Podcast Summary

WORK Conversations: "It's All A Mess - Meet Emily Kirkpatrick"

Podcast: Work with Erika Ayers Badan
Host: Erika Ayers Badan
Guest: Emily Kirkpatrick (Substack: I Heart Mess)
Release Date: February 2, 2026
Episode Theme:
An unfiltered, humorous, and candid look at the modern media landscape and the realities of going independent, featuring Emily Kirkpatrick, a former journalist turned Substack creator. This episode dissects the chaos in digital media, the collapse of traditional traffic models, the influencer economy, and what it's really like to build a personal brand (and living) as an independent writer today.

Main Discussion Points & Insights

1. The State of the Media Industry (00:00–06:36)

• Digital Media Decline: Erika opens with a comprehensive breakdown on why traditional digital media is "a mess" right now. She explains the collapse in website traffic due to declining Google search referrals and closed social media ecosystems:
  • "Google search is diminishing…companies in the media ecosystem are seeing the SEO search referral traffic really, really drop off. Their whole business model…there’s less impressions, less money to go around, less revenue to the bottom line." (01:25)
  • Social platforms like Facebook and Instagram have closed off, leaving fewer options for discoverability. TikTok is still more open, but all major players are trying to keep users inside their platforms.
• AI and Future Discoverability: There’s a new question of how writers and publishers will be found via AI and agents—and speculation that AI companies will eventually charge for that discoverability.
• Blurred Lines & Influence: Erika highlights the increasing overlap between political, corporate, and media interests, citing billionaire ownership (e.g., Jeff Bezos at The Washington Post) and growing skepticism in coverage.
• Influencer Struggles: Influencers are having a harder time reaching their communities, especially on algorithmic platforms like Instagram. Erika jokes about getting trapped in the dachshund algorithm loop.
  • “The worlds are getting smaller…you’re finding that traffic referral sources are depleting and new ones haven’t emerged.”

2. Meet Emily Kirkpatrick: The Leap from Traditional Media to Substack (06:36–11:22)

• Background: Emily grew up in Portsmouth, New Hampshire. She is now a full-time independent writer—her work split 50/50 between Substack and YouTube.

  • "Yeah, yeah. I mean, my job is like 50% substack, 50% YouTube." (06:49)

• Dramatic Exit from the New York Post:

  • Emily recounts her viral departure story: She tweeted a sarcastic response to an op-ed blaming millennials for “killing the power lunch,” noting that, ironically, millennials like her at The Post didn’t even get a lunch hour.
  • The tweet went viral. HR threatened to fire her if she didn’t take it down. She asked for 24 hours to decide, which became a pivotal moment.
    • "I don’t respond well to threats. I don’t really respond well to being told what to do, especially when I felt like I was in the right." (08:40, Emily)
  • Turns out, her complaint was about work conditions (no lunch break), which is legally protected. While she wasn’t fired, her work life became hostile, so she quit.

• Transition to Independence:

  • After quitting, Emily freelanced but then COVID-19 hit and freelance budgets vanished. She started focusing on growing her own audience on Substack, leveraging her pre-existing following from viral posts and Twitter.
  • "So I might as well work for myself… I was already tweeting stuff pretty similar to what I do in the newsletter." (09:53, Emily)
  • Now, she’s no longer active on Twitter, preferring to own her content/audience.

3. Building a Business on Substack (11:22–13:20)

• Monetization:
  • All of Emily’s newsletter income is from subscribers, not ads. YouTube has only limited ad support; her business is primarily direct audience revenue.
    • "I don't have any ads...Everything else is subscription." (11:15, Emily)
• Audience Engagement:
  • She values the control and authenticity that comes from direct relationships with readers.

4. Deep Dive: Celebrity Fashion Commentary (13:20–16:59)

• Bad Fashion Expertise:

  • Emily specializes in covering, and often lampooning, bad celebrity fashion.
  • Mount Rushmore of Bad Fashion: Kim Kardashian is foundational—Emily spent years covering her at tabloids—which leads to discussion of celebrity wig/hair secrets, then stylist antics, and extremes like Julia Fox (“expensive clown” aesthetic).
    • “She [Kim Kardashian] is just kind of a foundational text for me...” (11:33, Emily)

• Behind the Scenes:

  • On stylists: They frequently “misread the room”—either by safe, boring choices or over-the-top “rage bait” (outrageous, skin-exposing outfits).
  • On samples: Many red carpet “disasters” happen because celebrities are wearing sample sizes that don’t fit.
    • “Why aren’t you getting custom things made?...You don’t have to just do samples.” (15:37, Emily)
    • Shoes are also rarely the right size; stylists just make them work for photos.

5. Substack Community & Creator Culture (16:59–19:41)

• Emily’s View:

  • She’s ambivalent toward the broader Substack “scene”—online, it feels “smarmy,” but real-life events are more authentic and lead to genuine friendships and collaborations.
  • Meetings like Substack bestseller meetups and panels have been key for networking and community building.

• Key Connections:

  • Emily’s podcast co-host, Jess (of Flesh World), is also a top Substack creator in beauty. Emily notes that some prominent Substack writers like Emily Sundberg and Bari Weiss operate in a different “echelon,” but maintain authenticity.

• Creative Motivation:

  • Emily is focused on simply growing her newsletter and being herself: “I like doing it…people can tell when they read it. It is very much my train of thought.” (18:39, Emily)
  • Her brand (“I Heart Mess”) is trademarked—she’s invested in the business for the long haul.

Notable Quotes & Moments

• On media decline:

  • Erika: "Google search is diminishing…companies in the media ecosystem are seeing the SEO search referral traffic really, really drop off." (01:25)

• On quitting the Post:

  • Emily: "I don’t respond well to threats...I went home and I thought about it, and it went more viral overnight." (08:40)
  • Emily: "At first, incredibly scary. And then once I did it, it felt awesome and, like, exactly what I was supposed to be." (09:28)

• On building independent income:

  • Erika: “And you make a living from that?”
  • Emily: “Yeah, full time.” (06:54)

• On Substack community events:

  • Emily: "I've met so many cool people and, like, normal people. I don't know. It's like, nice to have that kind of [connection]." (17:18)

• On celebrity fashion’s unreality:

  • Emily: "Celebrities are weird to me because…none of it is real. I like kind of regular people’s clothes." (13:20)
  • Emily: "One of my favorite habits on the red carpet is you can look at the back of heels, and you can usually see about an inch more shoe than there is foot, because they're just giving them whatever." (16:12)

• On personal branding:

  • Emily: "I Heart Mess is trademark." (19:41)

Key Timestamps

• 00:00–06:36 — Industry overview: media traffic collapse, influence of AI, and the rise of personal, independent platforms.
• 06:36–09:40 — Emily’s background, her experience at the New York Post, and her viral exit.
• 09:40–11:22 — Struggles of freelancing during COVID, transition to independence, and revenue breakdown.
• 11:22–16:59 — Celebrity fashion: The art (and mess) of bad taste, stylist dynamics, “rage bait” dressing, and industry inside jokes.
• 16:59–19:41 — Inside Substack: creator connections, the “scene,” branding, and the business of authenticity.

Conclusion

This episode is a must-listen for anyone curious about:

• The rapid, chaotic transformation of the media industry
• The challenges and freedoms of being an independent writer in 2026
• The messy, funny truth behind celebrity fashion
• How authenticity and owning your audience are now key to creative success

Find Emily Kirkpatrick at "I Heart Mess" on Substack and @messworldwide on Instagram.