My Journey of Becoming Nomadic

My urge to have a nomadic lifestyle of moving from place to place began in my early 20’s when I would read books and short stories about women traveling all over the world.

Reading each story was like tossing a log on a fire that never knew existed. It started to burn deep down inside and before too long it became hard to ignore- and somehow I knew that the only way to satisfy the fire was to travel. I wanted to be like those courageous, adventurous women but comparing myself to them felt like crossing a gap as wide as the Grand Canyon. Impossible.

I grew up in a small town in Maine, none of my family members were adventurous and certainly NOT nomads. No one understood me much when I decided to spend my 20’s skipping from town to town, state to state, country to country.

I was alone in my goals, but strong in my choice.

Even my closest of friends didn’t see this lifestyle as an enriching, expressive, growth opportunity like I had described it. They saw it more as a concern and less as courageous.

Thinking back to before it all began I had absolutely no idea how to get to live a life of travel and this want need, took me on several odd and exciting routes to get there.

My first big travel leap of faith was when I bought a one-way ticket to Hawaii. Never been before, no job, no friends/family, nada. Alone with a one-way ticket and two suitcases because I heard it was awesome. Who wouldn’t want to live in a place where everyone loved? I was even more ready for the change after having lived in Boston 4 years prior.

I was ready for forever summers, happy people and the sand under my toes while the sun warmed my face.

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After living in the islands for two years, the urge to travel further still called me by name. I gave in nearly as effortlessly as I moved my life across the ocean. I created a pattern for the following 5 years by working really hard (not so much, smart) with at 2-3 jobs at a time (bar tending, nanny, bookkeeping, waitress, pharmacy tech- ANY job who hired me where I could gain more skills) I’d save enough money to travel for 6 weeks, quit whatever job was working at the time and travel until I ran out of money. Rinse and repeat.

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It was getting exhausting, not to mention hardly the best way to plan for a future. I realized that I should be focusing my efforts on a job where I could travel AND work. I looked into becoming a flight attendant, but decided to take flying lessons instead. Then there was ‘teaching English abroad’- which was out since I didn’t have a bachelor’s degree. Lastly the whole ‘blog and travel’ or ‘woofing’ or some other way to make inconsistent money or barter. But none of these really spoke to me.

Feverishly Googling ways to combine travel with work when I was working at my 9-5 office jobs. I always dreaded waking up, dreaded the commute, dreaded not being able to wear jeans on Tuesdays and dreaded taking a lunch since it would mean spending 30 more min at this land-locked, suffocating space. Working all year to get two weeks paid vacation, if you’re lucky- seemed more like a jail sentence to me.

I realized I didn’t want a JOB overseas, I wanted a FULL life and to be able to leave on my own terms.

Don’t get me wrong, I love WORKING. I have created and ran more positions in company’s than not by my sheer focus, hard work and results. I am a quick learner, good with people and love to see businesses be a TOTAL success. Alas, I could not find a way to feel truly happy in a cubical.

It’s almost like I was an Octagon trying to shove myself in a square and forcing a smile to prove I fit in.

After about 5 years of trial and refine, I finally made my OWN business around my passion of travel by combining all the skills I learned as a nomad and in business.

Hence Kaylee, the Digital Nomad was born, my truest path.

Now I read women who travel and say ‘ I will write a book.’ So who knows…… 🙂

Originally posted on my business page here.

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6 thoughts on “My Journey of Becoming Nomadic

    1. What an awesome question! Thank you for asking. I could not find one of the books I had read (as a nomad I pass my books along to the next reader) but a few I can recall are Eat, Pray, Love, WILD (newer read), A Year in the World, do you have any recommended reads?

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