Today's wise guest is an entrepreneurial business owner who has lived and worked in Chicago, London and San Francisco. Lindsay Yellin is creative and bold—and she keeps it very real. She's worked as an executive in high-pressure industries and now helps other executive leaders in similar environments to cope and thrive.

When you listen to this episode you will come away with …

Tips and techniques for dealing with fear.
Practices you can apply right now - today - for coping with stress and uncertainty.
Leadership practices and advice on leading your team during tumultuous times.

More About Our Wise Guest Lindsay Yellin

Lindsay Yellin is an executive leadership coach who helps high-achieving creative leaders move beyond fear and self-doubt to lead with possibility and self-trust. A former advertising executive, she's no stranger to high-pressure, high-visibility environments. And she understands firsthand the challenge of staying true to yourself while leading others.

Today, Lindsay is a passionate champion and challenger for her clients, helping them unlock their leadership potential through deep self-connection and intentional relationships. She's also host of a new podcast, "Unfiltered Leadership with Lindsay Yellin."

Beyond coaching, you'll also find her behind the espresso bar, where her love for sparking connection shows up just as strongly. Whether in a coaching session or over a cup of coffee, her mission is the same: to inspire clarity, courage, and conviction that drive meaningful, lasting change.

Lindsay joins us today from her home in Half Moon Bay, California - on the Pacific Coast midway between Silicon Valley and San Francisco.

Resources

Lindsay Yellin Coaching website

Lindsay's Podcast:

Watch on YouTube

Listen on Spotify or on Apple Podcasts

Credits

Editor + Technical Advisor Bob Hotchkiss

Brand + Strategy Advisor Andy Malinoski

PR + Partnerships Advisor Rachel Bell

Marketing, Social Media and Graphic Design Chloe Lineberg

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Episode Chapters

[0:03:41] - Meet Lindsay Yellin: A Journey from Agency Life to Coaching

[0:04:18] - Lindsay and Skip share how they are connected

[0:04:51] - The Power of Place: Chicago Roots and Career Growth

[0:05:51] - The Moment Everything Changed

[0:06:31] - Fear vs. Possibility: A Practical Reframe

[0:08:59] - Coaching for Creative Leaders [0:10:11] - When the Jenga Tower Shakes: Navigating Uncertainty

[0:14:59] - Lindsay Yellin Shares Her Main Thing

[0:15:18] - Who I Am, Who I Want to Be: Using Values to Lead Yourself [0:20:53] - Self-Compassion Isn't Soft—It's Strong

[0:25:42] - Final Thoughts: Humanity Over Perfection

Ep. 136: Choosing Possibility Over Fear with Lindsay Yellin