DiscoverPennie For Your Thoughts PodcastEP 81: CultureCon, Confidence & Comparison | How to Stop Feeling Small in Big Rooms
EP 81: CultureCon, Confidence & Comparison | How to Stop Feeling Small in Big Rooms

EP 81: CultureCon, Confidence & Comparison | How to Stop Feeling Small in Big Rooms

Update: 2025-10-08
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This week, Pennie unpacks the real conversation behind all the Culture Con discourse — the one that has less to do with influencers and everything to do with how we feel about ourselves.

She opens up about why she didn’t attend for years, what finally made her go, and what she learned about confidence, comparison, and walking in rooms like she already belongs there.

From social anxiety to the pressure of online visibility, Pennie shares her personal journey and offers tangible, psychology-backed tools to help you feel grounded, confident, and connected — even in spaces that once made you shrink

In This Episode:

Why so many people left Culture Con feeling disconnected

How comparison culture and social media distort our self-worth

Pennie’s story of finally attending after years of hesitation

What it means to build confidence through action, not validation

Practical ways to manage social anxiety and regulate your energy

The importance of networking across, not up

Highlights from Vic Mensa and 2 Chainz’s panels

How to remember that everything you’re looking for already exists within you

“Everything you’re searching for in those rooms — confidence, belonging, connection — already exists within you. You just have to know it, practice it, affirm it, and walk in it.” - Pennie Anassi

Mentioned:

Vic Mensa — on quitting drugs and redefining success

2 Chainz — on being a psych major and bridging intellect with artistry

Imani Ellis & Culture Con NYC — a creative homecoming and hub for Black excellence

IG: @penniepeace

TikTok: @penniepeaceful

YT: @peacepennie

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& We Back...Ego Death

& We Back...Ego Death

2023-11-0728:42

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EP 81: CultureCon, Confidence & Comparison | How to Stop Feeling Small in Big Rooms

EP 81: CultureCon, Confidence & Comparison | How to Stop Feeling Small in Big Rooms

Pennie Anassi