Could’ve, Should’ve, Would’ve

I’m currently in Mexico enjoying the last few days of a wonderful trip with my fiancée.  We started our adventure by spending some time with good friends in Cuernavaca – a picturesque city known for the filming of many Latin-American soap operas – and then Mexico City before heading down to the beautiful coast of the Mayan Riviera. 

After checking into our resort, ditching our bags and swapping out shorts and shoes for bathing suits and flip-flops, we headed down to the pool to soak up the balance of that days’ sunshine. We hadn't been in the pool more than 5 minutes when we met some nice people from Michigan that asked how long we were there for.  It was to be the start of standard resort chit chat that was about to quickly remind me that not everyone thinks the same way.

I explained that we were staying at that particular resort of 8 nights, however, we were in Mexico for a total of 3 weeks.

“Three weeks!”  They exclaimed!  “Must be nice!  You guys are so lucky!”  I didn't dare tell them that we've been basically travelling non-stop for the past 3 years.

“I wouldn't call it luck.” I said.  “I work every day of the year regardless of where I am.  I simply choose to work while traveling rather than in a static location.”

That opened up the usual barrage of questions like, ‘what do you do for a living?’, ‘how did you get into that business?’, and the ever-so-popular, ‘where all have you traveled?’  Then, after a few more feeling around questions, the really weighted question: ‘how do you afford so much travel?’

I can’t tell you how many times I've had that exact conversation over the past 5 years.  I probably had that conversation, or some variation of it, at least a dozen times just in that pool alone over those 8 days.  People love to chat while on holidays and especially when they think someone has a magic key to traveling more or breaking free from the typical confines of work.

And, every single time I answer their questions and give them a glimpse at my view of that magic key, explaining that a life like ours isn't that difficult to achieve nor is it expensive and especially compared to “the typical North American lifestyle”, I see their eyes start to drift and then they eventually go back to telling me that I’m lucky.

Even those that dare to tell me that one day they would like to work for themselves, or retire early to travel, or, buy that boat they've been talking about for two decades to sail the world, it always comes back to the same:  One day…

I’m here to tell you that I don’t buy into this business of ‘One day’.  I never have and I assure you that it will never come for the over-whelming majority of people.   And if they aren't telling me about their One Day plans, then they are telling me about the opportunities that past them by.  Stories like, “I remember when I was younger and had an opportunity to go work overseas, but…” Or, “My husband and I had a chance to buy a foreign piece of land for dirt cheap, but…”  Or, “I was going to start my own business, but…”

I've heard those stories my entire life and well before I started traveling and living the way I am.  Those stories always come with a long, deep sigh and are usually laced with regret.   That said, I understand that this lifestyle is not for everyone.  I get that people have mortgages, families, careers, I really do.  However, there are always ways to achieve what is most important to you.  When I have the opportunity to share a handful of easy suggestions on how one can do what we do without giving up their lives and with taking little to no risk, I really seem to capture their attention.  But after a few more minutes of talking, negative thoughts start to invade them, their shoulders slump once more and they then tell me that ‘it’s just not that easy’.  Well, it can be that easy, however, fear is a common out.

I’m not just referring to how one can break free of the cubicle and travel the globe, I’m talking about dreams in general.  How many people truly set important personal dream goals and then follow through?  We set serious goals at work and in other areas of our lives, but for ourselves?

Words like ‘should’ve’, ‘could’ve’ or ‘would’ve’ are all words that indicate one has let something important pass them by, however, it’s never too late to start living exactly how you've always wanted!  Don’t get caught up in the “how”.  Instead, think of your dreams, seriously consider what life would be like to live out those dreams and then start working on the how.  Instead of saying “I can’t” ask yourself, “What if I could.”  Think outside of the box, ask around; find someone who’s already achieving what it is that you want and approach them. Ask them how easy it was once they truly decided to take that first step, you might be surprised!    

So, my friend, it's time to take that first step!