion, self-advocacy, and authentic communication shape every area of our lives. Drawing from her experience living with cystic fibrosis and building a career around helping leaders communicate with confidence, Klyn shares why sales isn't about convincing people—it's about creating genuine connection and having the courage to ask for what matters.What You'll Take Away- Why confidence is built through action, not by waiting until you feel ready- How "rejection therapy" can help you become more comfortable asking for what you want- Why authentic conversations outperform traditional sales tactics every time- How avoiding difficult conversations creates resentment and holds back personal and professional growth- Practical ways to strengthen your communication, negotiation, and leadership skills every dayGuest BioKlyn Elsbury is a leadership sales trainer, speaker, and communication strategist who helps organizations build trust, strengthen influence, and communicate with confidence. Her work combines real-world sales experience with powerful lessons on courage, resilience, and authentic leadership.Connect with Klyn:https://www.linkedin.com/in/klynelsburywww.leadershipsalestraining.com Revenue Growth Roadmap  https://sales.leadershipsalestraining.com/sos-714503https://www.youtube.com/@realklynelsburyIf this conversation inspired you to have the conversations you've been avoiding, subscribe to I Can Fit That In and leave a review to help more leaders discover the show.Connect with Erin Coupe:Instagram: @authenticallyecLinkedIn: Erin CoupeChapters00:43 Meet Klyn Elsbury01:25 The Story That Shaped Her Life03:22 From Corporate Sales to Fighting for Survival05:23 Courage Starts With Asking07:04 Why People Struggle to Ask for What They Want11:30 Rejection Therapy and Building Confidence13:29 Why Selling Feels So Uncomfortable17:31 Difficult Conversations and Resentment19:23 Building a Business Through Authenticity21:14 Confidence Is Built by Winning23:03 Rituals for Intentional Leadership25:17 What to Do When You Feel Stuck26:58 Narrate Your Life Like the Hero27:56 Where to Connect with Kyln29:13 Outro