This show delivers entrepreneurship strategies around imposter syndrome, burnout, and mental health. If you’re looking for tips on overcoming obstacles in business from an award-winning female founder who’s passionate about pursuing ambition without sacrificing your self worth, you’re in the right place.
This show is for leaders, creatives and entrepreneurs who have wondered:
- What is imposter syndrome?
- Can our burnout symptoms help us evolve?
- Does an entrepreneurial spirit always come with anxiety?
- How do I execute my ideas about business in seasons of self-doubt?
41. Riff Over Recipe: Trusting Yourself & Embracing the Unknown
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 (https://www.paprikaapp.com/)
O’nr – A Nonprofit for Business Owners (http://o-nr.org/)
Episode with Shannon Miles (https://pod.link/1719538527/episode/9662ff0b21f1abc9ff6678dc2b459ebb)
Join Lindsey on Substack (https://lindseyepperly.substack.com/)
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 (https://lindseyepperly.substack.com/)!
19 Mar 2025
40. How to Stop People-Pleasing & Start Living on Your Own Terms
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 (https://lindseyepperly.substack.com/)!
12 Mar 2025
39. How Do You Stay Grounded While Chasing Big Dreams? Learn from Pauleanna Reid
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 (https://www.thewritersblok.com/), 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! (https://www.instagram.com/pauleannareid/?hl=en)
For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here (https://lindseyepperly.substack.com/)!
Inside a recent episode
25. Does Networking Really Make a Difference? Susan McPherson Will Transform How You Connect
Published 18 Sept 2024 · Transcript excerpt
[…] And that is yourself and do a steep self -reflection, determine what your goals are the next one year, three year, maybe even five years. And then you think about what your superpowers are. So you can think about how you can be supportive of others. You also think about who you can connect with or reconnect with that are going to help you not only meet your goals, but ways you can be supportive of others. And lastly, and this is probably something that's really, really important in the world we're living in today, where there is quite a bit of vitro and challenges in our public discourse. And that is to think about how to break out of that hermetically sealed bubble that so many of us find ourselves in, myself included, where we tend to attract people that look like us, sound like us, the same age, race, and color and career as us. […]
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