When do you choose risk over stability?  That was the question I had to answer when deciding whether or not I should leave my job to live out of a backpack while traversing across three continents for several months to eventually return to my point of departure (Upstate New York).

To some of the readers the dilemma of going on the trip of a lifetime or stay at home doesn’t seem like much of a dilemma at all.  Life is short, so you should go on the trip.  To others who value stability in their lives, the choice seems equally as obvious. I have it good now, don’t throw it away.

Because you’re reading our travel blog it’s obvious what choice I made.  After several long talks with Katie discussing the logistics of how we could make our trip possible, I had one internal hurdle that got me to the point where I said yes.  I asked myself, what would Pop Pop do?

Again, some backstory for the reader on who this man was and how he influenced my decision.  Pop Pop was my paternal grandfather.  He was a man who, as I knew him, was willing to take risks on the belief that through hard work and a smile on your face you can overcome the challenges that life will eventually present to you.  He passed away about two years ago, but prior to his passing I had the opportunity to spend some quality time  with him.  During our car rides to and fro he would tell me stories of his life.  Some I tend to believe were exaggerated (think of the movie “Big Fish”), while others seemed believable on face value.  From time to time I would recount the tales Pop Pop told me to other family members to validate if there was any truth behind the legend.  More often than not, his adventures in life were founded in truth.

I looked to my grandfather for wisdom when making the decision to partake on my own adventure because in the stories he told me, and even some of the ones he didn’t, I knew his life had its fair share of hardship and tragedy.  In the final years of his life  Pop Pop was still able to genuinely smile at me every morning when I would pick him up.  It’s my belief that he was able to wake up every morning with a smile on his face because he chose to live his life the way he wanted to; for better or for worse.

Should I have had the opportunity to ask Pop Pop his advice on my dilemma he would have smiled at me and said “go” and then after a brief pause “can I join you?”