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

18 Jun 2025 · 52 min

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In short

Podcast Episode Notes: The School of Greatness - Sailing With Phoenix

Episode Overview

  • Episode Title: Sailing With Phoenix: “I Quit My Job To Sail The World & Discovered My Purpose”
  • Host: Lewis Howes
  • Guest: Oliver Widger
  • Key Themes: Pursuing dreams, facing mortality, finding purpose, overcoming self-doubt.

Guest Introduction

  • Oliver Widger: Former corporate worker who transformed his life after a severe spine diagnosis led him to quit his job and sail across the Pacific Ocean with his cat, Phoenix. His journey has garnered a massive following on social media.

Key Topics Discussed

  1. Catalyst for Change
  2. Oliver's life-altering spine diagnosis at age 29 revealed he had the spine of someone over 120 years old.
  3. This diagnosis forced him to confront his mortality, leading to a three-year struggle with partying and self-doubt.
  1. The Turning Point
  2. A spontaneous video posted on TikTok, expressing his disdain for his corporate life, inadvertently went viral and reached his bosses.
  3. This embarrassing moment became a catalyst for his decision to quit and pursue sailing.
  1. Chasing Impossible Dreams
  2. Oliver liquidated his 401k, sold his possessions, and bought a sailboat to realize his dream.
  3. Emphasizes that anyone can achieve extraordinary things with determination, regardless of their past or perceived limitations.
  1. Overcoming Self-Doubt
  2. Shared a simple strategy: solve only the problem directly in front of you instead of becoming overwhelmed by the bigger picture.
  3. Oliver emphasizes that he had no prior sailing experience but learned through trial and error, mainly utilizing YouTube tutorials.
  1. Finding Your Purpose
  2. Suggests a ridiculous question to discover one’s purpose: "What crazy thing do you actually want to do?"
  3. Discussed how he embraced the concept of dying poor as a form of ultimate freedom.
  1. Lessons Learned from Sailing
  2. After 12 days at sea, Oliver feels healthier and more fulfilled than ever.
  3. Overcoming fears and self-criticisms has been part of the journey; he learned to trust himself and his ability to solve problems at sea.

Key Takeaways

  • Finding Purpose:
  • It's vital to identify what truly makes you happy, regardless of societal expectations.
  • Facing Fears:
  • Embracing the fear of failure can lead to profound personal growth and fulfillment.
  • Live Authentically:
  • Sharing one’s genuine experience can inspire others to take action in their lives.
  • Support Systems:
  • Family, friends, and online communities can provide crucial encouragement when pursuing dreams.

Final Thoughts

  • Oliver’s journey illustrates that taking risks, despite the fear of failure and judgment, can lead to extraordinary life changes.
  • Encourages listeners to chase their dreams and not to shy away from exploring their true desires.

Resources Mentioned

  • Oliver's TikTok: [Sailing With Phoenix](https://www.tiktok.com/@sailing_with_phoenix)
  • Oliver's Instagram: [Sailing With Phoenix](https://www.instagram.com/sailing_with_phoenix/?hl=en)
  • Lewis Howes' Book: *Make Money Easy* - [Link to book](https://lewishowes.com/money)

Conclusion

  • The episode serves as a powerful reminder of the importance of pursuing one's passions and being brave enough to take the leap into the unknown. Oliver’s story showcases resilience and the potential for transformation that lies within all of us.

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Transcript

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0:00I went to the doctor and they took some x-rays and the doctor said she was like your spine is like somebody who's over 120 years old. After the diagnosis, I spiraled completely. And then I finally one day I was like, my name is Oliver. I work a corporate job at a tire shop. I absolutely hate this life. Yeah, I'm gonna buy a sailboat and I'm going to sail around the world. That's Oliver Widger, who quit his job after he posted that video, liquidated his 401k, bought a sailboat, and started learning how to sail. Our guest for you guys today is the one and only Oliver Widger. I haven't told anyone this, but I was in special ed from first grade to senior in high school.

0:44There'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 I would stop the globe with my finger and I would buy a plane ticket, a one-way plane ticket, and go there. If there's somebody that is looking to chase their dream, find the point of no return.

1:23So I'm so excited, man, because I've been watching your journey over the last few days. My friend Tim was here, showed me your videos. and since three or four days ago when I started watching you, I think your audience has exponentially grown and I love seeing what you're doing. And so we have, if you can, share your full name because on Instagram you're sailing with Phoenix and you are changing and inspiring the world in a massive way. So if you can, share with your full name to the audience who's watching. Yeah, my name is Oliver Widger and yeah and so so you have this video of you working a corporate job and essentially hating your life and at at one point you decide because you have uh test results at the hospital right that yeah that something is something's off in your body is that correct yeah well so like i i had neck pain for a really long time like for a long time but like i don't like going to the doctor So I just, you know, put it off.

2:33And 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. And like hindsight is they could have like immediately paralyzed me. And I just got lucky that didn't happen. And none of that worked. and so i finally i finally like called my doc or i finally like called a doctor and i was like i need to i need to see like a doctor doctor i need to figure this out because it's insane and uh yeah i went to the doctor and they took some x-rays and then i um you know they didn't think anything 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 at work and 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 uh she like she was like freaking out like she didn't handle it very well because like she was the uh she was an orthopedic specialist so she wasn't like a neurologist um but yeah she like was like i don't know how you're here right now talking to me and not in excruciating pain i was like well i am in a bit of pain and that's why i am here and uh she was like your spine is like so i've never i've done this for 20 years i've never seen anything like this your spine is like somebody who's over 120 years old and um i uh uh 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 all long-winded and stuff but i went went through i had to see like four neurologists and uh all of it was really really bad and uh yeah so i 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 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 long like i can't do anything that like i can't do anything that involves any sort of impact right but um but i you know physically i can i you know i've got all my limbs you know and i'm losing and wasting it at work 29 29 yeah so you're getting you're getting all these doctors saying that you've got a spine of 120 year old yeah you were working a job that you didn't really fully love that you were just doing it because you thought you were supposed to do it i guess or you just yeah it's 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 it you know there's a lot of like potential for money within the job so i was like all right this is it this is i'm 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 but i don't really want to do any of that like this this actually sucks and uh um uh yeah and it was like three years i went through after the diagnosis it was like a three-year battle of like literally i completely lost myself and i went down this crazy rabbit hole 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 i spiraled completely um and then i I finally one day I was like, like I had, I, uh, so that video that I posted that you probably saw where I'm in that shirt, you're like my work shirt.

6:38You're like, I did it. Well, before like the, the original post where I'm in the uniform and I'm like, I absolutely hate this life. That full version of that is like two minutes and 35 seconds long. And it's, it's just, it's wild to watch. It is at the bottom of my TikTok. I'm, I've never taken it down. um but i said my brother i decided i i found a purpose i decided i wanted to sail around the world and um my brother convinced me to start documenting it and so 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 i never used tiktok before i didn't know how social media worked so i'm i i was on a tiktok and I put it in as a draft because I thought I could put it in as a draft.

7:30You 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. Then I show up to work the next day, totally oblivious to what's going on. And then one of the technicians comes up to me. 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.

8:07And so how I left, that video, that video is everything. That video is absolutely changed. Because who knows if I would have had the courage to lead. Who knows? To lead without that video. Because that video is the most embarrassing thing that's ever happened. And I was there for 11 years and it went to everybody that I know, you know, it was shared within the company and When did that be like I go first when did that video first get leaked to everyone in your context? It was this a year ago two years ago. When was it this was a year ago? but So you put you filmed this video which I'll put up on YouTube as well You film this video of you in your car saying I hate my life.

8:45Yeah, my life's miserable I've been working this job for whatever eight or ten 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 going to quit but it's one of those things where it's like i don't know you know i don't know if i would have had actually when i came down to it had the courage to 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 and wow man and so you went and so you went from oregon going on a sailboat that you've never been in the ocean before only in a river and you're going on a sailboat from Oregon to Hawaii and you're 12 days in.

9:52Is that right? Yeah, 12 days in, yeah. So I'm like almost a thousand miles away from... I'm basically closer to the people on the space station than I am to anybody on land. Dude, I love seeing the comments of everyone in here saying you're one of the most inspiring people in the world right now. Everyone's following your journey. They're rooting for you. they're cheering for you my my favorite part is the shirt of phoenix you know and everywhere this year was the cat um and i just think what you're doing 99.9 percent 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 yeah i figured When I quit my job abruptly like that, I had like, I don't know,$10 ,000 in debt or something.

10:53And 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 uh so i liquidated my 401k sold my cars i sold literally everything without even like my apartment was empty without even knowing what boat i was going to buy or before or how i was going to buy a boat and uh uh i i spent the following month just like searching for a boat and you see i just got really lucky that i got a good uh you know a capable boat because i could have that could have gone so wrong as well um and it didn't and uh uh yeah and then i just dived into it with 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 it was like basically youtube and uh i just like i just like uh as far as learning how to sail so i I got the boat.

12:01I didn't even watch that many YouTube videos. I bought the boat. I took it out. I made incredible mistakes. I'm lucky to still have the boat. So many things have worked out. There's just really high risk. It paid off. It worked out. Let me ask you, Oliver. You bought the boat and then you just got the keys to the boat and you just said, all right i'm just gonna 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 boat because the lines were all like 15 years old and chaked through so i and i replaced also all of the like rubber components and then yeah i took it out um i i love this for you i don't know why because i'm i love that you're documenting this and you're able to share it in such an authentic way again you've got almost a million followers in like 10 days something how is it how does it feel to know that putting out a few pieces of content and actually chasing your dreams is inspiring millions of people around the world how does that feel i haven't really even fully processed it like it's insane like it's it is it's dude like the the experience of i feel like the experience of like because i went viral on the day that i left and i'm also crossing an ocean you know what i mean two two insane things that i'm like that are like you know competing with i would literally fight for my life the other day while i'm going viral you know like it's it was it's just been so weird and there's not a lot of time to like because i'm still i'm you know obviously making the content 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 not a small thing you know yeah and uh it's been so it's been so cool too like the i that i don't know i've some of the comments that i've read and stuff that like you know it's like somehow some way it's like bringing people together that's the coolest thing in the world that it is man i'm reading i'm reading some of the comments here where one mom said my son and all his friends are glued to their phone waiting for your next video and they're all inspired so again you're you're helping kids you're helping adults again there's the compilation video you made i guess from all the either tiktoks or the instagram videos of people watching your journey that is inspiring because so many people from all walks of life different backgrounds different races different economic classes all feel the pain of not pursuing something yeah that they know they should be pursuing or they're stuck in a relationship that they know they need to get out of but they're afraid they're stuck of the job they they want to launch something on the side even just for fun it's not always about like leaving your job in the relationship but it's like maybe they just had a dream that they want to pursue on the side they're afraid of you just gotta jump like that is the hardest part how did you overcome the fear of being worried about what everyone thinks about you by doing so that was crazy idea that was the base thing that held me back because like i was super worried about like you know literally what solved all of my problems was like there's a few things that's all like but one of them was was like i literally completely came to terms with possibly being broke for the rest of my life until i died like being just poor and dying poor I absolutely became completely content with that idea.

15:47And once I became content with that idea, it was freedom. You know what I mean? I had freedom. And that's what it came down to because that was one of my fears. It's like I'm going to be poor. No one's going to – who's going to want to be with like a poor – I'm going to be single forever. Like all that stuff was the things running through my head. Who's going to want to date a guy, a bum on a boat, and all that stuff. you know i yeah and you just all of it is nonsense all of it is noise and um you just gotta i don't know you just gotta go for it i guess oliver what about your parents are your parents still around your siblings yeah most of my mom and brother live in the uk um and my yeah my dad is is in the u.s but and they're they're proud what did they say originally when you're like i'm gonna quit my job i'm gonna liquidate all my assets and 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 they saw how miserable i was and i had been you know it was like three solid years of being like at the lowest low and they could see it and so i think they they were probably like you know they were probably like i mean anything better you know and uh 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 all right and now that they know like just go that who cares yeah yeah yeah yeah this is incredible man um what is the you wrote about 15 20 days away from hawaii do you know which island you're turning the rain on 12 days of oahu you go to oahu yeah um do you know have you been to hawaii before i've been to maui before yeah i've got one of my other brothers his own maui actually gonna land in maui no i originally i wanted to go to maui because he's there um but i uh uh decided to go to oahu because ma in maui i would need a car to like drive around and so Oahu

18:03there's a marine story there too like a West Marine that's there within walking distance and everything's within walking distance so it just made more legislative sense I want like thousands of people to be there when you arrive and just I want the world to give you a big group hug and just congratulate you on taking the leap and taking the chance and going on the journey because most people in life will never take the leap and go for it yeah and it doesn't matter if like people succeed or fail it's really not it's about it's about going on the journey and seeing what you're made of and so i'm curious what's the biggest lesson about yourself you've learned in the first 12 days of traveling from oregon to hawaii on a sailboat alone with your cat what's the biggest lesson you've learned about you um i i don't know i learned a lot about me on the process over the last year like i am a different person over this last year and uh i i just like i've learned that i'm i i you know i've always had really really really intense like i'm like my hardest critic to the most intense level.

19:16And I just learned that I can do anything. Like, I've done the impossible. Like, I've done everything I've done. I thought it was impossible. So, yeah. Dude. What is your greatest fear?

19:36Falling off the boat. You jumped off the boat already, right? Yeah, but it was completely becomes yeah yeah yeah the falling off the boat but you've got a life jacket are you are you tying yourself up are you taking like there's no life jacket um just because if you fall in a life jacket just prolongs the inevitable so you know but i see for a harness there's a point wearing a life jacket there's nothing around here if i fell in the water the life jacket would just prolong the end wouldn't it help you swim back to your boat or something no the boat sails itself like i'm going it's going like right now i'm like six knots well unless it stopped and you had the sails down and you fell off like you did then it's fine but if you fall off when it's going you can't have to fell off yeah you're not getting back on oh snap yeah you better remember that harness yourself rope yourself yeah where i'm 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 would catch me before i i fall off i love one of the videos you posted where you said you know i can't remember your exact words i'm paraphrasing but you're like i'm an average guy i'm below average and if i can do this you don't want to 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 in special ed from uh first grade to senior in high school like i couldn't do school at all and um i can't write i've got every single like learning disability i 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 yeah so like i can't stress that enough is like all the only thing i can do there's only there's one thing in my life that i could do well and that is i can grind i can work so hard and that's the only thing if i lean into that i can do i can do anything so that's what it's come down to and that's what i've done what is here's a question for you maybe you've never been asked this when do you feel the most loved in your life when do i feel the most loved uh right now i feel pretty loved but uh i don't know it's when do i feel the most loved um

22:07I don't know. Or like when I, when I, when I talk to like my mom and brother, I guess, I don't know. 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? uh they just you know they just they're they're did my parents are separated and don't talk so it's like a weird different dynamic but like they just uh they just you know they've seen me go through some weird stuff you know what i mean and uh they've never they've just you know they've just the love is there always you know what i mean if that makes sense they've always unconditionally love me it doesn't matter where what's what's where i am in life they just have 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 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 yeah if you could go back uh to your 21 year old self knowing everything you've been through in the last almost decade what advice would you give i would literally i I tell people this that are young all the time that like message because, you know, I get messages and stuff.

24:01I 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 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.

24:41I'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?

24:54um hell yeah sweet

25:02oh man what about all the people you know again 12 days ago no one knew who you were and now you've got a million followers and again people are invested in your journey in your life they want to see you win because you're bringing so much hope and inspiration to the world what is it like going from you know nothing 12 days ago and having a dream and starting in the ocean to having a million followers in under two weeks and people so invested in your story how does that feel uh i don't know i haven't been able to process it like it's if it feels unreal It feels not real like it's it's it doesn't I'm literally sitting here watching these absolutely absurd sunsets with dolphins jumping and then you know with these insane sunsets and then And then I'm also viral at the same time and inspiring all these people All these things that are like not real, you know, I mean the old thing.

26:05It'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 it's just that it that it it worked all of it because social media I I've been I didn't know anything about social media or how to edit videos anything I spent I would spend like six hours a day editing six seven hours a day editing videos and just figure making the craziest videos and just figuring it out and uh and then also i would spend literally the rest of my waking moments working on the boat and learning how to sail and i did that for a year straight completely isolated completely locked from the outside world did it for a year straight and uh uh it's just so crazy that like the the it it all came you know it all blew up together at the same exact time you know where i left and i went viral you know i don't know it's crazy when you were when you were you know for the last year buying the boat and learning how to sail and doing all these things and learning how to edit videos were you posting any of these videos or were you just all of it it's all documented were you posting these on my tiktok or something or where were you posting these other videos last year oh so most of the videos are on tiktok and then right around when i got the boat uh a little after i got the boat i started posting on instagram so if you go to the bottom of my tiktok you'll see a crazy okay i got you man now i gotta ask you because again i'm seeing so many comments coming here people say they come and check on you every day just to see how you're doing i gotta ask how's phoenix can we see phoenix as well yeah let's let's see her you gotta figure out you have another question tim you want to ask one you want to come on and ask you want to come on and ask here she is saying it's kitty oh phoenix oh man we need to make phoenix shirts and just sell them online for you you know that's what i'm able to do yeah i'm working on it that's amazing man um and also for people that are out a lot of people are commenting how they've been waiting for you to go live they've been waiting for you to share more so maybe you got to go live on your own at some point once a day so people can be checked in on what you're up to i've been trying on tiktok it's just obviously i'm i am in in an ocean so i do have to like you know do you think and for those again for those that don't know who you are i want people to click on below.

28:47I'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 DoFundMe 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, five dollars. But if you've ever, for anyone watching this, and we're going to post this on YouTube in the audio later, but for anyone watching or listening, if you've ever had a dream that you've been afraid to take on. If you've ever had something like in your heart or your mind 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.

29:31You have to watch this journey because again, I cannot reiterate this enough, Oliver, that you speak about having learning disabilities your entire life, working a job that wasn't enjoyable for you, Maybe he was paying the bills and it wasn't affordable, 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.

30:11I literally feel healthier. Like, it's crazy. You feel physically. Not only do I feel healthier, but my lifestyle, because of the financial side of things, I've been eating 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 their dream like something that I realized is like I guess my recommendation would be to like find the point of no return and then cross that point as soon as you cross that point that's the hardest part as soon as you cross that line it's it's you're all in you're it's you go for it i mean it's the fear the fear will drive you 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 phone i've never advertised or talked about the go fund me because i think it's weird and uh but i did just put it up and i uh you know a bunch of people have obviously donated it and it's well so i've only put ten thousand dollars in there because that's i but when i left oregon i was ten thousand dollars in debt i've gone all in on everything this entire time that i've just you know and uh um now i'm not in debt and it's gone over that so i just wanted to say thank you to everybody for that.

31:59Oh, man. Yeah, again, for people that are, you know, just afraid to go for their dream, it's just inspiring to watch. And you talked about, like, it's really that point of no return. This may be the wrong analogy, but it's, you know, the analogy of burning the boats when you get on new land and you kind of, like, burn your boats. Wrong analogy if you're on a boat, right? Yeah. Where you can't go back. You can't go back to, like, safe land. you have to like take on the new journey conquer the new journey yeah move forward even though it's uncertain it's unknown yeah and and you're doing that and you're sailing in the ocean yeah and believe you can because the whole time i i had this incredible self-doubt the whole time of going through the process all of it is noise it's all it's all bullshit yeah it's all nice Can you quiet the critic or the doubt in your mind as a person that's, you know, struggled in school, didn't have the job that you wanted, you know, had back pain for the last 10 years?

33:01How did you overcome the self-critic and the doubt? I just, there was no option. I didn't have an option but to succeed. Like my hopes, yeah, I just didn't have an option to succeed. I just kept going. I just, one thing that I would do a lot, so I've tried to do this once before, a few, two years, like right after the diagnosis. But what I did was I thought about everything way too far ahead and I discouraged my, I would think about, you know, 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.

33:42I'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 in the head of like, when I get the boat, and what if I fall in the middle of the ocean, and what happens then?

34:23How do I save my life? Just one step at a time. Yeah, and so that's what I did. Whatever the problem was in front of me, I did that. So I got the boat, okay? Well, I don't know how to sail. All right, well, start sailing. And then it started sailing, okay? Well, I don't have any of the right equipment on the boat to cross the ocean. All right. Well, it's still the right equipment. You know, I don't have any money. All right. So social media was like I've always planned. Social media was my – this only will all work if social media came together because that could fund my expedition around the world.

34:58And so my plan was always that social media was going to work. It was always a plan. And I was going to keep going until it worked. I've posted every single day, terrible posts, good posts. I've done it every single day for a year. And with the intention of going forever, you know what I mean? And not stopping. Like, 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 a lot on instagram or to talk every day and document this or is this just not this is all on my mind this is all on my mind but you weren't really you weren't on social media before this for you no before a year ago now so you're just like yeah i'm gonna figure out social media you weren't on there maybe you're on there if you go to the bottom of my tiktok 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 be like you are you okay like dude i'm just trying to figure this out you know what i mean like and uh everyone thought i was insane everybody and it's so weird now because they're all now messaging me and going i always believed in you yeah then you didn't you had this the whole time I believed in you.

36:28Yeah. Wow, man. Yeah. And I just kept going through all that. And, you know, there's times where I thought I was insane myself. And I just kept going. What do you want people to know about the way you think, the way you feel, the way you act that maybe they don't know about yet? If you could share a little bit more about how you think about this process or what's going through your head. Again, it's probably lonely out there. even though you have tons of comments and people loving on you on social media you're alone in the middle of the ocean with a cat do you feel lonely or do you feel like how do you put yourself to sleep calmly and feel safe all that stuff i knew i was going to be fine with the isolation on this passage because i'm not kidding the past five months so i i spent i learned how to sail for the first like six months and that's when i taught myself how to sail and then the last five months i didn't sail at all and i spent every single day 10 hours a day working on the boat in complete isolation i didn't speak to another soul ever like i literally just uh the only people i spoke to were the people at the marine store really and that was it and so i've been completely isolated for um by the time i get to hawaii it'll be like six months um other than i did a send-off thing right before i left so i did have some people come to the boat but aside from that i've been in complete isolation and um uh i i i'm comfortable with my own thoughts alone you know what i mean so i'm fine and uh i do well oh i'm not a um it's it's weird because like i'm on social media but i'm i'm not i'm a keep to myself person i'm i am awkward and i'm if somebody you know come say says that says hello to me in person and stuff i'm totally weird so uh i don't remember what the question was but no it's good man it's just more like how do you think about it if you're being if you're alone in the ocean for all this time like is your mind okay do you feel like safe emotionally yeah yeah yeah i feel good i feel i trust myself and i trust my the work i've put into the boat and i trust my ability to solve pretty much every problem that can come up because when crossing an ocean it's not like what will break or it's not like if something will break it's what will break and being able to being able to have the resources on board and the the kind of the skills 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 uh 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.

39:19It's the sailor's, it's the sailor's worst curse is that the camera doesn't do waves any justice. And, um, so yeah, my rudder broke and it, it, it locked in the starboard position and it, which you're not supposed to go at, as to the waves on the side, on the side. And it positioned the boat, uh, to the waves on the side. So I was literally like the way it was the worst, absolute worst case scenario as far as when that was gonna happen and 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 loads of you up wow yes airboats cap science i it was like that for like three or four hours while i was trying to solve it and uh i i uh jumped into the engine room um and i'm in the engine room and i see the cable came off the quadrant and i'm literally getting thrown from one side to the other while i'm trying to fix this cable in the quadrant and not let the because as soon as you put the cable back on it it'll you know the rudder will like slam back and uh you know i was trying to not to like lose my fingers so i got a screwdriver down in the back and i tried to pry the the cable back around the quadrant it was crazy that was the scariest moment of my entire life hands down but yeah so what about phoenix during that time is is she like at that point she was already like well adjusted to the boat um so i'm sure she did you get merchant sickness too or no she only once when i first took the boat out like a year ago.

41:01She's an aqua-blown boat cat now. It's crazy. She gets around better than I do. She walks around like a gimbal. She anticipates the wave so well. She's like a gimbal cat. Do you have her harnessed up also if she's out on the deck? I'm the kind of guy that would absolutely walk my cat. She's seven years old now. She was a feral cat when I got her. I spent like three years trying to walk my cat. It's impossible. It is an impossible task. I can't get a harness on her. I don't let her out on the deck. You do? No, I don't let her out there unless it's really calm. And she doesn't leave the cockpit area.

41:47And she's my attention. You know what I mean? So that's always how I'm... When I'm on shore, yeah, she can get where I was. Sure, sure, sure. Dude, this is crazy, man. I got a few final questions, a few minutes left for you, if that's okay. A lot of people are asking, you know, if people go to your Instagram right now, do you have the location where you are, like, live on the map? Yeah, that's on my highlight. Okay. So if you click on my highlight. Do that. And, man, is this Starlink that you're using on the boat? Yes, we're having it well. There's, like, no lag. Yeah, I didn't know if it was going to work.

42:24So, like, I had to, like, literally, because I did have some followers. I had like 60 ,000 followers before I left. And so I had to like literally just tell him like, hey, look, I'm, you know, I know how deep this is going to work. Yeah. I don't know if it's going to work. And I'll see you guys probably in 30 days. But it's, dude, it's, it's worked really well this whole time. 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 to eight hours at once? I remember on like the weather, like there's no sleep schedule really.

42:55it's just you sleep when you can like if i after this call if i get a uh a wave of tiredness i'm gonna take advantage of that because right now the boat's balanced the boat's good so i'm gonna take advantage of that i'm gonna go to sleep for a couple hours and then um so yeah and it depends on the weather so like last night i stayed up till like 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 Yeah, but I get plenty of sleep. Like one of like the greatest, I once fell through a tree, a full tree coming through my apartment.

43:32It came through the roof of my apartment. I slept through the whole thing. And I don't know if you ever heard a tree fall because the next the following day I was outside and a tree fell. And it sounds like a freaking grenade goes off. Like it's insane. and so I could sleep through anything which is like a blessing and a curse because if something happens I'll probably sleep through it but I think the thing that that That where sailors meet their demise is because of sleep deprivation We'll not have that problem Your problem will be you won't wake up Yeah You gotta you gotta share one more time.

44:13You got to show the cat Phoenix the cat one more time Everyone who came on late is asking, where's Phoenix? Yeah. Yeah. There she is. Oh, such a sweetie. Does she sleep next to you also or no? Yeah, she sleeps next to me. And, yeah.

44:39She sleeps right here. I sleep right here. Oh, man. You're living the dream, man. Yeah. Yeah. Oliver, again, I know you've got a lot of activities you've got to do on the boat, but I'm glad we got connected, and I wanted to share your message with my audience. I'm going to make this out there on my podcast, but I wanted to just one more time say that it's really inspiring what you're doing. it again for those that are just tuning in oliver's from oregon he had a diagnosis about his back that was not good from the doctors and wasn't living the life that he envisioned you weren't living that beautiful healthy rich life internally and externally and he decided to quit his job because he wasn't fulfilled at the job he was at and really pursued the dream of traveling around the world on a sailboat and experiencing life to the fullest based on your dreams maybe it's not i wouldn't want to do that but your dream was to do that and you sold everything you liquidated your 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.

45:56I'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 because they're too afraid to fail or what if, or what if I go broke or what if I don't have any money or what if everyone laughs at me? And so what? You know, if they do, okay. Well, at least you will 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 is people laughing at you going broke and all that stuff because all that happened i yeah but it works 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 send you a FaceTime or a text when you land in Hawaii.

46:50But what's one final message for this conversation that you'd love to send to people? If they're struggling in a relationship where they feel like they know they've got to get out of, if they've got this artistic dream or music dream or something they want to pursue, but they've been too afraid of what people are going to think about them, what's one final piece of advice or wisdom you would share based on your journey? You know. You know the answers. You know the answers. you know the answers and if you're questioning the relationship or the job and you've been questioning the relationship, the job, that is the answer like you've got the answers it's that simple you've got the answers for a better life you just gotta do it and that will solve that problem you know, so I don't know, you have the answers I guess the hard thing for me because at the beginning of the spine thing at the very beginning i i and before that too i didn't know like i didn't have like uh it's really hard for me to find like a purpose you know what i mean because i think a lot of people are a lot like they think that's really cool and stuff what i'm doing and all that but they they don't know how to find their purpose or they don't know what the thing is they want to they want to do all the things but they don't know what it is what their purpose is and that I think a lot of people get trapped in that and um it's hard to find your purpose but in hindsight it's easy you know what I mean like it's like what do you what's the ridiculous thing you want to do like sailing around the world on a boat with my cat is ridiculous you know what I mean it's ridiculous but it's that's like a ridiculous dream that I had and so why don't I just make that my purpose it's it is simple you know what I mean like if what is it you want to do do that and just go for it.

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48:42I love that, man. It is Mother's Day today while we're recording this live. I'm curious. What's your message to your mom and the greatest lesson your mom's taught you? My mom is my biggest fan. She's my biggest fan. She loves me through and through. From the beginning, she's liked every single video. My mom doesn't have a lot of money at all. and she like she goes she goes into like go fund me and donate if you'll donate like 25 bucks 50 bucks and i literally have to be like mom stop stop doing that and uh um yeah she's the greatest she just is the greatest and uh yeah um i think i can't remember the rest of the question but yeah your mom that's a great uh that she supported you on this whole journey doing some crazy your aim that's amazing uh final question for you oliver because i want you to go call your mom and i know you got a lot to do on the boat um i asked this at the end of all my interviews uh what is your definition of greatness um my definition of greatness is just to be just being humble like a humble person you know regardless of what they're if they're worth millions of dollars or they're living a a life well below their means but like i just think somebody who's just kind and like humble and like just just overall you know the people that you meet and they're just like just really you could just tell they're really good people like that's that's greatness son oliver you're a really good person we appreciate you a lot of your fans and followers here are loving the journey and they're grateful that you're going live so i want to acknowledge you for taking the lead man it's a scary dream that you had and you're doing it and you're showing the world that people's dreams matter because they matter so we're grateful for you oliver we appreciate you been cheering you on if you need any support feel free to message me anytime and i can't wait to continue to watch the journey man yeah i appreciate you, man.

50:49Thank you very much for having me. That's cool. Well, stay in touch, man. And I can't wait to watch the next content. We'll see you, brother. All right, man. Thank you. I have a brand new book called Make Money Easy. And if you'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 makemoneyeasybook.com right now and get yourself a copy. I really think this is going to help you transform your relationship with money this moment moving forward.

51:27I hope you enjoyed today's episode and it inspired you on your journey towards greatness. Make sure to check out the show notes in the description for a full rundown of today's episode with all the important links. And if you want weekly exclusive bonus episodes with me personally, as well as ad-free listening, then make sure to subscribe to our Greatness Plus channel exclusively on Apple Podcasts. Share this with a friend on social media and leave us a review on Apple Podcasts as well. Let me know what you enjoyed about this episode in that review. I really love hearing feedback from you and it helps us figure out how we can support and serve you moving forward.

52:05And 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.

From the publisher

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 TikTok

Oliver's Instagram

In this episode you will learn:

  • How a devastating spine diagnosis became the catalyst for the greatest adventure of Oliver's life
  • Why accidentally posting your breakdown video to your bosses might be the best mistake you ever make
  • The simple strategy Oliver used to overcome overwhelming self-doubt: solve only the problem directly in front of you
  • How 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 freedom

For more information go to https://www.lewishowes.com/1786

For more Greatness text PODCAST to +1 (614) 350-3960

More SOG episodes we think you’ll love:

Pat Flynn  – greatness.lnk.to/1777SC

Muniba Mazari – greatness.lnk.to/1684SC

Mark Manson – greatness.lnk.to/1750SC

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