who is this guy?
A few months ago—probably late January—my Instagram feed showed me a reel of a young man sailing his boat along the Columbia River at sunrise. Living near Portland, I recognized his location right away. The man said he was on his way to the Oregon coast by himself, then proceeded to laugh nervously while trying to figure out how to pass under a train bridge for the first time. His laugh was unique—so much so, I couldn’t quite tell if he was being serious or not. He didn’t seem all that confident, in fact, he called himself an idiot for not knowing enough. Nevertheless, he seemed happy and I was happy for him. “Who is this guy?,” I asked myself, proceeding to click on his page.
His name, I discovered, is Oliver Widger. At the time I think he had somewhere around 20,000 followers. Oliver had only recently bought his sailboat and was still learning to sail (no wonder he seemed nervous sailing to the coast by himself). That’s not even the half of it though. You see, Oliver didn’t just buy a boat to learn to sail. He bought a boat to start a new life chapter.
. . .
from sales to sails
In his former life, Oliver worked a corporate job making decent money. However, wealth and status had lost their luster, and Oliver began dreaming of a different trajectory: being a full-time sailor. Mind you, Oliver had no prior sailing experience at this point.
Oliver’s dream was expedited when he was diagnosed with a serious spinal condition in his late 20s, potentially impacting his future quality of life. It was then when Oliver decided to earnestly seek after joy. With no time to waste, he abruptly quit his job, liquidated his 401k, and bought a sailboat. His goals were lofty and had to be achieved within one year: 1) learn to sail, 2) outfit his boat for ocean travel, and 3) leave Oregon for good.
First stop on his journey? Hawaii. After that? The world. What about a first mate? That would be Oliver’s beloved calico cat, Phoenix.
. . .
a chance to meet
I started following Oliver on Instagram out of curiosity, but to be honest I didn’t really pay much attention to him. Knowing a lot of social media is pretty exaggerated, I wasn’t sure what to believe, so I only half-heartedly watched his videos. Nonetheless, I’ve always loved content about boats and water activities, so I kept Oliver and his cat on the back burner of my mind. I checked his page every now and then to see how he was doing.
In March, as I was visiting some friends on the coast for a weekend getaway, the thought of Oliver popped into my mind. I knew he was relatively close by, continuing the work of outfitting his boat near Astoria. Coincidentally, I happened to have my camera with me. The dots connected. The more I thought about it, the more I realized what a perfect photography client Oliver would be. If you take a look at my website and Instagram page, you’ll get a feel for my brand and vibe pretty quickly. I’ve always loved working in outdoor settings with adventurous clients who don’t take themselves too seriously—people who exude light and joy with their laughter and candid expressions. To me, Oliver checked all the boxes, so I decided to reach out to him. “If he’s really serious about wanting to sail around the world,” I thought, “I want to be the one to help tell his story.”
In the end it all worked out. I met Oliver on the dock in front of his boat on the afternoon of March 23rd, in the middle of a gale with sideways rain. He was wearing his signature Sol Duc Hot Springs sweatshirt and grungy Dutch Bros beanie, the same things he had been wearing in his Instagram reels for the past week. It was obvious he wasn’t trying to put on a show or be someone he wasn’t. He was kind and grateful—and especially welcoming—giving me a tour of his boat and introducing me to sweet Phoenix. We chatted for about an hour and he let me ask him every question I could think of, so as to rid my mind of any doubts I had about his competency and intelligence. I then took his photos and he laughed that same laugh I had heard so many times before through my phone, with a smile so bright it could light up any room. “This guy is legit,” I thought to myself, “He really is going to sail the world—and sooner or later the world is going to fall in love with him.”
. . .
see for yourself
As I write this, Oliver and Phoenix are currently half way to Hawaii—a testament to Oliver’s hard work, courage, and focus. Since departing Oregon on April 30th, they have have amassed a following of over one million people. Feel free to follow their journey on social media: @sailing_with_phoenix
Below are some of my favorite photos from our shoot:
All images by Tracy Robyn Film & Photo.
. . .
