HeyJaredThe Pressures of Privilege
Conversations about mastery, family, legacy, and what success doesn't solve.Diana Oehrli talks with concert pianists, family wealth advisors, artists, and people who work quietly with successful families - from a cleaner in Gstaad who knows wealthy families from the inside,…
- Indexed episodes, last 90 days
- 10
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- Sep 8, 2026
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- Jul 6, 2026
Latest episodes
Why Work If You Don't Need The Money? (opens the original)
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What if "why work?" is the wrong question? In this solo episode of The Pressures of Privilege, host Diana Oehrli takes on a question she's heard more than once, from a relative who asked why she'd work when she didn't need the money and from an ex who said he'd take her back if she got a job. She traces it back to a call with her Swiss lawyer, who told her an inheritance meant a bigger social security bill unless she took a job. That contradiction sends her looking past the usual answer. She tal
Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement (opens the original)
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In this episode of Pressures of Privilege, host Diana Oehrli sits down with Howard Kaplan, CEO and founder of Personal Strategic Design, who spent 30 years as a Harvard MBA, CPA, and wealth manager telling accomplished people how to retire, before his own life forced him to admit that doing everything right hadn't delivered what he actually wanted. Now he helps successful people in the second half of life find health, happiness, and emotional prosperity, drawing on life design training with Stan
Ep49 Matt Grace—How to Set a Boundary With Someone You Love When You're Terrified It Will Hurt Them (opens the original)
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In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Matt Grace, founder of the family recovery practice, Saving Grace, who has spent more than twenty years sober and over ten thousand hours walking wealthy families through a child's, a spouse's, or a sibling's addiction. His memoir, God Doesn't Relapse, released on August 11 and traces his own years of active addiction, an overdose in his boss's office, and a father who paid his bills until he turned twenty-nine. Matt
Ep48 Anna Holtzman—How to Stop Earning Your Right to Belong When You Were Born Into Privilege (opens the original)
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In this episode of Pressures of Privilege, host Diana Oehrli sits down with Anna Holtzman, a psychotherapist in private practice in New York City who spent 15 years in publishing and television, including years as a reality TV editor at MTV, before debilitating migraines pushed her toward mind-body healing and an entirely new career in her 40s. Anna is trained in somatic experiencing, internal family systems, and pain reprocessing therapy, and she hosts the podcast How to Trust Yourself. Anna wr
Ep47 Jolanthe de Koning—How to Let Go of Perfect When Achievement Is Your Whole Identity (opens the original)
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In this episode of Pressures of Privilege, host Diana Oehrli sits down with Jolanthe de Koning, PhD researcher, yoga teacher, and founder of Amid the Mess, for a conversation that cuts well beneath the surface of wellness culture and gets honest about what it actually takes to feel well when real life keeps getting in the way. Jolanthe spent nearly nine years inside academia studying how physical activity and loneliness intersect in older adults. What she found surprised even her. The wealthiest
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