Designing Life on Her Own Terms: Michelle Carmack’s Journey with Oak + Pine Society

“Designing life on your own terms.”

That was the tagline for Michelle Carmack’s Oak + Pine Society—the one that resonated deeply with me and led me to join her community of female entrepreneurs. Since then, I’ve found myself steeped in conversations at Waioli Tea Room, savoring homemade dishes at Friendsgiving potlucks, and hosting mindfulness workshops at the House of SAVON—her co-working and event space created (but not limited to) Oak + Pine members.

“I wanted to build a space for women like me,” Michelle recalls, reflecting on what sparked both the Oak + Pine community and, later, the House of Savon, which officially opened its doors in 2022. At the time, she was questioning the traditional 9-to-5 trajectory. Working in the corporate world, she saw women forced to choose between working late or being home to tuck their children into bed. She knew she didn’t want to face those same difficult choices.

Inspired by her entrepreneurial mother and grandmother—who, despite their busy schedules, had the freedom and flexibility to be present—Michelle envisioned a life where she could prioritize both career and family. Growing up, she benefited from the care and attention of her family at her after-school performances and extracurriculars. As she got older, Michelle realized that wasn’t the reality for many children. She wanted to build a life where she could be fully engaged with her own family some day.

But as we all know, the path to living out a vision is rarely straightforward. What began as a baby boutique eventually evolved into a co-working and event space. Michelle had initially launched a maternity concierge service but found herself struggling to connect with the moms she was trying to serve—because she wasn’t a mom herself. (That’s since changed; Michelle is now in her final trimester, expecting a baby girl in April.)

“I lost energy in building the baby boutique and maternity concierge because I didn’t have a direct connection to being a mom,” she reflects.

But being an entrepreneur is in her blood, and she knew when to pivot. “When I lost momentum, I started asking myself: Who is an audience I can serve and feel connected to?” The answer was female entrepreneurs—women walking the same path she was. “Everything I wanted to learn, they wanted to learn. Everything I wanted to talk about, they wanted to talk about.” And so, her business evolved.

Now, with five years of experience, Michelle has insights to share with fellow entrepreneurs—much of it intuitive yet invaluable. When it comes to scaling your business, she emphasizes defining what scalability means for you.

“I didn’t want a lot of employees. I wanted a lean and mighty team,” she says.

Her marketing approach? Entirely conversational. “If you’re a stranger, I’m not going to ask you to sleep with me,” she jokes. (As an entrepreneur myself, I should probably heed this advice and stop asking strangers to sleep with me.) If someone isn’t interested in her services, she reframes the rejection: “Well, who do you know?” She also identifies advocates—people already invested in her membership or community—and encourages them to share her offerings with others.

As our interview wrapped up, Michelle left me with three essential skills for entrepreneurial women, regardless of industry: self-reflection, relationship-building, and discipline. And her guiding philosophy?

“Follow what energizes you. Trust that your energy is guiding you in the right direction—but don’t follow it blindly. Ask yourself: Why am I being pulled this way?”