Several years ago I wrote my dad a letter. It was a letter requesting his permission & support to buy a sailboat, take a semester off of college and go sailing. He was pretty shocked, but I already had my mom on board, so after a short family meeting I got the all-clear.

That letter was the beginning of one of the most influential times in my life. I bought that sailboat, took the semester off and went sailing. I left a shy, insecure kid and returned to the dock an outgoing, confident man.

Last year my parents noticed I again had that look in my eye. It was time to try something new…to begin another adventure. So we had another family meeting.

The past 12 months have been a bit of a blur. I had one of the greatest seasons of work ever, quit my job, took a road trip across the country, and moved onto a friend’s sailboat. I’ve spent the past few months writing, thinking, relaxing and dreaming. The dreams and thoughts always fall back to my goal of sailing around the world. I have the will, I just don’t yet have the way.

So I’ve written down tons and tons of ideas of ways to make enough money to take the trip. Most of which are legal.

But none of the ideas felt just right. And then I was talking with a sailor friend and he told me about a guy who he’d met years ago from New Zealand. So I looked up this New Zealand guy, and it seems that he’s in the business of helping people fund adventures.

And then that brought me back to my experience with Going to the ‘Ship and the trip I made to the BCS National Championship Game this year with my friend West. We allowed other people to take part by pitching in for gas & expenses in return for us sending them postcards and video updates and stuff.

It all seemed a bit vain at first…us asking people for their hard earned money so that we could enjoy the experience of a lifetime. But that trip became so much bigger than just West & me. I got email after email from people thanking us for including them in the adventure. I heard story after story from folks who were unable to make the trip themselves, but felt like they were there because of our posts & videos.

And that brings us to two weeks ago. I was sitting here at the marina talking with friends over happy hour. I threw out the idea of letting people sponsor a small portion of my sailing trip in exchange for postcards or videos or something.

I explained that I’m not trying to be a charity or anything…if you have $10 to give to the Red Cross or me, by all means give it to the Red Cross. But in the same way that people are willing to spend money on a fancy lunch or movie ticket or magazine or book, maybe people will be interested enough in my story and the trip I’m making that they’ll jump at the chance to be a part of said story.

As I worked through the idea aloud, I failed to notice my one friend reaching into his back pocket. Before I knew it, he shoved a $20 bill in my hand and said “I’ve known you for over 7 years, and by God if you say you’re going to sail around the world, then I have faith that you’ll do it. And I want to sponsor the first 2 miles.”

I was a little stunned at first…I even tried to hand him his money back. “Wait…I mean…I’m not quite ready to do this…I was just bouncing ideas around…”.

Accepting his $20 meant that it’s real. That somebody actually thinks I can do it. That this dream of sailing around the world isn’t just a dream anymore. It’s a goal.

He wouldn’t take the $20 back, so it sits in the front of my wallet as a reminder that now the story is bigger than just me. Moments later I looked up to see one of the most amazing sunsets I’ve seen in a long time (pictured above). In a weird way, it felt like some sort of confirmation that this was the next step…inviting other people along on the journey was exactly what I was supposed to do.

So I shared this with my family when they were in town visiting last weekend. We talked about it for a little while and I got their official all-clear to pursue this crazy dream of mine. I have a long way to go, but God willing, I’ll be ready to begin the trip next spring.

Until then, I’m making it my full-time job to figure out how to fund the trip, become a better writer, learn as much as I can from more experienced sailors, and do whatever I can to help others fulfill their dreams.

If you believe in what I’m doing and would like to be a part of my story, please consider sponsoring a mile or sharing this story with your friends.

If you have any suggestions, I’d love you to send them to contact@sailingbo.com.

And if you’re not convinced, here are a few posts that’ll help you get a better feel for me and my writing style…

Thanks for taking the time to read about my dream, and hopefully I’ll hear from you soon!