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Entrepreneurship, Insecurities, and What Growth Really Looks Like
Season 2 of The Boss Society Podcast is here (🎉) and we’re kicking it off with an honest behind-the-scenes look at what’s happening inside Olympia Boss Society.
In this episode, Megan shares February wins inside the community, lessons that surfaced along the way, and a powerful reframe about growth that many entrepreneurs experience but rarely talk about.
She also reflects on a question she was recently asked: How would you describe Olympia Boss Society to someone who has never experienced it before? The answer reveals why OBS is more than networking, more than education, and more than social connection. It’s a room where women are building businesses and building each other at the same time.
• Growth in business rarely looks clean or linear.
• Entrepreneurship often mirrors back the insecurities we didn’t realize we were carrying.
• Your abandonment wounds, scarcity mindset, control tendencies, and fear of being seen can all show up in how you run and market your business.
• The right room matters. The environment you build your business inside of impacts the depth of connection and conversation.
• Just because you want to do everything doesn’t mean you have the capacity to do everything well. Alignment beats overdoing.
• Early growth often looks like expansion and excitement, but long-term growth starts to look like discernment and sustainability.
• Olympia Boss Society isn’t just networking, education, or socializing. It’s a room where women build businesses and build each other.
Connection Night
Our monthly gathering where women entrepreneurs come together for conversation, collaboration, and education.
Coffee & Convos
A smaller member gathering designed for deeper connection and honest conversation.
She Blooms Spring Retreat
A powerful weekend experience where women step away from daily noise to reconnect with their vision, reflect on their next season of business, and build alongside other entrepreneurs.
A big thank you to Wildflower Estética, Olympia’s first certified sustainable skin, wax, and makeup studio, for sponsoring the food at this month’s Connection Night.
Owned by Bridget, Wildflower Estética offers massage-forward facials with visible results, inclusive gender-neutral services, and a warm botanical experience designed to help clients slow down and feel cared for.
As a Green Circle Certified business, Wildflower diverts up to 95% of salon waste from landfills, helping address the 877 pounds of beauty waste generated every minute in North America.
✨ Special offer for the OBS community:
Book a facial and use code OBS to receive a complimentary brow cleanup.
Learn more:wildfloweraestetica.com
Instagram: @wildflower.aestetica
This episode is supported by our OBSties, incredible women inside the Olympia Boss Society community who help share and grow this space with other women entrepreneurs.
A special thank you to:
• Amy Carlson – Marketing ecosystems built by women, for women who are done shrinking.
• April Porter – Human Design and soul-led leadership.
• Hilary Hopkins – Neurodiversity-informed real estate.
• Janis Sadoyama – Helping your brand wear what it’s best at.
• Kristy Cruz – Plant and succulent coach.
• Kyra Delaney – iOS and Mac app developer.
• Valerie Garretts – Owner of Cedar Flats Flower Farm and Olympia Speech & Language.
These women are builders, connectors, and leaders in our community, and their support helps Olympia Boss Society continue creating spaces where women entrepreneurs can grow together.
Each week on the podcast, Megan highlights one of the women helping support Olympia Boss Society behind the scenes.
This week’s spotlight is Sarah Hoium, our Story Catcher.
Sarah helps capture the stories unfolding within the community — collaborations, wins, growth moments, and breakthroughs that might otherwise go unnoticed. Her role celebrates what women in this community are building so those stories can inspire others.
Sarah is the owner and maker behind Moonstruck Studio in downtown Centralia, where she creates custom jewelry and hosts charm bar experiences, private parties, and creative gatherings.
Find Sarah here:
Instagram: @moonstruck.by.sarah
Share the Episode
If this episode resonated with you, send it to a woman in your life who might need the reminder that growth doesn’t always look the way we expect it to.
And if you enjoy the show, leaving a review helps more women discover the podcast and join the conversation.
Until next time… stay bossy. ✨
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!
View all episodes
By Megan GillespieSeason 2 of The Boss Society Podcast is here (🎉) and we’re kicking it off with an honest behind-the-scenes look at what’s happening inside Olympia Boss Society.
In this episode, Megan shares February wins inside the community, lessons that surfaced along the way, and a powerful reframe about growth that many entrepreneurs experience but rarely talk about.
She also reflects on a question she was recently asked: How would you describe Olympia Boss Society to someone who has never experienced it before? The answer reveals why OBS is more than networking, more than education, and more than social connection. It’s a room where women are building businesses and building each other at the same time.
• Growth in business rarely looks clean or linear.
• Entrepreneurship often mirrors back the insecurities we didn’t realize we were carrying.
• Your abandonment wounds, scarcity mindset, control tendencies, and fear of being seen can all show up in how you run and market your business.
• The right room matters. The environment you build your business inside of impacts the depth of connection and conversation.
• Just because you want to do everything doesn’t mean you have the capacity to do everything well. Alignment beats overdoing.
• Early growth often looks like expansion and excitement, but long-term growth starts to look like discernment and sustainability.
• Olympia Boss Society isn’t just networking, education, or socializing. It’s a room where women build businesses and build each other.
Connection Night
Our monthly gathering where women entrepreneurs come together for conversation, collaboration, and education.
Coffee & Convos
A smaller member gathering designed for deeper connection and honest conversation.
She Blooms Spring Retreat
A powerful weekend experience where women step away from daily noise to reconnect with their vision, reflect on their next season of business, and build alongside other entrepreneurs.
A big thank you to Wildflower Estética, Olympia’s first certified sustainable skin, wax, and makeup studio, for sponsoring the food at this month’s Connection Night.
Owned by Bridget, Wildflower Estética offers massage-forward facials with visible results, inclusive gender-neutral services, and a warm botanical experience designed to help clients slow down and feel cared for.
As a Green Circle Certified business, Wildflower diverts up to 95% of salon waste from landfills, helping address the 877 pounds of beauty waste generated every minute in North America.
✨ Special offer for the OBS community:
Book a facial and use code OBS to receive a complimentary brow cleanup.
Learn more:wildfloweraestetica.com
Instagram: @wildflower.aestetica
This episode is supported by our OBSties, incredible women inside the Olympia Boss Society community who help share and grow this space with other women entrepreneurs.
A special thank you to:
• Amy Carlson – Marketing ecosystems built by women, for women who are done shrinking.
• April Porter – Human Design and soul-led leadership.
• Hilary Hopkins – Neurodiversity-informed real estate.
• Janis Sadoyama – Helping your brand wear what it’s best at.
• Kristy Cruz – Plant and succulent coach.
• Kyra Delaney – iOS and Mac app developer.
• Valerie Garretts – Owner of Cedar Flats Flower Farm and Olympia Speech & Language.
These women are builders, connectors, and leaders in our community, and their support helps Olympia Boss Society continue creating spaces where women entrepreneurs can grow together.
Each week on the podcast, Megan highlights one of the women helping support Olympia Boss Society behind the scenes.
This week’s spotlight is Sarah Hoium, our Story Catcher.
Sarah helps capture the stories unfolding within the community — collaborations, wins, growth moments, and breakthroughs that might otherwise go unnoticed. Her role celebrates what women in this community are building so those stories can inspire others.
Sarah is the owner and maker behind Moonstruck Studio in downtown Centralia, where she creates custom jewelry and hosts charm bar experiences, private parties, and creative gatherings.
Find Sarah here:
Instagram: @moonstruck.by.sarah
Share the Episode
If this episode resonated with you, send it to a woman in your life who might need the reminder that growth doesn’t always look the way we expect it to.
And if you enjoy the show, leaving a review helps more women discover the podcast and join the conversation.
Until next time… stay bossy. ✨
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!