It’s 5 a.m. on a dark fall morning in Sioux Falls, South Dakota. With temperatures hovering just below freezing, I set out on my paper route. On evenings—weekday or weekend, rain or shine—I step out once again on foot for my second job, selling subscriptions to the same paper, Argus Leader. As a kid, I had one goal: to earn money and afford anything I could call my own. Well, maybe two—if I sold enough subscriptions, I could win prizes like a Walkman or tickets to see Cyndi Lauper. Looking back, this paper route was my first sales job.
There’s always another door
Even as a young teen, I learned to read subtle differences in the people behind each door. I adjusted my pitch to suit their unique personalities, came to understand their needs, and learned to accept rejection with grace. It was humbling, but it built the resilience to push forward after every “no” and knock on the next door. The previous door didn’t matter.
At 14, I started working in the service industry, first at Prime Time Burgers, then at TGI Fridays and Applebee’s. Moving into management, I learned invaluable lessons in accountability and customer service that became the foundation of my work ethic. One piece of advice from my Prime Time Burgers boss stuck with me: “If you give yourself five minutes extra, you’ll always be on time.” I’ve never been late since. Small habits, learned early, shape long-term success.
Sit on all sides of the table
Working in food service taught me that at its core, it’s a sales job. Like my paper route, it required understanding each customer’s story and developing an intuition for their needs. Instead of asking, “Would you like an appetizer?” I learned to say, “Can I get you started with some warm mozzarella sticks? My last table just had some and said they were amazing.” A story is always more compelling than a generic question.
As the daughter of Polish immigrants, I saw the fortitude required to forge a path in this country. My parents struggled to find work because their qualifications weren’t recognized. My mother, a former teacher, took a job in manufacturing to make ends meet. The determination of my parents, combined with my early work experiences, gave me a unique perspective on the challenges faced by those working in the gig-economy space. When I moved into tech—working at Airbnb, Uber Eats, and now Taskrabbit—I understood first-hand the challenges faced by hosts, drivers, food delivery workers, and Taskers.
Empathy is a superpower
Drawing upon past experience alone provides only a limited view of the gig economy’s ever-evolving challenges. In every corporate role, I signed up for jobs on the supplier side to understand their experiences on the frontlines. How does it feel to be delayed because there’s no parking? What if a client forgets to provide an entry code or a job runs overtime, throwing off the whole day’s schedule? Working in these roles, I saw how long deliveries actually take, how complex a single task can be, and how frustrating it could be to wait weeks for payment. Time and again, these experiences reinforced the essential role of empathy in business.
Many leaders focus on customers, but compassion for employees and partners is just as vital. Being on the frontlines builds an instinct for the challenges faced in the field, helping identify patterns and make informed decisions. At the C-suite level, business decisions are human decisions. Understanding the workforce—through their daily realities—is a leader’s greatest strength.
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