Dude Who Quit His Job, Bought A Boat, And Sailed To Patagonia Has Secret To Retiring At 25

This Dude Who Quit His Job, Bought A Boat, And Sailed To Patagonia Has The Secret To Retiring At 25 Years Old

Wrote a note said “Be back in a minute”
Bought a boat and I sailed off in it
Don’t think anybody’s gonna miss me anyway

Yeah, those Jimmy Buffett lyrics sound wonderful and all, but who actually has the stones to do that? I don’t, which is why I’m going to spend tonight sitting on my couch drinking half a bottle of red wine while I catch up on some Hulu.

But some dude named Dwyer Haney (or “Captain Dwayne after a few drinks” as he states on his website) did exactly that when he quit his job at the tender age of 25 only to buy a boat and head for the stormy seas. Simply put, he retired early and became happy as a clam in between sailing from the United States to Patagonia in Chile. His idea was easy:

The premise of this adventure is that I’ll quit my job, sell all of my worldly possessions, buy a boat, and take to the sea.

I’ll strive to live a simpler, more sustainable life.

I’ll see the world at a slower pace and be able to take in all that I pass.

I’m going to watch a hell of a lot of sunsets.

And now he’s been doing it for two years. Jealous? Me too. Just look at the photos he took along the fuckin’ way.

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Captain Dwayne’s got a ton of other photos of his journey on his Instagram account and his website, both of which are making me want to call it a day and tell Dave I’ll see him never. But the really interesting part about his entire journey is how he enabled himself to take this journey, or as he calls it, “How To Retire At 25 And Live The Dream.”

Step 1: Save Some Moolah

A lot of people are complete dumb-asses when it comes to managing money. My parents were fairly frugal as I was growing up and they gave me enough education to understand and control my spending. This doesn’t appear to be the norm, so I’ll try and impart some of the mindset that has allowed me to live off of savings for a couple years.

A lot of people in the US complain about not having enough money to “make ends meet”, but a lot of people in the US also have $600 smartphones, buy bottled water every day, and pay a hundred bucks a month for TV subscriptions that rots their brains. Over the course of my travels, I’ve met and talked with people that live on a couple of dollars a day. Lots of these people are totally satisfied with their lives. When you examine the lives of “poor” people in the US through the lens of people that are truly poor, you find that they’re actually living like kings. It is this perspective that sets you free.

Okay, so save a little money, stop paying for cable and internet, and grow my own food so I don’t have to spend $7.99 every night for a pre-made salad at a big box grocery store. Next.

Step 2: Make a Plan

You’ve got to make sure you’ve got a legit parachute before you jump out of the plane. Quitting your job with just the vague notion that you’re going to “travel the world!” or “ride a bike to India!” would be a pretty rash move. You should do some serious research, develop a budget, come up with a timeline, and really know what you’re getting yourself into.

He goes into much deeper detail about this here. Essentially what he’s saying is that you need to scour the internet for some strategies to make ends meet without dropping a fuckton of cash. And before you say, “But I just stopped paying for internet!”, remember that libraries offer that shit for free.

You can’t just Walter Mitty your way to the top.

Step 3: Retire with Tact

Everyone around you probably thinks you’re going to keep busting your ass until age 65 before taking a break. Your boss, your friends, and your family are probably all making plans based on this assumption, so when you break the news you’ve got to do it gently and hope they’re supportive instead of angry for “changing the plan”.

What you’re doing isn’t “normal”, so people won’t necessarily understand or agree with the decisions you’re making. The research you’ve done, the plan you’ve developed, and your realistic budget should help to persuade your friends and family that you haven’t totally lost your marbles. If they truly love you and care about your happiness they’ll support you and help you succeed. You are in charge of your life. You can’t let other people’s opinion’s dictate your happiness.

He even goes into enough detail that he suggests you throw yourself a retirement party, which is a real dick move at the age of 25 if you ask me. But that being said, I respect the hell out of it because it’s just rubbing it in all your coworker’s faces that you’ve got the nuts to quit your dead-end job and they don’t.

But finally, the fun stuff.

Step 4: Live the Dream

This is the easy part. Go out and put your plan into action! The first few weeks are kind of a rush as the truth of your new life sinks in. You’ll end up with some growing pains somewhere along the way, so try to remain flexible. It’s good to leave your plans a bit open ended as you adjust to realities that might be a bit different from your plan. The most important thing, in the end, is to have fun, and enjoy yourself. If you find that you need to alter your plans to realize the dream that you envisioned, leave yourself the flexibility to do that.

Being someone that has no idea what to do come Step 2, this seems pretty far off for anyone that’s only put a few minutes of thought into it (read: me). But I think I could get used to the life that he’s livin’. After all, he makes the outcome of it all sound pretttttty nice.

Step 5: Reap the Benefits

Each adventure will teach each individual something different. I’ll describe my experience to give you some idea of what you’ll get out of it in the end. I chose cruising on a sailboat for a number of reasons. A sailboat seemed like it would allow me to explore some beautiful parts of the world. I figured it would challenge me and stretch me beyond my comfort zone. I also reckoned that it would reduce my impact on the world around me. These precepts have all proven true over the course of the last year and a half, but there have been other benefits as well.

Me? I felt like Ernesto Guevara when I got back from spending Christmas in Mexico (humble brag) only to get back to my car and see that someone hit-and-run me, which totally threw off my chill vibe. So I’m not entirely sure how I’d deal with all life’s hurdles like Captain Dwayne has, but maybe that’s why I’m sitting at a desk typing about this guy and not chillin’ with two ladies on my arm in Patagonia. To each their own, I guess.

Sure, student loans and lengthy mortgages might have you down for the count at this point, but just live vicariously through our boy Captain Dwayne. He’s giving us hope that at least someone has it figured out.

But like I said, he’s got incredible detail on all of this on his website, which is worth a look if not for the landscape photos alone.

[via Imgur / Digg / Voyage Of The Rascal / Instagram]

Images via Imgur

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Will deFries (Twitter / Instagram) is a Senior Writer at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram). Email me at

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