This Entrepreneur Was at a Career Crossroads. Then, a Cabbie Gave Her the Perfect Advice

Before she founded accessories and clothing company Stella & Dot, Jessica Herrin had a difficult choice to make. One cab driver advised her to look for the upside–which she’s continued to do to this day.

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BY Christine Lagorio-Chafkin - 28 Feb 2019

Jessica Herrin.

CREDIT: Courtesy company

Stella & Dot isn't just a website to pick out a shiny cuff bracelet or customizable charm necklace. It's also a network of 30,000 women--who host gatherings to sell costume jewelry and accessories--many of whom are micro-entrepreneurs themselves. Before founding it in 2003, and before founding and selling her other venture,, Jessica Herrin was a driftless recent college graduate. Luckily, she had job options. Only, it took the sage advice of an Austin cabbie to pull her in the right direction--and change her thinking for the long term. --As told to Christine Lagorio-Chafkin

Sometimes the best advice in life comes from the unlikeliest of places. Like the front seat of a yellow cab.

When I graduated from college, I came to a fork in the road: Which job to take? I had a position lined up at an established investment bank that paid well and would offer good reference for business school. But then, on a whim, I took an interview with a software startup in Austin. I got the job on the spot. They wanted a fast answer. It was risky given how young the company was, but at the same time, all the unknown possibilities seemed exciting.

On the cab ride to the airport, I weighed the decision. The cab driver looked at me in the rearview mirror and asked what had me so worried. I explained the situation.

He responded, "Well, which job has the best upside to it? Is that extra upside worth the risk of the worst-case scenario if you make that choice?"

I thought about his question. The investment-banker financial analyst program was well defined. It was two grueling years and a path to a great business school. It paid well and would give me solid finance skills. The upside was predictable. That was not the case with the startup. That path was an absolute unknown to me--so, technically, it had to have even more of an upside. My role was less defined, but that also meant I could take on more responsibility. The future of the company was unknown, so it could grow quickly and I could grow with it.

The cabbie was right. Looking at it in that light, it became an easy decision. And one that I have never regretted. I use that framework to make difficult decisions to this day.

Example: A few years ago, we were trying to decide whether it was time to grow our mission impact by creating a Stella & Dot family of brands and by adding a totally new product line. This would allow more people to pursue different passions and earn incremental income.

To me, this potential upside impact to our mission--to engage more people in the world of flexible entrepreneurship--far outweighed the risk of taking on extra work and investment. Even years later, the cabbie's advice worked.


From the March/April 2019 issue of Inc. magazine


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