Meet our Kick-Ass New Orleans Host: Alyson Kilday

Creating Your Own “Real World” With The Lessons From Your Career Break

I grew up in a family that traveled. Having spent my first 18 years living in over half a dozen countries and having visited even more, you could say we were a family heavily infected with the travel bug. We weren’t “missionaries” or “military”, the two most common questions I’ve been asked growing up.

My parents are two of the original career breakers. My father quit his good corporate job in the mid-eighties to go sailing across the Pacific Ocean with his young family. (I was 2 when we left, and my little sister was born in the Pacific). As most travelers soon realize, there is no point in making concrete plans. My father’s plan to sail around the world took a detour in Japan where a short visit turned in to a decade long stay. After Japan, life took us to North America, South America, the Caribbean, New Zealand, and into South East Asia.

We ended up in the U.S. as my sister and I began university. In university my life was much like everyone elses. Broke, dreaming, and ready to get out to the “real world” and prove myself (meaning a big fancy job and a paycheck). Even at the dawn of the financial meltdown, thanks to good grades and the language skills I’d picked up in my earlier life, I was able to get that little corporate job. I was excited and looked forward to being able to finance my “adult” life. No more eating ramen noodles for weeks at a time!

This lasted just over a year before the very sight of the cubicle walls, the florescent lighting, the petty and surprisingly immature office politics, and the endless sheets of excel printouts began to drive me mad. I’ve always been a creative and active person, and this lifestyle was not meshing all that well. My longtime boyfriend and partner in crime was also starting to look around and wonder what we were working so hard for.

Maybe it was old, broke college habits or maybe we just never valued material goods as much as others, but unlike our co-workers we hadn’t gone out and bought the largest TV and nicest car with our paychecks. It was about this time that we began looking online at exotic locations, searching for sailboats, and coming up with crazy, little business ideas about running a bed and breakfast on a deserted island. We realized what we wanted was an adventure. We wanted something other than a 9-5 job and the toys with the monthly credit card bills attached. We decided one evening, naturally over the course of a few drinks, that we were going to go for it!

For the next year and a half we saved every penny we could. No cable TV, no shopping sprees, no cool new iPhone or gadget, not to mention no new cars and no vacations. We managed to live fairly comfortably on one paycheck and put the other into savings each month. This was doable I’m sure because we were fresh from being broke college kids and it still felt like we were living well.

We left in the spring of 2009 to go crew with my parents for a spell on their sailboat in the Caribbean while we learned the ropes. The plan being we would then find rides, work, and crew positions while working our way towards South America and beyond.

Like all good plans laid by mice and men our plans changed with the current, but what came out of our 9-month trip was the self confidence and knowledge that we can and will be able to create the life that we want. We are now based in New Orleans, working on Hop & Jaunt, our creative design and branding agency that we started while traveling. It’s been great, working at a job where you not only love what you do but you’re the only boss making you work late! We still have crazy ideas about adventures and places we want to go in the future, and thanks to the last career break we know that with a little luck it’s all doable!