This week, Megan sits down with financial advisor Anna Fanning to talk about what it really feels like to be underestimated at work. The conversation started at Coffee & Convos when a question about handling constant objections from men lit up the room. Anna shares how being underestimated began for her as a kid, how it shows up in male-dominated spaces, and the quiet confidence moves that shift the power back. You’ll hear practical language to use in the moment, how to balance authority with authenticity, and why money knowledge is confidence.Key PointsThe Coffee & Convos moment that sparked this episode and why it hit home for AnnaAnna’s early story of being underestimated and how she turned it into fuelWhat underestimation looks like in male-dominated industries and peer dynamicsPhrases and proof points that diffuse condescension without getting defensiveThe “Do you trust me?” question that resets the roomPersonal brand vs. professional authority and finding the sweet spotMoney as power for women, and why knowing your numbers builds confidenceChoosing clients who trust you, setting boundaries, and saying noHow community helps you quiet self-doubt and stop underestimating yourselfSpecial OfferReady for more of these conversations in real life? Join Olympia Boss Society to get access to member events like Coffee & Convos and Connection Night, our community chat, and ongoing support to grow your business with confidence. Perfect timing with our fall lineup.Links MentionedConnect with Anna Fanning: WebsiteJoin Olympia Boss Society membership: Join the CollectiveCome to our next public event: Events CalendarPreview for Next WeekWe’re keeping the spooky season energy going with a hair raising convo all about the fear of being seen!Enjoying the show?If this episode made you feel seen, tap the stars and leave a quick review. Share it with a friend who needs the reminder that her voice belongs in every room.Loved this episode? Make sure to subscribe so you never miss a conversation inside The Boss Society Podcast! If you found value in today’s episode, share it with a friend or leave a review—it helps more women like you find the show.✨ Stay connected:📲 Follow me on Instagram: @themegangillespie @olympiabosssociety📩 Join the community: www.olympiabosssociety.com🎙️ Want to be a guest? Apply HEREYour voice matters. Your seat at the table is waiting. See you next time!

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