https://www.listennotes.com/e/c6c20ec1f7e449ddb9ad8ffeb6e75d83

I went to the doctor and they took some X-rays and the, the doctor's like, 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, uh, 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, boat and started learning how to sail. Our guest for you guys today is the one and only Oliver Woodard. I haven't told anyone this, but I was in special ed from, uh, 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 ticket, 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—

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Uh, 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, at one point you decide because you have, uh, test results at the hospital, right? That, uh, 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, um, 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— 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 was at work like the next day and they called me when I was at work and the doctor's like, 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 Uh, she was an orthopedic specialist, so she wasn't like a neurologist. Um, 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, uh, she was like, your spine is like— so 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 phase, 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 4 neurologists. And all of it was really, really bad. And yeah, so I basically just stopped going to the doctor. And, uh, and then I went through this, uh, 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 long, 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've got all my limbs, you know, I'm improving and wasting it at work. 29.

29.

Yeah.

So you're getting, you're getting all these doctors saying that you got a, a spine of a 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's just like, like I jumped into it and, uh, I didn't have any, like, I barely graduated high school. And it was a good— as far as the money goes, it was a good job. There's a lot of potential for money within the job. So I was like, all right, this is it. I'm going to be able to buy the house and have the fence and kids and whatever. 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. This actually sucks. Uh, yeah, and it was like 3 years. I went through— after the diagnosis, it was like a 3-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, 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, and then, yeah, it just— I spiraled completely. And then I finally one day I was like, like I had— I saw that video that I posted 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 original post where I'm in 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'm, I've never taken it down. Um, but I said my brother, I decided 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 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, uh, 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 was on a TikTok and I put it in as a draft because I thought I could put it in as a draft. And, um, 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, when are you going to 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 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 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, uh, uh, when did that video first—

when did that video first get leaked to everyone in your context? Was this a year ago, 2 years ago? When was it?

This was a year ago.

So you put— you filmed This video, which I'll put up on YouTube as well, you filmed this video of you in your car saying, I hate my life.

Yeah.

My life's miserable. I've been working this job for whatever, 8 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?

Yeah, pretty much.

Yeah. Then you, you filmed it for yourself without the intention of putting it out. And then you put it out for 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 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, to quit. But that video is what went viral.

That's crazy.

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. And 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.

Yeah.

And you're going on a sailboat from Oregon to Hawaii, and you're 12 days in. Is that right?

Uh, yeah, 12 days in. Yeah. So I'm like almost 1,000 miles away from— I'm, I'm basically closer to the people on the space station than I am to anybody on land.

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. Um, and I just think what you're doing 99.9% 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.

Yeah, I figured out— 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 401(k). And so I liquidated my 401(k), 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 before or how I was going to buy a boat. And, uh, uh, I, I spent the following month just like searching for a boat. And you see, I just got really lucky that I got a good, uh, you know, a capable boat because that could have, that could have gone so wrong as well. Um, and it didn't. And, uh, uh, yeah. And then I just dived into it with knowing nothing.

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'd never sailed before.

Yeah, everything was like basically YouTube. And, uh, I just like, I just like, uh, as far as learning how to sail, so I, I, uh, uh, I got the— 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, uh, I just— it paid off. It worked out.

Wait a minute, 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 gonna 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. So I— and I replaced also all of the like rubber components. And then, yeah, I took it out.

Um, dude, I, 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?

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? 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, you know? 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 of time staying alive.

Yeah, yeah, yeah, not a small thing, you know?

Yeah. And, uh, 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 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, 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.

Yeah.

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, they wanna launch something on the side, even just for fun. It's not always about like, leaving your job and the relationship, but it's like maybe they just had a dream that they want to pursue on the side that they're afraid of.

You just got to jump. Like, that is the hardest part.

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That was a crazy idea. That was the biggest thing that, 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 solved all my problems, 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, um, uh, 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, uh, all that stuff, you know. I, you, and you just, all of it is nonsense. All of it is noise. And, um, you just gotta, I don't know, you just gotta 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, um, and my, yeah, my dad is, is in the US, but, and they're, 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 3 solid years of being like at the lowest low and they could see it. And so I think they were probably like, You know, they were probably like, I mean, anything better, you know? And, uh, so, um, but they've all— 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, 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, like, just go, that— who cares? Yeah, yeah, yeah.

Yeah, this is incredible, man. Uh, what is the— you, you wrote about 15, 20 days away from Hawaii. Do you know which island you're trying to land on? 12 days of Oahu. You're going 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.

You're not going to 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, um, I, uh, there's a Marine store 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 legit sense.

I want, 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, 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 what 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, I don't know. I learned a lot about me on the process for 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, 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, what, what's your greatest fear?

Um, 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 got a life jacket? Are you, are you tying yourself up? Are you taking like—

there's no life jacket, um, just because if you fall in, a life jacket just prolongs the inevitable. So, you know, but I see for a harness, there's no 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, going like 6 knots.

Well, unless it's stopped and you have 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—

I fell off. Yeah, you're not getting back on.

Oh snap.

Yeah, you better remember that. Hardened yourself.

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, 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 this.

I'm, I'm not like— I can't stress that I am as below— oh dude, I was in I wasn't— I haven't told anyone this, but I was in special ed from, uh, first grade to senior in high school. Like, I couldn't do school at all. And, um, I can't write. I've got every single, like, learning disability. I could— 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 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, when I, when I talk to like my mom and brother, I guess. 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 about me?

Is it about your relationship with your family that you appreciate so much?

Uh, 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 just, 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 loved me. It doesn't matter where— what's— what's where I am in life. They just to have.

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, 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 in these videos is really inspiring. And I'm curious, if you could go back, uh, you said you're 29, is that right, Oliver?

Yeah.

If you could go back, uh, to your 21-year-old self, knowing everything you've been through in the last almost decade, what advice would you give?

Literally, I tell people this, they're 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, oh, that's what I would've done. And I, I would've 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 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?

Hell yeah. Sweet.

Oh, man. What about all the people? 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 2 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. Like, it's, it's, it's, 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, uh, and then I'm also viral at the same time and inspiring all these people. All these things that are like not real, you know what I mean? Oh, 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 Hawaii. And then I'll probably be able to feel how real it really is. I mean, it feels unreal. It feels— it's absolutely insane. 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 6 hours a day editing 6, 7 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, 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, where I 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 were you just—

yeah, it's all, all of it is all documented.

Were you posting these on like TikTok or something, or where were you posting these other videos last year?

Oh, so most of the videos are on TikTok. And then right around when I got the boat, uh, 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—

Okay, I got you, man. 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 break— you gotta figure out— you have another question too? I'm gonna ask one. You want to come on and ask? You want to come on and ask?

Here she is, saying this, kitties.

Oh, Phoenix! Oh man, we need to make Phoenix shirts, just sell them online for you, you know? That's what you need to do.

Yeah, I'm working on it.

That's amazing, man. Um, 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'm, 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 and 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, 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, you know, 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?

100%. Yeah, I like literally feel healthier.

Like, I—

it's crazy.

You feel physically—

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, uh, 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 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, 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, and you're all in at that point. And, uh, and I went all in, uh, 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 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.

Tax and bonus season is one of those sneaky little moments. You check your account, you see a refund or a bonus, and for about 10 seconds you feel rich. Like, ooh, maybe I'll go buy some expensive gift for myself. Then reality kicks in. But here is the thing, that moment right there is actually kind of powerful for us. For most of us, extra money hits the account and suddenly it already has plans because something needs to be fixed. Something needs paid for, or something you've wanted for forever is calling your name. There's no shame in this. Life is full. Things break, plans pop up. But what if just for a minute you paused, like just for a second, not because you have to, but because you want to ask a better question. Not what can I buy right now, but what would actually feel good about this later? And instead of the moment running you, You make an intentional move, not a big dramatic one, just a simple decision that leaves you feeling a little more steady and a little more in control, specifically with your money. And if you get a tax refund or a bonus, try asking a different question. Not what can I buy today, but how can I give my bonus a bonus? Or how can I turn my tax refund into more funds? It's a small shift, but it changes the energy. And suddenly it isn't just extra cash. It's an opportunity. One simple, intentional decision can help you feel a little bit more in control, a little more steady. And honestly, that feels better than an impulse purchase you forget about in 2 weeks. And that's why I like how US Bank approaches tax and bonus season. They know these moments matter. US Bank Smart Lease Savings is designed for people who want flexibility while earning competitive promotional rates. And if you are in a place where you do not need immediate access to that money, US Bank CD Specials let you lock in a guaranteed rate for a set period of time. It's so simple, it's straightforward, and it's about saving your way. Growing your money without overcomplicating it. US Bank can be a trusted partner when you decide to be a little more intentional personal with a financial boost. Visit usbank.com/savings to get started. Savings rates vary based on the presence of an additional eligible product and combined qualifying balances. CD rates vary by term and location. Member FDIC. There's nothing that frustrates me more than when things don't move with speed. And when it comes to building a strong daily routine for your life, the tools that you rely on at home should make things run more smoothly without interruptions. and that's the thinking behind T-Mobile's 5G Home Internet. And big news, T-Mobile now has the fastest 5G Home Internet according to the experts at Ookla Speedtest. Setup is so quick and simple, no technician needed, and you're online in 15 minutes or less. And the price comes with a 5-year price guarantee, so you don't have to worry about unexpected price hikes down the road. And when I'm working from home, my internet does a lot of the heavy lifting. It's prepping for the next show on the School of Greatness, uploading files. I'm doing Zoom calls, I'm doing meetings. All these different things are all happening and I need them to happen fast. And with T-Mobile 5G Home Internet, things move fast and stay smooth. Pages load quickly, files upload successfully, and I can stay focused without constant interruptions. It makes a big difference. Visit t-mobile.com/homeinternet to check availability today. Price guarantee exclusions like taxes and fees apply. Fastest based on Ookla Speedtest Intelligence data, second half of 2025. All rights reserved. Beautiful, 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, but 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 you can, because the whole time I, I had this incredible self-doubt, the whole time of going through the process. All of it is noise. It's all, it's all bullshit. Yeah, it's all noise.

You quiet the critic or the doubt in your mind 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?

I just— there's no option. Like, I didn't have an option but to, to succeed. Like, my hopes— yeah, just didn't have an option to succeed. I, I just kept going. Just it— one thing that I would do a lot— so I've tried to do this once before, a few— 2 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 gonna know how to work on a boat. I'm not gonna— 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 adopted a sailor, all of these trades, and, um, within a year. Uh, 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.

Don't think 5 years 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 did. I like, whatever the problem was that in front of me, I did that. So I got the boat. Okay, well, I, I don't know how to sail. All right, we'll 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 works. I've posted every single day terrible posts, good posts, but I've done it every single day for a year. And, uh, and I, with, with the intention of going forever, you know what I mean? And not stopping, like, I just going forever. And, um, and it worked. It worked.

Did someone give you the, the blueprint of like, okay, if you're gonna do this, you gotta get the boat, and you have to go on Instagram or TikTok every day and document this, or is this just—

no, this is all in my mind. This is all in my mind.

But you weren't really— you weren't on social media before this, were you?

No, before a year ago now.

So you're just like, yeah, I'm gonna figure out social media. You weren't on there. 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, 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 to be like, dude, are you okay? Like, dude, I'm just trying to figure this out, you know what I mean? Like, and, uh, 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. You didn't.

You had this the whole time. I believed in you.

Yeah. Wow, man. Yeah. And, uh, I just, I just kept going through all that. And, uh, you know, there's times where I thought I was insane myself and, uh, I just kept going.

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.

I knew I was gonna be fine with the isolation on this passage because I'm not kidding the past 5 months. So I, I spent, I learned how to sail for the first like 6 months. And that's when I taught myself how to sail. And then the last 5 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 6 months. Um, 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, um, uh, I, I, I'm comfortable with my own thoughts alone, you know what I mean? So I'm fine. And, uh, I do well. Oh, I'm not a, um— 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, says something, says hello to me in person and stuff. I'm totally weird. So, uh, 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 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 have the resources on board and the kind of the skills to solve the issue. Like, the worst thing that could break is literally like the rudder. It's one of the worst things, and it broke. And, uh, on day like 6 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 you're— yeah, and you're not supposed to— the boat isn't— the camera doesn't do waves any justice. It's the sailor's— it's a sailor's worst curse is that the camera doesn't do waves any justice. And, um, so yeah, my rudder broke and it, it, it 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, uh, 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 gonna happen. And then so the boat like literally was— would go from this all the way to this within like 3 seconds. And it was just going like this, like parallel. And because that's— wow. Yes, that's cap science. I— it was like that for like 3 or 4 hours while I was trying to solve it. And, uh, I, I, uh, jumped into the engine room, um, and 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 the, you know, the rudder will like slam back. And, uh, 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.

So what about Phoenix during that time? Is she like flying?

She was at that point, she was already like well adjusted to the boat. Um, so I'm sure she get motion 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, 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, do you have her harnessed up also if she's out on the deck, or would she follow?

I, I'm the kind of guy that would absolutely walk my cat. So I spent like— like, she's 7 years old now, and she was a feral cat when I got her. And, um, she, uh— I spent like 3 years trying to walk my cat. Like, it's impossible. It is an impossible task.

So I can't get a harness on her, but does she know 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. Oh yeah, she can go on shore.

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, uh, right now, do you have the location where you are, like, live on— Yeah, on the—

That's on my highlight. Okay, so if you go, if you click on my highlight to that. And you—

and, man, is this Starlink that you're using on the boat?

Yes, we're having really well.

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, I had like 60,000 followers before I left, and so I had to, uh, like literally just tell them like, hey, look, I'm— you know, I may not hear— no idea if it's gonna work. Yeah, I don't know if it's gonna work, and, uh, I'll see you guys probably in 30 days, but Dude, it's, it's worked really well this whole time.

And what's your, what's your, 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 6 to 8 hours?

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, uh, a wave of tiredness, I'm gonna take advantage of that because right now the boat's balanced, the boat's good. So I'm gonna take advantage of that. I'm gonna go sleep for a couple hours. And then, so yeah, and it depends on the weather. So like last night, I stayed up till like 3 AM, 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 get plenty of sleep. Like 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, um, 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, um, I think the thing that, that that where sailors meet their demise is because of sleep deprivation. Yeah, we'll not have that problem.

Your problem will be you won't wake up.

Yeah, crash.

Yeah, 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, here she is.

Oh, such a sweetie. Does she sleep next to you also or no?

Yeah, she sleeps next to me and, uh, um, yeah, we are, we, she like, she sleeps right here and I sleep right here.

Oh man. You're living the dream, man.

Yeah. Um, yeah.

All around again, I wanna, I wanna, I know you got a lot of activities you gotta do on the boat, but I'm glad we got connected and I wanna, I wanted to share your message with my audience. And I'm gonna 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, uh, 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 everyone laughs at me? And so what, you know, if they do, okay, well, at least you won't regret it. Tax and bonus season is one of those sneaky little moments. You check your account, you see a refund or a bonus, and for about 10 seconds you feel rich, like, ooh, maybe I'll go buy some expensive gift for myself. Then reality kicks in. But here is the thing. That moment right there is actually kind of powerful for us. For most of us, extra money hits the account and suddenly it already has plans because something needs to be fixed, something needs paid for, or something you've wanted for forever is calling your name. There's no shame in this. Life is full. Things break, plans pop up. But what if just for a minute you paused, like just for a second, not because you have to, but because you want to ask a better question. Not what can I buy right now, but what would actually feel good about this later? And instead of the moment running you, you make an intentional move, not a big dramatic one, just a simple decision that leaves you feeling a little more steady and a little more in control, specifically with your money. And if you get a tax refund or a bonus, try asking a different question, not what can I buy today? But how can I give my bonus a bonus? Or how can I turn my tax refund into more funds? It's a small shift, but it changes the energy and suddenly it isn't just extra cash. It's an opportunity. One simple, intentional decision can help you feel a little bit more in control, a little more steady. And honestly, that feels better than an impulse purchase you forget about in 2 weeks. And that's why I like how U.S. Bank approaches tax and bonus season. They know these moments matter. U.S. Bank Smart Lease Savings is designed for people who want flexibility while earning competitive promotional rates. And if you are in a place where you do not need immediate access to that money, U.S. Bank CD Specials let you lock in a guaranteed rate for a set period of time. It's so simple. It's straightforward and it's about saving your way. Growing your money without overcomplicating it. US Bank can be a trusted partner when you decide to be a little more intentional with a financial boost. Visit usbank.com/savings to get started. Savings rates vary based on the presence of an additional eligible product and combined qualifying balances. CD rates vary by term and location. Member FDIC. Spring is the season for closet cleanouts. It's the perfect time to narrow down your wardrobe to pieces that are well-made and easy to wear all the time. And that's where Quince comes in. With Quince, you get fabrics that feel elevated and pricing that actually makes sense. They work directly with ethical factories and cut out the middlemen, so you're paying for quality, not brand markup. Everything is designed to last and make getting dressed easy. And it's not just their clothing. They have great bedding options too. And Martha and I actually have their European linen duvet cover set, and it's so soft and comfortable. We love it. Highly recommend doing a little spring cleaning and upgrading a few things you use every day. Just start small and keep it simple. Refresh your wardrobe with Quince. Go to quince.com/lewis for free shipping and 365-day returns. Now available in Canada too. Go to quince.com/lewis for free shipping and 365-day returns. Quince.com/Lewis. 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 a guarantee is, is people laughing at you going broke and all that stuff because all that happened. Yeah, but it works.

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, 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 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 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 a— 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, 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, um, 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 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. Yeah. And, uh, just, just go for it. So, um, I love that, man.

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?

Oh, my mom is 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 in like GoFundMe and donate. If you'll donate like $25, $50, 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 think—

I can't remember the rest of the question, but yeah, your mom, that's great that she supported you with this whole journey doing some crazy hearing. That's amazing. Uh, 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. Um, I asked this at the end of all my interviews, uh, what is your definition of greatness?

Um, uh, my definition 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 you're going live. So I want to acknowledge you for taking the leap, 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, I appreciate it, man. Thank you very much for having me. That's cool, man.

Well, stay in touch, man, and I can't wait to watch the next content. We'll see you, brother.

All right, man. Thanks. Thank you.

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