#257 Alison Stewart: The LinkedIn Message That Changed Everything — Part One

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 Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.
20 Million+ All-Time Downloads.
80+ Countries Reached Daily.
Global Top 1% Podcast.
Top 5 US Business.
Top 1 US Careers.

>>>180,000+ are outgrowing. Act Today.<<<