14. Rewriting the Rules: Courage, Self-Trust, and Leadership Beyond the Box with Lindsey Simmons

What happens when you stop trying to fit into a box and finally give yourself permission to be all of who you are?In this episode of Unfiltered Leadership, Lindsay Yellin sits down with Lindsey Simmons, founder of Linda in HR, fractional talent leader, career coach, stand-up comedian, avid hunter, fly fisher, and door mother at New York’s iconic MOTHERDISCO.Lindsey’s story is a powerful reminder that identity is not linear and leadership is not about perfection. It is about self-trust, resilience, and choosing courage over familiarity.Together, Lindsay and Lindsey explore what it really takes to navigate layoffs, career pivots, entrepreneurship, and identity shifts without losing yourself in the process. They talk candidly about grief, nervous system regulation, asking for help, redefining success, and why familiar discomfort often keeps us stuck.This conversation is for anyone questioning their next move, navigating career uncertainty, or craving permission to evolve.Episode HighlightsWhy “containing multitudes” is a leadership skillHow a layoff became a catalyst for reinventionFamiliar discomfort vs meaningful discomfortThe power of reframing without toxic positivityWhy you don’t get unless you askLetting go of people pleasing and external expectationsEntrepreneurship, risk tolerance, and trusting yourselfFilming a reality show for entrepreneurs and what it unlockedPractical job search and recruiting insights for today’s marketHow to protect your energy while navigating a toxic or uncertain workplaceAbout your host: Lindsay YellinLindsay Yellin is an executive leadership coach, dynamic speaker, and certified ACC and CPCC who helps high-achieving creative leaders trade fear for possibility and self-doubt for self-trust. A former advertising executive, she has led in high-pressure, high-visibility environments and knows the challenge of staying connected to oneself while leading others.✨ Book a Coaching Chemistry Call with Lindsay: ⁠https://calendly.com/yellin-coaching/...✨ Get your espresso shot of leadership insight, join the Grounds for Growth newsletter: https://yellingroundsforgrowth.myflod...About Lindsey Simmons:Founder of Linda in HR, providing Fractional Talent Leadership, Recruitment consulting and career coaching. Avid hunter, angler and board member of Juliana's Anglers & Sporting Club. GMHC & BTLM Volunteer. Dog mom to Wendell. Writer, Comedian, and Door Mother @ Motherdisco Find her on Instagram @linda.in.hr or at her website https://www.lindainhr.com/