Episode #24
Leadership Lessons Every Woman Business Owner Needs to Hear
What does it actually take to become a confident leader, especially when you don't feel completely ready for the role? In this episode of The Boss Society Podcast , we're continuing the Bare Minimum Summer Series with a conversation about a different kind of simplicity: trusting yourself enough to lead without believing you need to have every answer first. Megan sits down with Cheryl Selby , longtime Olympia community leader, former small business owner, and former Mayor of Olympia. Cheryl served two terms as Mayor from 2016 to 2023 after two years on City Council. Before stepping into public leadership, she owned Vivala, a women's clothing store in downtown Olympia. Today, she serves as President of the Olympia Arts & Heritage Alliance and remains deeply involved in community and civic leadership. Together, Megan and Cheryl talk about what it really looks like to step into leadership before you feel qualified, stay grounded when leadership gets difficult, navigate conflict with poise, and find your voice when you're the only woman in the room. In This Episode, We Talk About: Cheryl's journey from small business owner to Mayor of Olympia Why you don't have to feel completely ready before stepping into leadership The merit behind "fake it until you make it" How confidence is built through experience, not before it Staying inspired when leadership gets hard Navigating criticism and conflict without losing yourself in it What Cheryl learned from being the only woman in the room Why your motivations matter when stepping into leadership The importance of surrounding yourself with people who know more than you Leadership lessons women business owners can apply to their own businesses and communities Whether you're leading a team, growing a business, building a community, or simply trying to trust yourself in your next season, this conversation is a reminder that leadership doesn't begin when you finally feel ready. Sometimes it begins when you decide to step forward anyway. Connect with Cheryl Learn more about Cheryl's current work with the Olympia Arts & Heritage Alliance and the Olympia AHA Museum and Visitor Center HERE Connect with Olympia Boss Society Ready to stop doing business alone? Join us for our September Connection Night: Pleasure as Leadership Intelligence , featuring Shauna Stewart of The Pleasure Atelier. We're exploring a different kind of leadership conversation: what if the fuel you're missing isn't more discipline, drive, or resilience, but pleasure? Shauna will guide us through how expanding our capacity to feel, receive, desire, and experience pleasure can also expand our capacity for discernment, boundaries, creativity, connection, and leadership. And, of course, we'll have plenty of time for what Olympia Boss Society does best: Networking Without the Ick and meaningful connection with other local women in business. Grab your ticket to September Connection Night and come get in the room with us. This Episode is Sponsored By 9 Grand Events and Services 9 Grand Events and Services is an autism-owned company that works with people with physical and intellectual disabilities. Since 2000, 9 Grand has provided catering for weddings, corporate events, and social gatherings, along with unique character events featuring famous characters. Whether you're planning a wedding, business event, or celebration, 9 Grand Events and Services can help bring it to life. Learn more at 9grandevents.com . Listen + Subscribe If you enjoyed this episode, make sure you're subscribed to The Boss Society Podcast so you don't miss the rest of our Bare Minimum Summer Series. And if this conversation made you think of another woman who's stepping into a bigger season of leadership, send this episode her way. 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 HERE Your voice matters. Your seat at the table is waiting. See you next time!
