There are two ways that I see it, how a person becomes an entrepreneur.

1. Legally insane.
2. Rage.
3. The third option is via family. I leave this out of the discussion due to the extreme difference between creating a company versus being born into it. To me, it doesn’t count.

Imagine Fred. Fred is 35 years old, married, mortgage, kids, and a nice cushy corporate job. Fred dreams of someday owning a million dollar home, a Maserati, and the financial freedom to travel all over the world while not worrying about bills. If this dream doesn’t sound familiar, it should. It’s the dream of most every red blooded American around save for some philosophical types who see money as a means to independence rather than slavery.

First off, let’s examine Fred’s dream. Let’s start off by assuming (virtually 100% correctly) that everyone of Fred’s co-workers and employees at Fred’s company imagine and dream that someday they will own a million dollar home. How realistic is this dream?

Fred has 100 co-workers. Each of the workers right off the bat is limited in terms of salary. In other words, each of these 100 workers has a ceiling in terms of the amount they can hope to earn in any given year (I’m not including traders here because they are the exception not the rule). In addition, the max that any one of these 100 workers could earn in any given year in any position besides CEO would roughly be around $250k. How realistic is it that any one of these 100 workers will ever get to an upper position that earns $250k? Further, assume that 1 person out of the 100 workers gets the $250k job – do you think that this person will get it because they are the smartest/best worker or because they are either friends with someone up high or are just dumb enough not to pose a threat to the old order of things around the company? Also look at the percentage chance of being this person – it’s 1/100!  Mark Twain famously said in reference to groups of people who all think the same thing:

“Whenever you find yourself on the side of the majority, it is time to pause and reflect.”

Einstein also famously said that the definition of insanity “is doing the same thing over and over while expecting a different result”.

Now I ask you again, does it make sense to have these types of dreams while working at a company? Does everyone at your company continue to go to work each and every day, making sure to say yes sir and no sir continue to have the dream that they will one day be a millionaire? If so, what makes that person different from any of the others? Does he somehow deserve it more than the other 99 people?

Now let’s apply the above mentioned rubric to Fred and see how it may play out – Fred carefully observes his boss (Jared) in the following situations:

1. Fred’s boss’s (Jared) morning routine. Each and every morning, Fred notices that his boss parks in the same exact parking spot at exactly the same time every morning. Jared is wearing his standard button down shirt and slacks, along with his college ring he so richly cherishes. After that Jared sits down at his desk and carefully reads the WSJ with his cup of coffee. Upon finishing, he perfectly folds the paper, making sure to crease all the edges, and places it in the pocket of his leather company briefcase which he was awarded for having 20 years working for the company. Jared thinks that by staying tuned in to the news that he is somehow smarter than other people who don’t have a clue about what is going on in politics.
2. Jared’s weekly schedule. One thing to note about Jared is his extreme discipline in accounting and planning for every hour of every day in his schedule. His schedule runs his life. If he has even 1 hour open during the day, he freaks out because maybe his big boss will get mad that Jared isn’t in a meeting about where a fu$%ing comma should be placed in a meaningless document.
3. Jared’s communication skills. Fred in trying to talk to his boss Jared notices that Jared cannot hold a conversation. Jared constantly makes nervous gestures by placing fingers around his mouth and face. Sometimes however, Jared does the opposite and tries to stare Fred down. Either way, Fred determines Jared is an insecure weakling and quietly chuckles.
4. Jared’s personal life. Fred tries to ask Jared about his personal life, but to no avail. From what Fred can gather Jared doesn’t have a wife or any kids or even a girlfriend. Fred finds this easy to believe because of the difficulty he has in having a simple conversation with Jared. It seems as though Jared rarely leaves his house and pretty much just stays indoors when not at work. Fred imagines that his severe lack of communication skills, personal skills, and common sense may in fact result from many years of corporate drudgery.
5. The sky falls on Jared every day. Fred notices that for some reason the sky seemingly falls on Jared everyday. How can that be? Are the problems and issues that Jared quacks about each and every day really as important as he makes them sound? Is the placement of a period inside quotation marks or after quotation marks important? Hmmm, Jared wants to ask a lawyer what they think. However, since Jared lacks even basic common sense, something as easy as understanding that it doesn’t matter not one f’ing bit is very hard for him to understand. Therefore, to make sure that all his bases are covered, Jared asks a “lawyer”. If Jared had common sense he’d understand that just as anyone can graduate from college, virtually anyone can become a lawyer. It’s not hard- Fred knows idiots from college who went on to become lawyers. Jared also makes mountains out of molehills as evidenced by him taking offense at vague comments made by others. Jared AUTOMATICALLY assumes that every comment made is somehow directed at him or to subtly undermine him. He voices these concerns to his fellow “close” co-workers” and employees.
6. Jared’s demeanor in meetings. Jared’s demeanor in meetings is at the bare minimum uptight. Fred observes Jared’s face immediately become flushed when entering into meetings. Fred assumes it’s because Jared is fearful that someone may figure out he’s a dumbass and has no clue about what is going on. Jared takes his traditional place at the meeting table, and offers up an ignorant joke that’s not even funny (a weak attempt to try and please those sitting at the table). Fred notes how red Jared’s ears get and how bloodshot his eyes are. Fred correctly notes this results from high stress. When the meeting commences Jared attempts to stare down those who are at the table. Since Jared is older than the other’s at the table Fred guesses that Jared feels entitled to stare co-worker’s down while attempting to prove that he “knows” more than they do about the pointless shit they do at work. Fred determines that even if Jared does in fact know more about this, this stuff is stupid and has no value outside in the real world. Jared sits back and quietly chuckles some more while watching his boss squirm at the meeting table.
7. Jared blames everything on Fred. Jared’s boss, a big VP type, who knows incrementally more than a typical nerd off the street about valueless stuff, begins to look at Jared. Jared as described above is adept at political maneuvering, or cloak and dagger strategies. Afterall, Jared has to keep his job, he’s got a mortgage and he cannot let his boss figure out that he’s a dumbass! So Jared asks Fred why he hasn’t delivered an assignment he gave him yesterday. Fred responds that Jared never gave him an assignment to which Jared responds that he did and Fred should have completed it. And so the cloak and dagger maneuvering continues. The more time that passes, the more time Fred has to observe what working at a company looks like and entails. He takes it in at a high level and ponders life outside of a company. After all, Fred, like everyone else, has always been told that you need to go to college, and then work for a company to truly make it.

So following the first points made in this short story, Jared has some options to change his life. For example, if Jared was legally insane, he most likely would have quit immediately upon realizing the fact that having a ceiling limiting his income is stupid. So for those of you who are legally crazy, I’d bet heavily on you being super successful in your endeavors.

The point of this story is two-fold. One, to show you that if you don’t have any problems at your job, then chances are that you’ll stay in your safe job. The second is to show you that you do have a way out, but the only way is rage. If you’re insane in a good way, then you’d be out the door upon first blush with this ignorance.

In sum working at a company and becoming a millionaire are mutually exclusive for the most part. You won’t become a millionaire while working for a company and its crazy to work for a company and think for some reason if you just keep your head down and work hard you’ll earn financial freedom. Freedom doesn’t come from having ceilings and limitations placed on you. Freedom comes by breaking rules and grabbing your future with your own hands and then molding it to serve your goals.

On a personal note, I fall into the philosophical camp seeing money as a means to freedom rather than ability to buy material garbage.