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

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 +1 (614) 350-3960More 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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

• 0:26Speaker 01

  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.

• 0:33Speaker 00

  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 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 dreams, find the point of no return and then...

• 1:23Lewis Howes?

  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 @sailingwithphoenix 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.

• 1:58Speaker 00

  Uh, yeah, my name is Oliver Widger and...

• 2:02Speaker 00

  Yeah.

• 2:03Lewis Howes?

  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?

• 2:18Speaker 00

  Uh, yeah.

• 2:20Lewis Howes?

  That something is, something is off in your body. Is that correct?

• 2:23Speaker 00

  Yeah, well, so like I, I had neck pain for a really long time, like for a long time, but I like, I don't like going to the doctor. So I just, uh, um, you know, put it off and then it, it just got, started to get really, really bad. And, uh, so yeah, I went to finally, I went to like, I almost got, cause I can't go to a chiropractor. I started out going to a chiropractor and like, yeah, hindsight is they could have like immediately paralyzed me. And, uh, I just got lucky that didn't happen and, um, none of that worked. And so I finally, I finally like called my doc or I finally like called a doctor and I was like, I need to, I need to see like a doctor, doctor.

• 3:04Speaker 00

  I need to figure this out cause it's insane. And, uh, yeah, I went to the doctor and they took some x-rays. And then I, um, you know, they didn't think of any of it, you know, he's, I don't know. But, and then I, uh, I was at work like the next day and they called me when I was at, uh, at work. And the, the doctors, she was like, what are you doing right now? And I was like, I'm at work. She's like, you need to come in right now. And I was like, okay. So I go in and, uh, she like, she was like freaking out, like she didn't handle it very well. Cause like she, she was a, uh, she was orthopedic specialist. So she wasn't like a neurologist.

• 3:44Speaker 00

  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 a hundred and 20 years old. And, um, I, uh, uh, 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 four neurologists.

• 4:20Lewis Howes?

  Wow.

• 4:21Speaker 00

  And, uh, all of it was really, really bad and, uh, 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, right now I am physically capable of doing anything I want, really. As far as, like, I can't do anything that, like, I can't do anything that involves any sort of impact. But, um, but I, you know, physically I can, I, you know, I've got all my limbs, you know, and I'm ruined. And wasting it at work, twenty-nine.

• 5:01Lewis Howes?

  Twenty-nine.

• 5:02Speaker 00

  Yeah.

• 5:02Lewis Howes?

  So you're getting, you're getting all these doctors saying that you've got a spine of a hundred twenty-year-old.

• 5:07Speaker 00

  Yeah.

• 5:07Lewis Howes?

  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?

• 5:14Speaker 00

  Yeah, it was just like, like, I jumped into it and, uh, I didn't have any, like, I barely graduated high school. And it's a, it was a good, as far as like the money goes, it was a good job, like, you know, there's a lot of, like, potential for money within the job. So I was like, alright, this is it, this is, I'm gonna be able to do the, buy the house and have the, you know, the fence and kids and whatever. And, uh, and then that immediately after the diagnosis, I just started to question all of that. Now, I was like, I don't really wanna do any of that, like, this, this actually sucks. And, uh, um, uh, yeah, and it was like three year, I went through, after the diagnosis, it was like a three-year battle of like, literally I completely lost myself.

• 5:56Speaker 00

  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,

• 6:08Lewis Howes?

  This is after you knew about, this is after you knew about the condition?

• 6:12Speaker 00

  Yeah.

• 6:12Lewis Howes?

  Yeah.

• 6:12Speaker 00

  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, I spiraled completely. And, and then I, I finally, one day I was like, Like I had, I uh, so that video that I posted that you probably saw where I'm in that shirt. You're like, my work shirt.

• 6:38Lewis Howes?

  You're like, I did it.

• 6:40Speaker 00

  Well, before, like the, the original post where I'm in that, the uniform and I'm like, I absolutely hate this life. That full version of that is like two minutes and thirty five seconds long. And it's, it's just, it's wild to watch. It is at the bottom of my TikTok. I'm, I've never taken it down. Um, but I said, my brother, I decided I, I, 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.

• 7:24Speaker 00

  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,

• 7:30Lewis Howes?

  You posted on accident.

• 7:32Speaker 00

  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 uh, 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 uh, what's going on. And then one of the like, the technicians comes up to me. He's like, hey man, what are you gonna buy that boat? And I was like, what in the world are you talking about? And he's like, the boat, man. And then I made the realization and uh, so the, how I left, I had my video. That video is everything. That video is absolutely changed because who knows if I would have had the courage to leave, who knows?

• 8:16Speaker 00

  To leave without that video because, because that video was the most embarrassing thing that's ever happened. And I was there for eleven years and it went to everybody that I know, you know, and it was shared within the company. And uh,

• 8:28Lewis Howes?

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

• 8:35Speaker 00

  This was a year ago, in the deck, but.

• 8:37Lewis Howes?

  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.

• 8:45Speaker 00

  Yeah.

• 8:45Lewis Howes?

  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?

• 9:00Speaker 00

  Yeah, pretty much. Yeah.

• 9:01Lewis Howes?

  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.

• 9:13Speaker 00

  Yeah, I don't know. I don't think so. I mean, who knows? I knew I was gonna quit, but it's one of those things where it's like, I don't know. You know, I don't know if I would have had actually, when it came down to it, had the courage to quit. But that video is what went viral. 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.

• 9:38Lewis Howes?

  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.

• 9:47Speaker 00

  Yeah.

• 9:48Lewis Howes?

  And you're going on a sailboat from Oregon to Hawaii in your 12 days, is that right?

• 9:53Speaker 00

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

• 10:08Lewis Howes?

  Dude, I love seeing the comments of everyone in here saying, you're one of the most inspiring people in the world right now. Everyone's following your journey. They're rooting for you. They're cheering for you. My, my favorite part is the shirt of Phoenix. You know, whenever you wear the shirt with 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, it's so comfortable, even if they're miserable, they'd rather stay safe and miserable than actually go for it.

• 10:42Speaker 00

  Yeah, I figured I was like, I had, when I, when I quit my job abruptly like that, I had like, I don't know, ten thousand dollars in debt or something and with no plan with a twenty six hundred dollar 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.

• 11:28Speaker 00

  And see, I just got really lucky that I got a good, you know, a capable boat. Cause they could have, that could have gone so wrong as well and it didn't. And, uh, yeah, and then I just dived into it with no one, nothing.

• 11:44Lewis Howes?

  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.

• 11:51Speaker 00

  Yeah, everything was like basically YouTube and I just like, I just like, as far as learning how to sail. So I, I, uh, I got the boat. I literally wa- I didn't even watch that many like YouTube videos. I just wa- I bought the boat. In fact, 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.

• 12:22Lewis Howes?

  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 out the dock and just see what happens?

• 12:31Speaker 00

  Yeah, so like a month after, it was about a month after, cause I had to replace some of the lines and stuff on boats. The lines were all like fifteen years old and take throughs. But and I replaced also all of the like rubber components and then, yeah, I took it out.

• 12:49Lewis Howes?

  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 and like 10 days, 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?

• 13:13Speaker 00

  I haven't really even fully processed it like it's insane like it's it is it's it's dude, the like the the experience of I feel like the experience of like, because I went viral on the day that I left. And I'm also crossing an ocean. You know what I mean?

• 13:31Speaker 00

  Two insane things that I'm like that are like, you know, competing with, I was literally fighting for my life the other day while I'm going viral. 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, you know, obviously making the content take a lot of time and then the rest of my time goes towards like managing the both. So there's not a lot of time.

• 13:53Lewis Howes?

  Staying alive. Yeah. Not a small thing, you know?

• 13:56Speaker 00

  Yeah. And it's been so, it's been so cool to 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's.

• 14:13Lewis Howes?

  Is man, I'm reading, I'm reading some of the comments here where one mom said, my son and all his friends are glued to their phone, waiting for your next video and they're all inspired. So again, you're you're helping kids, you're helping adults. Again, there's the compilation video you made, I guess, from all the either TikToks or the Instagram videos of people watching your journey. That is inspiring because so many people from all walks of life, different backgrounds, different races, different economic classes. All feel the pain of not pursuing something that they know they should be pursuing, or they're stuck in a relationship that they know they need to get out of, but they're afraid.

• 14:54Lewis Howes?

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

• 15:06Speaker 00

  He's got to jump like that is the hardest part.

• 15:10Lewis Howes?

  How did you overcome the fear of being worried about what everyone thinks about you? By doing some crazy idea?

• 15:17Speaker 00

  That was the biggest 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 sold on me, but one of them was, was like, I literally completely came to terms with possibly being broke for the rest of my life until I died, like being just poor and dying poor. I could, I absolutely became like completely content with that idea. And once I became content with that idea, I was freedom. You know what I mean? I had freedom. And that's what it came down to, because that was one of my fears. It's like, I'm gonna be poor.

• 15:59Speaker 00

  No one's gonna, you know, who's gonna wanna 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 wanna date a guy on a bum on a boat? And all that stuff, you know, I, and you just, all of it is nonsense. All of it is noise. And you just gotta, I don't know, you just gotta go for it, I guess.

• 16:21Lewis Howes?

  Oliver, what about your parents? Are your parents still around? Do you have siblings?

• 16:24Speaker 00

  Yeah, most of my mom and brother live in the UK. And my, yeah, my dad is, is in the US. And they're, they're proud.

• 16:33Lewis Howes?

  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 did they say?

• 16:43Speaker 00

  They were, I think they, they saw how miserable I was. And I'd been, you know, it was like three solid years of being like, at the lowest low. And they could see it. And so I think they, they were probably like,

• 16:59Speaker 00

  you know, they were probably like, I mean, anything better, you know? And so. Um, but they've 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, alright.

• 17:20Lewis Howes?

  And now that they know, like, just go, that, who cares?

• 17:23Speaker 00

  Yeah, yeah.

• 17:24Lewis Howes?

  Dude, this is incredible, man. Um, what is the, you wrote about fifteen, twenty days away from Hawaii. Do you know which island you're trying to land on? Twelve days to Oahu. You go to Oahu.

• 17:37Speaker 00

  Yeah.

• 17:37Lewis Howes?

  Um, do you, do you know, have you been to Hawaii before?

• 17:41Speaker 00

  I've been to Maui before, yeah. I've got, one of my other brothers is on Maui, actually.

• 17:45Lewis Howes?

  Can I land in Maui?

• 17:47Speaker 00

  No, I, originally I wanted to go to Maui because he's there. Um, but I, uh, uh, decided to go to Oahu because Ma- 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 logistical sense.

• 18:12Lewis Howes?

  I want, I want like thousands of people to be there when you arrive and just,

• 18:17Speaker 00

  Yeah.

• 18:17Lewis Howes?

  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.

• 18:31Speaker 00

  Yeah.

• 18:32Lewis Howes?

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

• 18:54Speaker 00

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

• 19:19Speaker 00

  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.

• 19:29Lewis Howes?

  Dude.

• 19:31Lewis Howes?

  What what is your greatest fear?

• 19:34Speaker 00

  Um. Falling off the boat.

• 19:38Lewis Howes?

  You jumped off the boat already, right?

• 19:41Speaker 00

  Yeah, but it was completely become.

• 19:43Lewis Howes?

  Yeah, yeah.

• 19:44Speaker 00

  Yeah.

• 19:44Lewis Howes?

  Falling off the boat, but you've got a life jacket. Are you? Are you tying yourself up? Are you taking like?

• 19:49Speaker 00

  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 a point wearing a life jacket. There's nothing around here. If I fell in the water, the life jacket would just prolong.

• 20:04Lewis Howes?

  The. Wouldn't it help you swim back to your boat or something?

• 20:08Speaker 00

  No, the boat sails itself like I'm going. It's going like. Right now, though, like six knots.

• 20:14Lewis Howes?

  Well, unless it stopped and you had the sails down and you fell off like you did, then it's fine. But if you fall off when it's going. You can't.

• 20:21Speaker 00

  Now if I fell off, yeah, you not get back on.

• 20:24Lewis Howes?

  Oh, snap.

• 20:25Speaker 00

  Yeah.

• 20:25Lewis Howes?

  You better. Remember that harness. Rope yourself.

• 20:28Speaker 00

  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.

• 20:41Lewis Howes?

  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.

• 20:52Speaker 00

  You'd Alan can do it. I'm I'm not like, I can't stress that I am as below. I do. I wasn't. I wasn't. I haven't told anyone this, but I was a 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 like. This is this is how I organize my notes. You know what I mean? This is. Piece of paper. I can't. I can't even read it. It's not even right.

• 21:23Speaker 00

  Yeah, so like I can't stress that enough is like all the only thing I can do there's only there's one thing in my life that I could do well and that is I can grind I can work so hard and that's the only thing if I lean into that I can do I could do anything so that's what it's come down to and that's what I've done.

• 21:41Lewis Howes?

  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?

• 21:50Speaker 00

  When do I feel the most loved? Uh, right now I feel pretty loved but uh I don't know it's when do I feel the most loved? Um, I don't know or like when I when I when I talk to like my mom and brother I guess I don't know because they you know they they love me unconditionally they've loved me they you know they love and my dad they love me like through and through it doesn't really matter what frame of mind what where I'm at in life they've just you know loved me.

• 22:28Lewis Howes?

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

• 22:33Speaker 00

  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 uh they you know they've seen me go through some weird stuff you know what I mean and they've never they've just you know they've just the love is there always you know what I mean if that makes sense they've always unconditionally loved me it doesn't matter where what's what's where I am in life they just have.

• 23:08Lewis Howes?

  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 gotta 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 uh these videos is really inspiring and I'm curious if you could go back uh you said you're 29 is that right Oliver?

• 23:45Speaker 00

  Yeah.

• 23:45Lewis Howes?

  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?

• 23:56Speaker 00

  Literally, I tell people this that are young all the time that like message, because you know, I get messages and stuff. I tell them, dude, if I could go back in time and I was 18 or 20 or whatever. Because, you know, you see these guys, they're getting into the job. I was 18 when I got into my job. And like, I thought this is what I needed to do and like, I would literally get a globe. And I would spin the globe and then I would stop the globe with my finger. And I would have a, you know, buy a plane ticket, a one-way plane ticket and go there and sit with, you know, no money and figure it out. And go, that's what I would have done. And I would have done that for as long as I could. That's why, that's what I recommend people do is spin the globe, point and go, you know, go see the world.

• 24:40Lewis Howes?

  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?

• 24:52Speaker 00

  Um, hell yeah. Sweet.

• 25:03Lewis Howes?

  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?

• 25:39Speaker 00

  I don't know. I haven't been able to process it like it's if if it feels unreal. It feels not real like it's it's it doesn't. I'm literally sitting here watching these absolutely absurd sunsets with dolphins jumping. And then, you know, with these insane sunsets and then 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? The all 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 the the uh how real it really is. And it's I mean, it feels unreal. It feels it's absolutely insane like.

• 26:24Speaker 00

  It's just that it that it it worked all of it because it's 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. Edit it six, seven hours a day editing videos and 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 that came, you know, it all blew up together at the same exact time.

• 27:07Speaker 00

  You know, where I left and I went viral, you know, I don't know. It's crazy.

• 27:12Lewis Howes?

  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?

• 27:22Speaker 00

  Yeah, it's all all of it. It's all documented. Yeah.

• 27:25Lewis Howes?

  Posted these on my TikTok or something or where were you posting these other videos last year?

• 27:30Speaker 00

  So most of the videos are on Tik Tok 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 Tik Tok, you'll see a crazy.

• 27:43Lewis Howes?

  Okay, I got you. Now I gotta ask you because again, I'm seeing so many comments coming here. People say they come and check on you every day just to see how you're doing. I gotta ask, how's Phoenix? Can we see Phoenix as well?

• 27:55Speaker 00

  Yeah.

• 27:55Lewis Howes?

  Let's, let's see her. You gotta, you gotta figure out. Do you have another question too? You want to ask one? You want to come on and ask?

• 28:04Speaker 00

  Here she is, Santa's kiddies.

• 28:06Lewis Howes?

  Oh, Phoenix. Oh, man. We need to make Phoenix shirts and just sell them online for you. You know, that's the only thing to do.

• 28:17Speaker 00

  Yeah, I'm working on it.

• 28:19Lewis Howes?

  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 gotta go live on your own at some point, once a day, so people can be checked in on what you're up to.

• 28:34Speaker 00

  I've been trying on Tik Tok. It's just, obviously I'm, I am in, in an ocean. So I do have to like, you know, do things.

• 28:42Lewis Howes?

  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 fun, go fund me where people can donate to support you on this journey. I'm, 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, five dollars. 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, or 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

• 29:22Lewis Howes?

  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 of your investment money. And you're on this journey for the last 12 days from Oregon to Hawaii sailing by yourself with a cat.

• 30:02Lewis Howes?

  And from the looks of it, you look happier, healthier, and freer than you've ever been in your life. Is that correct?

• 30:09Speaker 00

  100%. Yeah, I like literally feel healthier. Like it's crazy.

• 30:14Lewis Howes?

  You feel this way.

• 30:16Speaker 00

  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. Like I feel so much better even then stopped working out because I had to use all that time to work on the boat. And I feel better. And I guess if I wanted to, I did give, you know, if there's somebody that is looking to to chase their their dreams, like something that I've I realized is like,

• 30:49Speaker 00

  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 I mean, it's the fear. The fear will drive you. And you're all in at that point. And and I went all in with like, I when I left Hawaii and I've I appreciate the I also do want to say thank you to everyone for like the the GoFund. I've never advertised or talked about the GoFundMe because I think it's weird. And but I did just put it up.

• 31:31Speaker 00

  And I, you know, a bunch of people have obviously donated it and it's well, I've only put $10,000 in there. Because that's I but when I left Oregon, I was $10,000 in debt. Well, 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.

• 31:59Lewis Howes?

  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, 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.

• 32:27Speaker 00

  Yeah.

• 32:28Lewis Howes?

  Move forward, even though it's uncertain, it's unknown.

• 32:31Speaker 00

  Yeah.

• 32:31Lewis Howes?

  And, and you're doing that. And you're sailing in the ocean.

• 32:34Speaker 00

  Yeah. And believe you can do, 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.

• 32:48Lewis Howes?

  Can you quiet the critic or the doubt in your mind?

• 32:51Speaker 00

  You keep going.

• 32:52Lewis Howes?

  As a person that's, you know, struggled in school, didn't have the job that you wanted. You know, had back pain for the last 10 years. How did you overcome the self critic and the doubt?

• 33:04Speaker 00

  I just, there's no option. Like, I didn't have an option but to succeed. Like, my, my hopes. Yeah, just didn't have an option to succeed. I, I just kept going. I just, it, one thing that I would do a lot. So I've tried to do this once before, a few, two years, 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'll, 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, I've adopted a sailor, all of these trades.

• 33:48Speaker 00

  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.

• 34:13Speaker 00

  Don't think about anything, get the boat. You don't have a boat. That's your problem.

• 34:18Lewis Howes?

  Don't think five years in ahead of like, when I get the boat and what if I fall in the middle of the ocean? And what happens then? How I save my life? Just one step at a time.

• 34:26Speaker 00

  Yeah. And so that's what I did. I like, whatever the problem was in front of me, I did that. So I got the boat. Okay. Well, I don't know how to sail. All right. We'll start sailing and 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. Social media was my, this, I did my, this all, only will all work if social media came together. Because that's, that could fund my expedition around the world. And so my plan was always that social media was going to work. It's always a plan. And I was going to keep going until it worked. I've posted every single day. Terrible posts, good posts, but I've done it every single day for a year.

• 35:12Speaker 00

  And, and I, with, with the intention of going forever. You know what I mean? And not stopping. Like I've just going forever and, and it worked. It worked.

• 35:26Lewis Howes?

  Did someone give you the, 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 Tik Tok every day and document this?

• 35:36Speaker 00

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

• 35:40Lewis Howes?

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

• 35:44Speaker 00

  No, before a year ago now.

• 35:47Lewis Howes?

  So you're just like, I'm going to figure out social media. You weren't on there. Maybe you're on there.

• 35:53Speaker 00

  If you go to the bottom of my Tik Tok, 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, 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 everyone thought I was insane. Everybody. And it's so weird now because they're all now messaging me and going, I always believed you.

• 36:24Speaker 00

  Then he didn't.

• 36:26Lewis Howes?

  This whole time I believed in you. Yeah. Wow, man.

• 36:29Speaker 00

  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.

• 36:41Lewis Howes?

  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?

• 37:08Speaker 00

  I knew I was gonna 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, the only people I spoke to were the people at the Marine Store, really. And that was it. And so I've been completely isolated for, by the time I get to Hawaii, it'll be like six months. Other than I did a send off thing right before I left, so I did have some people come to the boat. But aside from that, I've been in complete isolation.

• 37:54Speaker 00

  And I, I, I'm comfortable with my own thoughts alone, you know what I mean? So I'm fine and I do well. I'm not a, it's, it's weird because like I'm on social media, but I'm, I'm not, I'm a keep to myself person. I'm, I am awkward and I'm, if somebody, you know, comes to say, says, says hello to me in person and stuff, I'm totally weird. So I don't remember what the question was, but.

• 38:23Lewis Howes?

  No, excuse me. It was 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?

• 38:33Speaker 00

  Yeah, yeah, yeah, I feel good. I feel I trust myself and I trust my the work I've put into the boat. And I trust my ability to solve pretty much every problem that can come up. Because when crossing an ocean, it's not like what will break or it's not like if something will break. It's what will break and being able to being able to have the resources on board and the the kind of the skills to to to solve the issue like I I the worst thing like the worst thing that could break is literally like the rudder. It's one of the worst things and it broke and on day like six or something at the worst time. It was at the height of the storm that I was in. So the way I was like looking up at these waves. Come on.

• 39:14Speaker 00

  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 locked in the starboard position. And it which you're not supposed to go at as to the waves on the side on the side. And it positioned the boat to the waves on the side. So I was literally like the way it was the worst, absolute worst case scenario as far as when that was gonna happen. And then so the boat like literally was would go from this all the way to this within like three seconds. And it was just going like this. Like peril. And because that's.

• 39:59Speaker 00

  Well, to be up. Wow. Yes, I hear about cap science. I it was like that for like three or four hours while I was trying to solve it. And I I jumped into the engine room. 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 I 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. That was the scariest moment of my entire life. Hands down. Wow. But yeah.

• 40:44Speaker 00

  And what what about so what about a phoenix during that time is is she like.

• 40:50Speaker 00

  At that point, she was already like well adjusted to the boat. Um, so I'm sure.

• 40:54Lewis Howes?

  She get motion sickness too, or no?

• 40:56Speaker 00

  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 watch 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.

• 41:14Lewis Howes?

  That's amazing. What did I mean? Do you have her harnessed up also if she's out on the deck or would she follow?

• 41:21Speaker 00

  I'm the kind of guy that would absolutely walk my cat. So I spent like, like she's seven years old now and she was a feral cat when I got her. And um, she uh, I spent like three years trying to walk my cat. It's impossible. It is an impossible task. So I can't get a harness on her.

• 41:38Lewis Howes?

  But is she not out there on the deck? You do?

• 41:41Speaker 00

  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 that's the only time when I'm on shore. Oh yeah, she can go on.

• 41:55Lewis Howes?

  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?

• 42:10Speaker 00

  Yeah, it's on my highlight. So if you go, if you click on my highlight.

• 42:15Lewis Howes?

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

• 42:19Speaker 00

  Yes, we're having really well.

• 42:21Lewis Howes?

  There's like no lag, it's.

• 42:23Speaker 00

  Yeah, I didn't know if it was gonna work. So like I had to like literally, cause 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 know how people'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 it's dude, it's, it's worked really well this whole time.

• 42:44Lewis Howes?

  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 16 hours at once?

• 42:52Speaker 00

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

• 43:36Speaker 00

  And I don't know if you ever heard a tree fall? Cause the next, the following day I was outside and a tree fell. And it sounds like a fricking grenade goes off. Like it's insane. And, uh, so I could sleep through anything, which is like a blessing and a curse. Cause if something happens, I'll probably sleep through it. But, um, I think the thing that, that, that where sailors meet their demise is because of sleep deprivation. We'll not have that problem with us.

• 44:06Lewis Howes?

  Your problem will be you won't wake up.

• 44:08Speaker 00

  Yeah.

• 44:08Lewis Howes?

  Crash. Yeah, yeah.

• 44:09Speaker 00

  Yeah.

• 44:10Lewis Howes?

  Um, but you gotta, you gotta share it one more time. You gotta show the cat, Phoenix the cat one more time. Cause everyone's, everyone who came on late is asking, where's Phoenix?

• 44:18Speaker 00

  Yeah, yeah.

• 44:22Speaker 00

  Here she is.

• 44:24Lewis Howes?

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

• 44:29Speaker 00

  Yeah, she sleeps next to me and, uh, um.

• 44:35Speaker 00

  Yeah, we're we she like she sleeps right here and I sleep right here.

• 44:41Lewis Howes?

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

• 44:44Speaker 00

  Yeah.

• 44:44Lewis Howes?

  Um, yeah, all right. 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 make this out there on my podcast, but I wanted to just one more time say that it's really inspiring what you're doing. And again, for those that are just tuning in, Oliver's from Oregon, he had a diagnosis about his back that was not good from the doctors and wasn't living the life that he envisioned. You weren't living that beautiful, healthy, rich life internally and externally. And he decided to quit his job because he wasn't

• 45:24Lewis Howes?

  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 because again, 99% of people won't go after the big scary dream that they have

• 46:10Lewis Howes?

  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 will regret it.

• 46:22Lewis Howes?

  And you're happier and healthier than you've ever been in your life right now.

• 46:26Speaker 00

  Yeah, yeah.

• 46:27Lewis Howes?

  And that's amazing.

• 46:28Speaker 00

  I feel like all those things are guaranteed is is people laughing at you going broke and all that stuff because all that happened. I yeah, but. It works.

• 46:38Lewis Howes?

  What's one, what's, I mean, people are gonna be watching your journey every single day. Uh, and I can't wait to, and I can't wait to celebrate you and, you know, send you a, a FaceTime or a text when you land in Hawaii.

• 46:51Lewis Howes?

  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 journey?

• 47:10Speaker 00

  You know, you know, the answers. You know, the answers to clear, you know, the answers. And if, if, if you're, if you're questioning the relationship or the job and, and you've been questioning the relationship, the job, that is the answer. Like you've got the answers. It's that simple. You've got the answers for the, for, for a better life. You just got to do it. And, 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 at, at the, cause 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?

• 47:54Speaker 00

  Cause 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, 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, 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 a 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 I, 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.

• 48:38Speaker 00

  And, uh, just, just go for it. So, um.

• 48:42Lewis Howes?

  I love that, man. We are, it, it is Mother's Day today while we're recording this live. I'm curious, what's your message? What's your, what's your message to your mom and the greatest lesson your mom's taught you?

• 48:52Speaker 00

  Oh, my mom was my biggest fan. She's my biggest fan. She loves me. Through and through and she she's from the beginning, she's liked every single video. She's she even she my mom doesn't have like a lot of money at all and she like she goes she goes and like GoFundMe and donate. If she'll donate like twenty five bucks, fifty bucks. And I literally had 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 questions, but yeah.

• 49:27Lewis Howes?

  So your mom, that's great and that she's 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?

• 49:45Speaker 00

  Um, uh, my definition of greatness is just to be, uh, 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, 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.

• 50:19Lewis Howes?

  Um, Oliver, you're a really good person. We appreciate you. A lot of your fans and followers here are loving the journey and they're grateful that you're going live. So I want to acknowledge you for taking the lead, man. It's a, 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. 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.

• 50:48Speaker 00

  Yeah, appreciate it, man. Thank you very much for having me. That's cool.

• 50:51Lewis Howes?

  Man, we'll stay in touch, man, and I can't wait to watch the next content. We'll see you, brother. All right, man. Thank you. I have a brand new book called Make Money Easy. And if you're looking to create more financial freedom in your life, you want abundance in your life, and you want to stop making money hard in your life, but you want to make it easier, you want to make it flow, you want to feel abundant, then make sure to go to makemoneyleasebook.com right now and get yourself a copy. I really think this is going to help you transform your relationship with money this moment, moving forward. I hope you enjoyed today's episode and it inspired you on your journey towards greatness.

• 51:32Lewis Howes?

  Make sure to check out the show notes in the description for a full rundown of today's episode with all the important links. And if you want weekly exclusive bonus episodes with me personally, as well as ad free listening, then make sure to subscribe to our Greatness Plus channel exclusively on Apple Podcasts. Share this with a friend on social media and leave us a review on Apple Podcasts as well. Let me know what you enjoyed about this episode in that review. I really love hearing feedback from you and it helps us figure out how we can support and serve you moving forward. And I want to remind you, if no one has told you lately, that you are loved, you are worthy, and you matter. And now it's time to go out there and do something great.