The Unspeakeasy With Meghan Daum

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👉 https://www.theunspeakablepodcast.com

Meghan's guest this time is author, essayist, and friend of the pod Sarah Hepola, who returns to celebrate her long-awaited memoir, The Only Thing There is to Want. Having survived early drafts, financial close-calls, and late-night meltdowns together, Meghan was eager to sit down with Sarah to trace the book's arduous six-year journey to publication and explore its honest take on romantic solitude.

Together, they chart the cultural shift from Gen X dating norms to today's hyper-connected, yet deeply lonely, mating landscape. From the "ambiguous loss" of childlessness to the surprisingly sweet dynamics of older women dating younger men, this episode explores what happens when post-feminist independence meets the messy, unpredictable urge for partnership in midlife.

This conversation covers:

• The Craft and Chaos of Memoir: How Sarah navigated a six-year writing ordeal, DoorDash rejections, and major draft overhauls to capture the delicate anatomy of three defining relationships.

• Modern Fertility and the "Ambiguous Loss" of Singledom: A frank look at shifting marriage statistics, biological clocks, and how media myths surrounding late-in-life motherhood led a generation astray on IVF.

• Hypersexualization, Internet Brain, and New Mating Rules: Why modern dating apps, online gender wars, and changing standards around intimacy have turned modern courtship into a confusing battlefield for both men and women.

Want to support the show and join our off-the-record community hangouts? Become a paid subscriber to The Unspeakeasy on Substack.

👉 https://www.theunspeakablepodcast.com

Sarah Hepola is an essayist, journalist, podcaster, and New York Times best-selling author. She wrote the acclaimed memoir Blackout: Remembering the Things I Drank to Forget as well as The Only Thing There is to Want. Her writing on culture, addiction, relationships, and modern womanhood has appeared in The Atlantic, The New York Times, Salon, Texas Monthly, and Slate.

• Sarah Hepola's Book: The Only Thing There is to Want

• 👉https://sarahhepola.com/the-only-thing-there-is-to-want

• Sarah Hepola's Website:

• 👉 https://sarahhepola.com

• Sarah Hepola's Instagram:

• 👉 https://www.instagram.com/thesarahhepolaexperience

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members.

• 👉 https://www.theunspeakablepodcast.com

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

• 👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

• 👉 https://www.theunspeakablepodcast

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

• 👉 https://tinyurl.com/ystzc5yz

Meghan's guest is Emma Pettit, a former Chronicle of Higher Education reporter who moved into audio this year at Longview, the new independent media outlet founded by veteran podcast creator Andy Mills. Her new three-part series, Street Fight, looks at a conflict playing out on sidewalks across the country: the rights of people living on the street versus the rights of everyone else. Emma traces the tramps and hobos who followed the Civil War and the Skid Row "bum era" that lasted into the 1970s. She explains why the problem looked so different by the 1980s, when the asylums had emptied, cheap housing had been zoned away, and crack had arrived. Meghan and Emma talk about the 1987 case of Joyce Brown, a woman who lived on a Manhattan heating grate. Mayor Ed Koch had her involuntarily committed, and the NYCLU fought him in court, arguing that she wasn't crazy, just homeless. She won her release, and Ronald Reagan later cited her case as proof of American freedom.

From there the conversation moves to a topic Meghan has covered a lot lately: Los Angeles and the present day. Emma interviewed Estela Lopez, a past guest on The Unspeakeasy, about how Skid Row went from desperate to horrifying. They discuss the court rulings in Jones v. City of Los Angeles, Martin v. Boise, and Grants Pass v. Johnson that left cities unsure whether they could enforce anti-camping laws at all. They also examine what "available shelter beds" really means, how the new supply of methamphetamine and fentanyl has changed the street population, and why Meghan thinks we need to stop lumping every kind of homelessness together.

This conversation covers:

• From Hobos to Encampments: The evolution of street life in America, the deinstitutionalization of public psychiatric care, and how hyper-potent modern street drugs transformed the landscape.

• The Joyce Brown Precedent: How a 1980s court battle over a homeless woman sleeping on a Manhattan heating grate set the template for modern legal paralysis.

• Rights, Wrongs, and Sidewalks: The fallout of court rulings like Martin v. Boise, the limitations of the "Housing First" framework, and what genuine compassion actually requires.

Want to support the show and join our off-the-record community hangouts? Become a paid subscriber to The Unspeakeasy on Substack.

👉 https://www.theunspeakablepodcast.com

Emma Pettit is a reporter and audio producer at Longview. Before stepping into audio with her three-part podcast series Street Fight, she spent a decade in print journalism, serving as a senior reporter for The Chronicle of Higher Education where she covered campus politics, faculty disputes, and institutional meltdowns. She began her journalism career at the Arkansas Democrat-Gazette after graduating from Villanova University.

• Listen to Emma's full audio series Street Fight on Longview:

• 👉 https://www.longview.report/series/street-fight

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members.

• 👉 https://www.theunspeakablepodcast.com

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

• 👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

• 👉 https://www.theunspeakablepodcast

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

• 👉 https://tinyurl.com/ystzc5yz

Another episode about local politics that's really about so much more.

Meghan's guest is Tanya Tsikanovsky, a candidate for West Hollywood City Council. (West Hollywood is part of greater Los Angeles but functions as its own municipality.) Tanya came out at 14 and founded her high school's first Gay-Straight Alliance, was a die-hard liberal Democrat, and later worked on Hillary Clinton's 2016 campaign in Iowa. But everything changed after the attacks of October 7th, 2023, when she says her Zionism cost her friendships, a rec-league invitation, and access to LGBT community spaces. She eventually did something she never could have imagined: registered to vote as a Republican. Now she's entered politics herself.

They talk about West Hollywood's small-city politics, why Tanya opposes new bike lanes on Fountain Avenue (a surprisingly contentious issue), the difference between "safety ambassadors" and actual law enforcement, and a West Hollywood care team's success getting an unhoused, mentally ill woman into treatment and housing. They also get into Prop 47, the limits of housing-first policy, and the DSA's growing influence in LA city politics.

They close on a topic Meghan's listeners have heard her discuss a lot lately: the seeming intractability of chronic street homelessness, including animal abuse and neglect on Skid Row and in other encampments around the city.

Want to support the show and join our off-the-record community hangouts? Become a paid subscriber to The Unspeakeasy on Substack.

👉 https://www.theunspeakablepodcast.com

• Visit Tanya Tsikanovsky's YouTube channel.

• 👉 https://www.youtube.com/@Highlyjewish

• Follow Tanya Tsikanovsky on social media @HighlyJewish or learn more about her campaign online.

• 👉 https://tanyaforchange.org

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members.

• 👉 https://www.theunspeakablepodcast.com

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

• 👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

• 👉 https://www.theunspeakablepodcast

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

• 👉 https://tinyurl.com/ystzc5yz

Meghan's guest this week is journalist Michael Powell, a staff writer at The Atlantic and longtime former New York Times reporter whom she has admired for years for his willingness to report on thorny, third-rail cultural topics. She talked with him about his recent reporting on chronic street homelessness, drug addiction, and the real-world consequences of progressive governance. Specifically, they discussed how the "harm reduction" model plays out in cities like Burlington and Seattle, and why mainstream media newsrooms have become so hesitant to cover complex cultural realities.

This conversation covers:

• The Reality of "Harm Reduction": How an approach born during the AIDS crisis expanded into policies that enable public fentanyl use while leaving working-class neighborhoods to deal with the fallout.

• Navigating the "Third Rail" Beat: What Michael learned covering sensitive cultural flashpoints—from campus racial controversies to gender sports eligibility—at The New York Times.

• Ideology vs. Lived Experience: The disconnect between well-meaning policy rhetoric and the daily struggles of local residents, parents, and small business owners.

• The Culture of Modern Newsrooms: Why institutional conformity, luxury beliefs, and fear of social media backlash stifle honest journalism—and why independent inquiry matters.

Read Michael Powell's writing for The Atlantic:

👉 https://www.theatlantic.com/author/powell-michael

Michael Powell is a staff writer at The Atlantic. Prior to joining The Atlantic in 2023, he spent sixteen years at The New York Times, serving as a national reporter, metro columnist, sports columnist, and coverer of cultural "third rail" issues. Before his career in journalism, he worked as a cab driver, doorman, and tenant organizer, and previously reported for The Washington Post, The Bergen Record, and The Burlington Free Press.

• Michael Powell's writing for The Atlantic:

• 👉 https://www.theatlantic.com/author/powell-michael

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members.

• 👉 https://www.theunspeakablepodcast.com

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

• 👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

• 👉 https://www.theunspeakablepodcast

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

• 👉 https://tinyurl.com/ystzc5yz

Meghan's guest this week is Evan Barker, a former progressive operative, fundraising strategist, and author of Nothing Left: Confessions of a Democratic Operative. Meghan was eager to sit down with Evan after following her journey from a working-class Midwestern Obama campaign volunteer to a high-powered consultant who ultimately grew disillusioned with the modern Democratic machine. Together, they pull back the curtain on what actually goes on inside campaign "call time," how wealthy donor advisors hijacked progressive priorities, and why the party's relentless focus on identity politics alienated the very working-class voters it claims to represent.

In this conversation, they dive into:

• The Brutal Reality of Political "Call Time": What it's like to sit beside candidates for eight hours a day begging billionaires for cash, using psychological tricks, and maneuvering past corporate gatekeepers.

• How Identity Politics Captured the Donor Base: How wealthy donors, young staffers, and ideological consultants created race-based funding mandates and cultural litmus tests that backfired across the country.

• Behind the Scenes at the DNC Spectacle: Evan's bizarre encounters chaperoning TikTok influencers, dodging Chicago vasectomy vans, and realizing the party's messaging was completely detached from everyday economic strain.

• Marrying MAGA Populism with Bernie Sanders Economics: Why a working-class party offering real health reform alongside common-sense border control could dominate American politics—if the two-party monopoly ever allows it.

Grab Evan's book Nothing Left: Confessions of a Democratic Operative and check out her work: 👉 https://www.evanbarker.net

Evan Barker is an author, political strategist, and former Democratic campaign operative. Raised in a union family in the Midwest with a rare genetic lung condition, she got her start in politics volunteering for Barack Obama's 2008 campaign before rising through the ranks to direct high-dollar fundraising for progressive candidates across the country. A first-generation college graduate, she served as a director at the campaign consulting firm Left Rising, raising millions of dollars before publicly breaking with the progressive movement. She is the author of Nothing Left: Confessions of a Democratic Operative.

• Connect with Evan Barker: Grab a copy of her book Nothing Left and check out her latest writing. 👉 https://www.evanbarker.net

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members.

• 👉 https://www.theunspeakablepodcast.com

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

• 👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

• 👉 https://www.theunspeakablepodcast.com

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

• 👉 https://tinyurl.com/ystzc5yz

After a decade of ideological conformity, is American theater ready to laugh at itself again?

This week Meghan is joined by Broadway star, comedian, and producer PJ Adzima, founder of Stage Time NYC and producer of Slam Frank—a mind-melting new musical that reimagines The Diary of Anne Frank through "an intersectional, multi-ethnic, genderqueer, Afro-Latin hip-hop lens." (You read that right.)

Slam Frank was conceived by composer and lyricist Andrew Fox, who was stunned and inspired by a Twitter thread in which someone asked, "Did Anne Frank ever examine her white privilege?" (You also read that right.) A play within a play about a progressive theater company twisting itself into knots trying to stay on the right side of history, the show has provoked both walkouts and rave reviews—including in The New York Times. (Again, you read that right.)

PJ and Meghan discuss the transformation of the theater world over the past decade, the legacy of The Book of Mormon (in which he starred for many years), the "Dear White American Theater" manifesto, and why he believes great art cannot be created by checking ideological boxes. They also talk about what happens when artists prioritize pleasing everyone over having a point of view—and why live performance still matters in an era dominated by algorithms and social media.

PJ was recently added as a guest at The Unspeakeasy's Small Gathering for Big Ideas retreat, Oct 19-21 in Kingston, NY. He joins fellow speakers John McWhorter and Lisa Marchiano. Spaces are filling fast. Info here.

Slam Frank opens off-Broadway at New York's Orpheum Theater in September.

Guest Bio:

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members.

• 👉 https://www.theunspeakablepodcast.com/

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

• 👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

• 👉 https://www.theunspeakablepodcast.com

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

• 👉 https://tinyurl.com/ystzc5yz

This (almost) Fourth of July conversation originally appeared on Jenny Holland's channel, Saving Culture From Itself, but it's really a "collab," as they say in the pod-biz. Meghan has talked with Jenny before on YouTube livestreams, but this is the first time they've done an official podcast together.

This conversation kept circling back to the kinds of tripwires and trigger points that cause people to tune out ideas before they even hear them—for instance my advocacy for Spencer Pratt in the L.A. mayoral race a few months ago and Jenny's support of . . . Brexit. (She lives in Belfast in Northern Ireland.) We also talked about how Meghan began her career at the tail end of the golden age of magazine journalism, and what it was like watching that world start to shift around 2012-13.

Finally, in the spirit of the season, they talked about American exceptionalism, generosity of spirit, and Jenny's husband's 1987 trip to the US as part of the "Children of the Troubles" program — the trip that made him fall in love with this country.

Catch more of Jenny's cultural critiques directly on her YouTube channel:

👉 https://www.youtube.com/@SavingCultureFromItself

Jenny Holland is an Irish-American, Gen X writer, critic, and former speechwriter who currently writes and hosts Saving Culture (from itself) on Substack and YouTube. A true media journeyman, her first gig in the news business was working as an assistant at The New York Times in the final years before the digital revolution—an experience she likens to being among the last people to board the lifeboats on the Titanic. Now living in Northern Ireland, she is a frequent contributor to Spiked and writes widely about culture, journalism, and the strange ideological shifts of the modern Western world.

• Join The Club: Become a paid subscriber to The Unspeakeasy on Substack to unlock monthly hangouts for Founding Members and gain access to exclusive live stream recordings.

  👉 https://www.theunspeakablepodcast.com/

• Unspeakeasy Retreats: Off-the-record, curated conversations in beautiful settings. Registration for this fall's Small Gathering for Big Ideas in New York's Hudson Valley is now open.

  👉 https://tinyurl.com/573a9vnu

• Meghan's Writing Workshops: Featuring a coed summer Zoom course and a 3-night women's writing retreat in upstate NY this fall. Is one right for you?

  👉 https://www.theunspeakablepodcast.com

• The Audiobook: Meghan's most recent book, The Catastrophe Hour, is out now. It's narrated by Meghan herself, in case you still haven't heard enough of her voice.

  👉 https://tinyurl.com/ystzc5yz

Meghan's guest this week is Lisa Marchiano—Jungian analyst, author, and co-host of the popular podcast This Jungian Life.

She's long been intrigued by Carl Jung's ideas but also found them somewhat elusive. So she asked Lisa to help me understand why Jung resonates so deeply with so many people and why his work feels especially relevant today.

They discuss archetypes, the shadow, synchronicity, Jung's break with Freud, and how Jungian psychology can help us make sense of political polarization, ideology, loneliness, and our search for meaning in an increasingly fractured culture.

If you enjoyed this conversation, you can continue it in person! Lisa will join us this October at The Unspeakeasy's second annual Small Gathering for Big Ideas in Kingston, New York (October 19–21), alongside John McWhorter. Learn more at theunspeakeasy.com/retreats.

Guest Bio:

Lisa Marchiano is an award-winning author, certified Jungian analyst, and co-host of the popular depth psychology podcast This Jungian Life, which has garnered more than 10 million downloads. The author of several acclaimed books that draw on the healing wisdom of fairy tales, Lisa holds degrees from Brown University, Columbia University, and New York University, trained at the Inter-Regional Society of Jungian Analysts, and lectures and leads workshops internationally on Jungian psychology and personal growth.

Mark Oppenheimer spent decades thinking about Judy Blume before finally writing her biography — and the result is a book that is a serious inquiry into Blume's books, her personal story, and social and cultural dynamics of the 80-plus years in which she has lived. In this conversation, we talk about what it meant to be a boy who loved Judy Blume, why realist fiction for young people has largely given way to fantasy, and how Blume's work stirred up controversy even though she never courted it herself.

Paying subscribers to The Unspeakeasy on Subtack can hear an extra long version of this conversation. Go to https://www.theunspeakablepodcast.com/subscribe to join or upgrade your subscription.

Guest bio:

Mark Oppenheimer is a journalist, academic, and the author of several books including Squirrel Hill, about the 2018 Tree of Life synagogue shooting. His new biography, Judy Blume: A Life, is out now.

Adam Miller is one of more than a dozen candidates running for mayor of Los Angeles, but unlike some of his rivals, he comes from the worlds of tech and nonprofit management rather than politics. Miller founded the e-learning company Cornerstone and the homelessness prevention nonprofit Better Angels, and says he entered the race because he believes the city's failures — especially around homelessness — are fundamentally operational.

In this conversation, Miller explains why encampments persist outside housing facilities, why affordable housing costs have spiraled, why shelters can sit half-empty, and why the city still lacks basic real-time data on homelessness. He also addresses the strange dynamics of a campaign unfolding in an attention economy where reality star Spencer Pratt has emerged as a serious contender. Miller argues that while he and Pratt often identify the same problems, he has the management experience to actually implement solutions.

Guest Bio:

Adam Miller, a tech entrepreneur and chief executive of the nonprofit Better Angels, is running for mayor of Los Angeles.