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Recently I had a conversation with a potential  cruiser who, when we described our lifestyle, and our travel plans, asked me a series of “what if” questions. The conversation went something like this:

  • What if you don’t like it?
  • What if you get sick?
  • What if, what if, what if…

I felt that each of the questions being asked were based on fear, and responded as such, explaining that we were not interested in limiting our life based on negative outcomes that only had a slight possibility of occurring. The conversation ultimately got me thinking about the power of those two little words though.

What if?

In fact, what if instead of focussing on all of the bad things that might occur, we chose to instead focus on all of the wonderful outcomes that are far more likely?

  • What if, by taking XYZ action, you were able to make a lot of wonderful new friends?
  • What if you became healthier, and were able to use more of your body’s innate resources?
  • What if you created lifelong, positive memories, giving you countless stories that you could share with those you love?

The list could go on and on, couldn’t it?

Rebecca and I, through no real conscious effort, almost always focus on the positive “what if” questions. Will that prevent us from having problems? Of course not, but continually asking fear-based questions that limit what we attempt won’t stop that from occurring either.

Choose carefully the type of what if questions you’re asking yourself. Without realizing it, you could very easily be limiting your outcomes.


Note: The subject of this post has nothing to do with this What if post, or this one!


  1. As a would be cruiser waiting on the sale of our house before we buy our boat, it occurs to me that any goal should contain the reason(s) “why”.

    The lifestyle a person sees and desires is often a only perception of what it actually takes to maintain that lifestyle. Sundowners enjoyed while waiting for the green flash don’t tell the story of squalls endured while getting to the anchorage. Having the world as your oyster often requires maintaining your boat in exotic places and then, before collecting your pearl, you often need to make countless dinghy runs hefting jerry cans of fuel and water…and lets not forget laundry and provisioning!

    Unless you have a boatload of cash where you can fly to your vessel and tell the crew to cast off, every sailor will need their personal reasons to help endure the difficulties and frustrations that are every bit a part of sailing as waiting for that illusive green flash!

    And, by the way, I hope you will forgive me if I mention that you can send me a personal email if you know of anyone interested in buying a beautiful home in Colorado Springs, CO!

  2. A great insight – thanks for posting. “What if?” is the knife that neatly slices off the head of any speculative venture, because the negatives are almost infinite. Eventually you can talk yourself into being curled up in the fetal position in a locked room. More practical to concentrate on opportunity – and that fact that our lifetimes really are rather short.

  3. What if…you don’t try? What is the cost of *not* going?

  4. Great post Mike! As much as I prefer the mechanical posts, you have had a really great run of excellent philosophical posts!! 🙂

  5. I love doing this kind of mental exploration! Really thinking about what I want from life, what I have to give?

    It really has allowed me to be out cruising now. If I hadn’t known I want to sail around the world, when the opportunity came up, I don’t know if I would have taken it. And if I didn’t know how MUCH I want this, when we lost our sailboat (shipwrecked in Mexico), I might have taken some of the advise given, and run home.

    Instead, we’re in Central America waiting out hurricane season, then heading to the Pacific!

  6. I love this. I don’t cruise (as you know) but I travel a lot and pretty much always alone. My friends always ask me – aren’t you scared? Don’t you worry about (fill in the blank). What if (fill in the blank). Where do you get the courage?

    I always say, if I don’t go alone I wouldn’t be going. I want to travel so I don’t have a choice. And I actually LOVE IT!!! I meet so many people when travelling alone – something that I don’t think happens as much when you go with others. I can’t tell you how many times I walk into a beach bar (or a bar in Nashville this past Jan) and someone will say “Are you alone” when I say I am, I inevitably get asked to join them. If that doesn’t happen, I am sure to sit at the bar where it is easy to talk to strangers beside you.

    And sure, sometimes when I am walking back to my hotel in the dark, I get a bit nervous (Sosua DR!!!) but nothing has ever happened to me. I walk with purpose, am aware of my surroundings, and don’t wear jewelry or carry a big purse.

    I don’t let any fears stop me and YES – I have made many great friendships, fulfilled long held dreams of seeing amazing places (with many more to come), and MOST OF ALL – felt empowered and fulfilled!!

    I’ve made travel a priority in my life, so I live small and frugally as I am comfortable with. I don’t feel like I miss out on anything living this way.

    I love my life!!

  7. Amen! Brother…Amen!!

  8. The sailing bug is pretty much a sickness that I deal with and if you have it you understand and if you don’t then it makes no sense. 🙂 As for change lifestyles I think most people decide on a gut level ( maybe from fear, or hurt, or something else) and then figure out the reasons afterwards to support their decision. Rare are the people like you who consciously choose a course. And logic is a blade that cuts both ways.

  9. What if? How about answering:
    What if not?
    What if we (I) didn’t?
    When we (I) decided years ago not to stay the course laid out by others for our (my) life, wouldn’t we still be living on what we (I) could gather from the ground in Africa?
    Modern “western” life is forcing humanity back into the place from which it originated (and to this day, still exists).
    Don’t fear the sea, the wind, the rain, the earth; understand them, and rise above the scrabble that wishes you to return to your “roots” – for therein lies madness for an active mind.

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