
A 29-year-old man with a spine condition worse than a 120-year-old's quit his corporate job and is now sailing solo across the Pacific Ocean, inspiring millions with his authentic journey of courage over comfort. This conversation reveals how facing mortality can become your greatest teacher and why the scariest dreams often lead to the most extraordinary life.
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Oliver Widger
I went to the doctor and they took some X rays and the doctors, she was like, your spine is like somebody who's over 120 years old. After the diagnosis, I spiraled completely. And then 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 going to 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 boat, 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, that are 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 and I would spin the globe and then I would stop the globe with my finger and I would buy a plane, take a one way plane ticket and go there. If there's somebody that is looking to chase their. Their dream, find the point of no return. And.
Unknown Host
So I'm so excited, man, because I've been watching your journey over the last few days. My friend Tim who's 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, 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.
Oliver Widger
Yeah, my name is Oliver Widger. And yeah.
Unknown Host
And so you have this video of you working a corporate job and sexually hating your life. And at one point you decide because you have test results at the hospital, right. That.
Oliver Widger
Yeah.
Unknown Host
That something is. Something's off in your body. Is that correct?
Oliver Widger
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, you know, put it off and then it just got started to get really, really bad. And so, yeah, I went to finally, I went to, like, I almost got. Because I can't go to a chiropractor. And I started out, go to a chiropractor. And like, hindsight is they could have like, immediately paralyzed me. And I just got lucky. That didn't happen. And none of that worked. And so I finally. I finally like, called my doc or I finally, like, 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, yeah, I went to the doctor and they took some X rays and then I, you know, they didn't think anything of it. You know, he's. I don't know. But. And then I. I was at work like the next day, and they called me when I was at. At work and the, the doctors, 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, I go in and she, like, she was like, freaking out. Like, she didn't handle it very well because, like, she. She was a. She was orthopedic specialist, so she wasn't like a neurologist, but yeah, she, like, 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 and that's why I am here. And she was like, your spine is like, I've never. 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 I. And then I went through this, Faye. 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. Went through. I had to see like, four neurologists.
Unknown Host
Wow.
Oliver Widger
And all of it was really, really bad. And. Yeah, so I. I basically just stopped going to the doctor and. And then I went through this just like this, like, I don't know, like a crisis of some sorts where, you know, where my mortality was kind of like hitting me in the face. And I was realizing that I'm spending my, like, because 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. But I, you know, physically I can. I, you know, I've got all my legs. Yeah. Yeah. And wasting it at work 2929. Yeah.
Unknown Host
So you're getting. You're getting all these doctors saying that you got a spine of 120 year old.
Oliver Widger
Yeah.
Unknown Host
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.
Oliver Widger
Yeah, it's just like. Like I jumped into it and I didn't have any. Like, I 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, you know, there's a lot of like, potential for money within the job. So I was like, all right, this is it. This is. I'm going to be able to do the. Buy the house and have the, you know, the fence and kids and whatever. And. And then that immediately after the diagnosis, I just started to question all of that and I was like, I don't really want to do any of that. Like, this. This actually sucks. And. 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 too, of like just like partying on the weekends to try and like, feel alive and like, just party, doing all the bad things. And this is after you knew about.
Unknown Host
This is after you knew about the condition.
Oliver Widger
Yeah, yeah, yeah. And then of course, that just dug the mental hole deeper, you know, living like that. And. And then, yeah, it just. I spiraled completely. And then I finally one day I was like. Like, I had. I. So that video that I posted that you probably saw, where I'm in that shirt. You're like, my work shirt.
Unknown Host
You're like, I did it well before.
Oliver Widger
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 2 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 have never taken it down. But I said, my brother, I decided, I found a purpose. I decided I wanted to sail around the world. And my brother convinced me to start documenting it. And so that was the very first video I've ever taken ever of myself. And I. 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'm I, I. It was on a TikTok, and I put it in as a draft because I thought I could put it in as a draft. And you posted it on accident. 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, like, the technicians comes up to me. He's like, hey, man, what? Are you gonna buy that boat? And I was like, what in the world are you talking about? He's like, the boat, man. And then I made the realization. And so how I left that video. That video is everything. That video is absolutely. Because who knows if I would have had the courage to leave. Who knows to leave without that video because. Because that video was 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.
Unknown Host
When did that video first get leaked to everyone? In your context, was this a year ago? Two years ago? When was it?
Oliver Widger
This was a year ago, the day I quit.
Unknown Host
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. 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?
Oliver Widger
Yeah, pretty much. Yeah.
Unknown Host
Then you feel you 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.
Oliver Widger
Yeah, I don't know. I don't think so. I mean, who knows? I knew I was gonna 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.
Unknown Host
That's crazy.
Oliver Widger
That video is everything. That video is everything. It's everything. And it's also because My brother. My brother told me to start recording myself. And.
Unknown Host
Wow, man. And so you went. And so you went from Oregon, going on a sailboat that you've never been in the ocean before, only in a river.
Oliver Widger
Yeah.
Unknown Host
And you're going on a sailboat from Oregon to Hawaii, and you're 12 days in, is that right?
Oliver Widger
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.
Unknown Host
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. My favorite part is the shirt of Phoenix. You know, whenever you wear the shirt with, it's the cat. And I just think what you're doing. 99.99% of the world will never do what you're doing because most people lack the courage. It's so safe, so comfortable, even if they're miserable. They'd rather stay safe and miserable than actually go for it.
Oliver Widger
Yeah, I figured I was. And you are going for it. When I. When I quit my job abruptly like that, I had, like, I don't know, $10,000 in debt or something, and with no plan, with a $2,600 rent due, and I just 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 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 gonna buy or before or how I was gonna buy a boat. And I. 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 I could have. That could have gone so wrong as well, and it didn't. And. Yeah, and then I just dived into it with knowing nothing.
Unknown Host
So how did you. I mean, how did you learn how to sail a boat, though? Like, how did you know which boat to buy? How to sail? You've never sailed before.
Oliver Widger
Yeah, everything was like, basically YouTube, and I just, like, I just, like, as far as learning how to sail, so I, I, I got the boat. I literally want. I didn't even watch that many, like, YouTube videos. I just, I bought the boat and I just, I took it out. And I made incredible mistakes. I'm lucky to still have the boat. Like, it's. So many things have, like, worked out where. Where it's just. There's just, like, really high risk and I just. It paid off. It worked out.
Unknown Host
Wait a minute.
Oliver Widger
And I just went through.
Unknown Host
Let me ask you, Oliver, you. 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.
Oliver Widger
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 shake through side. And I replaced also all of the, like, rubber components. And then, yeah, I took it out.
Unknown Host
I love this for you. I don't know why. Because I'm. 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 in, like, 10 days or something. How does it. 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 for you?
Oliver Widger
I haven't really even fully processed it. Like, it's insane. Like, it's. It is. It's. Dude, like, the. The experience of. I feel like the experience of, like. Because I went viral on the day that I left. Wow. And I'm also crossing an ocean. You know what I mean? So the two. Two insane things that I'm like, that are, like, you know, competing with. I would literally fight for my life the other day while I'm going viral. Like, it's. It was. It's just been so weird, and there's not a lot of time to, like. Because I'm still. I'm, 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.
Unknown Host
Staying alive. Yeah.
Oliver Widger
Yeah, yeah.
Unknown Host
Not a small thing.
Oliver Widger
Yeah. And it's been so. It's been so cool, too, like, the. I. That. 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.
Unknown Host
It is, man. I'm reading. I'm reading some of the comments here where one mom said, my son and all of his friends are glued to their phone waiting for your Next video. And they're all inspired. So again, 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.
Oliver Widger
You just gotta jump. Like, that is the hardest part.
Unknown Host
How did you overcome the fear of being worried about what everyone thinks about you? By doing some crazy idea.
Oliver Widger
That was the biggest thing that held me back because, like, 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. 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 could. I absolutely became, like, completely content with that idea. And once I became content with that idea, I was freedom. You know what I mean? I had freedom. And that's what it came down to, because that was where my fears. It's like, I. I'm gonna be poor. No one's gonna. You know, I'm. How. Who's gonna want to be with, like, a poor. I'm gonna be single forever. Like, all that stuff was the things running through my head. You know, who's gonna want to date a guy on a. A bum on a boat and all that stuff, you know, I. You, and you just. All of it is nonsense. All of it is noise, and you just gotta. I don't know, you just gotta go for it, I guess.
Unknown Host
Oliver, what about your parents? Are your parents still around?
Oliver Widger
Do you have siblings? Yeah, most of my mom and brother live in the uk and my. Yeah, my dad is. Is in the US and they're. They're proud.
Unknown Host
What did they say originally? When you're like, I'm gonna quit my job. I'm gonna liquidate all my assets. I'm gonna essentially buy a boat and do something I've never done to go around the world by. What do they say?
Oliver Widger
I think they. They saw how miserable I was, and I've been, you know, it was like three solid years of being, like, at the lowest low, and they could see it. So I think they. They were probably like, you know, they were probably like, I mean, anything better, you know, and so. But they're. They've always been really. My brother's been, like, incredibly supportive. Like, I remember, like, being at work, and I'm like, dude, everybody knows every. 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, I'm like, just go.
Unknown Host
That. Who cares?
Oliver Widger
Yeah, yeah, yeah.
Unknown Host
Dude, this is incredible, man. What is the. You wrote about 15, 20 days away from Hawaii. Do you know which island you're turning? The Random Club, 12 days.
Oliver Widger
Oahu.
Unknown Host
You go to Oahu?
Oliver Widger
Yeah.
Unknown Host
Do you know. Have you been to Hawaii before?
Oliver Widger
I've been to Maui before, yeah. I've got. One of my other brothers is on Maui.
Unknown Host
Actually. Gonna land in Maui.
Oliver Widger
No, I. Originally, I wanted to go to Maui because he's there, but I decided to go to Oahu because in Maui, I would need a car to, like, drive around. And so Oahu, there's a Marine story there, too. Like a West Marine that's there within walking distance. And everything's within walking distance, so it just made more, like, legislative sense.
Unknown Host
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 sail, a boat alone with your cat? What's the biggest lesson you've learned about you?
Oliver Widger
I. 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 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 I. I just learned that I can. 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.
Unknown Host
What'S your greatest fear?
Oliver Widger
Falling off the boat.
Unknown Host
You jumped off the boat already, right?
Oliver Widger
Yeah, but it was completely becalmed.
Unknown Host
Yeah, yeah, yeah. Falling off the boat. But you got a life jacket. Are you. Are you tying yourself up? Are you taking. Like.
Oliver Widger
There's no life jacket just. Cause if you fall in a life jacket just prolongs the inevitable. So, you know. But as you wear 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.
Unknown Host
Wouldn't it help you swim back to your boat or something?
Oliver Widger
No, the boat sails itself. Like, I'm going. It's going, like, right now. Going like six knots.
Unknown Host
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 to. You fell off.
Oliver Widger
Yeah. You did not get back on.
Unknown Host
Oh, snap.
Oliver Widger
Yeah, you better remember that. Harness yourself.
Unknown Host
Rope yourself.
Oliver Widger
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. I fall off.
Unknown Host
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, I'm.
Oliver Widger
I'm not. Like, I can't stress that I am as below I'll do. I was in. I wasn't. I haven't told anyone this, but I was in special ed from first grade to a 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. I think, like, this is. This is how I organize my notes. You know what I mean? Piece of paper. I can't. I can't even read it. So I don't even write. Yeah. So, like, I can't stress that enough. Is like, all. The only thing I can do. 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, and that's the only thing, if I lean into that I can do. I could do anything. So that's what it's come down to. And that's what I've done.
Unknown Host
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?
Oliver Widger
When do I feel the most loved? Right now I feel pretty loved, but I don't know. It's. When do I feel the most loved? I don't know. Or like when I, when I, when I talk to like my mom and brother, I guess. I don't know because they, you know, they, they love me unconditionally. They've loved me. They, you know, they love and my dad, they love me like through and through. It doesn't really matter what frame of mind, what, where I'm at in life. They've just, you know, what love me.
Unknown Host
What is it about your relationship with your family that you appreciate so much?
Oliver Widger
They just, you know, they just, they're. They're. My parents are separated and don't talk. So it's like a weird different dynamic. But like they just, they, you know, they've seen me go through some weird stuff, you know what I mean? And they've never, they've just, you know, they've just. The love is there always. You know what I mean? If that makes sense. They've always unconditionally love me. It doesn't matter where what's, what's. Where I am in life. They just have.
Unknown Host
That's 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?
Oliver Widger
Yeah.
Unknown Host
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?
Oliver Widger
Literally, 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, take 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.
Unknown Host
I'm curious 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?
Oliver Widger
Oh yeah. Sweet. Yeah.
Unknown Host
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?
Oliver Widger
I don't know. I haven't been able to process it. Like it's. If it feels unreal, it feels not real. Like it's, it's, it doesn't. I'm literally sitting here watching these absolutely absurd sunsets with dolphins jumping and then, you know, with these insane sunsets and then, and then I'm also viral at the same time and inspiring all these people. This is 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 how real it really is. And it's, I mean it feels unreal. It feels, it's absolutely insane. Like, it's just that it, that it, it worked. All of it. Because social media, I, I've been, I didn't know anything about social media or how to edit videos, anything. I spent, I would spend like six hours a day editing six, seven hours a day editing videos and figure making the craziest videos and just figuring it out. And, 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 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, where I left and I went viral. You know, I don't know. It's crazy.
Unknown Host
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 were you just.
Oliver Widger
Yeah, it's all. All of it is all documented.
Unknown Host
Were you posting these on my TikTok or something? Or where were you posting these other videos last year?
Oliver Widger
So most of the videos are on TikTok. 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 Tik Tok, you'll see a crazy.
Unknown Host
Okay, I got you. Now I gotta 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 gotta ask, how's Phoenix? Can we see Phoenix as well? Yeah, let's. Let's see her. You gotta. You gotta figure out you have another question too. You want to ask one? You want to. Come on ask. You want to come on and ask?
Oliver Widger
Here she is, famous kitties.
Unknown Host
Oh, Phoenix. Oh, man. We need to make Phoenix shirts. Just sell them online for you, you know, that's what we have to do.
Oliver Widger
Yeah, I'm working on it.
Unknown Host
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.
Oliver Widger
I've been trying on Tick Tock. It's just obviously I'm. I am in. In an ocean, so I do have to like, you know, do you think.
Unknown Host
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. 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 and the audio later, but for anyone watching or listening, if you've ever had a dream that you've been afraid to take off, if you've ever had something, like, in your heart or your mind or your soul that 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, working a job that wasn't enjoyable for you. Maybe it 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 from the looks of it, you look happier, healthier, and freer than you've ever been in your life. Is that correct?
Oliver Widger
100. Yeah. I, like, literally feel healthier. Like, it's crazy. You feel physically, and it's not only 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. Their dream, like, something that I've. I realized is like, I. 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, it. 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, I. 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 and. But I did just put it up and I, you know, a bunch of people have obviously donated it and it's. Well, so I've only put $10,000 in there because that's. I. But when I left Oregon, I was $10,000 in debt. I've gone all in on everything this entire time that I've just been, you know, and now I'm not in debt and it's gone over that. So I just wanted to say thank you to everybody for that.
Unknown Host
Yeah, man. 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. If you're on a boat.
Oliver Widger
Yeah.
Unknown Host
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.
Oliver Widger
Yeah.
Unknown Host
Move forward even though it's uncertain, it's unknown.
Oliver Widger
Yeah.
Unknown Host
And. And you're doing that and you're sailing in the ocean.
Oliver Widger
Yeah. And believe you can do. 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 so bullshit. Yeah. It's all nice.
Unknown Host
You quiet the critic or the doubt in your mind as, as a person. That's the, 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?
Oliver Widger
I just, There was no option. Like I didn't have an option but to, to succeed. Like my, My hopes. Yeah. Just didn't have an option to succeed. I, I just kept going. I just. It one thing that I would do a lot. So I've tried to do this once before. Four, 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 discouraged my. I would think about, you know, 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 within a Year. But I, 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, the solution to that was literally what is the. What is the problem that is directly in front of you and solve that problem. So if you're, if you're, 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.
Unknown Host
Don't think five years and 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.
Oliver Widger
Yeah. And so that's what 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, install the right equipment. You know, I, you know, I don't have any money. All right, so social media was like, I've always planned on. Social media was my. This. I did my. 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 was 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. But I've done it every single day for a year. And, and I, with, with the intention of going forever, you know what I mean? And not stopping. Like, I just going forever. And, and it worked. It worked.
Unknown Host
Did someone give you the, the blueprint of, like, okay, if you're going to do this, you got to get the boat and, and you have to go on Instagram or TikTok every day and document this or this. Just not.
Oliver Widger
This is all in my mind. This is all in my mind.
Unknown Host
But you weren't really. You weren't on social media before this, were you?
Oliver Widger
No, before a year ago now.
Unknown Host
So you're just like, yeah, I'm gonna figure out social media weren't on there.
Oliver Widger
Maybe you're on there. If you, if you go to the bottom of my TikTok, you'll see it's. It's a disaster. It's like as cringy as it gets. It's terrible. But I, But I Was like. And it's only. The only people that are seeing it are people that I know. You know what I mean? So everybody thought I was unhinged. Everyone, every people were calling me be 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. Yeah, then you didn't.
Unknown Host
You had this the whole time. I believed in you. Yeah.
Oliver Widger
Yeah.
Unknown Host
Wow. Man.
Oliver Widger
Yeah. And I just, 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.
Unknown Host
And 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.
Oliver Widger
I knew I was going to be fine with the isolation on this passage because I'm not kidding, the past five months I learned to have a sale for the first 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. 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, 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. I'm not. I'm a keep to myself person. I'm. I am awkward and I'm. If somebody, you know, comes, say, says, 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.
Unknown Host
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?
Oliver Widger
Yeah, yeah, yeah. I feel good. I feel I trust myself and I trust my, 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. It's 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 wave. I was like, looking up at these waves come on. And then you're. 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 sailor's worst curse is that the camera doesn't do waves any justice. And so, yeah, my rudder broke and locked in the starboard position. And it. Which you're not supposed to go at as to the waves on the side. On the side. And it positioned the boat to the waves on the side. So I was literally like, the way. It was the worst, absolute worst case scenario as far as when that was going to happen. And then so the boat, like, literally was. Would go from this all the way to this within like, three seconds. And it was just going like this, like, peril. And because that.
Unknown Host
Wow.
Oliver Widger
Yes. Airboat's cap science. I. It was like that for like three or four hours while I was trying to solve it. And I, 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 in 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 to not to, like, lose my fingers. So I got a screwdriver down in the back and I tried to pry the, the cable back around the quadrant. It was crazy, man. That was the scariest moment of my entire life, hands down. Wow. But yeah.
Unknown Host
So what about Phoenix during that time? Is she like.
Oliver Widger
She was at that point, she was already, like, well adjusted to the boat, so. I'm sure.
Unknown Host
She get motion sickness too, or. No, she.
Oliver Widger
Only once when I first took the boat out, like a year ago. Cat now. It's crazy, like, watching her, like, she walks. She gets around better than I do, and she, like, walks around like a. Like a gimbal. Like, she. It's like she anticipates the wave so well. She's like a gimbal cat. That's amazing. Yeah. And it's what I mean.
Unknown Host
Do you have her harness up also if she's not on the deck, or would she follow?
Oliver Widger
I'm the kind of guy that would absolutely walk my cat. So I spent, like, when I. She's seven years old now and she was a feral cat when I got her, and she. I spent like three years trying to walk like cat. It's just impossible. It is an impossible task. So I can't get a harness on her.
Unknown Host
But is she. Not let her out on the deck? You do?
Oliver Widger
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. Oh, yeah, she can go.
Unknown Host
Sure, sure, sure. Dude, this is crazy, man. I got a few. I got a few final questions. Few minutes left for you, if that's okay. A lot of people are asking, you know, if. If people go to your Instagram right now, do you have the location where you are, like, live on. Yeah, on the.
Oliver Widger
That's on my highlight.
Unknown Host
Okay.
Oliver Widger
So if you go. If you click on my highlight.
Unknown Host
See that? And you. And. And, man, is this starlink that you're using on the boat?
Oliver Widger
Yes. We're having really well.
Unknown Host
There's, like, no lag. It's.
Oliver Widger
Yeah, I didn't know if it was gonna work, so, like, I had to, like, literally, because I did have some followers. I had like 60, 000 followers before I left. And so I had to, like, literally just tell them, like, hey, look, I'm, you know, work. 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. It's worked really well this whole time.
Unknown Host
And what's your. What's your, what's your day look like then? Are you sleeping a lot or is it like couple hours of sleep at a time or do you try to sleep six to eight hours?
Oliver Widger
Depends on 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 because 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. 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. So. Yeah, but I, I get plenty of sleep. One of 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 because the next, the following day I was outside and a tree fell and it sounds like a freaking grenade goes off. Like it's insane. And so I could sleep through anything, which is like a blessing and a curse because 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. Of sleep deprivation, will not have that problem.
Unknown Host
Your problem will be you won't wake up. Crash. Yeah, yeah, yeah, 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?
Oliver Widger
Yeah, yeah.
Unknown Host
Here she is a. Such a sweetie. Does she sleep next to you also or no?
Oliver Widger
Yeah, she sleeps next to me. And yeah, we are. We. She like, she sleeps right here. I sleep right here.
Unknown Host
Oh, man, you're living the dream, man.
Oliver Widger
Yeah, yeah.
Unknown Host
All around 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 put 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 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 it's an amazing journey, man. I'm so happy that you're documenting this. I'm so glad that you're taking the leap and you had 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 what if I want to. Laughs at me. And so what, you know, if they do, okay, well, at least you won't regret it. And you're happier and healthier than you've ever been in your life right now.
Oliver Widger
Yeah. Yeah.
Unknown Host
And that's amazing.
Oliver Widger
I feel like all those things are a guarantee. Is. Is people laughing at you going broke and all that stuff, because all that happened. Yeah, but it works.
Unknown Host
What's one. What's. I mean, people are going to 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?
Oliver Widger
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 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. 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, hard thing for me, it went at the. Because at the beginning of the spine thing, at the very beginning, I. I. And before that, too, I didn't know. Like, I didn't have. Like, it's 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. They don't know how to find their purpose or they don't know what the thing is. They want to. They want to do all the things that 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 do you. 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 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 just. Just go for it. So I love that, man.
Unknown Host
We are. It is Mother's Day today. While we're recording this live, I'm curious, what's your. What's your message to your mom and the greatest lesson your mom's taught you?
Oliver Widger
Oh, my mom was my biggest fan. She was my biggest fan. She loves me through and through, and she. She's. From the beginning, she's liked every single video. She's.
Unknown Host
She.
Oliver Widger
Even my mom doesn't have, like, a lot of money at all. And she, like, she goes. She goes into, like, GoFundMe and donate events. You'll donate, like, 25 bucks, 50 bucks. And I literally have to be like, mom, stop. Stop doing that. And, yeah, she's the greatest. She just is the greatest. And, yeah, I think. I can't remember the rest of the question, but, yeah, your mom.
Unknown Host
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 got a lot to do on the boat. I asked this at the end of all my interviews. What is your definition of greatness.
Oliver Widger
My definite true greatness is just 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.
Unknown Host
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 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 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, be 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.
Oliver Widger
Yeah, I appreciate, man. Thank you very much for having me. That's cool, man.
Unknown Host
Well, stay in touch, man. And I can't wait to watch the next content. We'll see you, brother.
Oliver Widger
All right, man. Thanks. Thank you.
Unknown Host
I have a brand new book called Make Money Easy and if you are 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 make moneyeasybook.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 free 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.
Podcast Summary: The School of Greatness – “Sailing With Phoenix: ‘I Quit My Job To Sail The World & Discovered My Purpose’ – Here’s The Secret To Finding Yours”
Podcast Information:
In this inspiring episode of The School of Greatness, host Lewis Howes interviews Oliver Widger, known online as "Sailing with Phoenix." Oliver shares his transformative journey of leaving a dissatisfying corporate job to embark on a solo sailing adventure around the world with his cat, Phoenix. The conversation delves into Oliver’s personal struggles, the pivotal moments that led to his life-changing decision, and the profound lessons he learned along the way.
Oliver begins by recounting his challenging educational years, stating, “I was in special ed from first grade to senior in high school. There’s only 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 anything” (00:00). His early life was marked by learning disabilities and a sense of being an outsider, which ultimately contributed to his later dissatisfaction with his corporate job.
A significant turning point in Oliver's life occurred when he faced a severe health diagnosis. At [04:20], he explains, “The doctor said my spine is like somebody who's over 120 years old.” This alarming news prompted a deep introspection about his life’s direction. Despite enduring chronic neck pain and dismissing initial medical advice, Oliver reached a crisis point where he questioned the very foundation of his existence and job satisfaction.
Struggling with his health and unfulfilled in his corporate role, Oliver made a bold decision: to leave his job and sail around the world. At [06:38], he reflects on his viral video confession: “I absolutely hate this life.” This video, initially meant to be a private rant, was inadvertently shared with his entire network, catalyzing his departure from his 11-year tenure at the tire shop.
The unintended viral spread of his emotional video played a crucial role in Oliver’s journey. At [08:35], he shares, “That video is everything. I don’t know if I would have had the courage to leave without that video.” The video not only served as a catalyst for his departure but also resonated with a broader audience, garnering support and admiration from strangers and acquaintances alike.
With no prior sailing experience, Oliver embarked on a steep learning curve. At [11:51], he admits, “I made incredible mistakes. I’m lucky to still have the boat.” Determined to pursue his dream, Oliver liquidated his 401k, sold his cars, and invested everything into purchasing and outfitting a sailboat suitable for an around-the-world journey. His preparation was largely self-taught through YouTube tutorials and hands-on practice, embodying his belief in relentless perseverance.
Now 12 days into his voyage from Oregon to Hawaii, Oliver shares the immediate challenges he faced. At [19:36], he candidly discusses his greatest fear: “Falling off the boat.” Despite this, his meticulous precautions, such as wearing a harness at all times, help mitigate these risks. Phoenix, his cat, proves to be an unwavering companion, adeptly navigating the boat’s movements and providing emotional support during solitary stretches.
A recurring theme in Oliver’s story is overcoming internal barriers. At [15:17], he reveals, “I completely came to terms with possibly being broke for the rest of my life until I died.” This acceptance of potential failure freed him from the paralyzing fear of judgment and financial insecurity, allowing him to fully commit to his dream. Oliver emphasizes the importance of taking incremental steps: “What is the problem that is directly in front of you and solve that problem” (34:18).
Throughout his journey, Oliver’s family plays a pivotal role. His brother’s encouragement was instrumental in initiating the project, while his mother remains his biggest fan. At [22:36], he shares, “They just, you know, they just, they’re my parents are separated and don’t talk. So it’s like a weird different dynamic. But like they just, they, you know, they love me unconditionally.” This unwavering support provides Oliver with the emotional backbone to pursue his unconventional path.
Oliver’s voyage has been as much about internal discovery as it is about physical adventure. At [33:04], he discusses silencing his inner critic: “It’s all his entire time of going through the process, all of it is noise. It’s all so bullshit.” By focusing on immediate challenges and practical solutions, he found clarity and purpose. His advice to listeners is straightforward yet profound: “Do whatever it is you want to do and just go for it” (24:41).
The unexpected viral nature of Oliver’s content has connected him with a global audience eager to follow his journey. At [13:13], he expresses his amazement: “I haven’t really even fully processed it. Like, it’s insane.” The support from millions of followers not only validates his decision but also serves as a beacon of hope for others contemplating significant life changes.
In closing, Oliver offers his personal definition of greatness. At [49:47], he articulates, “My definition of true greatness is 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 life well below their means.” For Oliver, greatness is rooted in humility, kindness, and genuine character, rather than material success.
Oliver’s journey is a testament to the power of following one’s passion despite overwhelming odds. His final message encourages listeners to trust their instincts and pursue their dreams relentlessly: “You've got to do it. And that will solve that problem, you know?” (47:10). His story exemplifies how embracing uncertainty and stepping outside one’s comfort zone can lead to profound personal fulfillment and inspire others to seek their own paths to greatness.
Notable Quotes with Timestamps:
Oliver Widger’s story, as shared on The School of Greatness, is a powerful reminder of the resilience of the human spirit and the importance of pursuing one’s true passions. His journey from a troubled corporate life to the vast, open ocean embodies the essence of greatness—living authentically, overcoming adversity, and inspiring others to do the same.