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Jenny’s Drastic Changes to Chase Her Nomadic Dreams

October 28, 2010


This week’s Great Life Experiences comes graphic designer, traveler, skateboarder, and blogger from Where is Jenny?.

Facing the Facts

It all started when life as I knew it began to fall apart. You see, I had always dreamed of long-term travel, but fell into a relationship with a boy I loved and planned on marrying. He wanted a traditional lifestyle, but promised me an unconventional one. We were great together, but after 4-years I realized that I was being duped.

He thought he wanted to live an unconventional life and travel like me, but instead wanted the traditional American Dream. Although I loved him, the life I wanted to live was not a compromise I was willing to make. Therefore, I ended the relationship. We just wanted different things out of life and we only live once.

Grabbing a Hold of Life

I had always told myself that if I weren’t with him I’d be fulfilling my dream of traveling the world indefinitely as a digital nomad. I’ve never worked for anyone in my adult life because I started Pirata Design (freelancing graphic design) straight out of college. When we broke-up I couldn’t break my promise to myself of becoming a digital nomad, that’s just the way I’m hardwired. I knew that fear would cause me to procrastinate so I set a deadline to depart in January of 2011 and told everyone I knew. There is no way in hell I wouldn’t do something once made public like that. I would feel like a complete and utter failure.

Taking Hold

Taking Hold

Fighting My Fears & Letting Go… of Stuff

I should have started selling my items 6-months before my departure, which is when I made the decision to become a digital nomad. However, my fears held me back. I came up with a thousand things I needed to do before I could focus on sorting and selling everything I owned.

When you think about it, it’s a daunting process to sort through every crevice of your apartment and watch other people take your items from you. It’s also very hard to let go of items that you have assigned sentimental value to. I found myself trying to come up with reasons to use items I haven’t used in several years.

I had to remind myself that if I haven’t used it in over a year, then I definitely didn’t need it now. Trying to narrow down your possessions to three Tupperware bins is no easy feat.

Jenny's Great Garbage Toss

Jenny's Great Trash Toss

Really Letting Go

You begin to purge items in layers. First you go through and trash everything that is considered trash. When it was all said and done, I had 15 bags of trash. I was mortified, but felt that this was part of the process I had to go through in order to become a minimalist. We all have it.

Then I parted with the items I absolutely did not need or cared about anymore. Those were easy. Lastly, I sorted through the items I really cared about and decided which were most important.

I’m going through his process because I don’t want to pay for a storage facility for a number of years only to come back and realize I didn’t need any of this stuff. Then I’d have paid several thousand dollars in fees to hold a bunch of useless items I didn’t even want. I’ve always looked at other travelers that had been on the road for several years with an insane sense of jealously.

Sealed with a Kiss

Sealed with a Kiss

Then I came to the realization that I only live once and it was up to me to make it happen. I decided to make active choices to move towards that lifestyle. I already have a sustainable business model for location independence so the only thing holding me back was myself.

Jenny on the Equator, near Quito, Equador

Jenny on the Equator near Quito, Equador

Starting My Dreams

In January 2011 I’ll be taking off for an epic road trip through the United States to see my friends, check out the best skateparks, and have a good time. Already I have offers for places to stay in Texas, Oregon, Florida, Oklahoma, Arizona, New Jersey, California, and Washington. My goal is to travel inside the United States without paying for accommodation and seeing where the offers of others, leads me.

If you’d like to follow my journey visit my blog at Where is Jenny? Or connect with me on Facebook and Twitter

One Comment leave one →
  1. November 1, 2010 8:04 am

    I am so proud of you Jenny!!! I am glad we have met and are helping each other achieve our dreams.

    I love the pics~

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