How a 76-year-old web designer stayed relevant by embracing change

Sobiloff’s transition from administrative roles to digital entrepreneurship began in 2000, when she took a webmaster course at the dawn of the commercial internet. The shift from manual typewriters to complex coding languages demanded more than just technical proficiency; it required a mindset shift. By launching her own freelance web design business, she began guiding small-business owners through the migration from Yellow Pages advertisements to social media marketing, learning every new platform in tandem with her clients.

The challenge of adaptation extended into her personal life, where she eventually embraced texting to maintain contact with her children and clients. In 2014, she pushed her boundaries further by launching "Two Grannies on the Road," a community television show that forced her to master video production and editing. Sobiloff maintains that while learning new systems becomes more difficult with age, the mental agility gained is vital. By documenting her travels on social media today, she serves as a practical counter-narrative to the idea that older generations are inherently disconnected from the digital world.