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Sometimes the Riskiest Choice is Playing It Safe

The following article was written by Jamie Shah, entrepreneur-in-residence at the Polsky Center for Entrepreneurship & Innovation and an adjunct professor at Chicago Booth School of Business, and originally published in Crain’s Chicago Business on January 20, 2025. Read the original article.


“I don’t envy you,” my father told me when I was graduating from the University of Chicago’s Booth School of Business. “You can do anything you want to do in life . . . but you’ll always wonder if you made the best choice.”

While he didn’t know it, his instinct was grounded in research. Psychologist Barry Schwartz’s “Paradox of Choice” explains how having too many options doesn’t free us — it paralyzes us. “With so many options to choose from,” Schwartz writes, “people find it difficult to choose at all.”

For high achievers, this uncertainty creates a hesitation to embrace the unconventional. As an entrepreneur-in-residence and adjunct professor at Booth, the question I hear most often from students is: “Should I take the risk and bet on myself, or stick with what’s known and familiar? Won’t I learn more working at a big-name company?”

The safe path is appealing. But what many don’t realize is that safety can be its own kind of risk.

Playing it safe can mean playing small. It can mean passing up the chance to define success on your own terms and falling into the trap of believing that others know more than you do.

For me, it meant turning down a job in venture capital to join my family’s business, Chem-Impex. It was an unknown brand, in an unnamed role, with unclear expectations. What gave me conviction to take a risk was remembering the story my father told me about starting his business in 1981. As immigrants who had recently moved to the United States, my parents had almost nothing: no internet, no connections; just the Whitepages, a jalopy of a car and boxes for furniture. My mom had just told him she was expecting their first child when he shared with her that he had quit his job working as a nightshift production chemist.

Faced with uncertainty, my parents took a bold step forward: They started their own business. When I ask my dad how he had the courage to begin when they had nothing, he says, “We started something because we had nothing.”

It was their lack of options that provided the clarity to focus on their strengths and build something true to themselves. With my dad’s expertise as a chemist, Chem-Impex took shape, a company designed to support scientific discovery through high-quality chemicals and thoughtful service. Grounded in what they knew best, they built a business that continues to reflect their commitment to empowering progress and innovation.

John Ward, a pioneering family business expert, called this “unconventional wisdom”: doing things differently because of who you are, not in spite of it. For family businesses — and entrepreneurs — the boldest moves often come from staying true to your values. Unconventional wisdom teaches us that the best choices aren’t always the obvious ones; they’re the ones that align with who you are and what you stand for. It’s about stepping forward with conviction, even when the way ahead is unclear.

As my dad reminds me today, the only real mistake is not trying. Everything else, you can figure out along the way. It’s a reminder that playing it safe can mean missing the chance to create something meaningful, because the boldest choices can have the power to transform ourselves and the world around us.

Jamie Shah is an entrepreneur-in-residence at the Polsky Center for Entrepreneurship & Innovation and an adjunct professor at Chicago Booth School of Business. She is president of her family’s business, Wood Dale-based Chem-Impex, and former chief operating officer of The Spice House. She was also previously lead associate at Hyde Park Angels and Hyde Park Venture Partners and was selected as a Kauffman Fellows finalist.

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