Investing | in-vest-ing (v), from the root word invest, which means:

  1. to keep oneself up at night with worry
  2. the topic of fancy, black-tie dinner parties where we impress each other with words no ones understands like disintermediation
  3. the vehicle that allows Wall Street bankers to thrive and stuff their pockets while people like us continue to … [see #1]

When I meet new people and tell them what I do, they usually take one of three sides when it comes to their own investing:

  • The I’ll start investing one day when I have money side


  • The I’ve tried investing and I can’t stomach the rollercoaster ride when it comes to my hard earned money side.


  • The I want something more, something different, something OFF Wall Street side

The first side folks are likely to never get off the sidelines and get in the game. They’d rather wait to invest their money “once they have it,” as if they already know they are going to lose money through investing and they want to make sure they have that money to lose. They don’t see investing as a way to make money. Fair enough.

The second side is so burned by Wall Street that their own jadedness won’t allow them to again try anything that resembles investing … maybe forever. If you’ve lost an obscene amount of money through stocks and bonds, I bet you can relate (I related hard when I was waking up from a nice fist-over-fist pummeling by the clenched hands of a brutal 2008. I’d pumped almost everything I had into investments and saved nothing. The real estate I owned became worthless. My retirement accounts crumbled).

The third side is ready for a different way to play the game.

The Norm (ahem, sucks, ahem)

Most of us take a path of going to school, getting a job, moving from hourly positions to salary positions and then spending all of our efforts advancing in our selected fields (but always thinking in terms of being an employee). This is the path most of us were taught from the time we mowed our first lawn and earned our first 50 cents. “Do good in school, kid. Get a good job, kid. You want to make a lot of money so you can vacation on beaches and wear nice watches don’t you?”

Well, kid, that’s not how it really works. It can–don’t get me wrong–but that’s a long, tiring, steep, avalanche-prone mountain to climb.

Enough Reading. Where Are All the Pictures in This Article?

Time for a picture. This is a great chart from one of the godfathers of personal finance, Robert Kiyosaki, and it’s called the “Cashflow Quadrant.”

When you boil it down, we all make money in 4 categories:

  1.    Employee (E). This could be you, with your high-paying job as the ultimate goal.
  2.    Self-Employed (S). Maybe this is you, if you are particularly brave and daring.
  3.    Business Owner (B). This may or may not be you (yet), but you’ve been dreaming.
  4.    Investor (I). This (along with #3) is the ultimate goal when it comes to becoming a money-making badass (in other words, when it comes to reaching Financial Freedom.)

The goal: Get to the bottom of the quadrant (the “I”), and get there fast. Don’t forever hang out in the same quadrant with the guys slinging sandwiches at SUBWAY (no judgement, that’s where I started). Moving on from “Employee” takes more courage than it does ice cream and dreams, I get it; I left a cushy government job four months before my first child was on the way–it took all I had to not throw up my guts from anxiety and panic (Stella Artois has a way of calming my nerves).

To get to the “I” you have to take the first step, which is breaking out of the traditional-savings-strategy jail cell and considering a new approach–an approach I’m thrilled to share with you in Part 2 of this article, found here.