Sailing with Phoenix
Why The Whole World Is Cheering For Oliver Widger
I’m lying in bed on a sunday morning scrolling tiktok when the rest of the world let me know that Sailing with Phoenix made it to Hawaii. I remembered the first video I saw from this account, what felt like barely a week before. The following video was posted May 1st. He did it. Oliver bought the boat and is setting out to sail around the world. His first initiation is to sail across the Pacific Ocean from Oregon to Hawaii. The “I did it” video is sitting at a cool 42+ Million views across platforms.
Documenting the highs, the lows, and the lulls of glassy ocean in between, Oliver shared his story every day for the following 25 days. On Day 3, a pod of whales joined the journey. On Day 10, Oliver takes his first swim in the open ocean despite a very ironic fear of deep waters. On Day 16, Oliver shares a surreal sunset and laughs about learning that airline pilots were telling passengers to look for him down below out their windows. Nearing Hawaii on Day 24, a plane (sent by a brand for pr) drops a package of spf products, snacks, and fan mail.
Oliver and his cat Phoenix have attracted a couple million followers, a few hundred millions of views, attention from media titans like Anderson Cooper, and have captured the hearts of most of America while they have documented their time sailing to Hawaii. People have said he’s become a source of inspiration and hope, expressing gratitude that they have made the right person famous this time.
We need to run this story back though, because in many ways the moral of this story is getting undermined by the effects of the virality aspect. The whole thing seems like a magic potion of chance. A lucky streak, and a sprinkle of internet fame. The real heart of this story is found in Oliver’s motivation and human spirit, which speaks volumes to the pulse of what our culture is experiencing.
Miserable with his job and overall lifestyle, and having just recently learned that he was at risk of going paralyzed from the neck down due to a spinal disorder, Oliver Widger became acutely aware that he might not be able to achieve his dream of sailing around the world when he gets older. His mortality stares him straight in the face and asks him what he wants of his life. Oliver seemingly doesn’t flinch. He quits his job in corporate America. He liquidates his 401k. He starts selling everything he owns too, to help fund the purchase of the boat he will soon live on.
At this point in time Oliver doesn’t know how to sail, let alone repair the boat if needed.
Is Oliver dumb? Reckless? Crazy? For hollowing out his 401k? For choosing to sail around the world without the qualifications?
Does your opinion even matter if Oliver is thriving (and it appears now that he really is)?
He spent a year getting comfortable being uncomfortable. Testing out the waters both literally in learning how to sail and figuratively in documenting his journey on social media before anyone was really even watching.
Months and months before he set sail, in a rather prophetic podcast interview with a friend, Oliver shared about his life in corporate America and how he ended up in the miserable position he was in before deciding to actualize his dream of sailing around the world. “I feel like we were fed propaganda, y’know. Like we were fed this dream. … That’s what happened to me, dude. I was sold this dream, this vision. I was sold it so well. Fully bit down on it, and then all of the sudden I’ve gotten older and I wake up one day and I’m like ‘this sucks!’ He says.
It’s the American dream that he was sold. Oliver’s current redemption arc, and most definitely the response to his story, is evidence that the American dream is dead. Or, at the very least, on it’s last few breaths.
On Day 25 of sailing from Oregon across the Pacific Ocean, Oliver and Phoenix arrive in Hawaii with an escort from the Hawaiian Coast Guard. The support Oliver attracted along the way speaks for itself. The warm welcome Oliver was met with when he got to Hawaii speaks for itself.
We think we’ve all become obsessed with watching this story unfold and come alive because we’re desperate for inspiration right now… but I see something else happening here.
Oliver’s story is a refreshing one that ignites inspiration and hope. I won’t discredit that. I mean, he made it out of the matrix right? He did indeed. I’m also going to adjust the mirror and bounce Oliver’s light back onto you, sweet reader.
On Day 9 of his journey Oliver talks about going all in on his dream, and what that really meant in his lived experience. Oliver shares his belief that “there is nothing special about him, except that one day he chose to put everything he had into this vision.” This is Oliver’s gift to us if we choose to receive it.
Oliver is revealing to each and every person that has become enamored by him & his story this: If you have a vision that you want badly enough, you do not need to be “special”. You do need to unflinchingly back yourself and the life you are called to create and live.
“The greatest form of activism is to be a living example of the type of people that you wish to see walking this earth.” - Ebonee Davis
Throughout his documentation of his journey Oliver has expressed being terrified every single day, being very aware of the risks he is betting on with his own life. Still, you can see it in his face that he is also having the time of his life. He is stoked to be on this truly authentic path of his own. He is fulfilling something dear to him — a vision he’s held since he was a young boy on sailing trips with his father.
In real time, we are watching Oliver Widger live his own hero’s journey, reclaim himself, and build a life that is on his own terms.
Oliver lived the default life for a while. It drained the light from his face and the joy from his spirit. Now, he is running toward something that makes him feel alive, and you can see the joy & wonder has flooded back to him.
We’ve fallen in love with Oliver through our screens because we cannot take our eyes off of his courage. We are magnetized to this story because we are watching Oliver live. We are witnessing what aliveness looks like. The very thing about the Sailing with Phoenix epic that you are “obsessed” with, is that he is ALIVE. And that, sweet reader, is also the very thing that you are aching to feel but afraid to be.
Wouldn’t you hate to wonder what Oliver’s unlived life would be if he chose to stay where he was? Wouldn’t you hate to wonder what your unlived life might be?
Because Oliver chose himself so wholeheartedly, he is living and breathing the good, beautiful, and fulfilling life that he deserves. And in doing so, he is giving the world around him some damn good light too. The Sailing with Phoenix story, which is only just beginning by the way, is not merely unfolding in front of our very eyes for hope-core vibes. It is a call to action to choose to participate fiercely in your own life.
And just like Oliver, the very self-proclaimed regular dude from Oregon, you hold the keys to your own freedom.
Get out there and make some Good Light.
Xx Riley Reign
To Oliver, may you stay protected & blessed with the resources you need during every step of your journey. Thank you for sharing yourself and your story with us. Thank you for chasing your dream, for showing others how to find our own way simply by doing it yourself, and for showing us what is possible. We admire your spirit and your unseen strength.
To Olivers brother (sorry I didn’t catch your name in any content), thank you for encouraging Oliver to do this wild thing AND for encouraging him to document it publicly. It sounds like some of the credit for this epic story animating itself before our eyes and getting to exist on social media at all is thanks to your encouragement. Whether you knew this would be the outcome or not, thank you for pouring into your brother. The ripple effect speaks for itself.
Content sources & where to find more of Oliver’s story —
— Sailing with Phoenix on TikTok, Instagram, and YouTube
— Oliver Widger on The Failure Podcast
— Oliver Widger interviewed by Anderson Cooper
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I love this story and wildly it’s the first I’m hearing of it… so thank you for sharing it!