A sailboat on the ocean.

How to Retire at 25 and Live the Dream

This post is an excerpt from Voyage of the Rascal.  It has been edited for length.  Check out the original post from May 23, 2015 at www.voyageoftherascal.com


18 months ago, I quit my job, sold all my possessions, and decided to buy a sailboat.  It was the hardest decision I’ve ever made and it took me almost a year before I finally built up enough courage to take the leap.

Have you ever thought about quitting your job for the trip of a lifetime? Here is the road map that will guide you to the good life!

Fish jumping out of the ocean.
Image: Dwyer Haney

Step 1: Save Some Moolah

A good place to start is your bank statement.  How much do you spend a month at coffee shops?  How much is your cell phone bill? Do these financial expenditures bring you proportional amounts of happiness?  Fulfillment?

Image: Dwyer Haney

Once you have a good understanding of where your money goes, you can start making decisions on where you can spend less.  Try to cut out all of the expenses that don’t truly enrich your life! Find a balance between austerity and happiness and don’t lose sight of the light at the end of the tunnel.

Step 2: Make a Plan

Do some serious research, develop a budget, come up with a timeline, and really know what you’re getting yourself into.

There are so many inspirational stories out there.  Read books, send emails, and learn as much as you can about your new life.  People are always eager to share their experiences, so take advantage of that.

The next step is cracking open a spreadsheet to figure out the financial realities of your dream.  What will your living expenses look like?  Will you have any residual income from investments?  How much does food cost in Tibet?  How many kilometers can your motorcycle go on a liter of fuel?

Once you know roughly how long you’ll be gone, give yourself some milestones – things you want to accomplish and a date to accomplish them by.   My initial milestones involved buying a boat and learning to sail and eventually evolved to things like sailing to the Sea of Cortez before hurricane season and arriving in Chile before winter set in.Man standing on rock outcrop overlooking the ocean.

Step 3: Retire with Tact

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.

It took me a long time to build up the courage to actually hand in my resignation.  It can be a really, really scary thing and the finality of it is resounding.  After you quit, there is no going back.  You’ve got to take a step back, however, and think of all the experiences you’re not having as you continue to amass your savings.  You can’t put a price on your time.

A man jumping off a cliff into the ocean.
Image: Dwyer Haney

Deep down inside, everyone is thinking (or has thought) about doing something like this and when they see you doing it, a little piece of them rejoices and they applaud you.  It’s like a switch has flipped and the entire universe is conspiring to help you towards your goal.  People will come out of the woodwork to lend advice, or introduce a contact, or just give you a pat on the butt when you need it.

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. .  The most important thing, in the end, is to have fun, and enjoy yourself.A man's legs propped up on a hammock.

Take plenty of pictures and make sure you don’t forget to sit back and smell the roses occasionally.  Try to include your friends and family in your plans, as sharing your adventures always makes them sweeter and more memorable.  It might be important to you to break away from your old life, but don’t lose touch with the things from your past that are important to you.

Step 5: Reap the Benefits

Each adventure will teach each individual something different.   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.

You frequently hear people saying how unhealthy it is to be constantly stressed out.   After making a fairly abrupt change from a stressful job (though not nearly as stressful as most of my friends’) to a really slow-paced, relaxed lifestyle, I can honestly say that there is a night-and-day difference.View of the moon over the ocean.

When I sailed away from the dock I immediately started losing weight and feeling healthier.  I used to come down with a cold or something every 3-4 months and in the last 18 months, I only got sick once.

I think my mental health has improved as well.  My sense of self-worth used to be really closely tied to my job performance and I found I’d get really frustrated and anxious if things weren’t going according to plan (even if it was totally beyond my control).  I’ve learned a lot about what really matters to me out here and I think I’m a more confident, balanced person because of that.

Sunset at sea.
Image: Dwyer Haney

I’ve met some fantastic people during this voyage and built some friendships that I really treasure.   There is a lot that you can learn from living in foreign countries and when I eventually head back to the states, I’ll have a different perspective, for sure.Man holding a fish on a sailboat.


I’ve been lucky enough to have several friends and family come down to visit me over the course of the last 18 months.  There is nothing quite like spending a week or two on a 30ft boat to really bond with someone.  I’ve built memories and relationships that are so much richer than they would have been with the occasional long weekend back in the states.

Sailing across oceans in a small sailboat teaches you a lot of skills.  There are obviously the hard skills, like learning to be a diesel mechanic, an electrician, or a navigator.  But more important than these hard skills are the intangibles that build within you along the way.  It took a long time to cultivate my will power, manage my fear, and focus my concentration enough to convince myself it was a good idea to cross the South Pacific in a 30 ft boat.

I truly wasn’t sure if I’d be able to make it to Chile.  I haven’t let on to many people, but there have been times along the way where I came really close to giving up and there have been times along the way when I’ve been truly scared.  In looking back on these last 18 months, it is exactly those experiences that have helped me grow the most.


Go big, you won’t regret it.


Related: Meet Dwyer Haney: Captain of the Rascal

Category: StoriesTravel Jobs



  1. This is awesome — I read these “how to quit your job and travel forever” posts and so many seem shallow and vapid. I feel like there is real meat here, and great advice for actually *doing* it, rather than just setting a few things into motion and not following through. Definitely the kind of inspirational piece you mention using to help form one’s own plans; I’ll be sharing it with my followers for sure!

  2. What do you do after you quit your job?

    How will you keep buying food?
    New sails? Boat repairs? Fuel? Slip Fees? Mooring rentals?

    How somehow the idea of being able to “retire”.. don’t really seem possible..
    How are you able to do anything of this stuff with no income?

    1. It looks like you might’ve missed Step 1, which was “Save Some Moolah”. None of this was possible (for me) without several years of frugality and hard work to put away a nest egg.

      Thats not to say that people don’t cruise while they’re still working. Working remotely or catering to the cruiser crowd (sewing, sail repairs, bottom scrubbing) is often times enough to get by.

  3. Retire at 25!
    Sounds good step 1.
    so you finish school (18), work 7 years and either luck out on some investments or retire for the next 65 years on what you saved in 8 years. Could I see your budget please. 🙂

    $15,000 a year times 65 years….. you saved almost a million dollars in 7 years whats your secret.
    Should it be, take off 2 years and see the world at 25.

    That said, congratulations. I once took off 6 months to relax and just take each day for what it was, People thought I was crazy. Now I am saving like crazy to get a new boat (old one was on25′). Have enough to live on until my pension kicks in (no RRSP, no company benefits, but thats another story). Then I will become the Old Man of the Sea. Sail down the west coast of N. American, through Panama and explore the Gulf of Mexico, Caribbean, Bahamas and up the east coast. Then do it all again backwrds.

  4. I left it until age 68, and it worked out fine. I sailed round thevworld in two years with paying guests, to offset the costs.

    The skill you need, is not sailing. The skill you need is how to fix things, because when sailing there is always something to fix. My book “Sailing in Stitches” might help you.

    Good luckJOHN

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