The Next Level, Ep. 1023: "Secret Podcast: Success in a Failing Country"

Hosts: Sarah Longwell, Tim Miller, and Jonathan V. Last
Release Date: October 11, 2025
Podcast by: The Bulwark

Overview

In this unique “Secret Podcast” episode, Bulwark veterans Sarah Longwell and Jonathan V. Last (JVL) set aside their usual political analysis to reflect candidly on their personal and professional journeys, the evolution of The Bulwark, and what it means to find success as the world seemingly veers into crisis. The central theme explores the irony and tension of personal and organizational growth amidst national and political decline, with revealing discussions about values, career choices, and staying true to mission over business or profit. Notably, Tim Miller is referenced but does not actively participate in this episode.

Key Discussion Points & Insights

1. Deciding to ‘Just Hang Out’ and Talk Shop

[01:04–02:34]

• The episode veers from political headlines; instead, Sarah and JVL decide to answer questions about their lives, careers, and their work relationship—spurred by audience curiosity during a recent live Q&A session.
• Quote:
  • JVL: “I think we have not done a just hangout show in a few years at this point where we just talk about stuff that doesn’t have to do with the news and politics. And I thought it would be nice to do that.” [01:08]

2. Revisiting Old Career Choices

[02:34–10:12]

• JVL asks Sarah, “If you had it to do all over again ... what would you do differently?” [02:34]
• Sarah describes the loneliness and difficulty of her early post-college years at ISI in Delaware, tied to her realization she was gay and the conservative social circles she found herself in.
  • These experiences, while painful, shaped her intellectual development and values.
  • She reflects on formative years reading conservative thinkers and dealing with the uncomfortable realization that many of them “went for Trump” later on.
  • Quote:
    • Sarah: “I went from having a million friends ... to like, a stack of conservative books ... It was when I’m realizing I’m gay ... like, the really tough—but I think about a lot those three years, how bad they were and how I wouldn’t trade them for anything, because that loneliness was a time of, like, tremendous intellectual awakening." [06:52]
    • Sarah: “The thing that I wasn’t prepared for ... is ... most of those people went for Trump, and most of those people moved in that direction and abandoned everything ... That was a tremendously destabilizing experience.” [09:20]
• JVL admits candidly that, had he known the U.S. would be facing democratic decline, and that so many admired public intellectuals would betray core values, he might have chosen something entirely different—like medicine.
  • Quote:
    • JVL: “If I had known that we were going to inhabit a world where I had to, like, pick up this shield every morning when I woke up ... no way I would have gone into political life ... I would have gone ... to medical school somewhere.” [10:12]
    • JVL: “I chose the writing life. And at a moment right before the writing life got blown up by the Internet, I was reading all of these people who I greatly admired, and 75 to 85% of them turned out to be cretins who did not believe any of the stuff that they were [writing].” [11:09]

3. On Fate, Skills, and Mission

[12:24–14:15]

• Sarah posits the counter-question: “Did it choose you?”—suggesting their unique blend of backgrounds and writing skill was perhaps suited for this difficult moment.
  • Quote:
    • Sarah: “Sometimes I can look back and marvel at the experience that I had that produced a set of skills that ... matches what we're doing in the moment pretty well ...” [12:24]
    • “To be you, you have to have both ... a somewhat ... bleak view of humanity ... combined with an ability to crank out 2,000 words a day. Don't you have a sense of, if not you, who?” [13:04]
• JVL downplays the notion of fate; he writes “because it’s the only tiny little thing that I can do to be one of 50,000 cogs in an ad hoc machine that’s trying to turn back fascism.” [13:35]
  • Quote:
    • JVL: “I would have been just as happy to have tried to add value to the world by helping sick people.” [14:03]
    • Sarah: “We also need people to diagnose accurately a sick country.” [14:15]

4. The Growth and Tensions of The Bulwark

[14:22–19:03]

• JVL raises the “central tension” of their success: “The worse things get for America, the better things get for The Bulwark.” [14:22]
• Sarah and JVL recall that The Bulwark actually grew during both the Trump and Biden presidencies, countering the idea that their relevance is tied only to crisis.
  • Quote:
    • JVL: “Things are pretty good for America during four years of Joe Biden, and The Bulwark grew like crazy.” [14:49]
    • Sarah: “We remained successful during the Joe Biden years ... because there’s a high quality of work being done ... An audience found us during those years of, ‘No, these guys know we’re not done yet.’” [15:16/15:23]
• JVL asks, "What worries you the most?" about The Bulwark’s future. [15:54]
  • Sarah discusses the challenges of scaling up without losing the “mission,” emphasizing the need to “chase more audience and more influence” without succumbing purely to commercial pressures.
  • She references pressures to sell out or focus on profit—as seen with other media personalities—stating firmly her desire “not to just be a business.”
  • Quote:
    • Sarah: “I don’t want to let anybody turn us into just a business where we are chasing the things that I think people who are in business chase and who, when they do that, sacrifice really important things about what they were supposed to be doing.” [18:02]
    • “We want to make sure we do both.” [18:40]

5. Light Moments of Banter

[02:12, 19:03, 19:14]

• Several segments of banter and self-deprecating jokes pepper the conversation, softening the heavy subject matter:
  • JVL and Sarah riff on JVL’s oversized, clashing hat and vest combination.
    • Sarah: “It’s very red and very blue.” [02:16]
    • JVL: “I was given this hat. It looks great and I want to rep it.” [02:27]
    • JVL: “I’m sorry, I have to take the hat on. I’m just feeling self conscious ... it’s too big, it’s too blue.” [19:03]
  • Sarah: “I'm just gonna look at your forehead now.” [19:14]

Memorable Quotes

• Sarah Longwell:

  • “That loneliness was a time of, like, tremendous intellectual awakening. ... I wouldn't trade them for anything.” [06:52]
  • “The thing that I wasn’t prepared for ... most of those people went for Trump ... That was a tremendously destabilizing experience.” [09:20]
  • “We want to make sure we do both [mission and smart business].” [18:40]

• JVL:

  • “If I had known ... I would have gone ... to medical school somewhere. ... I would never have chosen this.” [10:12]
  • “I do it because I feel like it’s the only tiny little thing that I can do to be one of 50,000 cogs in an ad hoc machine that’s trying to turn back fascism.” [13:35]
  • “Things are pretty good for America during four years of Joe Biden, and the Bulwark grew like crazy.” [14:49]

Timestamps for Important Segments

| Timestamp | Segment | Notes | |-----------|--------------------------------------------|---------------------------------------------------------------| | 01:04 | Show premise & break from politics | How the episode’s “personal” tone was selected. | | 02:34 | Sarah’s career path & conservative circles | Effects of early work at ISI and grappling with identity. | | 06:49 | Intellectual awakening & loneliness | Sarah’s post-college transformative years in Delaware. | | 09:20 | Betrayal by conservative mentors | Sarah on pain of seeing mentors support Trump. | | 10:12 | JVL’s hypothetical: alternate careers | JVL considers medicine if he’d known the future. | | 12:24 | Reflection on fate and preparation | Is this work a calling, or a product of unique skillsets? | | 13:35 | “Cog in the machine” comment | JVL on his personal motivation for continuing the work. | | 14:49 | Bulwark’s growth—Biden and Trump years | Rebutting the “Trump-only” relevance. | | 15:54 | Concerns about scaling The Bulwark | Sarah on mission vs. business tradeoffs and “secret sauce.” | | 18:40 | Commitment to balance | How leadership preserves both mission and sustainable growth. |

Tone and Atmosphere

The tone is frank, vulnerable, occasionally humorous, and marked by a sense of mission beset with ironic frustration. Both hosts blend warmth and seriousness, deftly balancing light candor with the existential stakes of their roles as journalists in troubling times.

Summary for First-Time Listeners

This episode is a rare, introspective detour that humanizes The Bulwark's key personalities. It’s ideal for listeners curious about the humans behind the headlines, the ethical dilemmas and emotional labor involved in a mission-driven newsroom, and the paradox of finding “success in a failing country.” The candid discussion offers insight into both professional and personal navigation of tumult in the political and media landscape.