What if the key to your next breakthrough wasn’t in another how-to guide, but in trusting yourself? In the Season 4 finale, host Lindsey Epperly challenges you to let go of the step-by-step formulas and lean into your own intuition.

This episode is for anyone who has ever felt stuck in the “supposed to” and is ready to explore what happens when you trust what you already know. If you’ve been waiting for a sign to step into something bigger, this is it.

What you'll learn in this episode:

• Why trusting yourself is the key to growth, both personally and professionally.

• How the "riff over recipe" mindset can apply to your career, leadership, and creativity.

• The staggering statistics on mental health struggles in entrepreneurship—and how O’nr is stepping in to help.

• What it means to be in an "open-handed" season and why forcing outcomes may be holding you back.

• How to recognize and embrace your next train car in life, even when you don’t know exactly where it leads.

  
  

Links & Mentions:

• Paprika Recipe App

• O’nr – A Nonprofit for Business Owners

• Episode with Shannon Miles

• Join Lindsey on Substack

  
  

ABOUT LINDSEY:

Lindsey Epperly is the founder and Chairwoman of Jetset World Travel, where she grew a one-woman business into a 100-person company, earning spots on the Inc. 5000 List. Named to Forbes' Next 1000 List, Lindsey is passionate about mentoring entrepreneurs, redefining leadership, and creating space for business owners to thrive.

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!

Are you constantly saying yes when you really mean no? Do you feel weighed down by expectations that aren’t your own? In this episode of Who Made You The Boss?, Lindsey sits down with author and podcast host Amy Wilson to unpack the deep roots of people-pleasing—why we do it, how it affects us, and, most importantly, how to break free. Amy shares eye-opening insights from her new book, revealing how societal pressures, self-help culture, and generational beliefs shape our ability to set boundaries.

Expect a candid, insightful conversation filled with practical strategies to reclaim your time, energy, and sense of self. Whether you struggle with saying no, feel guilty when prioritizing yourself, or want to support others facing the same challenge, this episode is packed with takeaways to help you redefine what it means to show up for yourself.

What you’ll learn in this episode:

• Why People-Pleasing Runs Deep: Explore the cultural and generational factors that make saying no so hard—and why it’s not your fault.

• Breaking the Cycle: Discover the turning point that led Amy to challenge her own people-pleasing tendencies and write a book about it.

• The Self-Help Trap: Learn how personal development culture can sometimes reinforce harmful patterns instead of helping you break them.

• Setting Boundaries with Confidence: Get actionable tips for saying no without guilt and creating space for what truly matters.

• Lifting Others Up: Find out how to support friends, family, and colleagues who struggle with people-pleasing.

  
  

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!

In this episode, you'll discover how to navigate the challenges of life and business with purpose and intention. Lindsey dives deep with Pauleanna Reid, a communications executive, celebrity ghostwriter, and new mom, to uncover actionable insights from her journey. Learn how to transform personal struggles into opportunities for growth, balance mental health while achieving big goals, and leverage mentorship to shape your future. From candid stories about career pivots and dating to practical advice on thriving as an entrepreneur and parent, this episode is packed with takeaways to help you align your passions with your purpose.

What you'll learn in this episode:

• How to Turn Struggles into Strengths: Discover actionable strategies for transforming personal challenges into career and personal growth opportunities.

• The Power of Intentionality: Learn how to align your goals, values, and actions to create a life and career that feels purposeful and fulfilling.

• The Role of Mentorship: Explore how finding the right mentors—and mentoring others—can shape your journey and impact future generations.

• Balancing Mental Health with High Performance: Get insights on managing mental health while maintaining focus and achieving success in both personal and professional life.

• Lessons from the World of Celebrity Ghostwriting: Gain a behind-the-scenes look at how Pauleanna carved out her niche and what it takes to build a unique, thriving career.

  
  

ABOUT PAULEANNA:

Pauleanna Reid is a celebrated celebrity ghostwriter, entrepreneur, and communications expert who helps high-profile leaders turn their personal stories into powerful brand assets. Founder of WritersBlok, a full-service ghostwriting agency, she leads a team of all-women creatives responsible for some of the most talked-about pop culture moments and books. Pauleanna is a sought-after speaker and media personality, passionate about mentorship, mental health, and empowering women to overcome life’s challenges. With a background in journalism and a commitment to social impact, she is dedicated to amplifying Black voices and supporting the next generation of leaders. Follow Pauleanna Here!

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!

This week, join Lindsey for a heartfelt and empowering conversation with Daisy Auger-Dominguez, a trailblazing author and leadership expert, as she shares strategies to combat burnout and reignite your passion for your work. Discover how to maintain your personal identity in leadership roles, foster empathy in communication, and handle the emotional toll of public criticism. With practical techniques for managing stress and inspiring stories—including a heartwarming moment from Daisy’s "happy folder"—this episode is packed with actionable advice to help you lead with purpose and resilience. Tune in for insights that will transform the way you approach leadership and self-care.

What you'll learn in this episode:

• Strategies for providing tough feedback with empathy to ensure it is constructive and well-received.

• Insights into reframing negative internal narratives and combating self-doubt to manage burnout effectively.

• Methods for creating nurturing workplace environments that prioritize employee well-being and productivity.

In this transformative episode, personal branding coach Allison Hare shares her powerful insights on navigating life’s biggest transitions and reinventing yourself with purpose. Discover her framework for addressing burnout, learn how to balance masculine and feminine energies for greater alignment, and uncover the key to setting boundaries that protect your time and energy. Whether you’re facing a major life change or simply looking to step into a more empowered version of yourself, this episode is packed with actionable advice and inspiration to help you thrive. Don’t miss this opportunity to redefine what’s possible for your life and career!

What you'll learn in this episode:

• Strategies like the "Happy Calendar Challenge" for assessing and rebalancing energy-draining and energizing activities.

• Insights into balancing masculine and feminine energies for a holistic approach to success.

• The importance of boundaries, creative experimentation, and finding energy through setting limits.

• The value of mentorship and having a trusted advisor to support transitions and break down emotional barriers.

  
  

ABOUT ALLISON:

Allison Hare is the creator and host of the award-winning globally ranked podcast, Late Learner. She is a former corporate sales executive who purposely left the corporate world to coach high-performing women to redesign their best lives without burnout. As a lifestyle and career coach and keynote speaker specializing in navigating transitions, personal branding, and even operates as an undercover podcast coach. Allison lives in Atlanta with her beloved husband and 2 children and is an endurance challenge fanatic, among other exciting hobbies keeping her dopamine levels high.

Connect with Allison:

Website

Podcast

For more information and to connect with our host, Lindsey Epperly,subscribe to our Substack here!

Join Lindsey for an inspiring conversation with accomplished author and storyteller Kimberly Stuart as they dive into the art of staying authentic in your creative and professional journey. Kimberly shares the highs and lows of rewriting her book after receiving pivotal feedback, offering powerful lessons on balancing external validation with personal purpose. This episode is a must-listen for anyone navigating the tension between creativity and business demands, looking to embrace grace amidst challenges, or striving to stay true to their passion while managing expectations. Tune in to reignite your purpose and approach your work—and life—with renewed authenticity.

What you'll learn in this episode:

• The importance of staying true to one's core motivations and how this focus can lead to unexpected successes.

• Strategies for managing the tension between seeking external validation and sticking to one's original purpose.

• Practical advice for aspiring writers on how to remain consistent and dedicated to completing a creative project.

• Reflections on the concept of grace and its significance in overcoming societal pressure for perfection and control.

  
  

ABOUT KIMBERLY:

Kimberly Stuart is an Iowa girl, a writer, a speaker, a podcaster, and a dark chocolate obsessive. She is the author of eight novels and a newly released nonfiction debut, Star For Jesus (And Other Jobs I Quit). Stuart's books have been featured in Cosmopolitan, Huff Post, and the Chicago Sun-Times. She and New York Times-bestselling author Bob Goff have coached hundreds of aspiring authors through their executive coaching, online courses, and live events in the San Diego area. Kim's solo podcast, For Real with Kimberly Stuart, launched in fall 2021. A joint podcast with Goff, The Writing Room, launched in fall 2022. Stuart has made her home in Minneapolis, Houston, Chicago, Costa Rica, Nebraska, and Iowa, where she now lives with her brave husband and three wily children.  Find Kim on Facebook,Instagram, and atkimberlystuart.com.

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!

Get ready for an inspiring and dynamic conversation as Lindsey sits down with her long-time friend, Matt Thomas, to explore how passion and philanthropy can drive life-changing achievements. From foundingBrawl for a Cause to becoming a Chess Boxing World Champion, Matt shares his incredible journey and reveals the secrets behind managing state changes and cognitive flexibility for peak performance. Whether you’re an entrepreneur, athlete, or someone striving to level up in life, this episode is packed with actionable insights to help you optimize your mindset, routines, and impact. Don’t miss this energizing discussion!

What you'll learn in this episode:

• The concept of state change management and its application in both sports and daily life.

• Techniques for cognitive flexibility and performance optimization, including breath work, visualization, and meditation.

• How to pursue philanthropy through our passions.

• How to reframe life's challenges as opportunities for growth and improvement.

ABOUT MATT:

Matt Thomas, aka @movingwithmat, is the USA’s first Chessboxing World Champion, a combat sports commentator, and a content creator focused on chessboxing, wellness, and peak performance. As the founder of Brawl for a Cause, he’s helped raise seven figures for over 150 nonprofits through first-time fighters. A former tech professional, Matt has traveled to 40+ countries, becoming a certified yoga instructor and creating Fight and Flow, a fitness concept blending calisthenics and yoga. His mission is to grow chessboxing, fuse Eastern wisdom with Western science, and generate over $1B for philanthropy.

CONNECT WITH MATT:

Instagram

X

For more information and to connect with our host, Lindsey Epperly,subscribe to our Substack here!

Join leadership expert Jenni Catron for a candid conversation that will challenge the way you think about leadership and connection. In this episode, Jenni dives into the often-overlooked struggles of loneliness at the top, offering actionable strategies for building meaningful peer relationships and fostering continuous growth. Learn how to embrace the sacred responsibility of leadership, create a culture of empathy and support, and lead with intention. Packed with personal stories and professional insights, this episode is a must-listen for anyone looking to lead with impact while staying grounded and connected.

What you'll learn in this episode:

ABOUT JENNI:

Jenni Catron is a leadership coach, speaker, and author passionate about helping leaders build thriving organizations. As Founder and CEO of The 4Sight Group, she consults on leadership, team culture, and organizational health, drawing on over 20 years of experience in corporate and non-profit settings. Jenni is the author of The 4 Dimensions of Extraordinary Leadership and the upcoming Culture Matters: A Framework for Helping Your Team Grow, Thrive, and Be Unstoppable. Find her at @jennicatron or www.get4sight.com.

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!

Kick off Season 4 with a powerful episode that will inspire you to turn your passions into a fulfilling career. Host Lindsey Epperly opens up about a pivotal moment in her life when an unexpected injury derailed her plans but ultimately taught her the importance of presence, resilience, and finding joy in the journey. Tune in to uncover how life’s disruptions can lead to deeper clarity, reflect on your own passions, and gain practical insights for embracing the messy, fun, and authentic pursuit of your dreams. This episode is your invitation to step into a life of purpose and play—don’t miss it!

What you'll learn in this episode:

ABOUT LINDSEY:

Lindsey Epperly is the founder and Chairwoman of Jetset World Travel, which she grew from a one-woman operation into a team of 100, earning two consecutive spots on the Inc. 5000 List of fastest-growing companies. Named to the Forbes Next 1000 List, Lindsey is passionate about championing entrepreneurs, addressing burnout and imposter syndrome, and turning obstacles into opportunities. Through her podcast, Who Made You the Boss?, and her in-progress fiction book, she shares the highs and lows of entrepreneurship to inspire others to lead with purpose and resilience.

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!

In this deeply personal episode, Lindsey shares a monumental moment from her journey as she steps back from the company she founded, Jetset World Travel. She discusses the winding path that led her to make this decision, the personal and professional experiences that shaped her, and how bravery sometimes means letting go. Lindsey reflects on losing a dear friend, becoming a mother, and overcoming a health scare—all of which shifted her perspective on success and leadership. Tune in as she explains how this shift is not just about stepping back but about creating space for others to lead and expand into their own purpose.

This episode is for you if you’ve wondered:

ABOUT LINDSEY:

Lindsey Epperly is an entrepreneur, writer, and the founder of Jetset World Travel. With over a decade of leadership experience, Lindsey is passionate about helping others believe in their unique value and guiding them to lead with purpose.

Additional resources from this episode:

⁠Jess Ekstrom's interview⁠ 

⁠Shannon Miles’ interview⁠

For more information on lindsey, visit  www.lindseyepperly.com 

Looking to turn your Imposter Syndrome into Inspiration? Grab the workbook here!

Join the Who Made You the Boss? Substack Community here!