Want to Live More Fully Alive?

Try the 5-Day Meaning Design Experiment: one mindset and practice per day to help you design a more meaningful life.

Includes an exclusive preview from Bill & Dave’s new book How to Live a Meaningful Life.

Coaching

Cindy Mascheroni

United States of America
Accepting Clients
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The leaders I work with have already won by most measures. What brings them to coaching isn’t failure. It’s the quiet sense that achievement and meaning are not the same thing, and the growing cost of ignoring that.

That gap is where I work.

For 25 years, I’ve coached CEOs, founders, and executives through growth, transition, succession, and the moments that reveal what actually matters. I’ve lived my own version: career pivots, a 37-year marriage, three kids, and a lifelong immersion in learning and inner work. I’m coaching from presence, backed by intuition, and informed by wise teachers.

Living in Sun Valley, Idaho teaches me something daily. We don’t design a life in isolation. Leadership, business, and life are interrelated and are most powerful when coherent. They’re part of a larger, dynamic, generative ecosystem. The mountains make it impossible to forget.

I love skiing, hiking, and deep conversation. Most of all, I love playing with my four grandkids, who remind me that wonder is not a small thing.

Coaching Types

Business & Entrepreneurship Executive and Leadership Retirement

Language Spoken

English

Group Sizes Available

Individual Small Group (10 or less)