In 2013, Jill Sessa took off on what has turned into a 20,000-mile-plus road trip, first by bicycle, then cross country on a Vespa, and then moving into a tiny RV. A serial entrepreneur with a number of prior businesses, Jill now manages her website maintenance service, UltimateWPHelp, while enjoying an ever-changing view from the “office” window.

Jill Sessa

In This Episode

  • How a big birthday and an even bigger storm changed her life
  • Why she focuses on being content, not happy
  • One of her must-see places in the United States
  • Living in an RV full-time
  • Mobile Internet solutions
  • Tips for outsourcing effectively
  • Keeping online information secure
  • And much more

Most Memorable Location-Independent Experiences

Spending my 42nd birthday at Badlands National Park, starting with a morning at the world-famous Wall Drug store and the afternoon and evening riding my Vespa around the park. I met a nomadic couple enjoying sunrise in the park and treated them to breakfast before we each took off to explore the outrageously beautiful landscape of the park. A far cry from my 40th, the day Hurricane Sandy hit NYC.

Biggest Surprise along the Way

After a lifetime of being a leader-type, public figure, and rather outgoing, my introverted side is blossoming. I’ve realized how much I was struggling and uncomfortable in my previous roles and have fully embraced being alone a majority of the time.

Resources We Talked About

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