21. The Messy Middle: 4 Lessons I’m Learning in a Season of Change (Espresso Shot) episode artwork

EPISODE · Mar 30, 2026 · 27 MIN

21. The Messy Middle: 4 Lessons I’m Learning in a Season of Change (Espresso Shot)

from Unfiltered Leadership with Lindsay Yellin · host Lindsay Yellin

In this solo episode of Unfiltered Leadership, Lindsay shares real-time reflections from a major season of change. Instead of waiting until everything is figured out, she talks about what it looks like to lead yourself in the messy middle.This episode explores the emotional and mental challenges that come with transition, identity shifts, uncertainty, and growth. Lindsay shares four lessons she is actively learning right now, including how to stop comparing yourself to past versions, how to avoid “double suffering,” how to stay present when you feel pressure to be productive, and why the hardest part of change is rarely what you expect.If you are navigating a transition in your career, your identity, your relationships, or your life, this episode is a reminder that you don’t have to have it all figured out to lead yourself well.Episode HighlightsWhy we romanticize past versions of ourselves during hard seasonsThe concept of double suffering and how we create extra stress in our mindsStruggling with productivity, identity, and feeling valuable during changeWhy the hardest part of transition is rarely what you expectHow to stay present instead of wishing yourself into the futureLeading yourself through uncertainty with compassion and resilienceWhy growth often happens in the messy middle, not the finished chapterAbout your host: Lindsay 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/chemistry-call ✨ Get your espresso shot of leadership insight, join the Grounds for Growth newsletter: https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth

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21. The Messy Middle: 4 Lessons I’m Learning in a Season of Change (Espresso Shot)

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