Lily Stewart on Quitting Your 9-5 Job to Build a Pilates Studio

In this episode of First Round’s On Me, Hannah sits down with Lily Stewart — creator, style muse, “walking Pinterest board,” and one half of the internet’s most wholesome roommate duo.From NYC nightlife to the Soft Girl era, performative vulnerability, modern dating dynamics, and the chaos of Gen Alpha memes, this conversation is funny, warm, and surprisingly introspective. Lily opens up about friendship loyalty (including that dartboard incident), leaving the 9–5 world, building community, chasing creative freedom, and why confidence in dating is disappearing.The episode also dives deep into the “soft era of men,” performative therapy culture, emotional intelligence, parasocial relationships, and why—despite everything—real connection still matters more than ever.💬 In the comments: Are men really in their “soft era,” or is it just social-media performance?00:00 – Meet Lily Stewart & NYC creative life01:00 – Music taste, nostalgia & personality03:30 – Dating red flags & the dartboard story07:00 – Career pivots: leaving 9–5 for creativity10:00 – Entrepreneurship vs corporate life12:00 – Freedom, fulfillment & taking risks14:30 – Building community & true support17:00 – Social media: connection vs burnout20:00 – Parasocial dynamics & craving IRL community23:00 – Modern dating struggles & overthinking25:30 – Men’s “soft era” & performative vulnerability28:00 – Approaching people in public: why confidence is disappearing31:00 – Emotional intelligence, therapy culture & accountability34:00 – What women actually want: honesty, strength & maturity37:00 – Ending situationships respectfully40:00 – Lily’s next chapter & Freeform Studio42:00 – Outro