I have met Kerwin several times over the years and he is a airline geek with the softest heart. He left his airline job over 4 years ago and has been travelling ever since. So how does this gentleman make Living The Dream work for him?
What was the first country you visited? Who with and why did you choose it?
In 1985, I visited Martinique in the French Caribbean for 17 days as a French Exchange Student; on my way back to Jamaica we stopped in Haiti. I had to speak French the entire time I was there; on the last day, the kid next door told me that my host father is an English teacher. I always wanted to get on an airplane and go somewhere so when that opportunity came along I jumped at it and my parents supported it.
When did you start a travel lifestyle? What inspired that change?
I've been traveling for as long as I can remember. I'm an aviation geek so travel comes with that territory. Full time travel started in June of 2011 when I left my airline job of 14.5 years. The company was merging and all the planets aligned, well, almost all of them. So I gave away almost everything I owned, rented a car with the rest and headed to a friend's house and have been staying with different friends and families and hotels around the world ever since. I tell you, it's really difficult to give your stuff away and I've learned how much my friends and family really means to me.
Do you have a base you travel from? Or is it continuous travel? And why do you choose that style?
Houston, Atlanta and New York are kind of my bases, but I flip flop all over. I literally have friends all over the world so that makes it easy. Ever so often I do a continuous travel like at the time of this writing. I chose the lifestyle as I hate to be in one place for too long. For me, its all about the journey, meeting new people, talking with them, finding out what makes them tick. Oddly enough, without asking almost everyone I meet in my travels invites me to their house the next time I'm in their city; its very strange and I've not been able to figure out why they do this. Most recently was an American couple I met at my hotel in Jerez, Spain.
How do you fund your travel lifestyle? Is it something you do when travelling or are you a saver?
The big question huh? It's tough, but for some reason I make it happen. Its a combination of savings (I'm a terrible saver so there's not much there), 401K, severance pay, ebook sales, income from my blogs and consulting. Staying with friends and family is a huge part of the funding as well.
If you could tell yourself one tip before you started your travel lifestyle, what would it be?
You know, I wouldn't change anything. My life is already recorded, I'm just playing it back.
What does "Living The Dream" mean to you?
The ability to not know what's next. Being able to stay in a place as little or as long as you need to and then choose a mode of transportation, air preferably and go. Plus being able to help others as they need it and you are able. I'm a simple guy; I don't need much.