Sailing With Phoenix

I don’t know about you, but there are certain social media accounts I follow that have become part of my daily routine. Some make me laugh. Some make me think. Others have me questioning humanity.

And then there are the accounts that remind me just how extraordinary ordinary people can be. A little over a year ago, I stumbled upon an Instagram account called Sailing With Phoenix.

At the time, it was a brand-new account belonging to a then 28-year-old young man named Oliver Widger, who had just quit his job as a tire salesman.

Now, most people who quit their jobs might take a little vacation, update their résumé, or spend a few days in their pajamas contemplating their next move. Not Oliver.

Oliver decided to buy a sailboat and sail across the Pacific Ocean.

With his cat.

Naturally, I was intrigued.

A few years earlier, Oliver had been diagnosed with Klippel-Feil syndrome, a rare congenital condition in which two or more vertebrae in the neck are fused together. Depending on the severity, it can create serious neurological complications, including a risk of paralysis. Yes, I had to consult the World Wide Web for that explanation. Kiki knows a few things, but rare spinal conditions aren’t exactly in my wheelhouse.

Faced with the uncertainty of what his future might hold, Oliver made a decision.
He wasn’t going to spend his life wondering what if. He was going to find out what’s next.

So he bought a sailboat, named it after his beloved cat Phoenix, and taught himself to sail.

How?

YouTube.

Yup. The same platform I consult when I can’t figure out how to assemble something from IKEA or properly shuck a clam was going to teach this guy how to navigate the Pacific Ocean.

I was hooked.

In April 2025, Oliver and Phoenix set sail from Oregon, bound for Hawaii.

And just like that, I became an unofficial member of the crew.

Every single day, I checked Instagram for updates. Some nights, when sleep eluded me, I’d find myself watching Oliver somewhere in the middle of the Pacific Ocean, talking to his phone, navigating the waves, and chatting with his cat.

It was like watching a real-life version of The Truman Show – except Truman had absolutely no idea people were watching him. Oliver knew and he was bringing us along for the ride.

I couldn’t wait to hear what this dude would say next. How was the weather? How were the waves? Was he eating? Was Phoenix behaving? Did he sleep? Was the boat okay?

Good grief. I was worrying about a complete stranger and his cat somewhere in the Pacific Ocean while sitting comfortably in my own home on Long Island.

That’s what I do, folks.

I become invested.

Oliver had family members helping him behind the scenes, and fundraising accounts were established to support his journey. I even purchased some merch.
That’s right. Kiki was financially invested in this adventure.

Friskies eventually came aboard as a sponsor, which was a pretty sweet deal for Oliver, Phoenix, and the folks who manufacture cat food.

On May 24, 2025, Oliver and Phoenix finally arrived in Hawaii. Safe. Healthy. Happy. I was absolutely thrilled.

Watching this young man accomplish something so enormous, something most people wouldn’t even consider attempting, was incredibly gratifying.

He had a dream. He had a reason. And he refused to let fear make the decision for him.

But apparently, sailing across the Pacific Ocean wasn’t quite enough for Oliver.

Oh, no.

This kid was just getting warmed up.

He decided his next adventure would be to sail around the entire world, nonstop, while raising awareness and money for the rare condition that had changed the course of his life.

Around. The. World.

Without stopping.

Excuse me?

I get annoyed when I have to drive around the block twice looking for a parking space.

Oliver sold his original sailboat and purchased another vessel better equipped for the demands of such an extraordinary voyage.

Naturally, his loyal followers, including yours truly, were glued to our phones watching him prepare the new boat. Every modification, every repair, every piece of equipment had a purpose.

And then there was Phoenix. Oh, my heart.

This time, his beloved feline companion would not be joining him. Phoenix would remain safely at home with Oliver’s brother until his return.

There is even an Instagram account called Waiting With Phoenix.

Of course I follow that one, too. Did you honestly think I wouldn’t?

Watching Oliver say goodbye to his furry first mate was difficult. I know how deeply our pets become part of our lives, and I could only imagine what it felt like to leave behind the one companion who had shared his first great adventure.

But I was relieved to know Phoenix would be safe, loved, and waiting for him.

Today marks Day 14 at sea for Oliver.

Fourteen days.

Alone.

On a sailboat.

In the middle of an ocean.

And here I sit, patiently waiting for today’s report.

I worry about him. I really do. Not just about the weather, the waves, or the mechanics of his boat.

I worry about the silence.

The solitude.

The sheer enormity of being alone with your thoughts for that length of time.

Could I do it?

Absolutely not.

Listen, Kiki is strong like bull. I’ve faced some pretty formidable challenges in my life. I’ve pushed myself physically, emotionally, and mentally through situations that required every ounce of strength I could muster.

But I also know my limits. Being alone in the middle of an ocean with nothing but my thoughts for company? Good Lord. My squirrel brain would stage a mutiny before we cleared the harbor. I’d be having full-blown conversations with the GPS by Day 3.

Still, I cannot help but admire this young man. His courage. His determination. His willingness to trade the familiar for the unknown. More importantly, his decision to turn a frightening medical diagnosis into an opportunity to inspire others. There’s something incredibly powerful about that.

We live in a world where negativity seems to be available in unlimited quantities. Open any social media platform and you’ll find plenty of anger, division, and people arguing over things that won’t matter five minutes from now.

Lately, I’ve been making a conscious effort to look for the good. The people who remind us that kindness, courage, and determination still exist.

So here’s what I’ve learned from Oliver Widger. You don’t have to sail around the world to find your courage. Sometimes you just have to stop allowing fear to steer the boat. We all have oceans to cross, dreams waiting to set sail, and a few storms to navigate along the way. The trick is knowing when to untie the ropes and leave the safety of the harbor.

As for Kiki? I’ll be cheering Oliver on from dry land, iced Americano in hand, Wi-Fi fully charged, and both feet planted firmly on the ground. Because somebody has to stay ashore and worry about the captain.

Smooth sailing, Oliver. I’m rooting for you. ❤️