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

Episode Date: June 18, 2025

Leave an Amazon Rating or Review for my New York Times Bestselling book, Make Money Easy!What happens when a spine diagnosis worse than you can imagine forces you to confront your mortality at 29? Oliver Widger went from working a corporate job he hated to sailing solo across the Pacific Ocean with nothing but his cat Phoenix and an unshakeable belief in chasing impossible dreams. After learning he had the spine of someone over 120 years old, Oliver spiraled through three years of partying and self-doubt before accidentally posting a video of himself in his work uniform declaring he "absolutely hated this life" - a mistake that changed everything when it went to all his bosses. Now weeks into a solo voyage from Oregon to Hawaii, Oliver has gained nearly a million followers while proving that the most below-average person can achieve extraordinary things through pure determination. This conversation reveals how facing your mortality can become the greatest gift, why crossing the point of no return is the only way to truly live, and how anyone brave enough to spin a globe and jump can transform their biggest fears into their greatest adventures.Oliver's TikTokOliver's InstagramIn this episode you will learn:How a devastating spine diagnosis became the catalyst for the greatest adventure of Oliver's lifeWhy accidentally posting your breakdown video to your bosses might be the best mistake you ever makeThe simple strategy Oliver used to overcome overwhelming self-doubt: solve only the problem directly in front of youHow to find your purpose by asking yourself one ridiculous question: what crazy thing do you actually want to do?Why becoming completely comfortable with dying poor is the secret to unlimited freedomFor more information go to https://www.lewishowes.com/1786For more Greatness text PODCAST to [phone]More SOG episodes we think you’ll love:Pat Flynn  – greatness.lnk.to/1777SCMuniba Mazari – greatness.lnk.to/1684SCMark Manson – greatness.lnk.to/1750SC Get more from Lewis! Get my New York Times Bestselling book, Make Money Easy!Get The Greatness Mindset audiobook on SpotifyText Lewis AIYouTubeInstagramWebsiteTiktokFacebookX

I went to the doctor and they took some x-rays and the doctor was like, your spine is like somebody who's over 120 years old. After the diagnosis, I spiraled completely. And then I finally, one day I was like, My name is Oliver. I work a corporate job at a tire shop. I absolutely hate this life. Yeah, I'm 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 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 a special ed from first grade to senior in high school. There's only, there's one thing in my life that I could do well and that is I can grind. I can work so hard. If I lean into that, I can do, I can do anything.

I tell people this, they're young all the time, that like message, I tell them, dude, if I could go back in time and I was 18 or 20 or whatever, I would literally get a globe and I would spin the globe and I would stop the globe with my finger, and I would buy a plane ticket,

a one-way plane ticket, and go there. If there's somebody that is looking to chase their dreams, find the point of no return, and then... So I'm so excited, man, because I've been watching your journey over the last few days. My friend Tim was here, showed me your videos. And since three or four days ago, when I started watching you, I think your audience has exponentially grown.

And, and I love seeing what you're doing. And so we have, if you can share your full name because on Instagram you're sailing with Phoenix and you are changing and inspiring the world in a massive way. So if you can share with your full name to the audience who's watching. Yeah, my name is Oliver Widger. Wittjer and yeah and so you have this video of you working a corporate job and essentially hating your life and at one point you decide because you have test results at the hospital right that yeah that something is something's off in your body is that correct yeah well so like I 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. I started out go to a chiropractor. I started out going 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. Cause it's insane. And yeah, I went to the doctor and they 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 of any 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 that at work in the the doctors that 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 a she was an orthopedic specialist so she wasn't like a neurologist but But yeah, she was like, I don't know how you're here right now talking to me and not in excruciating pain. I was like, well, I am in a bit of pain. And so I am here. And she was like, your spine is like, I've done this for 20 years,

I've never seen anything like this. Your spine is like somebody who's over 120 years old. And I, like somebody who's over 120 years old and I and then I went through this say you know I had to wait it's a long story I don't want to like just be a long winded and stuff but I went went through I had to see like four neurologists and all of it was really really bad and Yeah, so 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 sort right you know where my mortality was kind of like hitting me in the face and I was realizing that I'm Spending my like right now I am physically capable of doing anything I want really, as far as like I can't do anything that, like I can't do anything that involves any sort of in power. But, but I was, you know, physically I can,

I, you know, I've got all my limbs, you know what I mean? And wasting it at work, 29. 29. Yeah. So you're getting all these doctors saying that you've got a spine of 120 year old yeah you were working a job that you didn't really fully love that you were just doing it because you thought you were supposed to do it i guess or you just yeah it's just like like i

jumped into it and uh i didn't have any like i barely graduated high school and it's it was a good as far as like the money goes it was a good job like it you know there's a lot of like potential for money within the job so I was like all right this is it I'm gonna be able to do the by 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 now but 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, um, this is after you knew about, this is after you knew about the condition. Yeah. Yeah. Yeah. And then of course that just dug the mental hole deeper, you know, living like that. And, um, uh, and then,

yeah, it just, uh, 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. You're like, I did it. Well before, like the original post where I'm in now, the uniform and I'm like absolutely hate this life that full version

of that is like two minutes and 35 seconds long and it's it's just It's wild to watch it is at the bottom of my tick-tock. I'm I've never taken it down But I said my brother I decided I found a purpose. I decided I wanted to sail around the world. Mm-hmm and 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. I never used TikTok before. I didn't know how social media worked. So I was on a TikTok and I put it in as a draft because I thought I could put it in as a draft. 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 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 changed. Cause who knows if I would have had the courage to leave, who knows to leave without that video. Cause 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, it was shared within the company and uh when did that video first when did that video first get leaked to everyone in your context was this a year ago two years ago when was it this was a year ago it's a deck but 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? Yeah, pretty much. Then you fill it for yourself without the intention of putting it out

and then you put it out to your bosses, right? They all see it on accident. Had you not done that, you would not be on this boat right now. Yeah, I don't know. I don't think so. I mean, who knows? I knew I was gonna quit,

but it's one of those things where it's like, I don't know. I don't know if I would have had, actually, when I came down to it, had the courage to quit but Video is what went viral. That's great. That video is everything that video is everything. It's everything and it's Because my brother my brother told me that to start recording myself and wow man And so you went and so you're 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? 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 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, it's the cat. 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 is so safe. It's so comfortable. Even if they're miserable, they'd rather stay safe. A visual that actually go for it. Yeah. I figured I was in you or go go for it. Yeah, I figured I was in you. I are going for it when I when I quit my job abruptly like that. I had like, I don't know, a $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, capable boat because that could have gone so wrong as well. And it didn't. And yeah, and then I just dived into it with no and nothing. So how did you, 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.

Yeah, everything was like basically YouTube and I just like I just like as far as learning how to sail so I I got I literally want I didn't even watch them any like YouTube videos. I just want I bought the boat. I just I took it out and I made the boat. I literally want I didn't watch them any like YouTube videos I just what I bought the boat. It's 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 there's just like really high risk and I just it paid off it worked out and I just went very let me, Oliver, you you bought the boat and then you just got the keys of the boat and you just said, I'm just going to push it off the dock and just see what happens.

Yeah. So like a month after there's about a month after, because I had to replace some of the lines and stuff on the books. The lines were all like 15 years old and take throughs. And I replaced also all of the like rubber components and then yeah I took it out um I yeah 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 and like 10 days something how does it feel to know that putting out a few pieces of content and actually chasing your dreams is inspiring millions of people around the world? How does

that feel? I 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 cuz I went viral on the day that I left and I'm also Crossing an ocean. You know me to do Insane things that I'm like that are like, you know competing with I would literally fight for my life the other day Well, I'm going viral. I hear like It was it's just been so weird and there's not a lot of time to like cuz I'm you know obviously making the content take 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 kind of small thing you know yeah and it's been so it's been so cool to you like the I that I'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 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 want to 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 I feel afraid of he's got a jump like that is the hardest part How did you overcome the fear of Being worried about what everyone thinks about you by doing so that was a crazy idea That was the base thing that helped 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 over my,

but one of them was like, I literally completely came to terms with possibly being broke for the rest of my life until I die, like being just poor and dying poor. I absolutely became like completely content with that idea and once I became content with that idea I was freedom you know I mean I had freedom and that's what it came down because my that was my fears it's like I I'm gonna be poor no one's gonna you

know 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 yeah who's gonna want to be with like a poor me to be single forever like all that stuff was the things running through my head Yeah, who's gonna want to date a guy on a bum on a boat and all that stuff, you know I yeah, and you just all of it is nonsense. All that is noise and You just got a I don't know you just got to go for it I guess Oliver What about your parents if your parents still around your siblings? Yeah, my mom and brother live in the UK and my dad is in the US and they're frowning. What did they say originally when you were 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 myself and my cat? What do they say? I think 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 were probably like You know, they were probably like the I mean anything better, you know, and You know, they were probably like, I mean, anything better, you know? And so, but they've always 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 so now like, just go that who cares? Yeah. Yeah. Yeah. This is incredible, man What is the here you wrote about 15 20 days away from Hawaii? Do you know which island you're trying to rain on? 12 days a while. Oh, you're going to a while. Who yeah

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 Yeah, I been to Maui before. Yeah, I've got one of my other brothers is on Maui. Actually, I landed Maui. No, I originally wanted to go to Maui because he's there. But I decided to go to a while who because now in Maui, I would need a car to like drive around. And so a while who I there's a marine story there too like a Western rain that's

there too it's been walking distance and everything's within walking distance so it just made more like legends 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 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 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? 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. Like I am a different person over this last year and I just like

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

You jumped off the boat already, right? Yeah, but it was completely becalmed. Yeah, yeah. Yeah. So 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 think we're a harness there's a point we're in a life jacket there's nothing around here if i fell in the water the life jacket would just prolong the am wouldn't help you swim back to your boat or something

Yeah, the boat sails itself like I'm going it's going like right now though my six not be done Well, unless it stopped and you had the sails down and you fell off like you did then it's fine But if you fall off when it's going you pay down I fell off. Yeah, you're not getting back on. Oh snap Yeah, you better remember that harness 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 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, you're down on some duets. I'm, I'm not like, I can't stress it, I am as below, I was in, I wasn't, I haven't told anyone this, but I was a special ed from first grade to senior in high school. Like I couldn't do school at all.

And I can't write about every single like learning disability. I think like this is this is how I organize my notes. You know what I mean? This is a piece of paper. I can't I can't even read it. It's not even right. Yeah, so like I can't stress read it, it's not even right. 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 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 it when do I feel the most love I don't know. When do I feel the most alone? I don't know. Like when I, when I, when I talk to like my mom and brother, I guess, cause 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 of me is it about your relationship with your family that you appreciate so much? They just, you know, they just, they're there. Did 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 I mean and they've never they've just you know they've just the love is there always you know I mean 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. 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 and these videos is really inspiring. And I'm curious if you could go back You said you're 29. Is that right all over? Yeah, if you could go back to your 21 year old self Knowing everything you've been through in the last almost decade What advice would you give?

So the leader 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 time, and I was 18 or 20 or whatever, because you see these guys, they're getting into the job. I was 18 when I got into my job. And I thought this is what I needed to do. And 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 and sit with, you know, no money and figure it out and go, oh, that's what I would have done. And I would have done that for as long as I could. That's why, that's what I recommend people do is spin the globe, point and go, you know, go see the world.

I'm curious, 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? Oh, yeah. Sweet. Oh, man. What about all the people, you know, again, 12 days ago, no one knew who you were.

And now you've got a million followers. And again, people are invested in your journey in your life. They want to see you win because you're bringing so much hope and inspiration to the world. What is it like going from, you know, nothing 12 days ago and having a dream and starting in the ocean to having a million followers in under two weeks and people so invested in your story. How does that feel? 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 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, all these things that are like not real.

And I mean, the, all, all the, like not real. And I mean, it's great. It's like everything's a bit of a fog. It's a bit of a dream. 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 how real it really is. I mean, it feels unreal. It feels it's absolutely insane. Like it's just that it that it it worked all that work is that 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 a Edit it six seven hours a day editing videos and figure making the craziest videos and just figuring it out and editing videos and just 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 locks from the outside world did it for a year straight and It's just so crazy that like the The it all that 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 all of it is all documented all documented. Were you posting these on my tick tock or something? Or where were you posting these other videos last year? Oh, most of the videos are on tick tock. And then right around when I got the boat little after I got the boat, I started posting on Instagram. So if you go to the bottom, my tick tock, you'll see a crazy.

OK, I got you. Now 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 have a break. Yeah You have another question to ask one. You're coming. We come on ask here. She is saying this kid is Oh Phoenix oh the amazing man. And also for people that are out a lot of people are commenting how they've been waiting for you to go live. They've been waiting for you to share more. So maybe you got to go live on your own at some point, once a day so people can be checked in on what you're up to. I've been trying on TikTok. It's just obviously I'm I am in an ocean. So I do have to like, you know, do things. Yeah, do you think? 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 front go fund me where people can donate to support you on this journey. I'm going to make a donation right after this. 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 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, you know, working a job that wasn't enjoyable for you. Maybe he was paying the bills and it wasn't horrible, but it was not feeding your soul.

And you took a risk. You sold everything, you took out all your investment money, and you're on this journey for the last 12 days from Oregon to Hawaii, sailing by yourself with a cat. And 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 this way and it's not only i feel healthier but my lifestyle because of the financial side of things has been i've been eaten terribly, you know what I mean? But I feel so much it's amazing. 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 dreams. Something that I realize is like, I guess my recommendation would be to find the point of no return and then cross that point. As soon as you cross that point, that's the hardest part. As soon as you cross that line, you it's you're all in you're it's you go for it I mean you 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 the go fund I've never advertised or talked about the go fund me because I think it's weird and but I did just put it up and I you know a bunch of people obviously donated it and it's well so I only put ten thousand dollars in there because that's I but when I left Oregon I was ten thousand dollars in debt well I've gone all in on everything this entire time. I've just made, you know, and, um, now I'm not in debt and it's gone over that.

So I just wanted to say thank you to everybody for that. Yeah. Oh man. Yeah. Again, for people that are, you know, just as afraid to go for their dream, it's just inspiring to watch. And you talked about like, it's really that point of no return. This may be the wrong analogy, but it's, you know, the analogy of burning the boats when you get on new land and you kind of like burn your boats.

Wrong analogy here on a boat, right? Where you can't go back. You can't go back to like safe land. You have to like take on the new journey, the new journey. Yeah move forward even though it's uncertain It's unknown. Yeah, and and you're doing that and you're sailing in the ocean Yeah, and believe you can because the whole time I had this Incredible self-doubt the whole time of going through the process all that is noise it's all it's all bullshit yeah it's all nice you quiet the critic or the down in your mind as a person that's you know struggled in school

didn't have the job that you wanted you know had back pain for the last ten years how did you overcome the self-critic and the doubt? I just, there was no option. Like I didn't have an option, but to succeed. Like my hopes, yeah, just didn't have an option to succeed. I just kept going. Just one thing that I would do a lot, so I've tried to do this once before, a few, two years ago, like right after the diagnosis.

But what I did was I I thought about everything way too far ahead and I would I discouraged my I would think about you know I like I'll fall and hit the boat wrong and I'll go paralyzed or I'll I'm not 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 an electrician, a diesel mechanic, I've become a plumber, I've literally, I've adopted a sailor, all of these trades, and within a year. But I would, my point is I would discourage myself, I discouraged myself, and then I couldn't even, I was like, you know, I couldn't even get past the bridge

of what boat to buy. I guess the solution to that was literally what is the problem that is directly in front of you and solve that problem. So if you don't have a boat, don't think about anything, get the boat. You don't have a boat, that's your problem. Don't think five years 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 I saved 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 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.

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 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 is always that social media was gonna work It's always a plan and I was gonna 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 with the intention of going forever. You know what I mean? And not stopping. Like I'm just going forever and it worked. It worked. Did someone give you the blueprint of like, okay, if you're going to do this,

you got to get the boat and you have to go on Instagram or TikTok every day and document this or is this just not? 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 weren't really you weren't on social media before this for you. Now before a year ago now. So you're just like, yeah, I'm going to figure out social media.

You weren't on there. Maybe you're on there. If you go to the bottom, my tech talk, you'll see it's, it's a disaster. It's like, it's 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, are you OK? 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 messaged me and going, I always believed you. Yeah. We made. They didn't. You had this the whole time I believed in you. Yeah. Wow man. 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. 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 quite 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. You feel lonely or do you feel like how do you put yourself to sleep calmly and feel safe? All that stuff.

I knew I was going to be fine with the isolation on this passage because I'm not kidding. The past five months. So I spent I learned how to sail for the first like six months. And that's when I taught myself how to sail. And then the last five months I didn't sail at all and I spent every single day 10 hours a day working on the boat in complete isolation I didn't speak to another soul ever like I literally just those 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. Oh, I'm not a it's it's weird because like I'm on social media, but I'm not I'm a keep to myself person. I'm I am awkward. And if somebody comes, says that says hello to me in person and stuff, I'm totally weird. So I don't remember what the question was, but no, it's good, man.

It's just more like how do you think about it? If you're being if you're alone in the ocean for all this time, like is your mind OK? 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 I the worst thing like the worst thing that could break is literally like the rudder is one of the worst things and it broke and On day like six or something at the worst time It was at the height of the storm that I was in so the way 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 sailors worst curse is that the camera doesn't do waves any justice and so yeah, my rudder broke and it it it walked in the starboard position and

It which you're not supposed to go at it as to the waves on the side on the side and it positioned the boat 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 this to 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's well to be up Wow Yes, they're both cap science. I it was like that for like three or four hours while I was trying to solve it and I jumped into the engine room And in the engine room and I see the cable came off the quadrant

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 cable back around the quadrant. It was crazy, man. That was the scariest moment of my entire life.

Hands down. But yeah. So what what about Phoenix during that time is she like flying on you make sure that at that point she was already like well adjusted to the boat and so I'm sure she get motion sickness too or no she only wants my first took the boat out like a year ago I mean she's an actual blown boat cat now it's crazy like watch here like she walks she gets around better than I do and she like walks around like a like the she I I'm the kind of guy that would absolutely walk my cat so I spent like like she's seven years old now and she was a feral cat when I got her and she I spent like three years trying to walk my cat it's just isn't possible it is an

impossible task so I can't get a harness on her but if she knew I'll let her out in 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 get where she is 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 people go to your Instagram right now, do you have the location where you are like live on?

Yeah, it's on my highlight. Okay. So if you go, if you click on my highlight. To that. And man, is this Starlink that you're using on the boat? Yes, we're having it. There's like no lag. Yeah, I didn't know if it was gonna work.

So like I had to like literally, cause I did have some followers, have a lot. in 30 days, but it's students. It works 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 six, eight hours? And one like the weather, like there's no sleep schedule, really. It's just you sleep when you can. Like if I after this call, if I get a a wave of tiredness, I'm going to take advantage of that, 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 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 get plenty of sleep. I'm 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 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's where sailors meet their demise is because of sleep deprivation will not'll not have that problem with. Your problem will be you will wake up. Yeah, yeah. Yeah. But you gotta you gotta share one more time. You gotta show the cat face the cow one more time. Everyone's everyone who came out late is asking where's Phoenix?

Yeah. Yeah. She is. Oh, such a sweetie. Yeah. Here she is. Oh, such a sweetie. Does she sleep next to you also or no? Yeah, she sleeps next to me. And, um, yeah, we're like, she sleeps right here. I sleep right here.

Oh, man. You're living the dream, man. Yeah. Yeah. All right. Again, I want to I want to I know you got a lot of activities you got to do on the boat. But I'm glad we got connected and I want to I wanted to share your message with my audience and I'm going to make this out there on my podcast. But I want 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 pursue 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, your your funds, all your savings to buy a boat. And for a year you were taught yourself how to sail a boat and you went you're now 12

days in the middle of the ocean on your way to Hawaii. And 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 have the courage to actually do it. Cause again, 99% of people won't go after the big scary dream that they have because they're too afraid to fail or what if, or what if I go broke or what if I don't have any money or whatever. Everyone laughs at me. And so what, you know, if they do, okay.

Well, at least you won't regret it. And you're happier and healthier than you've ever been in your life right now. Yeah. Yeah. And that's amazing. I feel like all those things are guaranteed is 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 gonna be watching your journey every single day. I can't wait to and I can't wait to celebrate you and 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 gonna think about them What's one final piece of advice or wisdom you would share based on your Johnny, you know, you know the answers You know the answers to clear you know the answers and if if you're if you're questioning the relationship or the job and And you've been questioning the relationship the job. That is the answer like you've got the answers It's that simple. You've got the answers for the for a better life you just got to do it and uh

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 a hard thing for me it went at the because at the beginning of the spine thing hard thing for me at the beginning of the spine thing, at the very beginning and before that too, I didn't know, like, I didn't have like 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 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. Yeah, I mean like it's like what do you what's the ridiculous thing?

You want to do like? Failing around the world on a boat with my cat is ridiculous. You know what I mean? It's ridiculous. But it's that's like a ridiculous dream that I had. And so why don't I just make that my purpose? It's it is simple. You know what I mean? Like if what is it you want to do? Do that. And just just go for it. So I love that man. We are it is Mother's Day today while we're recording this live. I'm curious. And what's your what's Go for it. So I love that man. We are. It is Mother's Day today while we're recording this live. I'm curious.

What's your message to your mom and the greatest lesson your mom's taught you? My mom is my biggest fan. She's my biggest fan. She loves me through and through. And she's from the beginning. She's liked every single video. She's even my mom doesn't have like a lot of money at all. And she like she goes, she goes, isn't like go

fund me and donate a picture 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 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. 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? interviews, what is your definition of greatness? My definition of greatness is just being humble, like a humble person, you know, regardless of what their, if they're worth millions of dollars or they're living a life well below their means, but like, I just think somebody who's just kind and like humble and like 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 greatness. Oliver, you're a really good person. We appreciate you. A lot of your fans and followers here are loving the journey and they're grateful that you're going live.

So I want to acknowledge you for taking the lead, man. It's a scary dream that you had and you 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. We're 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 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. Of course, man. Well, stay in touch, man. And I can't wait to watch the next content. We'll see you, Bradley. All right, man, thanks.

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