With Yahtzee’s anchor set, I attached the snubber to bow cleats and rolled out the last few feet of chain. Though our family has anchored in this spot dozens of times over the past year-and-a-half, it felt different this time. Very different. Looking at the familiar shoreline, at the green trees above it, at the rock walls reaching skyward, at the craggy snow-capped peaks and a brilliant blue sky, I smiled. The difference is that we’re no longer merely here for a weekend. We’ve hit the play button and the dream continues—we’re cruising again and this is just the first stop on our newest journey.

Soaking in the moment, my mind shot back nearly 16 years to when this whole dream was but a flicker in my imagination. I’d grown up sailing, but after a summer of working on sailboats in Newport, Rhode Island, I’d returned for my sophomore year at the University of Oregon with an ignited passion for it. My adventurous spirit insatiably craved a life under sail, of seeing new places, of meeting new people, of visiting far flung anchorages and ports, of cruising on my own terms. I was determined to make it happen.

To do so, I decided to blend jobs in the sailing industry with another passion—writing—and with that I set my mind on turning my goals and dreams into reality. When I shared the idea with my advisor while choosing a fall class schedule, I thought he was going to burst out laughing. I never saw him again. Friends and family had doubts, too, some of which were shared openly. I knew people thought I was just a starry-eyed college kid with an overly idealistic dream that would soon pass and certainly never happen. Sail and write for a living? Get real. You’re dreaming! You have to get a real job, and a house, and a car, and so on and so on. Not me. Not us.

Fortunately, in this same timeframe I’d found the perfect adventure partner to believe in and share the dream with, and over the years Jill and I have made it happen together. Now, seven years after buying Yahtzee and cruising to Alaska, we find ourselves pushing off for the next adventure. On Friday afternoon we waved heartfelt goodbyes to friends on the dock, pulled out of Seward Harbor and set sail back into the cruising life. Back into our dreams. Because, above all else, life’s short, and it’s not going to live itself.