Jenny Leonard – Living A Great Life With No Job [Interview]

24 June 2011 Interviews


This interview was conducted by Stephen Perkins and was originally posted on his blog.

Jenny Leonard got out of college not looking for a job, but looking for a life. And ever since then, it’s safe to say that her life has been far from boring. Between amazing travels, business success, and landing a spot on TV, Jenny is truly someone to learn from. In this interview, Jenny talks about how she went from an interest in “far-away places” to actually visitng those places and having a job that she doesn’t view as a job at all.

Tell us about yourself and your background

My name is Jenny Leonard and I’ve never had a job. I started my freelance graphic design business straight out of college in 2003 and have been successful despite everyone telling me I’m crazy. In 2006 I left to volunteer in Vanuatu for 6-weeks and backpacked South America for 5-months in 2008-2009. In December of 2010 I broke up with my boyfriend, sold everything I owned, and set off for an indefinite trip around the world. I’m currently 6-months into that journey. I started my blog Where is Jenny? in September of 2010, but am moving it over to Never North this summer to focus more on the reader.

How did your interest for traveling start?

As a kid I always had an interest in seeing far-away places, but never had the opportunity. Our family never traveled anywhere. In 2004 I went on a cruise to the Caribbean and saw for the first time something so vastly different than anything I’d seen before. Up to that point I’d only been to a few US states (Texas, Oklahoma, and Louisiana) It was there that I realized I needed to see and explore the world in which I lived. My wanderlust was just beginning.

What gave you the idea to start a blog?

I was searching online about travel and found a blog of a guy who was traveling around the world. Not only did I get the idea to do an extended backpacking trip I got the idea to start a blog as well. I originally started Where Is Jenny? in 2005 to document my day-to-day travels, but relauched it in September 2010 with a new direction.

How is your blog different from other travel blogs?

My blog is not just a travel blog. I do talk about travel and give travel tips, but I’m more focused on helping others live life to the fullest. My target audience is other service based freelancers that want more flexibility (location independence) in their life. That could mean spending more time with their family, traveling around the world, or time to pursue their hobbies.  Too many of us focus on working and having jobs rather than having fun and living life. 2-weeks of vacation is not acceptable.

How have you been able to turn your passion into an income?

I love to be creative so I’ve built my freelance graphic design business in addition to selling my travel photography online on micro stock sites. I also started making money on my blog in my second month by using affiliate links for products I recommend. Eventually, I want to create my own products and streamline my income even more.

What was one of your biggest setbacks and what did you learn from that?

My biggest setback was a car accident. I know it has nothing to do with business, but it greatly affects my life. I have a rare injury called Thoracic Outlet Syndrome and it causes me to be in pain every second of my life. Learning how to overcome and deal with that injury has made me a very strong person.

What was one of your biggest accomplishments and what did you learn from that?

Getting on National Geographic’s reality tv show, FleaMan. My episode is entitled, “Rock and Roll Riches” and it will air on July 1st, 2011 at 8PM EST. I learned that if you follow your heart and your passion good things will continue to come your way. You never know what will happen, what opportunities will present themselves, or where you will end up. I’ve learned to have blind faith that everything will turn out epic and awesome and it usually does.

What advice would you give to young entrepreneurs?

Always have an open mind and learn something from every person you encounter. You will never know everything so don’t act like you do. When something isn’t working, learn when to quit or change directions. Failure is part of the game. All successful people have failures. It’s the getting back up and trying again that make you successful.

Created By:

Stephen Perkins is a Young Entrepreneur, Business & Technology Blogger/Vlogger, Founder of LittleAlien, Editor-In-Chief of ReactrMag, and Managing Editor of EpicLaunch

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