The Pressures of Privilege

Privilege gives you more. What will you do with it? The Pressures of Privilege Show explores class, achievement, family legacy, and the responsibilities that come with advantage — through conversations...more

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Latest Episodes

Ep51 Dr. Louise Stanger—Keep Falling Up: Addiction, the Myth of Rock Bottom, and How to Help Someone You Love Before It's Too Late

September 13, 2026

Ep51 Dr. Louise Stanger—Keep Falling Up: Addiction, the Myth of Rock Bottom, and How to Help Someone You Love Before It's Too Late

What actually happens inside a family when someone is drowning in addiction... and everyone around them is quietly drowning too? In this episode of...

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00:44:31

Why Work If You Don't Need The Money?

September 08, 2026

Why Work If You Don't Need The Money?

What if "why work?" is the wrong question? In this solo episode of The Pressures of Privilege, host Diana Oehrli takes on a question...

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00:07:46

Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement

September 06, 2026

Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement

In this episode of Pressures of Privilege, host Diana Oehrli sits down with Howard Kaplan, CEO and founder of Personal Strategic Design, who spent...

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00:58:22

Ep49 Matt Grace—How to Set a Boundary With Someone You Love When You're Terrified It Will Hurt Them

August 31, 2026

Ep49 Matt Grace—How to Set a Boundary With Someone You Love When You're Terrified It Will Hurt Them

In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Matt Grace, founder of the family recovery practice, Saving Grace,...

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00:50:25

Ep48 Anna Holtzman—How to Stop Earning Your Right to Belong When You Were Born Into Privilege

August 23, 2026

Ep48 Anna Holtzman—How to Stop Earning Your Right to Belong When You Were Born Into Privilege

In this episode of Pressures of Privilege, host Diana Oehrli sits down with Anna Holtzman, a psychotherapist in private practice in New York City...

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00:58:39

Ep47 Jolanthe de Koning—How to Let Go of Perfect When Achievement Is Your Whole Identity

August 16, 2026

Ep47 Jolanthe de Koning—How to Let Go of Perfect When Achievement Is Your Whole Identity

In this episode of Pressures of Privilege, host Diana Oehrli sits down with Jolanthe de Koning, PhD researcher, yoga teacher, and founder of Amid...

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00:54:28

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