Diana Oehrli

The Pressures of Privilege

Privilege is supposed to set you free. So why doesn't it? The Pressures of Privilege goes inside the worlds of wealth, status, achievement, and family legacy—with inheritors, founders, advisors, doctors, artists, observers, and the ones who got out. Hosted by Swiss-American writer Diana Oehrli, the show explores the private pressures that accompany advantage and asks what it takes to build a life that is healthy, meaningful, and truly your own. Every episode is about one thing: freedom. New episodes twice a week.

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Author

Diana Oehrli

Category

Education

Podcast website

feeds.castos.com

Latest episode

Nov 2, 2026

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Episodes

Ep58 LaVonne Chastain and Gaylynn Kapri—How to Get Up When Your Worst Chapter Starts to Feel Like Your Whole Story 02.11.2026

In this episode of The Pressures of Privilege , host Diana Oehrli sits down with cousins LaVonne Chastain and Gaylynn Kapri, the writer and the subject of the memoir Get Up , for a conversation about what it takes to stand back up after childhood abuse, addiction, the loss of a daughter, and stage four cancer. Gaylynn lived through all of it and is still here. She recently married and is starting...

Ep57 Peter Holmes à Court—How to Put Your Privilege to Work for Other People When the Career You Love Costs You Your Family 26.10.2026

In this episode of The Pressures of Privilege , host Diana Oehrli sits down with Peter Holmes à Court, author of Riding with Giants , co-owner of the South Sydney Rabbitohs alongside Russell Crowe, a media leader at Davos since 2012, and today the Chief Convener of Afrika House in Nairobi, for a conversation about what a person with a lot of opportunity owes to the people who never got the same ch...

Ep56 Dr. Jud Brewer—How to Stop Anxiety From Running Your Life Even When Control Has Stopped Working 18.10.2026

In this episode of The Pressures of Privilege , host Diana Oehrli sits down with Dr. Jud Brewer, a psychiatrist and brain scientist who runs research at the Mindfulness Center at Brown University and wrote the New York Times bestseller Unwinding Anxiety, for a conversation about why money and control fail to quiet an anxious mind. Dr. Brewer's lab began with smoking, then moved to eating, and foun...

Ep55 Mark Drax—How to Stop Believing You Are a Monster When an Abusive Childhood Taught You to Hate Yourself 11.10.2026

In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Mark Drax, an ICF-certified addiction recovery coach and a disciple of Dr. Gabor Maté, for a conversation about what happens when a boy from a secure home, with private schools and every advantage on paper, grows into a man who spends decades hiding. Mark was never into drink or drugs. At six foot eight, with white hai...

Ep54 Tammy Buss—How to Hand Down a Family Business When Everyone Is Quietly Assuming a Different Plan 05.10.2026

In this episode of The Pressures of Privilege , host Diana Oehrli sits down with Tammy Buss, founder of BlueRoots and a family enterprise advisor, for a conversation about what happens to a family when a business gets handed down and the hard conversations never get had. Tammy spent more than 30 years building her own business in financial services, then lived through her own succession, selling p...

The Consumer and the Steward 30.09.2026

In this solo episode of The Pressures of Privilege, the third in her stewardship series, host Diana Oehrli returns to a February night in 2012 in the Swiss Alps, when snow kept piling up outside her chalet in Gstaad, her phone stayed silent, and an iced-over windshield made the two-hour drive to Geneva almost impossible to see through. Diana was in the middle of a painful breakup, barely sleeping,...

Ep53 Dr. Lindsay Emmerson—How to Stop Chasing Perfect Parenting 27.09.2026

In this episode of Pressures of Privilege, host Diana Oehrli sits down with Dr. Lindsay Emmerson, a psychologist and mother of four who has spent her career turning decades of parenting research into tools that hold up in the middle of a real meltdown, not just on a whiteboard. Lindsay's research points to something most parents have never been told: getting it right about half the time is enough...

Ep52 Sara Vetter—How to Heal Your Relationship With Money When Having Plenty Still Feels Like Not Enough 20.09.2026

In this episode of Pressures of Privilege, host Diana Oehrli sits down with Sara Vetter, CEO of the Soul of Money Institute and a longtime work partner of Lynne Twist, author of The Soul of Money, for a conversation about what it takes to feel at home with yourself when a full bank account has never been able to do that for you. Sara grew up in a big Italian ranching family in Central California t...

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 13.09.2026

What actually happens inside a family when someone is drowning in addiction... and everyone around them is quietly drowning too? In this episode of Pressures of Privilege, host Diana Oehrli sits down with Dr. Louise Stanger, who is a nationally recognized interventionist, licensed clinical social worker, founder of All About Interventions, and author of six books, including her most recent, Trauma...

Why Work If You Don't Need The Money? 08.09.2026

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 secu...

Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement 06.09.2026

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 hal...

Ep49 Matt Grace—How to Set a Boundary With Someone You Love When You're Terrified It Will Hurt Them 31.08.2026

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,...

Ep48 Anna Holtzman—How to Stop Earning Your Right to Belong When You Were Born Into Privilege 23.08.2026

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 fam...

Ep47 Jolanthe de Koning—How to Let Go of Perfect When Achievement Is Your Whole Identity 16.08.2026

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...

Ep46 Todd Sarner—How to Raise Resilient Kids When You're Already Doing Everything Right 09.08.2026

Why do children who have every advantage in the world still struggle to handle a simple no? In this episode of Pressures of Privilege, host Diana Oehrli sits down with Todd Sarner, a licensed therapist who trained under attachment expert Dr. Gordon Newfeld and has spent 22 years working with more than 2,000 families, many of them among the most resourced in the country. Todd is the author of The C...

Ep45 Jeanne Omlor—How to Find What You Truly Want When Money and Power Still Feel Like Isolation 03.08.2026

What happens when everything you've worked to acquire starts working you instead? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Jeanne Omlor, a business coach who has been an actress, a fashion designer, and a Wall Street recruiter before building a coaching practice that has served seven hundred clients in seven years without spending a dollar on ads. Jeanne also...

Ep44 Graham Hawley—How to Take Your Health Back When the System Profits From You Staying Sick 26.07.2026

What if the exhaustion, the cravings, and the diagnoses you've been told are just "getting older" are actually working exactly as designed? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Graham Hawley, a certified health and wellness coach and founder of Simply Health Conscious, who has spent the last six years helping Americans get back something he never had to t...

Ep43 Dr. Gloria Vanderhorst—How to Raise a Son Who Can Actually Feel When Boyhood Teaches Him Not To 20.07.2026

What if the wider emotional range boys are born with is trained out of them before they can talk? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Dr. Gloria Vanderhorst, a psychologist who has spent over 30 years working with kids, parents, and couples and is currently finishing a book for fathers on raising sons who are both strong and whole. Dr. Vanderhorst has sp...

Ep42 Todd Ormiston—How to Raise Resilient Kids When the World Keeps Selling Them Outcomes Over Character 06.07.2026

What if the biggest gift you could give your child is the chance to fail safely, in public, and get back up? In this episode of Pressures of Privilege, host Diana Oehrli sits down with Todd Ormiston, executive director of North Country School and Camp Tree Tops in Lake Placid, New York, a place Diana attended as a child, alongside three generations of her family before her. Todd grew up on a farm...

Ep41 Lynne Harlow—The Art of Taking Away: Discovering How Giving More Means Doing Less 29.06.2026

What if taking something away could be the most generous thing you do? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Lynne Harlow, a reductive artist with work in the Met, MoMA, and the RISD Museum, who has also spent twenty-six years inside the philanthropy world managing grants for the Lily Auchincloss Foundation in New York and now runs her own advising firm, T...

The Art of Showing Up Every Day 24.06.2026

What if hitting the target was never the point? In this solo episode of The Pressures of Privilege, host Diana Oehrli revisits a discipline she has kept since childhood: an art practiced every single day, the way her sensei once told her to brush her teeth. Drawing on Eugen Herrigel's 1948 classic Zen in the Art of Archery, the karate teachers who shaped her, and the piano instructors who caught h...

Ep40 Eames Yates—How to Find Peace When Every Achievement Still Feels Like a Fraud 22.06.2026

What happens when the chase that built your entire career stops making sense? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Eames Yates, the journalist who landed interviews most reporters only dream of: CIA directors, Navy SEAL commanders, Alec Baldwin, and, eventually, the Dalai Lama himself, in his home in India. Then he walked away from all of it to open a yog...

Switzerland Is Counting The Wrong Foreigners 17.06.2026

What happens when an entire country is certain something is disappearing but is wrong about who took it? In this solo episode of The Pressures of Privilege, host Diana Oehrli returns to Gstaad, the Swiss village where her grandparents lived and where she watched the butcher shop, the bakery, and the dining room at the Olden close one by one. After Swiss voters rejected an initiative to cap the cou...

Ep39 Deborah Delaney—How to Answer "Is This It?" When You Already Have Everything You Were Supposed to Want 14.06.2026

What do you do with the rest of your life once you already have everything you were taught to want? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Deborah Delaney, a woman who spent 16 years as a London broker before she woke up one morning, looked out at the beautiful home, the six Arabian horses, the successful business, and the family she had built, and asked he...

”You're American” 10.06.2026

Where do you belong when every answer feels only partly true? In this solo episode of The Pressures of Privilege, host Diana Oehrli explores the world of adult third culture kids, or ATCKs: people who grew up between their parents' culture and the culture of the country where they lived and formed a third culture of their own. Diana shares what happened when she moved to Gstaad in 2002 and her nei...

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