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The Boss Society Podcast
Megan Gillespie
34 episodes
5 days ago
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.

Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.

Pull up a chair—your voice belongs in this conversation.
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Entrepreneurship
Business,
Marketing
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All content for The Boss Society Podcast is the property of Megan Gillespie and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.

Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.

Pull up a chair—your voice belongs in this conversation.
Show more...
Entrepreneurship
Business,
Marketing
Episodes (20/34)
The Boss Society Podcast
Her Season: Behind the Scenes of Our First Retreat and the Magic That Sparked She Blooms

You know that feeling when everything finally clicks... when you realize you’re exactly where you’re meant to be? That’s what Her Season felt like.

In this episode, Megan and Stef pull back the curtain on Olympia Boss Society’s first-ever retreat: a weekend filled with transformation, laughter, late-night breakthroughs, and the kind of connection that changes you from the inside out.

They share what really happened behind the scenes — the nerves, the lessons, the tears, the lip sync battles — and how this experience sparked something bigger coming Spring 2026 👀


If you’ve ever felt the pull for deeper connection or the need to reconnect with yourself, this conversation will remind you what’s possible when women gather with intention.


Key Points:

  • What it really takes to host a transformative retreat (and the moments that made it magical)
  • The power of creating space for both strategy and stillness
  • Why community connection is the foundation for lasting growth
  • Real stories of breakthroughs, healing, and next-level business momentum
  • How the energy of Her Season is evolving into She Blooms — a retreat for rooted, sustainable growth


✨ Special Offer:

Applications for the She Blooms Retreat (March 19–22, 2026) are officially open!

Join us at the beautiful Semiahmoo Retreat House for a weekend of renewal, sustainable strategy, and community connection.

🌸 $200 Fast-Action Bonus if you apply by November 15th.

→ Apply Here


 Links Mentioned:

  • Learn more about She Blooms Retreat → HERE
  • Follow Stef at @soundstrategymarketing
  • Follow Megan at @olympiabosssociety
  • Join the Olympia Boss Society
  • Check out the Union Sky House
  • Connect with Elizabeth Second Shift Cook



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!

Show more...
1 week ago
1 hour 10 minutes 41 seconds

The Boss Society Podcast
Networking Horror Stories: The Spooky Side of “Putting Yourself Out There

Episode Description:

It’s Halloween week and what better way to celebrate than with a few truly terrifying tales from the world of networking? 👻

In this special spooky-season episode, Megan shares her own “introvert’s nightmare” story from the buttoned-up, performative networking days that inspired Olympia Boss Society, along with real stories from local women about the awkward, cringey, and downright scary side of building connections.

You’ll laugh, you’ll cringe, and you’ll definitely feel seen... because we’ve all been in those rooms that made us question why we showed up in the first place.


But by the end, these stories remind us why we keep showing up anyway… and what happens when you finally find yourpeople. 🤍


✨ Key Points

  • Megan’s personal story: from cliquey luncheons to cold coffee conference rooms
  • The truth about how intimidating networking can feel for introverts
  • Real community-submitted “networking horror stories” (and a few anonymous icks we can all relate to)
  • The importance of human-first connection and why authenticity always wins
  • A redemption story that reminds us: the scariest part of networking isn’t showing up, it’s thinking you don’t belong

🎄 Special Feature: Project Cheer

We’re partnering with members Katie Fama-Silver + Bryn from the Fama-Silver Agency and Heather Foster on Project Cheer... a community initiative to gift a fully decorated Christmas tree to a local family in need this holiday season.

🎁 Know someone who could use a little extra light and love?

Nominate them for Project Cheer before November 15th.

👉 HERE


🤍 Links Mentioned

  • Olympia Boss Society Membership: Become a Member
  • Project Cheer Nomination Form: Nominate HERE
  • Follow Megan on Instagram: @megangillespie
  • Follow Olympia Boss Society: @olympiabosssociety


🌙 Next Week on The Boss Society Podcast

We’re shifting from spooky to thankful as we head into November & Stef and I are recapping the entire Her Season retreat + are announcing something very exciting! 👀

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!

Show more...
2 weeks ago
33 minutes 26 seconds

The Boss Society Podcast
The Fear of Being Seen

This October, we’re diving into spooky situations in business... the ones that make us squirm a little but hold so much power when we finally face them.

And this week’s fear? Being seen.

Megan sits down with Amy Carlson, founder of Sand & Pine Creative, to talk about what it really takes to show up in your business with authenticity, vulnerability, and self-trust.


Amy helps women-owned and community-based businesses build marketing ecosystems that actually make sense, feel sustainable, and reflect who they are. In this conversation, she shares how she shifted from social media management to a more holistic, connection-driven approach to marketing... and how women entrepreneurs can do the same. They dig into the evolution of marketing, the fear that comes with visibility, and the role of consistency, reciprocity, and community in building a brand that lasts.


This one will have you rethinking not just your marketing, but how you show up as a leader.

✨ Key Points

  • How Amy transitioned from social media management to ecosystem marketing
  • The evolution of marketing since COVID and what’s working now
  • The difference between visibility and vulnerability (and why both matter)
  • How authenticity and self-trust drive sustainable business growth
  • Why consistency and boundaries build trust with yourself and your audience
  • The power of reciprocity and connection in business relationships
  • The “marble jar theory” and what it teaches us about mutual trust
  • How sharing your story creates deeper connection and community
  • Why taking care of yourself makes you a stronger leader


Special Offer

Want to join the conversation beyond the podcast? Come connect with the women behind the mic inside Olympia Boss Society ✨ our local and online community for women building businesses through connection, not competition.

✨ Join the community here


Links Mentioned

  • Connect with Amy Carlson: @sandandpinecreative
  • Read Amy’s Substack: HERE
  • Learn more about Sand & Pine Creative: sandandpinecreative.com
  • Connect with Megan: @themegangillespie
  • Learn more about Olympia Boss Society: olympiabosssociety.com


Next Week on The Boss Society Podcast

We’re keeping the spooky season going with a collection of stories that’ll hit close to home... a mash up of Networking Horror Stories! You won’t want to miss it 👻


Enjoying the show?

If this episode inspired you, please leave a review or share it with a friend who’s been afraid to show up online. Every share helps more women find this community and this conversation.

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!

Show more...
3 weeks ago
1 hour 8 minutes 40 seconds

The Boss Society Podcast
Tales of Men Not Taking You Seriously at Work... and What To Do About It

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 Points

  • The Coffee & Convos moment that sparked this episode and why it hit home for Anna
  • Anna’s early story of being underestimated and how she turned it into fuel
  • What underestimation looks like in male-dominated industries and peer dynamics
  • Phrases and proof points that diffuse condescension without getting defensive
  • The “Do you trust me?” question that resets the room
  • Personal brand vs. professional authority and finding the sweet spot
  • Money as power for women, and why knowing your numbers builds confidence
  • Choosing clients who trust you, setting boundaries, and saying no
  • How community helps you quiet self-doubt and stop underestimating yourself


Special Offer

Ready 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 Mentioned

  • Connect with Anna Fanning: Website
  • Join Olympia Boss Society membership: Join the Collective
  • Come to our next public event: Events Calendar


Preview for Next Week

We’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 HERE

Your voice matters. Your seat at the table is waiting. See you next time!

Show more...
4 weeks ago
43 minutes 51 seconds

The Boss Society Podcast
Quarterly Planning That Actually Works (Because Not Having a Plan Is the Scariest Thing of All!)

It’s spooky season 👻 and here on The Boss Society Podcast, October is all about spooky situations ... from networking horror stories to next week’s conversation about being underestimated by men.

But before we dive into all of that, we’re starting the month with one of the scariest things in business: not having a plan.

In this solo episode, Megan walks you through her simple method for quarterly planning. You’ll learn how to reflect, audit, and reset in a way that feels doable, without locking yourself into a rigid year-long plan. Because when the world feels chaotic, creating structure you can actually stick to is one of the best gifts you can give yourself and your business.


Key Points

  • Why quarterly planning beats yearly planning (and keeps overwhelm low)
  • Reflection prompts to start with before you set new goals
  • How to lightly audit your systems, social media, and offer suite
  • Using the Do / Delegate / Delete filter to avoid overload
  • The power of theme days for more flow and less chaos
  • How to map your quarter and build in monthly/quarterly reviews
  • Why quarterly planning is about clarity... not perfection

Special Offer / Community Update

Want to plan your quarter with support, accountability, and a community of women who get it? Here’s what’s happening inside Olympia Boss Society this month:

  • October 2 – Halloween Connection Night: Come dressed as your favorite iconic woman for a night of connection and strategy, featuring Aypril Porter teaching The Business of Being You.
  • October 17– Content & Co-Working (members only): A working session to create and plan your content with accountability.
  • October 23 – Coffee & Convos Open House: A cozy, conversation-first event perfect for new and familiar faces.

✨ The OBS Membership includes three in-person events every month, our private Circle community, weekly Q&A, and more.

✨ Inner Circle applications are now open 🤩 our ambassador + leadership team inside OBS for women ready to step into visibility, shape the community, and access extra perks.


Links Mentioned in This Episode

  • Olympia Boss Society Events
  • Collective Membership
  • Inner Circle Applications


👀Preview for Next Week

Next week we’re leaning fully into spooky situations with a powerful conversation about what it’s like to be underestimated by men — and how women are rising above it. You don’t want to miss this one.


Call for Reviews

If you loved this episode, let us know by leaving a review on Apple Podcasts or Spotify. Your reviews help more women find the show and join the conversation!

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!

Show more...
1 month ago
1 minute 40 seconds

The Boss Society Podcast
How Do You Sell When the World’s on Fire? The Weight of Showing Up

What does it mean to keep showing up for your business when the world feels unbearably heavy?

In this candid roundtable conversation, Megan sits down with Olympia business owners Nicole Pate and Melanie Asher to unpack the tension between running a business and holding space for humanity in difficult times. Together, they explore how to market with integrity, lead with responsibility, and protect your energy when social media feels overwhelming.

This conversation isn’t about quick fixes... it’s about navigating the paradox of being a leader, a human, and a business owner all at once.


Key Points

  • The pressure and paralysis of posting on social media during heavy news cycles
  • Fear, leadership, and the responsibility that comes with building a personal brand
  • Why empathy can keep us stuck, and how to reframe into responsible marketing
  • Real talk about doom scrolling, boundaries, and nervous system care
  • Leading in circles: from yourself, to your clients, to your wider audience
  • The difference between performative action and meaningful leadership
  • Practical tips for showing up with respect, relevance, and resonance


✨ If you’re craving real community in the middle of it all, you don’t have to navigate this alone. Join Olympia Boss Society to find connection and support with women who get it.


Links Mentioned

  • Follow Nicole Pate on Instagram: @travelagentnicole
  • Connect with Melanie Asher on LinkedIn: https://www.linkedin.com/in/omicle/
  • Learn more about Olympia Boss Society: olympiabosssociety.com
  • Want support moving away from social media? Download my free Newsletter Template HERE & start growing your community in your inbox!


Next Week on the Podcast

Megan returns with a solo follow-up to this conversation, sharing her personal reflections and a practical framework for responsible visibility you can use right now to show up with integrity, even when the world feels heavy.


Leave a Review

If this episode resonated with you, the best way to support the show is to leave a review on Apple Podcasts or share it with a friend. Your reviews help more women find these conversations and join the community

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!

Show more...
1 month ago
1 hour 1 minute 49 seconds

The Boss Society Podcast
Owning Your Spotlight: Imposter Syndrome, Introversion, and the Courage to Be Seen

This week on The Boss Society Podcast, Megan sits down with Inner Circle member and boutique insurance brokerage owner Katie Fama-Silver for a raw, heartfelt conversation about stepping out from behind the scenes and into your own spotlight.

Katie opens up about what it was like to stand behind more extroverted women in the past, why she finally decided to build her own brand, and how joining Olympia Boss Society helped her grow into a true pillar of community. From navigating introversion and vulnerability to battling imposter syndrome, Katie’s story is a powerful reminder that your name, your voice, and your presence matter.

If you’ve ever wondered whether you’re really ready to step out, this episode will meet you right where you are.


Key Points

  • Why Katie describes herself as a “recovering introvert” and how she’s pushed herself into the spotlight.
  • The lessons she learned from standing behind extroverted women, and why she chose to make her own name.
  • How joining OBS as a member and stepping into the Inner Circle shifted her confidence and leadership.
  • The role vulnerability plays in building trust and authentic relationships.
  • How she navigates imposter syndrome and reminds herself of her skills and experience.
  • What “owning your spotlight” really looks like... for business, family, and community.


Links Mentioned in the Episode

  • Connect with Katie on Instagram: @thefamasilveragency
  • Visit The Fama-Silver Agency in Tumwater, WA
  • Learn more about Olympia Boss Society: www.olympiabosssociety.com


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!

Show more...
2 months ago
39 minutes 52 seconds

The Boss Society Podcast
Human Design & Healing for Entrepreneurs

If you’ve ever tried all the business strategies and still felt like something was off, this episode is for you.

Megan sits down with Aypril Porter—life and business coach, grief guide, Human Design expert, and projector—to talk about how understanding your energetic blueprint can change everything. From unlearning burnout to working through invisible fears, this is a conversation about coming home to yourself while building the business you're meant to lead.


They also explore the intersection of Human Design and reparenting, how unhealed childhood patterns sneak into your launches, and why success doesn’t have to come at the cost of your well-being.


Key Points:

  • What Human Design actually is (and why it’s not just another personality test)
  • The difference between pushing harder vs. honoring your energy
  • How childhood patterns and fears sneak into our business decisions
  • The five Human Design types, and how they show up in entrepreneurship
  • Why “doing it differently” doesn’t mean doing it wrong
  • Rapid-fire insights on how different design elements might explain common business struggles
  • What shifts when you name your fears instead of avoiding them
  • The power of building a business that supports you


Special Offer from Aypril:

✨ Grab her free Fear Report to see which fears may be baked into your chart and how to work with them instead of against them.

Snag it HERE


Links Mentioned in This Episode:

  • Aypril’s website
  • Follow Aypril on IG, FB, and TikTok
  • Snag the LAST SPOT at the OBS Her Season Retreat in October. Apply HERE🍂✨
  • Join us in October for Connection Night where Aypril digs deeps into Human Design. Tickets will go on sale soon. Stay tuned HERE


Leave Us a Review:

Love the show? Leave a review and help us keep sharing honest conversations like this one. Your words mean the world.

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!

Show more...
2 months ago
48 minutes 37 seconds

The Boss Society Podcast
38 Lessons from 38 Years🎉

Megan’s birthday is on Saturday (🥳), and she’s marking the moment by sharing 38 of the most powerful lessons she’s learned in 38 years. This milestone episode of The Boss Society Podcast blends personal growth, motherhood, and entrepreneurship, reflecting on how these experiences have shaped her life and business.

From redefining success and building community, to setting boundaries, honoring seasons, and remembering it’s never too late to start again... this episode goes deeper than strategy to explore what it really means to build a business and life that feel aligned.

Listeners will also hear updates on the Her Season Retreat, September Olympia Boss Society events, and the special birthday gifts Megan is offering this month.


Key Points

  • Success is personal and doesn’t look one way.
  • Community is the foundation of lasting growth.
  • Burnout isn’t a badge of honor; rest matters.
  • Boundaries protect time, energy, and relationships.
  • Vulnerability builds trust and connection.
  • Sustainable businesses are built around life.
  • Permission to pivot and reinvent is always available.
  • It’s never too late to start again.


Birthday Gift 🎉

To celebrate her 38th birthday, Megan is giving back to the community:

  • Connection Night: Register for September Connection Night HERE by August 30 for a chance to win a free month inside the Collective.


Special Offer

✨ Only 1 spot remain for Her Season Retreat this October. Doors close September 14. Apply HERE


Links Mentioned in This Episode

  • Olympia Boss Society Membership
  • September Connection Night
  • Apply for Her Season Retreat

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!

Show more...
2 months ago
51 minutes 49 seconds

The Boss Society Podcast
Midlife Clarity: Burnout, Boundaries, and Becoming Yourself Again

In this week’s episode of The Boss Society Podcast, Megan sits down with West Olympia real estate guide and community connector Heather Foster for an honest, funny, and deeply relatable conversation about what it means to reinvent yourself — again and again — until it finally feels right.

From raising three kids as a military spouse to moving 20+ times and walking away from her career when it no longer aligned, Heather’s story is a powerful reminder that midlife isn’t a decline... it’s a chance to rise. Together, they unpack what it looks like to rediscover your identity after motherhood, shed people-pleasing, build a business on your own terms, and why collaboration and community are essential for sustainable success.

Whether you're in real estate or not, this episode is full of grounded wisdom for any woman navigating a new season, especially if you're craving space to show up as your truest self.


Key Points:

  • Why reinvention is often just rediscovery
  • What 20+ moves taught Heather about letting go and starting fresh
  • The power of walking away from a business that no longer aligns
  • Midlife as a season of expansion, not invisibility
  • How to stop performing and start leading with truth
  • Why surrounding yourself with the right people changes everything
  • Redefining success outside of hustle culture and industry standards


Special Offer:

If you’re local to the Olympia area and want a real estate guide who sees the whole person, follow Heather at @heathertinolympia or reach out at HeatherFoster@bhhsnw.com. Whether you’re buying, selling, downsizing, starting fresh, or need some recommendations around town... she’s in your corner.


PS: Heather is also joining us at Her Season 🍂✨ a cozy, in-person fall retreat for women entrepreneurs who are ready to reset, reconnect, and rise into what’s next. It’s happening this October on the water in Hood Canal, and you can learn more and apply to join us HERE


Links Mentioned:

  • Follow Heather on Instagram
  • Connect on Facebook
  • Apply for the Her Season Retreat
  • Local shoutouts: Stef McDonald, Olympia Dust Market, Lovely & Dapper Bakery


Chapters:

00:00 Introduction and Personal Journey

06:18 The Impact of Frequent Moves

16:03 Reinvention and Rediscovery

25:13 Navigating Identity Beyond Labels

32:36 Embracing Failure as a Learning Tool

34:07 Navigating the Chaos of the Real Estate Market

36:18 Personal Accountability and Ethical Business Practices

38:24 The Importance of Integrity in Business

41:07 Setting Boundaries for Sustainable Success

44:22 The Power of Collaboration and Delegation

49:41 Finding the Right Mentor and Support System

54:27 Building a Supportive Community

58:29 Taking Charge of Your Business Journey


✨ Leave a Review:

Loving the show? Don’t forget to follow, leave a review, and share this episode with a friend who’s in the middle of their own reinvention.

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!

Show more...
2 months ago
1 hour 9 minutes 55 seconds

The Boss Society Podcast
The Episode Where Megan Models a Mid-Season Pivot

When I recorded this episode a few weeks ago, I was in full “no launches, just nurturing” mode for the rest of summer. But as you’ll hear in the disclaimer, business moves fast, and sometimes the right opportunity changes everything. Mid-summer, the Her Season retreat went from “I’ll do it later” to “I need to do this now,” and this episode is the perfect example of why I decided to pivot.

Today, I’m sharing how I’m closing out summer with intention, creating space before fall, and resisting the pressure to overextend myself... all while staying open to the magic of aligned opportunities. Whether you’re in a slow season or in the middle of a big decision, this conversation will help you see how to stay grounded and ready to move when the moment is right.


Key Points:

  • Why strategy isn’t set in stone, and how to pivot with intention
  • The power of staying grounded in your plan while leaving room for aligned opportunities
  • How I’m using August as a soft runway into fall without scrambling
  • Simple ways to nurture your audience and business without overextending
  • The mindset shift that makes it easier to change direction without guilt

Special Offer:

Join us for Her Season, a three-day, all-inclusive October retreat in Union WA for the Olympia Boss Society community. It’s designed to help you finish the year grounded in clarity, aligned with your next season, and stepping into who you’re meant to become. Half the spots are already full! Apply now via the link in the show notes.


Links Mentioned in this Episode:

  • Apply for Her Season: HERE✨
  • Learn more about Olympia Boss Society: HERE

Next Week on The Boss Society Podcast:

We’re back with a guest episode you don’t want to miss... a conversation about reinventing yourself until you get it right, leveling up through collaboration and delegation, and embracing midlife as an opportunity to be your truest self. You’ll leave feeling inspired to trust your own path, build relationships that lift you higher, and take bold steps toward the life and business you really want.


Leave a Review:

If you loved this episode, please leave a rating and review on Apple Podcasts or Spotify. Your reviews help more women find this show and grow in community.

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!

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3 months ago
19 minutes 58 seconds

The Boss Society Podcast
Her Season: A Retreat for Women Entrepreneurs

In this episode, Megan sits down with her friend and fellow OBS member Stef McDonald to share something that’s been years in the making: the launch of Her Season ✨ a cozy, intentional retreat designed to help women reconnect with themselves and rise into their next season of life and business.

They dive into how the vision finally came to life, why October is the perfect time to pause before the end-of-year rush, and what makes this retreat feel so different from any other business event. From hot seat masterminds to forest walks, silent mornings to pajama game nights, Her Season blends strategy and restoration in a way that feels grounded, nourishing, and honest.


This isn’t about cramming in more info or pushing harder. It’s about stepping away long enough to hear yourself again.

If you’ve been craving space, support, and a room full of women who get it ... this one’s for you.


✨ Key Takeaways

  • Her Season is designed to support both personal restoration and business clarity...without the pressure.
  • October is a powerful transition month, a chance to reset before holiday overwhelm.
  • This retreat is for the woman who leads everything… but rarely pauses for herself.
  • It’s not a conference. It’s an intimate, in-house experience with 10–14 women.
  • The retreat includes hot seat masterminds, solo reflection, workshops, journaling, and connection.
  • Visibility support is available without pressure to perform or show up a certain way.
  • Participants leave with a personalized Q4 plan, a message to their future self, and restored energy.
  • The retreat offers a rare opportunity to be held, witnessed, and supported by women who understand.
  • This experience is about coming home to yourself... and rising from that place.

💥 Fast Action Bonus — Ends in 24 Hours!

Apply within the first 24 hours and receive:

✔️ A 30-minute 1:1 Strategy Session with Megan

✔️ Early access to bed selection if you pay in full

This bonus ensures you’ll arrive already supported, grounded, and ready to make the most of your retreat experience.


Her Season: An OBS Retreat

October 10–12, 2025 | Union, WA

A weekend of deep connection, personal restoration, and aligned business strategy

→ Click here to apply now


Have questions? Looking for creative payment options? Not sure if this is the right time? Let's talk about it! Send us a message hello@olympiabosssoceity.com

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!

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3 months ago
29 minutes 24 seconds

The Boss Society Podcast
Scaling Speed or Staying Power?: Summer Success Blueprint FINAL Episode

In this final episode of the Summer Success Blueprint series, Megan Gillespie gets real about what summer revealed, and why building a business with vision is the only way forward. From simplifying your offers to embracing the clarity that comes with slowing down, this conversation is a powerful reminder that you get to evolve. You’ll hear Megan reflect on the past few months, the lessons that surfaced, and how focusing on local impact, intentional visibility, and values-based leadership is the path to long-term success.


If you’ve been craving a nudge to get honest about what’s working—and what isn’t—this one’s for you.


✨ Key Points:

  • This series was a pivot to lead from values.
  • Summer reveals clarity about what works and what drains you.
  • Define what you're scaling: speed or staying power?
  • Stop chasing vanity metrics; focus on engagement.
  • You are allowed to evolve and simplify your business.
  • Success can look like clearer offers and aligned marketing.
  • You are the CEO of your business and have the final say.


Chapters:

00:00 — Introduction to the Summer Success Blueprint Series

01:04 — The Importance of Vision in Business

07:39 — Embracing Change and Growth

11:14 — Conclusion and Looking Forward


Links Mentioned in This Episode:

  • Join Olympia Boss Society
  • Work with Megan


Next Week:

We're kicking off a new season with a MASSIVE ANNOUNCEMENT that you will not want to miss 📣


If this episode resonated with you, leave a review and share it with a fellow entrepreneur. Your support means everything!

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!

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3 months ago
13 minutes 1 second

The Boss Society Podcast
Monetize What You Already Know: Summer Success Blueprint

This one is for every woman who’s ever second-guessed whether she had anything worth selling. In this episode of the Summer Success Blueprint series, Megan is breaking down how to generate real income from the skills, ideas, and experience you already have, without launching a course, building a funnel, or burning yourself out.

We’ll walk through the 3-lens framework Megan uses with her clients to help them find their most aligned (and easiest) offers, plus shares the exact offers she's monetizing this summer to keep her business moving while her capacity is low. If you’ve been waiting for clarity, this is your moment.

Let’s make money in a way that actually works for you.


✨ Key Points:

  • You’re already sitting on something worth selling
  • Why we associate income with overexertion—and how to unlearn that
  • The 3-lens framework to find your quick-win offer
  • 6 micro-offer ideas that don’t require a big launch
  • Real talk: what I’m monetizing this summer and why it works
  • Local visibility = overlooked revenue
  • The reminder we all need: your circle can't buy what you never talk about
  • 3 action steps to implement right now


Special Offer:

If this episode sparked an idea for your own summer offer, my Voxer Intensive is the perfect way to refine it and get it out into the world. You’ll get real-time voice support and direct feedback so you can move forward fast.

DM me on Instagram to book yours.


Links Mentioned:

  • Olympia Boss Society: olympiabosssociety.com


Coming Next Week:

We’re closing out the Summer Success Blueprint with a big one: legacy, longevity, and building a business that’s designed to last. You won’t want to miss it.



Loving the podcast? Leave a review or tag us on social with your favorite takeaways and who you’d love to hear from as we head into fall.

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!

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3 months ago
21 minutes 40 seconds

The Boss Society Podcast
Resilience is a CEO Skill, Not a Survival Response: Summer Success Blueprint

In this episode of the Boss Society podcast, we’re getting honest about what it really means to lead through the mess... not just when everything’s going well. Megan shares her own experience navigating energy dips, personal struggles, and unexpected curveballs this summer, and offers a powerful framework for redefining resilience as a CEO skill, not just a survival response.

You’ll walk away with three tangible ways to build a business that supports you through the hard seasons, not just the highlight reels.


Key Points:

  • Why reactive decision-making keeps us stuck in hustle mode
  • The difference between hustler energy and resilient CEO identity
  • What it really means to lead with grounded clarity (even when life is lifing)
  • Three practical ways to build resilience into your business now
  • Why a resilient business isn’t built alone—and why your community matters


Links Mentioned:

  • Olympia Boss Society


👀 Next Week:

Get ready! We’re shifting gears to talk about how to monetize your expertise in a way that feels light, aligned, and totally doable, especially during summer. Don’t miss it.


📣 Loving this series? Your reviews mean the world. Leave a quick review on Apple Podcasts and help more women find this community of support and strategy.

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!

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4 months ago
17 minutes 40 seconds

The Boss Society Podcast
How to Scale with Purpose (Not Pressure): Summer Success Blueprint

In this freeing episode of the Summer Success Blueprint series, Megan unpacks why the traditional idea of “scaling” might be holding you back, and how to grow your business with more intention and less overwhelm. From simplifying offers to repurposing with strategy, this conversation is your permission to ditch hustle culture and choose sustainable growth that actually fits your life.

If you’ve been asking yourself how to stay visible without adding more to your plate, this episode is for you.


Key Points:

  • Why the traditional scaling narrative is broken
  • The truth about “doing more” vs. “doing better”
  • 3 ways to scale this summer without burning out:
  1. Audit & Elevate what’s already working
  2. Simplify your offers to fit your summer hours
  3. Repurpose with intention to amplify your message
  • Real-life examples from Megan’s own business
  • A reflection prompt to redefine growth on your terms

Special Offer:

Want help simplifying your business and scaling what actually works? Email hello@themegangillespie.com the word “ease” for details on 1:1 mentorship or the 2-week Voxer intensive.


Get Connected:

  • Olympia Boss Society Membership
  • Upcoming Events


Next Week:

We're diving into resilience... what it really looks like in business and why it’s the quiet backbone of your summer success.

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!

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4 months ago
10 minutes 57 seconds

The Boss Society Podcast
What To Do "In The Room" - Summer Success Blueprint

You walked into the room. Maybe for the first time. Maybe after a long hiatus. And maybe... it actually felt good. So now what?

This week, we’re diving into what happens after the yes in part two of our networking redefined chat. Because it’s not just about showing up. It’s about how you hold your energy, carry the conversation, and follow up with intention. This episode is your practical guide to networking in a way that’s rooted in real confidence, quiet leadership, and meaningful results.


If you’ve ever left a room feeling drained, awkward, or unsure of your next move… this one’s for you.


Key Points:

  • Why confidence doesn’t have to be loud... and how to walk in with grounded energy
  • Easy, non-awkward conversation openers that create real connection
  • What to do after the event to turn that moment into momentum
  • How to build a networking strategy that actually works for you
  • The true ROI of relationships and how one connection can change everything

✨ Special Offer + Links Mentioned in This Episode:

Grab the Networking Without the Ick freebie — your audio + digital guide to building a networking strategy that aligns with your energy, goals, and schedule.

  • Networking Without the Ick Freebie


Chapters

00:00 Introduction to Networking Transformation

01:26 Building Comfortable Confidence

04:0 Effective Networking Strategies

06:33 The Importance of Follow-Up

08:34 Networking for Business Growth

10:47 Reframing Your Networking Approach

14:09 Creating a Sustainable Networking System

16:10Conclusion and Resources

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!

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4 months ago
17 minutes 51 seconds

The Boss Society Podcast
Redefining Networking for Women Entrepreneurs - Summer Success Blueprint

In this episode of The Boss Society Podcast, host Megan Gillespie gets real about what networking should feel like for women entrepreneurs—especially in the summer. If traditional networking gives you the ick, this conversation will feel like a breath of fresh air. Megan shares why connection over competition is the future, how to make networking feel more human, and the mindset shift that helps you show up with confidence (no perfect pitch required).


Plus...big news! The new Q3 Olympia Boss Society event schedule is here, and we’re simplifying everything to make space for more meaningful connections. What does that mean? Get all the tea in this episode!


Key Points:

  • Ditch the pressure to prove yourself
  • Connection > competition
  • Focus on relationships, not results
  • Summer is made for casual, powerful conversations
  • Support first, sell later
  • Authenticity always wins
  • One brave yes can open big doors


Chapters:

00:00 – Redefining Networking for Women

03:22 – The Power of Connection Over Competition

06:23 – Networking in the Summer: A Unique Opportunity

09:47 – Transforming Networking from Transaction to Transformation

10:59 – Building Meaningful Connections


Special Offer:

Ready for real connection? Join Boss Society Collective to access the new simplified Q3 event lineup—more intentional gatherings, member perks, and a low-pressure way to grow your network. Membership is open now. - 📣PRICES INCREASE IN JULY📣


Links Mentioned in the Episode:

  • Join Olympia Boss Society
  • Q3 Event Schedule

Next Week:

This is part one of our networking redefined series. In part two, we’re diving into how to build visibility and connection if you're an introvert, a busy mom, or just tired of being "on" all the time. You don’t want to miss it.

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!

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4 months ago
16 minutes

The Boss Society Podcast
Time Management That Actually Works in Summer - Summer Success Blueprint

In this episode of The Boss Society Podcast, host Megan Gillespie unpacks what it really looks like to manage your time as a business owner during summer. Spoiler alert: it’s not about doing more or sticking to strict routines.

Instead, she shares how to shift into rhythms that actually work so you can grow your business and enjoy your life. You’ll learn how to ditch the guilt, use the Summer Three Method to stay focused, and create white space that gives you clarity.

If you’ve been feeling stretched thin or out of sync, this episode is your gentle reset.


Key Takeaways:

  • Summer throws off traditional time management...flexibility is key.
  • A break down of the Summer Three Method to keep your priorities focused.
  • Letting go of “non-essential” tasks creates clarity and energy.
  • Routines don’t have to be rigid, try rhythm-based planning.
  • Guilt doesn’t serve you. Rest fuels your momentum.

Episode Chapters:

00:00 – Navigating Summer’s Time Dynamics

Why summer feels like a paradox and how that impacts your productivity.

04:14 – Overcoming Guilt and Embracing Rest

Why rest isn’t lazy and how to reframe guilt around doing less.

07:06 – The Summer Three Method for Productivity

Megan’s go-to time management tool that helps you focus without the pressure.

09:57 – Shifting from Rigid Routines to Flexible Rhythms

How to work with your energy and your season instead of forcing old habits.

14:07 – Letting Go of Non-Essentials

What’s really necessary, and how releasing the rest creates room to grow.

18:23 – Creating White Space for Clarity

The power of pause and why every entrepreneur needs margin this season.



Links Mentioned:

  • Join Olympia Boss Society here

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!

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4 months ago
18 minutes 31 seconds

The Boss Society Podcast
Your Summer Visibility Blueprint: A Series to Keep You Growing Without Burning Out

Welcome to The Boss Society Podcast and the kickoff of our brand new summer mini-series ✨The Summer Success Blueprint✨. In this episode, Megan shares a behind-the-scenes look at what shifted in her life and business this season, why summer requires a different kind of strategy, and what you can expect from this powerful 8-part series.

If you’re a woman entrepreneur craving more visibility but less burnout this summer, this is your blueprint. We’re redefining success with bite-sized, mindset-shifting episodes that help you stay present, grow with ease, and feel supported by real relationships (not hustle and algorithms).


Key Points:

  • A personal story about burnout and the pivot that led to this reimagined series
  • Why traditional strategies don’t always work in summer...and what to do instead
  • What this 8-part series will cover, including time management, visibility, resilience, and aligned growth
  • Who this series is for: women craving freedom, connection, and a business that actually fits their life
  • What makes this series different: honest conversations and grounded frameworks from the messy middle
  • A summer challenge: what can you simplify in your business without losing momentum?


Feeling this conversation? Join us inside the Olympia Boss Society! Our local community for women entrepreneurs craving connection, strategy, and visibility that feels real. You belong here.

Links Mentioned:

  • Follow Megan on Instagram
  • Join Olympia Boss Society
  • Tag Megan in your summer shift @megangillespie and share what you’re releasing or reclaiming


Next Week:

In Episode 2, we’re digging into what networking can look like...especially if you’re introverted, exhausted, or just over the traditional way of doing it. If the words “connection” and “community” feel good, but “networking” makes you cringe, you’re going to love this one.


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!

Show more...
5 months ago
12 minutes 36 seconds

The Boss Society Podcast
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.

Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.

Pull up a chair—your voice belongs in this conversation.