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Every big win starts with a first paycheck. Today's feature comes from Reina Silvante in Chicago, who started a dog-walking business called Day Job Dogwalking during the early part of the pandemic, while still working her day job remotely.
Reina picked dog walking because it felt accessible and unintimidating; she'd started other side projects before without following through, and this one didn't require overthinking. Her neighborhood had plenty of dog owners, and remote work during the pandemic left her with free time in the middle of the day. She started with flyers at local coffee shops and posts on Nextdoor, which brought in a handful of customers.
The turning point came when she formalized the business and registered it as Day Job Dogwalking, a name that played on the fact that she'd sometimes take work calls while walking dogs. The name itself drew in new customers, and before long she'd made her first $1,000. She also hired a neighborhood assistant, a high schooler with free time thanks to school closures, and still turned a profit after paying her.
Reina kept the business running for more than six months, until her employer ended remote work, clearing more than $15,000 in unexpected extra income along the way. She can't point to anything she'd do differently. The biggest shift wasn't the money; it was realizing she could be an entrepreneur at all, something she hadn't considered despite holding a master's degree and a solid day-job income.
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