The Pressures of Privilege

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...

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...

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...

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...

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...

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...

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...

What happens when the most important healing knowledge in the world stays locked in the rooms of the people who already know it? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Araminta Jonsson, CEO of Mint Partnership, Executive Director of the Trauma Research Foundation, and the force behind Transform Trauma Oxford, Europe's largest trauma conference, for a conver...

What if the work that holds your family together has been deliberately erased from the official record? In this solo episode of The Pressures of Privilege, host Diana Oehrli follows a thread from Forbes cast iron sales data to a conversation with her 80-year-old friend Henry in his garden, where seeds and soil count as consumer spending while the labor he puts in every day vanishes from any ledger...

What happens when wealth passes from one generation to the next, but the wisdom doesn't come with it? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Tyler Osborne, financial educator, podcast host of Money Master, and self-described hope dealer who grew up sleeping on a couch in East San Jose and went on to work at JPMorgan before walking away to build something of...

When someone says "tax the rich," do they mean you? In this solo episode of The Pressures of Privilege, Diana Oehrli starts with Jeff Bezos and his proposal to exempt the bottom half of American earners from federal income tax and uses it to trace something far more uncomfortable. The federal income tax was built to reach visible money: salaries, bonuses, and realized gains. The wealthiest America...

What happens when you carry something forward that came through years of relationship and transmission rather than anything you earned alone? And what does it really mean to steward that? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Yanti Amos (former international lawyer, founder of Earth Yoga NYC, and global ambassador for the WTKO) for a conversation about lin...

What does it feel like when genuine kindness tips into rescue? In this solo episode of The Pressures of Privilege, Diana Oehrli draws on Dr. Jud Brewer's habit-loop research and 20 years watching people she loves get rescued until there was nothing left to rescue. She traces the enabling crisis to its source: generations of people with enough resources to avoid correction, who perfected the habit...

What do you do with a legacy you didn't build in a family that expects you to carry it? In this episode of Pressures of Privilege, host Diana Oehrli sits down with Ashley D. Varnado, former managing director at Bank of America's private bank, where she oversaw $25 billion in assets across 18 markets and became one of the youngest African American female managing directors at the firm. She stepped...

In May 2026, the largest review of medicinal cannabis ever conducted concluded that the drug is ineffective for treating anxiety, depression, or PTSD. Millions of people are using it for exactly those reasons. In this solo episode of The Pressures of Privilege, Diana Oehrli traces the real epidemic running beneath the addiction crisis: loneliness. She opens with her own story, from roaming the hal...

The proposed New York pied-à-terre tax on luxury secondary properties has rattled a certain class of people, and the conversation has already moved in its usual circles: Monaco, Palm Beach, and the calculus of 183 days south of the Mason-Dixon Line. In this solo episode, Diana Oehrli asks the harder question: not whether you can leave, but what you're actually trading away if you do. Diana traces...

What happens when the same resources that promise to protect you are quietly making your most dangerous habits easier to sustain? In the sixth and final essay of her Health-Wealth Divide series, host Diana Oehrli examines the pillar that lifestyle medicine calls "avoidance of toxic substances and behaviors," bringing to it 20 years of personal sobriety and a lifetime inside the systems of inherite...

What happens when you do everything right, the meetings, the steps, and the service, and still get close to losing it all? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Sean Dugan, a sober companion with 35 years of sobriety, nearly 20 years of professional recovery work, and a board seat at the Global Recovery Initiatives Foundation. Sean has worked with clients...

She had 400 people at her birthday party. Flew them in. Put them up. Open bar, live music, a toast that made the room cry. Three days later, she called Diana and said she felt completely alone. In this episode of The Pressures of Privilege, Diana Oehrli continues The Health-Wealth Divide series with Part 5: Connectedness. The American College of Lifestyle Medicine recently renamed this pillar, fro...

What do you do when the finish line is long past, and the feeling of enough still hasn't arrived? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Lindsey Frances, a legacy and wealth psychologist based between London and Switzerland who works with some of the world's most successful people, the ones who have more than they could spend and still cannot locate a sense...

What if every stress solution money can buy is actually making things worse? In this solo episode of The Pressures of Privilege, Diana Oehrli unpacks what she calls the stress paradox—the counterintuitive truth that wealth, despite giving access to the world's best therapists, elite retreats, psychedelic ceremonies, ketamine clinics, and expert coaches, often leaves high-achieving families more wo...

What happens when you're given every advantage—the education, the connections, the career, the passport—and still end up at 27 with a one-way ticket and no idea what you're actually for? In this episode of The Pressures of Privilege, host Diana Oehrli sits down with Chris Blachut, creator of Innate Edge and the writer behind The Zag. Chris walked away from a promising corporate finance career, spe...

In this episode of The Pressures of Privilege, host Diana Oehrli confronts one of the most overlooked health crises facing high-net-worth individuals: the slow, invisible erosion of sleep. Despite having every conceivable advantage — custom mattresses, blackout curtains, wearable trackers, and the freedom to architect their own schedules — wealthy people are sleeping worse than ever. Diana explain...

In the second installment of her six-part Health-Wealth Divide series on The Pressures of Privilege, executive coach Diana Oehrli tackles the pillar of physical activity — and the deeply counterintuitive ways that wealth erodes it. On paper, ultra high net worth individuals have every advantage. Personal trainers charging hundreds of dollars an hour, private Pilates studios, Pelotons in the guest...

In this episode of The Pressures of Privilege, executive coach Diana Oehrli opens a conversation that almost never happens in high-net-worth circles — the one about food. Not processed junk or tight budgets. The harder conversation: what happens when you have access to every nutritional resource money can buy, and your health still tells a different story. Drawing on her training through Harvard M...