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 thought to myself as I clicked on his page.
His name, I discovered, is Oliver Widger. At the time he had around 20,000 followers on Instagram. 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 brand 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.
The realization of 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 in the back of my mind. I checked his page every now and then to see how he was doing.
In March, some friends and I were on the coast for a weekend getaway. While in bed at the hotel, tired from a long day, I scrolled through my phone one last time before drifting off to sleep. That’s when Oliver’s face appeared. I was then struck by a crazy thought. I knew Oliver was relatively close by, continuing the work of outfitting his boat near Astoria . . . coincidentally, I had my camera with me.
The dots began to connect. 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 social media pages, you’ll get a feel for my brand and vibe pretty quickly. I love working outdoors 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—without thinking too hard, I reached 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 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 hoodie and grungy Dutch Bros beanie, the same clothes he had been wearing on social media for the past week. I knew in an instant he wasn’t putting on a show. His sincerity was apparent; his demeanor, quiet and confident.
Oliver welcomed me onto his floating abode and introduced me to sweet Phoenix. We chatted for about an hour as he fielded my nonstop questions. “How did you learn?,” “What is your plan?,” “What happens in an emergency?” . . . and so on. Oliver was prepared with answers and patient in giving them, melting away any doubts I had about his competency and intelligence.
Meanwhile, Phoenix was still warming up to me. I gave her a pat on the head and let her sniff my hand. Oliver gently scooped her up and laughed without hesitation—the same unforgettable laugh I had heard so many times before in his videos. I began taking photos and he offered a bright smile. And as for Phoenix? Well, she eventually came out of her shell!
Honestly, the rest of the shoot felt easy, with Oliver in his element and me pretending to be a fly on the wall. “This guy is legit,” I thought to myself, “He really is going to sail around 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 already half way to Hawaii—a testament to Oliver’s hard work, courage, and focus. Since departing Oregon on April 30th, they 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.
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