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Am I lucky? I suppose so. I was lucky (if that’s the word you want to use) to have been born healthy, to some loving parents, in a functional family, in Canada. I was not born to some crack heads, or into some war-torn country, or worse.

Compared to most families though, we were in no way well off. Only my dad worked and he had a blue-collar job. We had no car, ever, and we had only one working TV with no cable. To pay for college and accommodations while studying, I had to rely upon student loans. No, my parents couldn’t pay for that for me. In spite of that lack of an abundance of money, I’d still consider myself lucky, or fortunate. That said, I really hate it when people use that word to describe us, especially relating to what we’re doing. It implies that we received some gift of the gods and that is what has allowed us to go sailing.

Everyone who has read this blog knows the most recent steps of how we made it happen (post 2008), but we still get emails and messages from people asking how we (or they) can afford it? Here is the back story… it’s really not that complicated.

  1. Work.
  2. Don’t spend everything that you make.
  3. Save and invest the difference.
  4. Live reasonably frugally.
  5. Do not borrow money for non-appreciating assets.
  6. Buy a boat, with cash.
  7. Go sailing.
  8. Repeat as necessary.

Assuming you were “lucky” like I was, is it more complicated than that?

If you need help with the money bit, buy and read this book: The Richest Man in Babylon


  1. I have yet to understand why some people in this world just can’t accept that you or anyone else dares to do something out of the norm. And those that feel there is no way you worked hard to get where you are today. I admire those that do what you & Rebecca have done-worked to live a dream. Happy for you two, have enjoyed following your life and appreciate your sharing. One day when you are old and sitting in a chair somewhere, you’ll at least have the memories rather than saying “wish we had sold everything and went sailing”. It comes down to what you really want in life!! I applaud you!!!!!!

    • I think people sometimes just don’t get it. No one has ever explained it to them. It’s also important to understand that focussing on anything beyond our own actions and decisions is not empowering.

    • My take on the ones that don’t accept it:
      Most people just do what they are told. They work like dogs and borrow tons to buy the big house and fancy cars and keep up with the Jones’ only to spend their time dreaming of retirement when they can stop the treadmill of misery. People who ‘do their own thing’ – whether it is buying a ‘micro’ house or a boat to go cruising – threaten them. They turn the whole idea that the treadmill of misery is the only path to ‘success’ (whatever that is) on it’s head. Essentially it shows these people that the only thing really stopping them from achieving their dreams is themselves. It doesn’t fit with the narrative of ‘how it works’….and that is scary (to some).

  2. I would also recommend reading Ed Robinson’s book “Leap Of Faith”. You can find it by typing the title in the Amazon box over on the right of this blog. It is a simple and easy to follow story of Ed and Kim’s journey.

  3. …amazing how the harder you work, the luckier you get.

  4. Love this post. I am often told that I am lucky as well, but it’s about hard work and being a little risky at times (if you wish).

  5. I am so sick and tired of the “lucky” thing myself. It negates the hard work it took to get where we are. I grew up in similar circumstances. Did not go to college until I was 37. Yes, we had some good breaks and ran with them, but we had some awful things happen too.

    Many people would have called it quits after your recent bad experiences. Instead you look at other ways to make it happen. For example you figured out that a cat was out of your price range so you are looking at monohulls. Many people would not get past the “must have a cat” thing. Or course it’s easy to find excuses to not do anything.

    It’s reached the point that when I hear people complain I ask if they really want to hear about solutions or if they just want me to make sympathetic noises.

  6. It is my experience that most people don’t sit back and look at their lives from a 10,000 ft view and analyze where they are, how they got there, where they want to be and how do they plan to get there. I am pretty sure that being able to think at that level is a prerequisite to pulling off these types of life changes.

    So they spend day in and day out and continue on the path that society has laid out for them. It never occurs to them to stray from that path. When they come across people like you, most point and think “wow they are in a nice spot over there! How lucky!” and they shrug their shoulders and continue on their path.

    Others, stop and add one more though… “How do I get there?” A few of these people execute diligently and end up far off the beaten path.

    And the whole cycle repeats as more people continue on this path laid out by society.

    I agree with you. You were lucky in that you were blessed with the same good fortune as many others in the western world. Good health, safety, education, prosperity. If others in the same situation envy you, they shouldn’t consider you luckier than them, but instead should ask themselves… “If I like where they are at more than where I am at… how did they get there and what can I do to join them?”

  7. You are right Mike. I have spent my career in financial planning. Some people are ready to learn. Some have entrenched thoughts and patterns and snap back to what’s familiar. Notice I didn’t say what worked prior for them. Owning your stuff changes your life. Now you are responsible. Then things can and will happen.
    When the students are ready, the teacher will appear!
    My favourite question, “how’s that been working for you?”


  8. As a longtime aspirational reader of your blog (meaning that I expect to follow in your footsteps in the not too distant future), the steps you have identified are precisely those that I have been employing myself during my own lucky life (with one trivial difference, I happened to be born in the USA).

    Another excellent link on this topic is the Mr. Money Mustache blog written by a guy who ‘retired’ in his 30s. In addition to the usual work/save/invest advice, he also has some good tactical advice as well (specific ways to invest and save, including good phone service plans, credit cards, etc.).

    Many thanks for the work you put into your blog.

    Do enjoy your hard-won ‘lucky’ lifestyle,
    Andy A.

  9. Well said !! I had a similar upbringing (ie:no extra money) and am told frequently how lucky I am to have retired at 44. It’s not luck, it’s hard work and being frugal on the wants versus needs. My wife and I sell everything we don’t use and constantly analyze even those that we do. We’re just counting down till our youngest is off to life in 3 years when we can buy a boat and explore the world. You and Rebecca are our living examples of how to live life.

  10. Mike, I loved this post, smiling as I read it. I, too, am happy to have been born into a family without much drama, but lucky? Lucky is winning the gene lottery by being born into a wealthy family and getting whatever you want without working for it. But that too has its pitfalls! The rest of us, make our own “luck”! My students sometimes tell me I’m lucky when I share some of my experiences. I tell them that I am just like them, and these experiences were born out of choices. Period. Continued good luck to you! 😉

  11. Sounds very familiar. Study, work, save, go climbing/sailing. Repeat.

    Dependable, too, or at least you know what to do when it goes badly; back to step 1.

    I like the way it feels.

  12. That’s great simple advice

  13. There’s the easy luck (like inheriting an estate), and then there’s the earned luck. The earned luck (like you I hate that term) is when preparation meets opportunity…and taking that leap of faith to go for it. Mike and Rebecca, thank you for sharing your adventures. You’ve inspired many to follow their dreams. Best wishes in your continued journey.

    • “You’ve inspired many to follow their dreams.”

      If that is true, then it makes the work invested in this blog entirely worth it the time and effort! Thank you.

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