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.

• 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.

• 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!

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.

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!

This week on The Boss Society Podcast, Megan sits down with Inner Circle member and boutique insurance agent 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.

• 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.

• 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!

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.

• 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

✨ 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

• 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

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!

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.

• 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.

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.

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

• 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!

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.

• 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

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 [email protected]. 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

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

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

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!

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!

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.

• 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.
• 
  

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.

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 [email protected]

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!

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!

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!

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.

• 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

• Olympia Boss Society

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.

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!