Not all career changes are dramatic. Some are deeply deliberate—and a little serendipitous.

In Part One, Alison Stewart, COO of Overalls, walks us through her transition from 10+ years in the financial sector to co-founding a startup she discovered on LinkedIn. With two kids at home and a stable job in a Fortune 100 company, Alison didn’t jump recklessly. Instead, she asked the hard questions: Am I fulfilled? What do I want next? And how much risk am I really willing to take?

This episode unpacks what happens when you combine career intuition with operational precision—and how a well-timed DM can change everything.

Key Highlights of Our Interview:

From Corporate Climb to Personal Wake-Up Call

“Time started blending together during the pandemic. I had to ask: Am I actually happy? Or just coasting in a cycle of constant resets?”

The Treadmill of Big Company Life

“With every leadership change, we took ten steps back before we moved one forward. I was learning—but I wasn’t growing.”

Childhood Moves, Adult Adaptability

“Moving five times by age 14 taught me to see change as an opportunity. That mindset still guides me today.”

The Pregnancy + Merger Combo

“Just weeks before giving birth to my second child, my business unit was sold. The uncertainty could’ve been paralyzing—but I chose to treat it as a new beginning.”

Risk—But Not Reckless: Mapping a Smarter Pivot

“I didn’t quit cold. I asked: What am I good at? What fulfills me? What can my family support? I gave myself permission to explore—and permission to say no.”

The Non-Obvious Job Search Strategy

“Instead of applying for jobs I knew I could do, I reverse-engineered what I wanted: values, pace, purpose. I wasn’t chasing a title—I was chasing a fit.”

The Moment Overalls Popped Off the Screen

“When I read about Overalls, something clicked. I didn’t even know if they were hiring. I just knew I had to reach out.”

Why LinkedIn Isn’t Just Noise

“It wasn’t a random scroll. I used LinkedIn intentionally—to research, reflect, and eventually connect. That DM changed everything.”

Communicating Across Industries

“Moving out of insurance meant translating my skill set. I had to show how what I did mapped onto what I wanted to do.”

Community + Clarity = Career Confidence

“A networking group of MBA alumni helped me spot my own excitement. They said, ‘This one lights you up. Go for it.’ That feedback made all the difference.”

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Host: Vince Chan | Guests: Alison Stewart

--Chief Change Officer--
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