#257 Alison Stewart: The LinkedIn Message That Changed Everything — Part One
#257 Alison Stewart: The LinkedIn Message That Changed Everything — Part One  
Podcast: Chief Change Officer
Published On: Wed Mar 26 2025
Description: Most people scroll through LinkedIn to procrastinate. Alison Stewart used it to land her next big thing. In Part One of this two-part series, Alison shares how she left her comfy finance job mid-pandemic to join a 16-person startup she found—wait for it—through networking online. We talk about career pivots, gut instincts, and how she slid into her co-founder’s inbox like a pro. Tomorrow, we dig into Overalls, the startup that thinks your benefits should actually benefit you. Novel, right?Key Highlights of Our Interview:"What Am I Doing?” – Hitting Pause on the Corporate Grind“During the pandemic, time started blending together. I had to stop and ask, what am I doing? Am I happy?” Those months at home made me realize how I’d been running on autopilot, stuck in a cycle of new leadership teams and constant resets. With every change, it felt like we were taking ten steps back just to make one forward."“The Safety Net of a Strong Company” – Navigating Stability vs. Fulfillment“You can get caught up in…having a strong company, great group of colleagues…new opportunities coming at you. But it might not be what truly motivates you.”“Controlling for Risk Factors” – Making Thoughtful Career Moves“I was trying to control for those risk factors, or at least account for them…what was I comfortable with? How would it impact my family?”“Overalls Caught My Eye” – The Power of an Unexpected Spark“I was sitting at work…reading about the launch of Overalls, and I got really excited. People almost stopped me, saying, ‘Allison, nothing gives you as much excitement as this opportunity."“Taking Skills Beyond Insurance” – Exploring New Industries on LinkedIn“I was interested in exploring something outside the insurance industry…how does my experience, how do my skills translate, and how do I communicate them effectively?”____________________Connect with us:Host: Vince Chan | Guests: Alison Stewart  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.