I often daydream about what it would be like if I lived on a boat that was constantly sailing from place to place.  Everything I need would be on that boat, and I could call any location my “home.”  What would it be like to live life without an anchor? (Ha!)

You see, I’ve realized that over the course of my life, I’ve grown more independent, earned more money, and consequently, accumulated more crap I probably don’t need.  First-world society tells me that because I have a smartphone (which talks back to me), a car, a decent apartment, and not one, but two computers, I must be doing pretty well for myself.

In retrospect, I’m disappointed that I couldn’t fit my entire life into a backpack when I was moving from New York to California.

Do I need a laptop AND a desktop computer?  Do I need a car?  Do I need three music keyboards when all I use is one?  (It just looks cooler, OK?)

It feels like every time I “improve” some aspect of my life, I’m just moving further away from the freedom of time and freedom from money I crave.  And its not just the physical weight and space of everything I own… its also the mental stress that comes with keeping track of it and protecting it.

Because I’m a visual learner, I went ahead and drew out a super corporate-looking chart that kind of looks like a stump (which represents “me”) with a whole lot of deep roots (which represents my sh*t).  Each box below the intial item is something I had to add in order to “improve” or “protect” the box above it.


It would be tedious to go item by item, but I think you get my point:

The more stuff I own or “improvements” I purchase, the more restricted and tied down I actually feel.  I even put a question mark next to “Promotions” under “Jobs,” because unless I’m working toward a passionate goal, a promotion may mean more time dedicated to something that doesn’t get me closer to that goal.

For example, if I wanted to move to Australia tomorrow (because I love world travel), it’s daunting to think about what I would do with all my stuff.

I’d have to:

  • Pay for rent when I’m not even here (or find a long term subletter)
  • Find a place to store everything
  • Cancel or adjust my car insurance, health insurance, renter’s insurances, etc.
  • Break my cell phone contract (and pay a heavy fine)
  • Keep track of my loan payments no matter where I would be
  • Cancel my credit cards or find new ones that could be used internationally
  • Store my car somewhere
  • Cancel my Internet and any other subscription services I’ve signed up for


Luckily (yet, unluckily), I’m not moving to Australia any time soon.  But wait… if I didn’t have all these things to worry about, would I move to Australia?  That’s the freedom I wish I had!

I know for some, their goal may not be freedom, but rather a stable foundation.  I can dig that… “to each, his own.”

But in my mind, “home” is where your stuff is.  If my stuff was contained on a boat or in a backpack, my “home” could be everywhere!  Do I sound like a complete vagabond yet?!

I challenge you to take a look at the things you own.  Do you need all of it?  Does it help you reach your goals?  Where can you trim the fat so that you’re not fighting through it instead?

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Jake is the younger, yet taller and more dashing brother between “Jake and Chad.” He’s the voice of reason behind every one of Chad’s audacious ideas, as he puts the “calculated” in “calculated risk.” He also writes songs and makes videos for the joy of the Internet. Jake is currently redeeming the millions of airline points he’s racked up through mad travel hacking techniques and is probably on a plane somewhere.


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