Sailing With Phoenix: “I Quit My Job To Sail The World & Discovered My Purpose” - Here’s The Secret To Finding Yours
52:24 Share

I went to the doctor and they took some x-rays and the doctor, she was like, "Your spine is like somebody who's over 120 years old." After the diagnosis, I spiraled completely and then I finally one day I was like, "My name is Oliver. I work a corporate job at a tire shop. I absolutely hate this life. Yeah, I'm gonna buy a sailboat."

and I'm going to sail around the world. That's Oliver Widger who quit his job after he posted that video, liquidated his 401k, bought a sailboat and started learning how to sail. Our guest for you guys today is the one and only Oliver Widger. I haven't told anyone this but I was in Special Ed

from first grade to senior in high school. There's only, there's one thing in my life that I could do well, and that is I can grind. I can work so hard. If I lean into that, I can do, I can do anything. I tell people this, they're young all the time, that like message. I tell them, dude, if I could go back in time and I was 18 or 20 or whatever, I would literally get a globe that

I would spin the globe and I would stop the globe with my finger and I would buy a plane ticket, a one-way plane ticket and go there. If there's somebody that is looking to chase their dream, find the point of no return and...

Are you ready to level up your business? Intuit QuickBooks has got your back. Forget stressing over unpaid invoices or tracking expenses. QuickBooks takes care of all that so you can focus on growing. Let QuickBooks be your all-in-one tool to help with the day-to-day tasks so you can stay focused on the big picture. Manage and grow your business all in one place. Intuit QuickBooks. Your way to money.

And now that everyone's up, you might as well make breakfast sandwiches topped with Land O'Lakes cheese.

Here's another hack. By buying Land O'Lakes products, it benefits over 1,000 farmer owners and their communities. Find it in the dairy aisle. ♪

This podcast is sponsored by Northwestern Mutual. Everyone wants to feel good about their finances, right? Well, that's why I've had life insurance with Northwestern Mutual for years. Their financial professionals ask the right questions, truly listen, and help uncover opportunities most people miss. I've seen it firsthand. Northwestern Mutual has been a part of my journey from the very beginning, providing the security and peace of mind I need as a human and an entrepreneur.

Find a better way to money at NM.com. The Northwestern Mutual Life Insurance Company, Milwaukee, Wisconsin. Paid testimonial by a Northwestern Mutual policy owner. So I'm so excited, man, because I've been watching your journey over the last few days. My friend Tim was here, showed me your videos.

And since three or four days ago when I started watching you, I think your audience has exponentially grown and I love seeing what you're doing. And so we have, if you can, share your full name because on Instagram you're sailing with Phoenix and you are changing and inspiring the world in a massive way. So if you can, share with your full name to the audience who's watching. Yeah, my name is Oliver Widger and

Yeah. And so, so you have this video of you working a corporate job and essentially hating your life. And at one point you decide because you have, uh, test results at the hospital, right? That, yeah, that something is, something's off in your body. Is that correct? Yeah. Well, so like I, I had neck pain for a really long time, like for a long time, but like, I don't like going to the doctor. So I just, uh, uh,

you know, put it off. And then it just got started to get really, really bad. And, uh, so yeah, I went to finally, I went to like, I almost got, cause I can't go to a chiropractor. I started out, go to a chiropractor and like hindsight is they could have like immediately paralyzed me. And, uh, I just got lucky that didn't happen. And, um, none of that worked. And so I finally, I finally like called my doc or I finally like, uh,

called a doctor and I was like, I need to, I need to see like a doctor, doctor. I need to figure this out because it's insane. And, uh, yeah, I went to the doctor and they took some x-rays and then I, um, you know, they didn't think of any of it, you know, he just,

I don't know. And then I was at work, like, the next day, and they called me when I was at work, and the doctor, she was like, what are you doing right now? And I was like, I'm at work. She's like, you need to come in right now. And I was like, okay. So I go in, and she, like, she was, like, freaking out. Like, she didn't handle it very well, because, like, she was the...

She was an orthopedic specialist, so she wasn't like a neurologist. But yeah, she was like, I don't know how you're here right now talking to me and not in excruciating pain. I was like, well, I am in a bit of pain. That's why I'm here. And she was like, your spine is like, I've done this for 20 years. I've never seen anything like this. Your spine is like somebody who's over 120 years old. And then I went through this.

You know, I had to wait. It's a long story. I don't want to like just be all long winded and stuff. But I went through, I had to see like four neurologists. Wow. And all of it was really, really bad. And yeah, so I basically just stopped going to the doctor. And then I went through this, just like this, like, I don't know, like a crisis of some sort, you know, where my mortality was,

Kind of, like, hitting me in the face. And I was realizing that I'm spending my... Like, right now, I am physically capable of doing anything I want, really. As far as... Like, I can't do anything that... Like, I can't do anything that involves any sort of impact. But, um...

but I, you know, physically I can, I, you know, I, I've got all my limbs, you know, and wasting it at work. 29, 29. Yeah. So you're getting, you're getting all these doctors saying that you've got a spine of 120 year old. Yeah. You were working a job that you didn't really fully love that you were just doing it because you thought you were supposed to do it, I guess. Or you just, yeah, it was just like, I jumped into it and, uh, I,

I didn't have any, like a barely graduated high school. And it's a, it was a good, as far as like the money goes, it was a good job. Like it, you know, there's a lot of like potential for money within the job. So I was like, all right, this is it. I'm going to be able to do the, buy the house and have the, you know, the fence and kids and whatever. And, uh, and then that immediately after the diagnosis, I just started to question all of that. Now, but I don't really want to do any of that. Like this, this actually sucks. And, uh,

Yeah, and it was like three years. I went through after the diagnosis, it was like a three year battle of like, literally, I completely lost myself. And I went down this crazy rabbit hole to have like, just like partying on the weekends to try and like feel alive and like just

Party doing all the bad things. And, um, this is after you knew about, this is after you knew about the condition. Yeah. Yeah. Yeah. And then of course that just dug the mental hole deeper, you know, living like that. And, um, and then, yeah, it just, uh, it's, I spiraled completely. Um, and then I, I finally, one day I was like, like I had, I, uh, so that video that I posted, um,

that you probably saw where I'm in that shirt. You're like my work shirt. You're like, I did it.

well before like the the original post where i'm in that the uniform and i'm like i absolutely hate this life that full version of that is like two minutes and 35 seconds long and it's it's just it's wild to watch it is at the bottom of my tiktok i'm i've never taken it down um but i said my brother i decided i i found a purpose i decided i wanted to sail around the world and um my brother convinced me to start documenting it and so

And so that was the very first video I've ever taken ever of myself. And I sit there and I record myself and I say all those things. And my plan was to at some point, like, just document everything and at some point post it all. And I never used TikTok before. I didn't know how social media worked. So I was on a TikTok and I put it in as a draft because I thought I could put it in as a draft. You posted it on our Instagram.

Yeah, I ended up posting it on accident. And then it went to, so I didn't know that also TikTok syncs with everybody in your contacts. So it went to all of my bosses and it went to everybody. And so, yeah, just this crazy, you know, rant went to every single one of my bosses. I show up to work the next day, totally oblivious.

to what's going on and then one of the technicians comes up to me and he's like, "Hey man, when are you gonna buy that boat?" And I was like, "What in the world are you talking about?" And he's like, "The boat, man!" And then I made the realization and so how I left... I think that meant video?

That video is everything. That video is absolutely changed. Because who knows if I would have had the courage to leave. Who knows? To leave without that video. Because that video is the most embarrassing thing that's ever happened. And I was there for 11 years. And it went to everybody that I know. You know? And it was shared within the company. And... When did that video first get leaked to everyone in your context? Was this a year ago? Two years ago? When was it? This was a year ago. Wow.

So you put, you filmed this video, which I'll put up on YouTube as well. You filmed this video of you and your car saying, I hate my life. My life's miserable. I've been working this job for whatever, eight or 10 years. I've got this spine condition. Yeah.

I'm not happy. I've been working hard. I've been doing all the right things, but I still don't feel good. I just still don't feel fulfilled and happy. Is that right? Yeah, pretty much. Then you fill it for yourself without the intention of putting it out. And then you put it out to your bosses, right? They all see it on accident. Had you not done that, you would not be on this boat right now. Yeah, I don't know. I don't think so. I mean, who knows? I knew I was going to quit, but it's one of those things where it's like,

I don't know. You know, I don't know if I would have had actually when it came down to it, had the courage to quit. But that video is what went viral. That video is everything. That video is everything. It's everything. And it's all because my brother, my brother told me to start recording myself. Wow, man. And so you went and so you went from Oregon to.

Going on a sailboat that you've never been in the ocean before only in a river Yeah, and you're going on a sailboat from Oregon to Hawaii and your 12 days in is that right? Yeah, yeah 12 days in yeah, so I'm like almost a thousand miles away from ammo. I'm basically closer to the people on the space station than I am to anybody on land and

- Dude, I love seeing the comments of everyone in here saying you're one of the most inspiring people in the world right now. Everyone's following your journey. They're rooting for you. They're cheering for you. My favorite part is the shirt of Phoenix. You know, whenever you wear the shirt with Phoenix, the cat. And I just think what you're doing, 99.9% of the world will never do what you're doing 'cause most people lack the courage.

It's so safe. It's so comfortable. Even if they're miserable, they'd rather stay safe and visible than actually go for it. Yeah, I figured I was like, when I quit my job abruptly like that, I had like

I don't know, $10,000 in debt or something. And, uh, with no plan with a $2,600 rent due. And, uh, I just, it was like, dude, all I know is I'm buying a boat and I'm sailing around the world. And then a week after quitting my job, I had the brilliant idea of liquidating my 401k. And, uh,

So I liquidated my 401k, sold my cars. I sold literally everything without even... Like, my apartment was empty without even knowing what boat I was going to buy or how I was going to buy a boat. And I spent the following month just, like, searching for a boat. And I just got really lucky that I got a good, you know, a capable boat. Because that could have gone so wrong as well. And it didn't. And...

Yeah, and then I just dived into it with no and nothing. So how did you learn how to sail a boat, though? How did you know which boat to buy, how to sail? You'd never sailed before. Yeah, everything was basically YouTube. And I just like... As far as learning how to sail, so I...

I got the boat. I didn't even watch that many YouTube videos. I bought the boat. I took it out. I made incredible mistakes. I'm lucky to still have the boat. So many things have worked out where there's just really high risk

And I just, it paid off. It worked out. Wait a minute. Let me ask you, Oliver. You bought the boat and then you just got the keys to the boat and you just said, all right, I'm just going to push it off the dock and just see what happens? Yeah. So like a month after, it was about a month after, because I had to replace some of the lines and stuff on the boat because the lines were all like 15 years old and chafed through. And I replaced also all of the like rubber components. And then, yeah, I took it out.

- I love this for you. I don't know why, because I love that you're documenting this and you're able to share it in such an authentic way. Again, you've got almost a million followers and like 10,000 something. How does it feel to know that putting out a few pieces of content and actually chasing your dreams

is inspiring millions of people around the world how does that feel i haven't really even fully processed it like it's insane like it's it is it's like the the experience of i feel like the experience of like because i went viral on the day that i left and i'm also crossing an ocean you know what i mean two two insane things that i'm like that are like you know competing with

I was literally fighting for my life the other day while I'm going viral. You know what I'm saying? Like, it's just been so weird. And there's not a lot of time to, like... Because I'm still, you know, obviously making the content takes a lot of time. And then the rest of my time goes towards, like, managing the boat. So there's not a lot of time. Staying alive. Yeah. Not a small thing. Yeah. And it's been so cool, too. Like, the...

i don't know i've some of the comments that i've read and stuff that like you know it's like somehow some way it's like bringing people together that's the coolest thing in the world that it is man i'm reading i'm reading some of the comments here where one mom said my son and all his friends are glued to their phone waiting for your next video and they're all inspired so again you're you're helping kids you're helping adults again there's

The compilation video you made, I guess from all the either TikToks or the Instagram videos of people watching your journey, that is inspiring because so many people from all walks of life, different backgrounds, different races, different economic classes, all feel the pain of not pursuing something that they know they should be pursuing or...

they're stuck in a relationship that they know they need to get out of but they're afraid they're stuck of the job they they want to launch something on the side even just for fun it's not always about like leaving your job in the relationship but it's like maybe they just had a dream that they want to pursue on the side they're afraid of you just gotta jump like that is the hardest part

Maine, where life the way it should be transforms all who encounter its spectacular landscapes. Rugged coastlines, pine-scented trails, sandy beaches, sparkling lakes, and tranquil forests inspire you to reflect and make meaningful moments. They offer endless opportunities for adventure and exploration. Whether pedaling or paddling, hiking or biking, Maine has more than enough outdoor spaces to make the most of long summer days.

relish in exquisite flavors harvested from the ocean and the rich soils of orchards and fields. Maine's makers are rooted in its heritage while boldly branching into new ways of thinking, doing, and being. Connect with its people in warm and authentic towns, which beckon you to stroll art galleries and locally owned shops, where generations of artists, writers, entrepreneurs, and craftspeople see the world anew. It's tempting to do it all when you visit, but take a beat and

and a breath get a feel for the time and tempo of maine simple pleasures scenic adventures where every route is the scenic one discover more at visitmaine.com you ever walk out of the grocery store or fill up your tank and just think

How is everything this expensive? Feels like prices are going up everywhere. And how great would it be if just once something actually just went down in price? Well, at Metro, that's exactly what's happening. They've lowered their prices and are giving you a five-year price guarantee on talk, text, and data. One line, now 20% lower. Family plans, also lowered. Oh, and you also get a free 5G phone.

all with no ID required and no activation fees. Stop by your neighborhood Metro store, visit Metro by T dash mobile.com or call to find out about their amazing offers. Bring your number not available. If currently at T mobile or with Metro in the past 180 days guarantee covers monthly price of on network, talk text and 5g data for customers activating on an eligible plan exclusions,

Apply. Details at Metro by T dash mobile dot com. When I got injured playing football, everything in my life changed. My dream disappeared overnight. I was broke, crashing on my sister's couch, stuck feeling sorry for myself. But then I made a choice. Stay stuck in that pain or adapt a no bull mindset and build something new. And that choice changed my life.

The No Bull mentality is what No Bull is all about. No Bull is the footwear brand for those committed to getting stronger physically, mentally, and emotionally. Known for their award-winning shoes, No Bull continues to raise the bar with the all-day Ripstop

I am a huge fan of these. Engineered for versatility, the all-day ripstop is designed to perform from early workouts to late nights and everything in between. With a soft foam midsole for comfort, targeted breathability, and a ripstop upper for extreme durability. They keep me moving comfortably all day long. I am a huge fan of these shoes. No shortcuts, no excuses, just commitment.

That's the No Bull mindset. Exclusively for our listeners, No Bull is offering 30% off your order. Visit NoBullProject.com slash greatness for 30% off your entire order. That's NoBullProject.com slash greatness for 30% off. How did you overcome the fear of being worried about what everyone thinks about you by doing some crazy idea? That was the biggest thing that held me back because I was super worried about like, you know,

Literally what solved all of my problems was like, there's a few things that's all I put, but one of them was, was like, I literally completely came to terms with possibly being,

broke for the rest of my life until I died. Like, being just poor and dying poor. I absolutely became, like, completely content with that idea. And once I became content with that idea, it was freedom. You know what I mean? I had freedom. And that's what it came down to. Because that was one of my fears. It's like, I...

I'm going to be poor. No one's going to, you know, who's going to want to be with like a poor, I'm going to be single forever. Like all that stuff was the things running through my head. Yeah. Who's going to want to date a guy on a, a bum on a boat and all that stuff. You know, I, and you just, all of it is nonsense. All of it is noise. And you just got to, I don't know. You just got to go for it. I guess. Oliver, what about your parents? Are your parents still around? Do you have siblings? Yeah. Most of my mom and brother live in the UK.

And my dad is in the US. And they're proud. What did they say originally when you were like, I'm going to quit my job. I'm going to liquidate all my assets. I'm going to essentially buy a boat and do something I've never done to go around the world by myself and my cat. What did they say? I think they saw...

how miserable I was. And I had been, you know, it was like three solid years of being like at the lowest low and they could see it. And so I think they, they were probably like, you know, they were probably like, I mean, anything better, you know? And so, yeah,

But they've always been really, my brother's been like incredibly supportive. Like I remember like at being at work and I'm like, dude, everybody knows. You know, I texted my brother and he like replies. He's like, now's the time. And I was like, all right. And now that they know, like just go. Who cares? Yeah. Yeah. This is incredible, man. What is the, you wrote about 15, 20 days away from Hawaii. Do you know which island you're trying to land on? Yeah.

12 days of wahoo to go to oahu yeah um do you do you know have you been to hawaii before i've been to maui before yeah i've got one of my other brothers is on maui actually gonna land in maui no i originally i wanted to go to maui because he's there um but i uh uh decided to go to oahu because now in maui i would need a car to like drive around and so oahu uh

There's a Marine story there too, like a West Marine that's there. It's within walking distance and everything's within walking distance. So it just made more like legislative sense. I want like thousands of people to be there when you arrive and just, I want the world to give you a big group hug and just congratulate you on taking the leap and taking the chance and going on the journey because most people in life will never take the leap and go for it.

And it doesn't matter if like people succeed or fail. It's really not. It's about, it's about going on the journey and seeing what you're made of. And so I'm curious, what's the biggest lesson about yourself you've learned in the first 12 days of traveling from Oregon to Hawaii on a sailboat alone with your cat? What's the biggest lesson you've learned about you? Um,

I don't know. I learned a lot about me on the process over the last year. Like I am a different person over this last year. And, uh, I, I just like, I've learned that I'm, I, I, you know, I've always had really, really, really intense. Like I'm like my hardest critic to the most intense level. And, uh,

I just learned that I can do anything. Like, I've done the impossible. Like, I've done everything I've done I thought was impossible. So, yeah. Dude, what is your greatest fear? Falling off the boat. You jumped off the boat already, right?

Yeah, but it was completely becalmed. Yeah, yeah. Yeah. Falling off the boat. But you've got a life jacket. Are you tying yourself up? Are you taking like... There's no life jacket. Just because if you fall in, a life jacket just prolongs the inevitable. So, you know. But I see for a harness...

There's a point wearing a life jacket. There's nothing around here. If I fell in the water, the life jacket would just prolong the end. Wouldn't it help you swim back to your boat or something? No, the boat sails itself. Like, I'm going, it's going like, right now it's going like six knots. Well, unless it stopped and you had the sails down and you fell off like you did, then it's fine. But if you fall off when it's going...

You can't catch what fell off. Yeah, you're not getting back on. Oh, snap. Yeah. You better rope yourself. Yeah, wear a harness. So every time I go out in the cockpit, I clip in.

And anytime I move forward, I'm clipped into the boat. So if I do lose my footing or something, the harness will catch me before I fall off. I love one of the videos you posted where you said, you know, I can't remember your exact words. I'm paraphrasing. But you're like, I'm an average guy. I'm below average. And if I can do this, anyone can do it. I'm not like, I can't stress that. I am as below. I haven't told anyone this, but I was in special ed.

from first grade to senior in high school. Like, I couldn't do school at all. And I can't write. I've got every single, like, learning disability. Like...

This is how I organize my notes. You know what I mean? This is a piece of paper. I can't even read it, so I don't even write. So, like, I can't stress that enough. The only thing I can do, there's one thing in my life that I can do well, and that is I can grind. I can work so hard, and that's the only thing. If I lean into that, I can do anything. So that's what it's come down to, and that's what I've done.

What is, here's a question for you. Maybe you've never been asked this. When do you feel the most loved in your life? When do I feel the most loved? Right now I feel pretty loved. But I don't know. When do I feel the most loved? I don't know. Like when I talk to like my mom and brother, I guess. I don't know.

They love me unconditionally. They've loved me. And my dad. They love me through and through. It doesn't really matter what frame of mind, where I'm at in life. They just love me. What is it about your relationship with your family that you appreciate so much? My parents are separated and don't talk. It's a weird, different dynamic. They just...

They've seen me go through some weird stuff. You know what I mean? And they've never... They've just... The love is there. Always. You know what I mean? Does that make sense? They've always unconditionally loved me. It doesn't matter where I am in life. They just have...

Beautiful, man. Again, Oliver, you're one of the most inspiring people on the internet right now and people are watching your journey. And I was like, I got to reach out to this guy because I just want to know what's more on your heart and hear more of your story because I think people are fascinated by your story.

And they want you to win. They want you to succeed. They want you to thrive. And I think you being so unapologetically you and authentic to who you are while you're sharing these stories, these videos is really inspiring. And I'm curious if you could go back. You said you're 29. Is that right, Oliver? Yeah.

If you could go back to your 21-year-old self, knowing everything you've been through in the last almost decade, what advice would you give your 21-year-old self? I tell people this that are young all the time that, like, message... Because, you know, I get messages and stuff. I tell them, dude, if I could go back in time and I was 18 or 20 or whatever... Because, you know, you see these guys, they're getting into the job. I was 18 when I got into my job. And, like, I thought this is what I needed to do. And, like...

I would literally get a globe and I would spin the globe and then I would stop the globe with my finger and I would have a, you know, buy a plane ticket, a one-way plane ticket and go there and sit with, you know, no money and figure it out and go. That's what I would have done. And I would have done that for as long as I could. That's why, that's what I recommend people do is spin the globe, point and go, you know, go see the world. I'm curious.

So if you could go into the future and you're 40, you know, 11 years in the future and you're 40, what do you think your 40 year old self would be saying to you now? Um, hell yeah. Sweet. Oh man. What about all the people, you know, again, 12 days ago, no one knew who you were and now you've got a million followers.

And again, people are invested in your journey, in your life. They want to see you win because you're bringing so much hope and inspiration to the world. What is it like going from, you know, nothing 12 days ago and having a dream and starting in the ocean to having a million followers in under two weeks and people so invested in your story? How does that feel? Uh,

I don't know. I haven't been able to process it. It feels unreal. It feels not real. I'm literally sitting here watching these absolutely absurd sunsets with dolphins jumping and then with these insane sunsets. And then I'm also viral at the same time and inspiring all these people. It's all

all these things that are like not real. You know what I mean? It's great. It's like, everything's a bit of a fog. It's a bit of a dream. It's, I don't feel like it'll be real until I put my feet on, on Hawaii. And then I'll probably be able to feel the, the, uh, how real it really is. Um, I mean, it feels unreal. It feels, it's absolutely insane. Like,

It's just that it worked. All of it, because social media, I didn't know anything about social media or how to edit videos, anything. I would spend like six hours a day editing

edited six seven hours a day editing videos and just figure making the craziest videos and just figuring it out and uh and then also i would spend literally the rest of my waking moments working on the boat and learning how to sail and i did that for a year straight completely isolated completely locked from the outside world did it for a year straight and uh

It's just so crazy that like the the it it all Came, you know, it all blew up together at the same exact time, you know, right left and I went viral You know, I don't know. It's crazy When you were when you were you know for the last year buying the boat and learning how to sail and doing all these things and learning how to edit videos were you posting any of these videos or you just All of it. It's all documented. Well, yeah

Posting these on my tick tock or something or where we opposed to these other videos last year So most of the videos are on tick tock and then right around when I got the boat

A little after I got the boat, I started posting on Instagram. So if you go to the bottom of my TikTok, you'll see a crazy amount. Okay, I got you. Now, I got to ask you because, again, I'm seeing so many comments coming here. People say they come and check on you every day just to see how you're doing. I got to ask, how's Phoenix? Can we see Phoenix as well? Yeah. Let's see her. You got to figure out. You have another question, too? You want to ask one? You want to come on and ask?

You want to come on and ask? Here she is, the sanus kitty. Oh, Phoenix. Oh, man. We need to make Phoenix shirts and just sell them online for you. That's what we have to do. Yeah, I'm working on it.

That's amazing, man. And also for people that are out, a lot of people are commenting how they've been waiting for you to go live. They've been waiting for you to share more. So maybe you got to go live on your own at some point once a day so people can be checked in on what you're up to. I've been trying on TikTok. It's just obviously I am in an ocean, so I do have to like, you know, do things.

And for those, again, for those that don't know who you are, I want people to click on below. I've got you pinned on there in the comments. If you click on Oliver's page, it's Sailing with Phoenix.

You also have a GoFundMe where people can donate to support you on this journey. I'm going to make a donation right after this. And I want people to go there. I want people to go there and donate and support you. You can give a dollar if you want to, $5. But if you've ever... For anyone watching this, and we're going to post this on YouTube in the audio later, but for anyone watching or listening, if you've ever had a dream that you've been afraid to take on, if you've ever...

had something like in your heart or your mind, your soul, you're like, I really want to do that. But you've been afraid or you've been scared or you're worried about what your family or friends are going to think about you. You have to watch Oliver. You have to watch this journey because again, I cannot reiterate this enough, Oliver, that you speak about having learning disabilities your entire life.

you know, working a job that wasn't enjoyable for you. Maybe he was paying the bills and it wasn't horrible, but it was not feeding your soul. And you took a risk. You sold everything. You took out all your investment money and you're on this journey for the last 12 days from Oregon to Hawaii, sailing by yourself with a cat. And, uh,

From the looks of it, you look happier, healthier, and freer than you've ever been in your life. Is that correct? 100%. Yeah. I literally feel healthier. It's crazy. You feel physically healthier.

It's not only do I feel healthier, but my lifestyle because of the financial side of things has been, I've been eating terribly. You know what I mean? But I feel so much. It's amazing. Like I feel so much better even then. Stopped working out because I had to use all that time to work on the boat and I feel better. And I guess if I wanted to, I did give, you know, if there's somebody that is looking to

to chase their dream. Like, something that I've realized is, like, I guess my recommendation would be to, like, find...

the point of no return and then cross that point. As soon as you cross that point, that's the hardest part. As soon as you cross that line, it's, it's, you're all in. You're, it's, you go for it. I mean, it's the fear, the fear will drive you. You're all in at that point. And, and I went all in with like, when I left Hawaii and I've, I appreciate the, I also do want to say thank you to everyone for like the,

The GoFundMe, I've never advertised or talked about the GoFundMe because I think it's weird. But I did just put it up and a bunch of people have obviously donated it. Well, I only put $10,000 in there because when I left Oregon, I was $10,000 in debt. I've gone all in on everything this entire time that I've just made.

you know and uh um now i'm not in debt and it's gone over that so i just wanted to say thank you to everybody for that

Maine, where life the way it should be transforms all who encounter its spectacular landscapes. Rugged coastlines, pine-scented trails, sandy beaches, sparkling lakes, and tranquil forests inspire you to reflect and make meaningful moments. They offer endless opportunities for adventure and exploration. Whether pedaling or paddling, hiking or biking, Maine has more than enough outdoor spaces to make the most of long summer days.

relish in exquisite flavors harvested from the ocean and the rich soils of orchards and fields. Maine's makers are rooted in its heritage while boldly branching into new ways of thinking, doing, and being. Connect with its people in warm and authentic towns, which beckon you to stroll art galleries and locally owned shops, where generations of artists, writers, entrepreneurs, and craftspeople see the world anew. It's tempting to do it all when you visit, but take a beat and

and a breath. Get a feel for the time and tempo of Maine. Simple pleasures, scenic adventures, where every route is the scenic one. Discover more at visitmaine.com.

At 42 years old, I'm pursuing my dream of returning to the USA National Handball Team to compete in the 2028 Olympics. I'm putting in hours of handball practice every week, so I've been extra intentional about how I'm taking care of my body on and off the court to support my energy and my recovery levels. And one thing I've been adding into my routine lately and loving is I Am 8's Daily Ultimate Essentials. I Am 8 is a daily all-in-one wellness drink that gives your body the support it needs

without juggling a bunch of different supplements. They use effective ingredients backed by real research. And it's not just hype. Clinical trials showed 95% of participants felt more energetic and 85% said their digestion improved with less bloating. Feel your best self every day with IM8. Go.

Go to im8health.com slash greatness and use code greatness for a free welcome kit, five free travel sachets, plus 10% off your order. That's I-M number eight, H-E-A-L-T-H dot

These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure, or prevent disease.

Yeah, again, for people that are, you know, just afraid to go for their dream. It's just inspiring to watch. And you talked about like, it's really that point of no return. This may be the wrong analogy, but it's, you know, the analogy of burning the boats when you get on new land and you kind of like burn your boats.

Wrong analogy here on a boat, right? Yeah. Where you can't go back. You can't go back to like safe land. You have to like take on the new journey, conquer the new journey. Yeah. Move forward, even though it's uncertain, it's unknown. Yeah. And, and you're doing that. I mean, you're sailing in the ocean. Yeah.

And believe me, because the whole time I had this incredible self-doubt, the whole time of going through the process, all of it is noise. It's all bullshit. Yeah, it's all noise. Can you quiet the critic or the doubt in your mind as a person that's, you know, struggled in school, didn't have the job that you wanted, you know, had back pain for the last 10 years? How did you overcome the self-critic and the doubt?

I just... There was no option. I didn't have an option but to succeed. Like, my hopes... Yeah, I just didn't have an option to succeed. I just kept going. I just... One thing that I would do a lot... So, I've tried to do this once before. A few... Two years ago. Like, right after the diagnosis. But what I did was I...

I thought about everything way too far ahead and I would, I discourage my, I would think about, you know, I like I'll fall and hit the boat wrong and I'll go paralyzed or I'll, I'm not going to know how to work on a boat. I'm not going to, I don't know anything about, I've done, I've become an electrician, a diesel mechanic. I've become a plumber. I've literally, I've, I've, I've adopted a sailor, all of these trades and, um, within a year, um,

But I would, my point is I would discourage myself. I discouraged myself. And then I couldn't even, I was like, you know, I couldn't even get past the bridge of what boat to buy. I guess the solution to that was literally what is the problem that is directly in front of you and solve that problem. So if you don't have a boat,

Don't think about anything. Get the boat. You don't have a boat. That's your problem. Don't think five years in ahead of like, when I get the boat and what if I fall in the middle of the ocean and what happens then? How do I save my life? Just one step at a time. Yeah. And so that's what I...

I did. I like whatever the problem was in front of me. I did that. So I got the boat. Okay. Well, I don't know how to sail. All right. Well, start sailing. And then it started sailing. Okay. Well, I don't have any of the right equipment on the boat to cross the ocean. All right. Well, it's still the right equipment, you know?

I don't have any money. All right. So social media was like I've always planned. Social media was my this. This all only will all work if social media came together because that's that could fund my expedition around the world. And so my plan is always that social media was going to work. It's always a plan. And I was going to keep going until it worked. I've posted every single day. Terrible posts.

Good posts. I've done it every single day for a year. And with the intention of going forever. You know what I mean? And not stopping. Like, just going forever. And it worked. It worked. Did someone give you the blueprint of like, okay, if you're going to do this, you've got to get the boat. And you have to go on Instagram or TikTok every day and document this. Or is this just me or not?

This is all in my mind. This is all in my mind. But you weren't on social media before this, were you? No. Before a year ago, no. So you were just like, I'm going to figure out social media. You weren't on there. Maybe you were on there. If

If you go to the bottom of my TikTok, you'll see it's a disaster. It's like as cringy as it gets. It's terrible. But I was like, and it's only people that are seeing it are people that I know. You know what I mean? So everybody thought I was unhinged. Everyone. People were calling me and being like, dude, are you okay? Like, dude, I'm just trying to figure this out. You know what I mean? Like,

And everyone thought I was insane. Everybody. And it's so weird now because they're all now messaging me and going, I always believed in you. Then you didn't. You had this the whole time. I believed in you. Yeah.

Wow, man. Yeah. And I just kept going through all that. And, you know, there's times where I thought I was insane myself. And I just kept going. What do you want people to know about the way you think, the way you feel, the way you act that maybe they don't know about yet? What's...

if you could share a little bit more about how you think about this process or what's going through your head. Again, it's probably lonely out there. Even though you have tons of comments and people loving on you on social media, you're alone in the middle of the ocean with a cat. Do you feel lonely? Or do you feel like, how do you put yourself to sleep calmly and feel safe? All that stuff. I knew I was going to be fine with the isolation on this passage because I'm not kidding. The past five months, so I spent...

I learned how to sail for the first like six months. And that's when I taught myself how to sail. And then the last five months, I didn't sail at all. And I spent every single day, 10 hours a day working on the boat in complete isolation. I didn't speak to another soul ever. Like I literally just, uh,

The only people I spoke to were the people at the Marine store, really. And that was it. And so I've been completely isolated for, by the time I get to Hawaii, it'll be like six months. Other than I did a send-off thing right before I left. So I did have some people come to the boat. But aside from that, I've been in complete isolation. And I'm comfortable with my own thoughts alone. You know what I mean? So I'm fine. And I do well.

I'm not a it's it's weird because like I'm on social media, but I'm not I'm a keep to myself person I'm I am awkward and I'm if somebody you know come say says that says hello to me in person and stuff I'm totally weird. So I Don't remember what the question was, but no, it's good man It's just more like how do you think about it? If you're being if you're alone in the ocean for all this time like is your mind? Okay, do you feel like safe emotionally?

Yeah, yeah, yeah. I feel good. I trust myself and I trust the work I've put into the boat and I trust my ability to solve pretty much every problem that can come up. Because when crossing an ocean, it's not like...

what will break or it's not like if something will break, it's what will break and being able to, being able to have the resources on board and the, the kind of the skills to, to, to solve the issue. Like I, I, the worst thing, like the worst thing that could break is literally like the rudder is one of the worst things. And it broke.

And on day like six or something, at the worst time, it was at the height of the storm that I was in. So the waves, I was like looking up at these waves. Come on. And then, yeah, and you're not supposed to, the boat isn't, the camera doesn't do waves any justice. It's the sailors, it's the sailors' worst curse is that the camera doesn't do waves any justice. And so, yeah, my rudder broke and it locked in the starboard position.

And it... You're not supposed to go to the waves on the side. And it positioned the boat to the waves on the side. So I was literally like...

It was the worst, absolute worst case scenario as far as when that was going to happen. And so the boat literally would go from this all the way to this within like three seconds. And it was just going like this. Wow. Yes, airboat's cap science. It was like that for like three or four hours while I was trying to solve it. And I jumped into the engine room.

And I'm in the engine room, and I see the cable came off the quadrant. And I'm literally getting thrown from one side to the other while I'm trying to fix this cable on the quadrant and not let the – because as soon as you put the cable back on it, it'll – you know, the rudder will, like, slam back. And, you know, I was trying not to, like, lose my fingers, so I got a screwdriver down in the back, and I tried to just pry the cable back around the quadrant. It was crazy, man.

That was the scariest moment of my entire life. Hands down. But yeah. So what about Phoenix during that time? Is she like... At that point, she was already well-adjusted to the boat. So I'm sure... Did she get merchant sickness too or no? She...

Only once when I first took the boat out like a year ago. She's a full-blown boat cat now. It's crazy. She gets around better than I do. And she walks around like a gimbal. It's like she anticipates the waves so well. She's like a gimbal cat. That's amazing. I mean, do you have her harnessed up also if she's out on the deck or when she falls off? I'm the kind of guy that would...

absolutely walk my cat so i spent like like she's seven years old now and she was a feral cat when i got her and um she uh i spent like three years trying to walk my cat it's impossible it is an impossible task so i can't get a harness on her but if she knew i let her out on the deck you do no i don't i don't let her out there unless it's like really calm and i'm and she doesn't leave the cockpit area and i'm she's my my attention you know what i mean

so yeah that's the only time when i'm on shore i'll yeah sure sure sure dude this is crazy man

I got a few final questions, a few minutes left for you, if that's okay. A lot of people are asking, you know, if people go to your Instagram right now, do you have the location where you are, like, live on? Yeah, it's on my highlight. Okay. So if you go, if you click on my highlight. And, man, is this Starlink that you're using on the boat? Yes, we're having it right now.

There's like no lag. It's yeah, I didn't know if it was gonna work So like I had to like literally because I did have some followers had like 60,000 followers before I left and so I had to Like literally just tell him like hey look, I'm yeah, I know how deep is what works Yeah, I don't know if it's gonna work and I'll see you guys probably in 30 days, but it's dude. It's I

It works really well this whole time. And what's your day look like then? Are you sleeping a lot or is it like a couple hours of sleep at a time or do you try to sleep six to eight hours at once? One, like the weather. Like there's no sleep schedule really. It's just you sleep when you can. Like if I, after this call, if I get a,

a wave of tiredness, I'm going to take advantage of that. Cause right now the boat's balanced, the boat's good. So I'm going to take advantage of that. I'm going to go to sleep for a couple hours. And then, um, so yeah, and it depends on the weather. So like last night I stayed up till like 3am because through the night, the winds got all weird and shifty. So I had to like, you know, be there to adjust the boat. Um, so yeah, um,

But I get plenty of sleep. Like the greatest, I once fell through a tree, a full tree coming through my apartment. It came through the roof of my apartment. I slept through the whole thing.

And I don't know if you ever heard a tree fall. Cause the next, the following day I was outside and a tree fell and it sounds like a fricking grenade goes off. Like it's insane. And so I could sleep through anything, which is like a blessing and a curse. Cause if something happens, I'll probably sleep through it. But I think the thing that, that,

that where sailors meet their demise is because of sleep deprivation we'll not have that problem your problem will be you won't wake up yeah crash yeah yeah um all right you gotta you gotta share one more time you gotta show the cat phoenix the cat one more time everyone's everyone who came on late is asking where's phoenix yeah yeah she is such a sweetie

Does she sleep next to you also or no? Yeah, she sleeps next to me. And yeah, we're, we, she like, she sleeps right here and I sleep right here. Oh man. You're living the dream, man. Yeah. All right. Again, I want to, I want to, I know you got a lot of activities you got to do on the boat, but I'm glad we got connected and I want to, I wanted to share your message with my audience and I'm going to make this out there on my podcast, but I wanted to just,

One more time, say that it's really inspiring what you're doing. And again, for those that are just tuning in, Oliver's from Oregon. He had a diagnosis about his back that was not good from the doctors and wasn't living the life that he envisioned. You weren't living that beautiful, healthy, rich life internally and externally.

And he decided to quit his job because he wasn't fulfilled at the job he was at and really pursued the dream of traveling around the world on a sailboat and experiencing life to the fullest based on your dreams. Maybe it's not, I wouldn't want to do that, but your dream was to do that. And you sold everything. You liquidated your funds, all your savings to buy a boat,

And for a year, you were taught yourself how to sail a boat and you went. You're now 12 days in the middle of the ocean on your way to Hawaii. And is

It's an amazing journey, man. I'm so happy that you're documenting this. I'm so glad that you're taking a leap and you have the courage to actually do it. Because again, 99% of people won't go after the big scary dream that they have because they're too afraid to fail or what if, or what if I go broke or what if I don't have any money or whatever, everyone laughs at me. And so what, you know, if they do, okay, well, at least you won't regret it.

This episode is brought to you by Square. Your favorite neighborhood spots run on Square. And did you know Square can help you turn your small business idea into a big success? Yes, even that wild idea for Squirrel Fuel, your squirrel-themed coffee bar.

Square is so much more than just a point of sale for local businesses. What started as a little white card reader is now powering things behind the scenes, helping you manage finances, schedule staff, and cover cash flow gaps. With Square, you could keep things at squirrel fuel running like clockwork, no caffeine needed, well, except for your baristas, and good luck finding one's

willing to wear a squirrel costume. Square gets it. Local businesses can be big business, yet with growth comes complexity. But whether you're expanding to new locations or building your loyal following, Square meets you at every opportunity. Square helps you handle today and dream bigger for tomorrow. Go to square.com slash go slash greatness to learn more. That's S-Q-U-A-R-E dot com slash G-O slash G-R-E-A-T-N-E-S-S.

Square. Meet you there. You spend a third of your life in bed. Shouldn't you get a pillow that's customized to your sleep? Upgrade your pillows with Coop Sleep Guaranty.

They design adjustable sleep products that accommodate to your unique size, shape, and sleep position, so you can rest comfortably and wake up feeling your best every day. And whether you're a side sleeper, a back sleeper, or even a starfish sleeper, Coop makes it easy to find the perfect pillow for you with their sleep quiz. They even offer free pillow consultations with their sleep expert so you can optimize your sleep. Martha and I just took Coop's sleep quiz, and we learned that the cool pillow

Plus pillow is the best choice for us. I hate feeling like I'm overheated while I sleep. And this specific pillow is made with gel infused memory foam, which is designed for 50% more breathability. So I'm super excited to try these pillows out. Visit coop sleep goods.com slash greatness to get 20% off your first order. That's C O O P sleep goods.com slash greatness.

And you're happier and healthier than you've ever been in your life right now. Yeah. Yeah. And that's amazing. I feel like all those things are guaranteed is, is people laughing at you going broke and all that stuff. Cause all that happened. I, yeah, but yeah,

It works. What's one, what's, I mean, people are gonna be watching your journey every single day. And I can't wait to, and I can't wait to celebrate you and, you know, send you a FaceTime or a text when you land in Hawaii. But what's one final message for this conversation that you'd love to send to people if they're struggling in a relationship where they feel like they know they've got to get out of, if they've got this

artistic dream or music dream or something they want to pursue, but they've been too afraid of what people are going to think about them. What's one final piece of advice or wisdom you would share based on your journey? You know, you know, the answers, you know, the answers to clear, you know, the answers. And if, if, if you're, if you're questioning the relationship or the job and, and you've been questioning the relationship, the job, that is the answer. Like you've got the answers. It's that simple. You've got the answers for the, for, for a better life.

You just got to do it. And that will solve that problem. You know? So, like, I had, you know, I don't know. You have the answers. I guess the hard thing for me, because at the beginning of the spine thing, at the very beginning, and before that, too, I didn't know, like, I didn't have, like, it was really hard for me to find, like, a purpose.

You know what I mean? Because I think a lot of people are a lot like, they think that's really cool and stuff, what I'm doing and all that, but they don't know how to find their purpose or they don't know what their thing is. They want to. They want to do all the things, but they don't know what it is, what their purpose is. And that, I think a lot of people get trapped in that and it's hard to find your purpose, but in hindsight, it's easy. You know what I mean? Like, it's like, what's the ridiculous thing you want to do? Like,

sailing around the world on a boat with my cat is ridiculous. You know what I mean? It's ridiculous, but it's, that's like a ridiculous dream that I had. And so why don't I just make that my purpose? It's, it is simple. You know what I mean? Like if, what is it you want to do? Do that. And, uh, just, just go for it. So, um,

I love that, man. It is Mother's Day today while we're recording this live. I'm curious, what's your message to your mom and the greatest lesson your mom's taught you? My mom was my biggest fan. She's my biggest fan. She loves me.

through and through and she she's from the beginning she's liked every single video she's she even she my mom doesn't have like a lot of money at all and she like she goes she goes and like go fund me and donate if you'll donate like 25 bucks 50 bucks and i literally have to be like mom stop stop doing that and uh um yeah she's the greatest she just is the greatest and uh yeah um

I can't remember the rest of the question, but yeah. Your mom, though, that's great that she supported you on this whole journey, doing some crazy hearing. That's amazing. Final question for you, Oliver, because I want you to go call your mom, and I know you've got a lot to do on the boat. I asked this at the end of all my interviews. What is your definition of greatness? My definition of greatness is just to be...

just being humble, like a humble person, you know, regardless of what they're, if they're worth millions of dollars or they're living a, a life well below their means. But like, I just think somebody who's just kind and like humble and like, just, just overall, you know, the people that you meet and they're just like, just really, you could just tell they're really good people. Like that's, that's greatness. Um,

Oliver, you're a really good person. We appreciate you. A lot of your fans and followers here are loving the journey and they're grateful that you're going live. So I want to acknowledge you for taking the lead, man. It's a scary dream that you had and you're doing it. And you're showing the world that people's dreams matter because they matter. So we're grateful for you, Oliver. We appreciate you. Been cheering you on. If you need any support, feel free to message me anytime. And I can't wait to continue to watch the journey, man. Yeah, appreciate it.

Thank you very much for having me. That's cool. Well, stay in touch, man. And I can't wait to watch the next content. We'll see you, brother. All right, man. Thank you. I have a brand new book called Make Money Easy. And if you were looking to...

create more financial freedom in your life, you want abundance in your life, and you want to stop making money hard in your life, but you want to make it easier, you want to make it flow, you want to feel abundant, then make sure to go to makemoneyeasybook.com right now and get yourself a copy. I really think this is going to help you transform your relationship with money this moment moving forward.

I hope you enjoyed today's episode and it inspired you on your journey towards greatness. Make sure to check out the show notes in the description for a full rundown of today's episode with all the important links. And if you want weekly exclusive bonus episodes with me personally, as well as

ad free listening, then make sure to subscribe to our greatness plus channel exclusively on Apple podcasts. Share this with a friend on social media and leave us a review on Apple podcasts as well. Let me know what you enjoyed about this episode in that review. I really love hearing feedback from you and it helps us figure out how we can support and serve you moving forward. And I want to remind you if no one has told you lately that you are loved, you are worthy, and you matter.

And now it's time to go out there and do something great.

I have a podcast that's called Literally with Rob Lowe. And basically, it's conversations I've had that really make you feel like you're pulling up a chair at an intimate dinner between myself and people that I admire, like Aaron Sorkin or Tiffany Haddish, Demi Moore, Chris Pratt, Michael J. Fox. There are new episodes out every Thursday. So subscribe, please, and listen wherever

wherever you get your podcasts. At Capella University, you can learn at your own pace with our FlexPath learning format.

Take one or two courses at a time and complete as many as you can in a 12-week billing session. With FlexPath, you can finish the bachelor's degree you started in 19 months and under $19,000. A different future is closer than you think with Capella University. Learn more at capella.edu. Fastest 25% of students. Cost varies by pace, transfer credits, and other factors. Fees apply.