Why Rejection Is the Fastest Path to Confidence | #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 day

Guest Bio

Klyn Ellsbury 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/klynelsbury

https://kelsbury.wixsite.com/missklyn

https://www.youtube.com/@realklynelsbury

If 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: @authenticallyec

LinkedIn: Erin Coupe

Chapters

00:43 Meet Kaylin Ellsbury

01:25 The Story That Shaped Her Life

03:22 From Corporate Sales to Fighting for Survival

05:23 Courage Starts With Asking

07:04 Why People Struggle to Ask for What They Want

11:30 Rejection Therapy and Building Confidence

13:29 Why Selling Feels So Uncomfortable

17:31 Difficult Conversations and Resentment

19:23 Building a Business Through Authenticity

21:14 Confidence Is Built by Winning

23:03 Rituals for Intentional Leadership

25:17 What to Do When You Feel Stuck

26:58 Narrate Your Life Like the Hero

27:56 Where to Connect with Kaylin

29:13 Outro

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