Episode 70

full
Published on:

30th Dec 2025

Stop Waiting & Start Creating with Katie Sampayo

What if success wasn’t about fitting into someone else’s box? What if it’s about building a life that’s entirely your own?

On this episode of She Wears the Pants, Ashley sits down with Katie Sampayo, a transformational coach, elite strategist, bestselling author, and retreat leader, who has been fully nomadic since 2018, running her business everywhere from the beaches of Costa Rica to the backcountry of Utah.

Katie helps entrepreneurs and high-achievers redesign their lives so they don’t just look good on paper, but actually feel aligned, fulfilling, and free. She’s living proof that freedom and success aren’t separate paths. They are one and the same.

In this powerful conversation, Ashley and Katie dive into:

  • Katie’s journey from corporate marketing to global entrepreneur and retreat leader
  • Why waiting for the “perfect moment” will keep you stuck, and how to build your own table instead
  • The importance of identity shifts when scaling a business and life you actually want
  • How limiting beliefs around love and money are deeply connected, and what to do about it
  • The surprising role that simplicity and boundaries play in sustaining success
  • Katie’s “flex week” practice that allows her to scale while staying grounded, creative, and energized

Katie’s story is a masterclass in courage, alignment, and intentional design. If you’ve ever felt like you were waiting for permission to start living the life you want, this episode is your reminder to stop waiting and start creating.

Learn more about our guest:

With over nine years of global experience and through dozens of retreats and coaching sessions, Katie Sampayo has empowered hundreds of high-achieving women to achieve deep fulfillment and lasting success.

Website: https://katiesampayo.com/

Instagram: https://www.instagram.com/katiesampayo/


Remember, stay confident, stay focused, and keep wearing those pants with pride.

Be sure to rate, review, and subscribe!


Grab Ashley’s free 5 Day Podcast Series, “The Unstoppable CEO Mindset”, https://ashleydeland.com/unstoppable-ceo-mindset 

Follow Ashley on Instagram https://www.instagram.com/ashleydeland/ 

Schedule a Consultation: https://ashleydeland.com/inquire 




Mentioned in this episode:

VIP Weekend Experience

https://ashleydeland.com/vip-weekend-experience

Next Episode All Episodes Previous Episode

Listen for free

Show artwork for She Wears the Pants

About the Podcast

She Wears the Pants
She Wears the Pants is the podcast for the women building more than businesses—they’re building identities, empires, and legacies.

Hosted by globally recognized business advisor, multi-business founder, and start-up investor Ashley Deland, this show lives at the intersection of strategy, structure, and self. Each week, Ashley pulls back the curtain on what it truly takes for women to scale companies that are financially sound, spiritually aligned, energetically sustainable, and structurally unshakeable.

This is where high-growth women founders come for boardroom-level strategy, identity evolution, feminine leadership, and the inner work required to hold the success they’re building.

Because strategy means nothing if the woman behind it can’t hold it.

Continue the Work with Ashley:

Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power.
→ https://ashleydeland.com/inquire

Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth.
→ https://ashleydeland.com/inquire

Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram.
→ https://www.instagram.com/ashleydeland/

She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

About your host

Profile picture for Ashley Deland

Ashley Deland