My career looks successful — why doesn't it feel right? If career change feels scary, this is how to redesign your work life without starting over.

If you're a high achiever wondering whether to stay, quit, or start over, this conversation is for you. Lindsay Yellin sits down with Ronnie Dickerson Stewart to break down the You Inc. mindset — how to treat your employer as a client, define your non-negotiable career requirements, and build career options BEFORE layoffs, burnout, or automation force you to.

📕 ABOUT THE NEW BOOK:

Work Life Remix by Ronnie Dickerson Stewart is launching now! It's the playbook for mid-career professionals who want to redesign their work life without throwing away everything they've built. Learn how to create choice, self-trust, and future provision in an era where loyalty no longer equals security.

✨ Book a Coaching Chemistry Call with Lindsay: ⁠https://calendly.com/yellin-coaching/chemistry-call?month=2025-09⁠ 

ABOUT RONNIE DICKERSON STEWART:

Former C-suite executive, executive coach, and author of Work Life Remix. Ronnie now helps leaders navigate career burnout, career planning, and life design without starting over.

LinkedIn: ⁠https://www.linkedin.com/company/ohheycoach/⁠

Instagram: ⁠https://www.instagram.com/ohheycoach/?hl=en⁠

Get the Work Life Remix Book https://workliferemix.com/

This is for mid-career professionals and high achievers wondering whether to stay, quit, or start over — and how to improve work-life balance without quitting everything you've built.

✨ Get your espresso shot of leadership insight: ⁠https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth

Feeling lost while navigating a big life transition? You've outgrown the identity that got you here — not failed it.

✨ Get your espresso shot of leadership insight: https://yellingroundsforgrowth.myflodesk.com/groundsforgrowth

Major life transitions can create a profound loss of identity, leaving high achievers desperate to find themselves again by returning to who they were. Leadership coach and author of Work Life Remix, Ronnie Dickerson Stewart, challenges that instinct: the identity that carried you through a former season may be unqualified for the life you’re building now.

In this conversation with Lindsay Yellin on Unfiltered Leadership, Ronnie shares how she navigated parenthood, leaving corporate life, and building a business — and how to process grief, name what you’re losing, and reclaim agency in your next chapter. If you’re moving through career change, parenthood, layoffs, or any season where familiar roles no longer fit, this is how to stop chasing your old self and start meeting the person this season requires.

This is just a portion of the larger conversation Lindsay and Ronnie had on this powerful topic. If you’re hungry for more, listen to the whole conversation here.

How to Lead Yourself When You Feel Lost with Ronnie Dickerson Stewart:

YouTube: https://www.youtube.com/watch?v=U3WzFoxKnQw

Spotify: https://open.spotify.com/episode/6U4Eg88vSh316GhxkEM6Ip?si=rfPajXO2QvCjrxYCQ-Q2TQ

Your core values can evolve, leaving your decisions aligned with a version of you that no longer exists.

Core values are often treated as permanent, but Lindsay Yellin argues that they can change as your life, priorities, beliefs, and needs evolve. That matters because values misalignment can surface as frustration, depleted energy, strained relationships, or difficulty making decisions without revealing its true source. 

Drawing on her work as an executive leadership coach, Lindsay shows how personal values influence self-leadership, leadership identity, and the choices you make under pressure. Her core values audit starts with two revealing questions: What brings you the most joy or contentment, and what frustrates you most? From there, she shows how to identify your core values, notice where your actions contradict them, and define what living in alignment looks like now.

This is for leaders and professionals who have changed without reevaluating the internal compass guiding their work and lives. You’ll leave with a clearer way to audit what matters now and make decisions that honor the person and leader you have become.

Description

My dad's leadership legacy changed how I define success and what I believe ambition should never cost us.

More than 16 years after my father Norm passed away, a recent trip to Hawaii with my brothers brought his example back into focus. Reflecting on him has changed how I understand leadership legacy: it lives not only in what we achieve, but in how consistently we treat people.

He showed me what authentic leadership looks like — respect, curiosity, partnership, and the commitment to live your principles whether people are watching or not. But his life also left me with harder questions about the cost of professional success when work begins to consume our health, presence, and relationships.

As a leadership coach, former corporate leader, and business owner, I'm sharing these lessons for ambitious leaders who want sustainable leadership without losing themselves to their work. If you've felt the pull of leadership burnout — or watched ambition quietly crowd out the life you're building — this one is for you.

I hope you leave ready to lead with integrity, remember what your success is for, and build a life and legacy you are present enough to enjoy.

Stop trying to "skill" your way out of burnout. Most leadership frameworks you’re following are actually sabotaging your ability to scale.

In this episode of Unfiltered Leadership, host Lindsay Yellin sits down with executive coach Christi Pizarek to challenge everything you think you know about leadership development. If you’ve been chasing "skill-based frameworks" to fix burnout or navigate complex challenges, you’re missing the point.

Christi Pizarek, founder of inTension Coaching and Consulting, shares her transformative journey from the advertising world to executive coaching, explaining why true leadership impact isn’t about adding more tools to your belt—it’s about deep, intentional capacity building.

In this video, you will learn:

• Why the "time is money" mindset is sabotaging your long-term organizational health.

• The "operating system upgrade": How to build foundational resilience to thrive in perpetual swirl.

• Why tension is actually the most fertile ground for innovation and leadership growth.

• How to cultivate curiosity and agency to navigate complexity without losing your groundedness.

About Christi Pizarek: Christi is an executive, team, and systems coach who blends depth, wisdom, and systems thinking. After a distinguished career in advertising (Starcom), she transitioned into internal and later independent coaching, focusing on helping leaders leverage discomfort for possibility and sustainable development.

• LinkedIn: https://www.linkedin.com/in/christi-pizarek/
• inTension's Website: https://www.intensioncoaching.com/
• inTension's IG: @inTensionCoaching

Setting boundaries at work doesn't threaten your career, it strengthens your leadership. Morgan shares how she went from burning out in her early career in advertising to leading authentically without sacrificing her values, her voice, or her influence.

In this episode, Morgan Pomish, a leader in the advertising industry breaks down what it really takes to set professional boundaries in a hustle culture without losing credibility, connection, or career momentum.

Drawing from her own experience of burnout, stress-induced health issues, and navigating male-dominated rooms, Morgan shares the exact approach that helped her lead authentically while staying true to her values.

What You'll Learn: 

• Why workplace boundaries feel impossible early in your career  and when they start to work for you 

• How to speak up for what you need without being labeled "difficult" 

• Why managing your energy matters more than managing your time 

• The truth about women and emotion in leadership 

• How consistent boundaries build trust and psychological safety on your team 

• The thermostat vs. thermometer leadership model 

• Why "being fun to work with" is an underrated leadership strategy 

• How your personal values shape your leadership style and why that influences everyone

This episode is for high-performing professionals, especially women in leadership, who want to build a career that doesn't cost them their well-being.

What happens when you give 11 years to a company and then get a calendar invite that changes everything? 

Kelly Nash spent over a decade at Salesforce, building a career coaching business on the side as her "just in case." When the layoff finally came, she didn't panic; she saw it as permission. In this episode, Kelly shares how to stop letting your job title define your identity, why the "meaningful middle" between jobs matters more than rushing into the next role, and how to build a portfolio career that no single company can take away. 

If you're navigating a layoff, rethinking your career identity, or wondering how to create more security through multiple income streams, this conversation is for you.

I spent years making everyone comfortable, and for a long time, it worked. It made me good at reading rooms, smoothing tension, staying dependable, and being the person people could count on. But as I sat down for this solo birthday episode, reflecting on one of the hardest years of my life, I realized how much of that “strength” was actually my people pleaser trying to keep me safe.

What I’m learning is that people pleasing can look like leadership, kindness, and strength from the outside, while underneath it can become self-abandonment. When your need to be liked starts overriding your values, your presence, your boundaries, and your ability to ask for help, something has to change.

If you are a high-achieving people pleaser who is exhausted from fixing, managing, performing, and keeping everyone else comfortable, I hope this feels like a hand on your shoulder. We’re talking about how to stop people-pleasing, how to sit with the discomfort of disappointing others, and how to reclaim your needs before burnout makes the choice for you.

Inside this episode

• Why this birthday reflection brought my people-pleasing into focus

• Why people-pleasing can become a career survival strategy • The leadership cost of staying silent to keep the peace

• How managing everyone’s emotions keeps you from being present

• Why is no one pleased when you stop pleasing

• How to reclaim your values, boundaries, and needs without losing your worth

In this episode of Unfiltered Leadership, Lindsay sits down with Caitlin Golden, HR executive and longtime friend, for a deep conversation about coaching, leadership, vulnerability, and what it really means to lead people well.

Lindsay and Caitlin first met through the Co-Active Training Institute during coach training while both were still working in advertising and marketing. What started as professional curiosity evolved into a years-long friendship grounded in shared values around people-centered leadership and personal growth.

Together, they explore how coaching fundamentally changed the way they lead, listen, communicate, and show up in relationships at work.

This conversation dives into:

• why most people hear but don’t truly listen

• how curiosity creates stronger leadership

• the difference between fixing and supporting

• vulnerability, accountability, and trust in leadership

• why great managers see people as whole humans

• and how self-awareness changes the way we lead others

Caitlin also shares practical examples from her experience leading HR teams, conducting exit interviews, managing talent, and helping people grow through feedback and recognition.

This episode is a powerful reminder that leadership isn’t about having all the answers. It’s about being willing to listen deeply, stay curious, and create spaces where people feel seen, heard, and understood.

About your host: Lindsay Yellin

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 

About Caitlin Golden

Caitlin is a senior HR executive with nearly two decades of experience building people-first cultures inside fast-moving agencies and startups. A Co-Active trained coach, she brings that same whole-person philosophy into her leadership work — helping organizations and the individuals within them grow from the inside out. Her practice sits at the intersection of strategic HR and human development, with a particular focus on leadership, engagement, and building the kind of environments where people genuinely thrive.

Episode Highlights

• How Lindsay and Caitlin met through coach training

• Why coach training was “life changing” for both of them

• The difference between hearing and truly listening

• What “powerful questions” actually look like

• Why curiosity is one of the most underrated leadership skills

• How coaching changes the way you manage teams

• The danger of leaders trying to fix everything

• Why strong leaders guide instead of control

• The connection between self-awareness and emotional intelligence

• How to “read the room” by understanding yourself first

• Why great leaders admit when they don’t know something

• The role of vulnerability, accountability, and repair in leadership

• How acknowledgment and recognition transform team culture

• Why people-centered leadership creates stronger engagement and trust

• Letting go of ego, perfectionism, and control as a leade

In this solo episode of Unfiltered Leadership, Lindsay reflects on five leaders who fundamentally changed the trajectory of her life and career by believing in her before she fully believed in herself.

From her early days in advertising to her transition into coaching and leadership development, Lindsay shares the moments, conversations, and leadership behaviors that shaped how she leads today.

This episode is both deeply personal and highly practical, unpacking what great leadership actually looks like in action:

• Sponsorship over surface-level mentorship

• Creating psychological safety

• Championing the whole person

• Speaking possibility into others

• Helping people step into rooms before they feel fully ready

Through stories about 5 leaders who impacted her career, Lindsay explores how belief can change someone’s trajectory and how leaders have the opportunity to create those moments every single day.

If you’ve ever wondered what truly impactful leadership looks like, this episode is a reminder that sometimes the smallest moments of belief become the biggest turning points.

• Why the best leaders don’t just mentor, they sponsor
• The difference between giving advice and creating access
• How Jessica Henrichs helped Lindsay see her own leadership potential
• Why speaking your ambitions out loud can change your life
• Ronnie Dickerson Stewart’s role in Lindsay becoming a coach
• The power of sharing your goals with the right people
• How Amy Cheronis helped Lindsay launch her coaching career
• Why leaders should create environments where people feel safe asking before they’re ready
• Chris Loeffler’s approach to people-first leadership
• Why some performance problems are actually role-fit problems
• Joan Vivaldelli’s role in Lindsay becoming a leadership facilitator
• Why confidence comes after action, not before
• The importance of believing in others before they fully believe in themselves

About your host: Lindsay Yellin

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