Man, Kelsey and I are planners to a fault. We're your stereotypical Type-A couple and then some. And by then some I mean I grew up in a military household then spent 5 years in the service myself, where my branch's motto was about always being prepared and having a plan. Now being prepared and things having a place works incredibly well with living on a sailboat. Plans, however, do not.

Our lovely sailboat we call home is not a planner. By her nature, she is always going wherever the wind takes her. Plans are not something she controls but something Mother Nature does. She's a stoic who knows what's in her sphere of influence and what isn't.

For us, this lesson has been a hard taught one. For example, when we bought Lucidity about a year ago we planned on keeping her on the hard in Indiantown for a month to do a bottom job and install an ice box conversion. Didn't happen. Bottom job is now overdue and we own an Engel. How about our first year cruising plans? Ha! We were bound for Havana & Dry Tortugas by last Fall at the absolute latest. Poor Luci hasn't left the dock in 11 months!

I could go on and on sharing our other best-laid plans since moving aboard but I'll spare you the monotony. We can plan all we want but at the end of the day, old man universe is going to do whatever the hell he wants. We've found what works best for us is having a few loose plans in place so that way when it comes time for one to come to fruition, it usually involves either a combination or deviation of all of them.

Sailing the Caribbean by the end of 2017 was admittedly a very loose plan. After founding an early-stage tech company this past October, the Caribbean seemed more like a distant dream than anything reminiscent of a plan. 6 months out it's looking like our reality now. But who knows. We've learned to take after Luci and just go wherever the wind blows us.

I recently watched Live like Alex and it left me questioning if what we were going to do was going to give me the answers I so relentlessly sought. Alex, someone who I could relate to in numerous ways, circumnavigated and did it in unprecedented style. I by no means am as charismatic or downright risky as he is but a lot of the things he was searching for I find myself seeking. What impact, if any, am I going to leave behind on this earth? Why am I here? What is my purpose and how can I live a fulfilled life?

Alex did it all, man. He brought people who have never even considered they would be lucky enough to be on a real boat and let them get behind the helm, just so he could bask in the joy they experienced. During his circumnavigation, Alex did something very few sailors actually do, he got to know this world's people. Yet after all of this, he completed his journey and was left feeling unfulfilled. During the film Alex says before he left he was confused, he didn't know what he wanted out of life and thought once the trip was complete he'd have all the answers. In reality, the exact opposite happened. He was more confused when he came back than he was when he left.

This left me questioning a lot of what we had planned to do. If this guy, someone I could only hope to emulate, was unfulfilled after a 3+ year circumnavigation, how could I be fulfilled after sailing the Caribbean for a year? Maybe I wasn't making the right move. Maybe traveling isn't meant to be fulfilling in this way, just rewarding and thought provoking? Once Alex arrived back home after his trip all I was thinking was he needed to do something like his Dad did - embrace his entrepreneurial spirit and do something centered around social impact. For those who haven't seen the film, Alex's Dad was an extremely successful entrepreneur who founded one of the nation's largest egg producers. Now I never had the pleasure of meeting Alex so I can't say for sure but for me as the viewer, I felt like that was what he was missing.

The company Alex's Dad founded

I tried to keep my doubts off my mind. We were pretty much on cruise control at this point, we had enough saved for our trip and were just waiting until next Fall to cast off. Then old man universe decides to throw me a curve ball.

As I'm talking about Abandon Comfort in my graduate class, a classmate of mine pitches me his business idea revolving around sparing Millennials from the burden of student debt. He knew it'd be right up my alley and he was right. Kelsey and I paid off our 50k in debt and we can't recommend it enough to anyone else who feels tied down by their finances and wants to travel. Fast forward 6 weeks and we have an incorporated business ready to launch this week. Our mobile application, known as Spared, has the potential to save our average user $9,000 in interest payments and get them debt-free 7 years faster. I want my friends and my generation to relish in the freedom that living debt-free awards them. I want to stop seeing people put up travel quotes and inspirational videos of people living life on their terms on social media, and start to see videos of them actually doing it themselves. I feel fulfilled in knowing I can get them there quicker and I can't wait to see my fellow Millennials actually out there doing the things they've always dreamed of doing.

So what does this mean for sailing the Caribbean for a year or Abandon Comfort in general? As of right now all of my time is being dedicated to Spared but Kelsey and I are by no means giving up on our plans. Sure the majority of my funds have been thrown at the business but I can recuperate if Spared fails and we have the time to sail as planned. But for right now I know I feel fulfilled and am overjoyed at the opportunity that has been laid out in front of me. Who knows what the next few months will hold or even the next year for that matter. All I know is I'm moving towards making my days count and leading a life of purpose.

For those who haven't seen it, carve out 1.5 hours of your time and learn about Alex and his adventures.

Sailing Plans, An Oxymoron

Potential Social Impact