Archive for the ‘Philosophy’ Category
Practicing The Art of Not-Planning

Everyone seems to be asking me where I’m going on this road trip. The truth is, I don’t really know. “Well, you must have some idea…” Okay. Yeah. I do. However, I like not getting my heart set on anything too specific. When I was backpacking through South America for 5-months I had a really good idea of where I wanted to go and all the exact places I wanted
The Secret to Happiness

Everyone has people who influence their lives from time to time. For me, mine was named Miles. Like many others in the United States I was taught that I was supposed to follow a certain path in life. Go to college. Get a job. Buy a house. Get married. Have kids. Retire. I wasn’t too excited about that path. Maybe you aren’t either. When I was on a celebratory cruise
The Lies Society Tells Us.

As you know from my (almost) 3 Month blog update which was just a few weeks ago I decided to refocus Where is Jenny to be more about living a freedom lifestyle than only being travel-centric. However, that tuning process is evolving as I learn, grow, and find my place in cyberspace. Right now, I feel as if I’m sending off mixed signals, a bit of confusion.
Why I’ll Never Have a Job

Everett Bogue at Far Beyond the Stars recently wrote an article entitled, “How to run forever and never” which made me reflect on my own life. What am I running from? Why do I want to travel the world? Am I crazy? Back in 2003 when I was just weeks away from graduating from the Art Institute of Dallas I met a guy named David. He worked at one of
Defining Moments from 27 Awesome Bloggers

The source of inspiration for this post comes from two places. The first is my own reflection on my life and what brought me to where I am today. When I was a distraught 18-year old I would have never in a million years thought I'd of volunteered in Vanuatu, backpacked South America, or run a successful location independent business for 8-years and
OMG… In 46 Days, I Won’t Have a Home

Over the last few weeks I’ve been charting my process here as I work to sell everything I own and move towards digital nomad status. My first step is to leave Houston on December 23rd where I will head to Plano (Dallas, TX) to spend Christmas with my family. After the holidays I’ll stay with my parents and work on transitioning my dogs to their new home. A process that
















