2026 Ins & Outs for Mom Entrepreneurs (Part 2): Capacity, Community & Letting Your Tomatoes Ripen
Thu Jan 29 2026
What happens when motherhood collides with neurodivergence, entrepreneurship, and a culture that still expects women to “do it all”?
In this powerful conversation, Megan sits down with Bailey Gordon, photographer, founder of the Mom Boss Meetup, and community builder, to talk honestly about what 2026 actually needs to look like for mom entrepreneurs.
From late ADHD diagnoses and PMDD, to why nap-time businesses create burnout, to redefining success through capacity, seasonality, and support, this episode is a deep exhale for moms who are tired of pretending they have the same bandwidth they had before kids.
Bailey introduces her unforgettable Tomato Theory for business growth, explains why smaller, more intentional rooms matter more than ever, and makes a compelling case for slowing down, pruning the offshoots, and letting what already exists finally ripen.
This episode is part of the ongoing 2026 Ins & Outs Series, and it’s a must-listen for moms building businesses while carrying the invisible load.
Key Topics We CoverWhy so many women don’t recognize neurodivergence until motherhoodADHD, dopamine, PMDD, and why cycles matter more than hustleThe emotional cost of building a business only during nap timeCapacity as a leadership skill, not a limitationWhy pretending you’re “fine” creates isolationHow community changes when vulnerability leadsSupporting mom entrepreneurs without minimizing their workThe Tomato Theory: pruning ideas so your best work can ripenWhy 2026 is about sustainability, routine, and honest pacingRedefining success without comparison to pre-kid productivity
2026 Ins & Outs for Mom EntrepreneursIN:
Capacity-based planningRoutines that support your nervous systemSmaller, intentional community spacesDelegating at homeHonest conversations about motherhood + businessCelebrating slow, steady growthAsking for help without apology
OUT:
Hustle cultureComparing yourself to who you were before kidsNot feeding yourselfTalking poorly about yourself or othersPretending you have the same bandwidth as someone without caregiving responsibilitiesConnect With BaileyPhotography: @photosbybailey on InstagramCommunity: @themombossmeetupWebsite: themombossmeetup.comBailey hosts monthly meetups for moms in business and moms exploring entrepreneurship, creating spaces rooted in honesty, connection, and real life.
What’s Coming NextMore conversations in the 2026 Ins & Outs Series, featuring women redefining leadership, success, and sustainability in business.
Final ReminderYour capacity is not a flaw.
Your season matters.
And you don’t need to grow new things to prove you’re moving forward.
If this episode resonated, share it with a mom who’s been pruning herself instead of her business.
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!
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What happens when motherhood collides with neurodivergence, entrepreneurship, and a culture that still expects women to “do it all”? In this powerful conversation, Megan sits down with Bailey Gordon, photographer, founder of the Mom Boss Meetup, and community builder, to talk honestly about what 2026 actually needs to look like for mom entrepreneurs. From late ADHD diagnoses and PMDD, to why nap-time businesses create burnout, to redefining success through capacity, seasonality, and support, this episode is a deep exhale for moms who are tired of pretending they have the same bandwidth they had before kids. Bailey introduces her unforgettable Tomato Theory for business growth, explains why smaller, more intentional rooms matter more than ever, and makes a compelling case for slowing down, pruning the offshoots, and letting what already exists finally ripen. This episode is part of the ongoing 2026 Ins & Outs Series, and it’s a must-listen for moms building businesses while carrying the invisible load. Key Topics We CoverWhy so many women don’t recognize neurodivergence until motherhoodADHD, dopamine, PMDD, and why cycles matter more than hustleThe emotional cost of building a business only during nap timeCapacity as a leadership skill, not a limitationWhy pretending you’re “fine” creates isolationHow community changes when vulnerability leadsSupporting mom entrepreneurs without minimizing their workThe Tomato Theory: pruning ideas so your best work can ripenWhy 2026 is about sustainability, routine, and honest pacingRedefining success without comparison to pre-kid productivity 2026 Ins & Outs for Mom EntrepreneursIN: Capacity-based planningRoutines that support your nervous systemSmaller, intentional community spacesDelegating at homeHonest conversations about motherhood + businessCelebrating slow, steady growthAsking for help without apology OUT: Hustle cultureComparing yourself to who you were before kidsNot feeding yourselfTalking poorly about yourself or othersPretending you have the same bandwidth as someone without caregiving responsibilitiesConnect With BaileyPhotography: @photosbybailey on InstagramCommunity: @themombossmeetupWebsite: themombossmeetup.comBailey hosts monthly meetups for moms in business and moms exploring entrepreneurship, creating spaces rooted in honesty, connection, and real life. What’s Coming NextMore conversations in the 2026 Ins & Outs Series, featuring women redefining leadership, success, and sustainability in business. Final ReminderYour capacity is not a flaw. Your season matters. And you don’t need to grow new things to prove you’re moving forward. If this episode resonated, share it with a mom who’s been pruning herself instead of her business. 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!