How to Become an It Girl with Vogue Fashion Photographer Olivia Bossert

EPISODE SUMMARYChelsea sits down with brand photographer and artist Olivia Bossert for a rich conversation about identity, visual expression, and what it really means to be an “IT girl.” Together, they explore how visual identity can act as a catalyst for confidence, clarity, and creative leadership — especially at the start of a new year when goals, reinvention, and becoming are top of mind. This episode is a deep dive into identity work, embodiment, and why personal branding isn’t about becoming someone else, but about amplifying who you already are.IN THIS EPISODE YOU’LL LEARN…What the “IT girl” movement actually means (and how it can help you achieve your business goals in 2026)How Olivia redefined the concept of an IT girl into grounded, embodied identity workWhy brand photoshoots can function as powerful rituals for identity shiftsThe difference between transformation and excavation when it comes to personal brandingHow visual identity supports confidence, visibility, and leadership in businessWhy multi-passionate founders don’t need to fragment themselves to have a cohesive brandHow clothing, environment, and ritual can help you step into (and out of) different rolesWhy standing out visually is becoming more important in an oversaturated digital worldHow embodiment and self-expression can reduce comparison and strengthen boundariesKEY TAKEAWAYS AND CONCEPTSThe IT Girl (Redefined): An IT girl isn’t someone unapproachable or polished to perfection — she’s someone fully embodied, self-trusting, and unapologetically herself.Identity Work Through Visuals: Brand imagery isn’t about becoming someone new; it’s about amplifying what’s already true and letting yourself be seen in it.Excavation vs. Reinvention: Great personal branding pulls from who you already are rather than layering on trends, archetypes, or expectations that don’t fit.Embodiment as Strategy: What you wear, how you move, and the rituals you use to start and end your workday all shape how you show up as a leader.Multi-Passionate Cohesion: A cohesive brand doesn’t come from hiding your interests — it comes from letting your humanity be the throughline.Visual Differentiation: In a world of identical “black blazer + laptop” brand photos, standing out visually becomes a signal of confidence, clarity, and authority.Ritual and Boundaries: Costume, clothing, and daily transitions help mark when you’re “on,” when you’re off, and protect your nervous system from being always visible.WHERE TO FIND OLIVIAYou can explore Olivia’s work, writing, and the IT Girl universe here...WebsiteInstagramEffortless Creativity SubstackDiscover Your It Girl ArchetypeFollow along for visual inspiration, It Girl identity work, long-form writing, and behind-the-scenes looks at her creative process.WORK WITH CHELSEAThe Empathy Edge (1:1 Mentorship)Your signature offers deserve more than word-of-mouth and make or break launches. Build a human-first sales system that balances strategy and nervous system safety. Learn to sell on evergreen, simplify your campaigns, and stay consistent, without launch stress or relying on referrals.→ Learn MoreSay Less Sales Messaging SprintA one-week sprint to fix stagnant or plateaued sales with emotionally intelligent, conversion-ready messaging that speaks to strangers, not just referrals.→ Book a SprintMarked Up Copy AuditGet detailed, personalized feedback on your sales page or email sequence so you can see exactly what’s working, what’s not, and what to say next.→ Book an Audit