The first time this magazine considered writing about Michelle Wax ’12 (BUS), it was three years after graduation and she had started a successful Boston-area company, Kitchen Millie, baking “two-bite cookies” that she sold at farmer’s markets before branching out to retail stores, restaurants, event catering, online sales, and a subscription service.

The next time Wax came on our radar, it was 2019 and she had left what was now two successful businesses in the hands of the teams she’d built to travel through all 50 states in her Jeep Wrangler. Despite having no film training, she interviewed hundreds of regular folks for “The American Happiness Project,” a documentary she later spun off into a coaching business.

Now, nearly a decade after this serial entrepreneur left her first day job to pursue a dream, she’s still going all in on the next big idea with her multifaceted business Everyday Vibrancy, which offers corporate happiness workshops, private dating and life coaching, networking and social events, and more — all aimed at helping people find themselves and connect with others.

“It took me quite some time to even have the courage to think about pivoting from the cookie company because I was very stuck in that identity. People knew me as the cookie lady,” says Wax, who in summer 2024 opened The City Retreat, a coworking and event space for paying members of her Boston Babes Social Club. “I was very attached to it. But since then, what I’ve noticed in myself is every few years or so, I have this kind of inner desire to bring something new to life and create something from nothing, which is something I really like doing.

“I’ve identified that pattern now, but at the start I thought something was wrong.”

Who could blame her? Kitchen Millie and The Local Fare, a storefront and commercial kitchen where small food businesses could learn and grow, were turning comfortable profits. She had dreamed of owning a baking business since she was a kid operating an annual lemonade stand with her two brothers, selling little homemade chocolate chip cookies for 25 cents apiece.

“It was kind of what I’d been going after for quite some time,” she says. “And I didn’t really feel the happiness and fulfillment that I thought I would.”

After creating her documentary and developing workshops based on what she learned from neuroscientists and through her interviews, she sold the food businesses.

“The question I always heard was, like, isn’t this what you wanted?” Wax says. Now, she reassures her clients and the student entrepreneurs she mentored as the Werth Institute’s 2022–2023 entrepreneur-in-residence that it’s OK not to know exactly what the future holds — and it’s OK to pivot.

“Everything does come together, everything does interconnect, and it’s often in ways you can’t even predict at this moment,” she says. “Looking back, it makes sense, I can weave the story.” But in the moment, she says, it felt like, “What the hell am I doing?”