Wednesday, May 22, 2013

Take a walk in my shoes...





Green Grass.

I have been a full-time entrepreneur for almost 8 years.  That fact continues to shock me because it means that for nearly decade, my full-time job has been a job that I’ve created for myself.  I don’t set my alarm clock, I work from home, I start and stop my day when I choose and I don’t have to ask for a day off.  On countless occasions, others have told me how great my life must be and how incredible it is to be your own boss.  There is truth to that; being in control of your own career is very fulfilling and satisfying but this perception of my life is a prime example of the grass on the other side appearing to be greener.  There’s a reason why there’s thousands of motivational quips, mantras and mottos created to encourage business owners; in between all of those awesome moments, being an entrepreneur can really suck… a lot.

Most people don’t understand just how hard it is to be an entrepreneur.  The failure rate of businesses beyond 5 years is astonishing (let’s just say the universe is exceptional at weeding out unsuccessful entrepreneurs).  The truth of the matter is, you have to be a little bit insane to believe that you will find the needle in the haystack or that you will be the guy that beats the house in Vegas… every time.  One of my favorite scenes in television history is during an episode of Entourage where Turtle (the perpetual slacker/gopher for his movie star friend) asks Ari (the high priced Hollywood agent who fits every possible stereotype) to assist him with raising money for his company.  Ari, who bootstrapped his way to the top, asked Turtle why he doesn’t just ask his rich friend for the money and Turtle replied, “I think It’s time for me to make something of myself.”  With a dismissive tone as if he had been personally offended, Ari replied, “Do you know what it takes to make something of yourself?”  Ari then goes into this beautiful yet spastic tirade where he hits Turtle with every question from what’s your breakeven point, to asking about office space and insurance.  He even uses his extremely competent and incredibly abused assistant to prove that “making it” requires a lot more than just having a good idea. 

[Witness it here.  Try and see the entire scene if you can.]

I’ve had a few “Turtle” moments when you realize that what you’re doing isn’t enough to get it done and that you have to regroup, refocus and bring more to the table.  Starting a business just because you want to be your own boss or because you want to be rich is the surest way to be out of business in 12 months or less.  You have to be way more dedicated with a deep-rooted passion that supersedes any superficial desire and even that doesn’t guarantee success.  The number one reason most new businesses fail is the lack of capital.  Not having enough money, as a cause of failure is fairly straightforward so there’s no need to harp on it further.   However, there are two much less discussed psychological causes that force people to close the doors, even if there is capital readily available: uncertainty and insecurity.

It is easy to see why it would be great to be your own boss but you must keep in mind that on your “less greener” grass, your boss gives you the one thing that an entrepreneur can never give herself, the certainty of a paycheck.  As long as you have your job there and you handle your duties, you can reasonably expect to get a paycheck several times a month.  You know how much it will be and almost exactly when it will come.  As an entrepreneur, even when you’ve finally made it, there’s still plenty of doubt because you don’t always know when you are going to see another payday or how much it will be.  If you own a restaurant, you can project how many paying customers will come through your door but you can never be sure.  What if your city has a horrible winter that keeps would be customers inside to order delivery or cook more?  How will you handle the lack of revenue?  Many deal-based industries like real estate force you to rely on the funds of a deal that doesn’t exist yet and there’s no way to guarantee when, where or how it will come.  Imagine being trapped in a room with very little oxygen and you have to figure a way out before you run out of air.  That’s what it feels like to be an entrepreneur when the bills are piling up and you don’t know when the next check is coming.

As bad as that can be, the worst feeling of all to deal with is insecurity.  If you save enough before you begin your venture or raise enough capital, you can temporarily reduce the feeling of uncertainty, but there’s no cure for the feeling that you aren’t good enough.  From day 1 until the day that you’ve “made it” (I put it in quotes because those two words represent a very subjective goal that can’t possibly be quantified in a universal term) you are constantly reminded that you haven’t made it and that you are always one bad break from everything falling apart.  Insecurity is not exclusive to entrepreneurs; folks with jobs can feel it too but the significant difference is that when you are the boss, the line between business and personal is blurred.  So if you fail as an entrepreneur, you feel like a failure rather than just not being able to execute a task.  Also when you start out, you have to simultaneously convince others that you are credible while mentally dealing with the fact that you don’t technically have the credibility that you are promoting.  When you haven’t made it, every single person you come across looks more stable and more successful than you.  Having a conversation with your lawyer friend can really ruin your day once you take into account his nice salary and hefty bonus.  It’s those moments when his grass is much greener than he will ever know.  If uncertainty is being trapped with no air, then insecurity is without a question, quicksand – knowing that you are inevitably going to sink to your death and realizing that any movements you make will only make you drop faster.

The suffocation of uncertainty and the hopelessness of insecurity is enough to make the greenest of grasses appear brown even after you’ve perfectly seeded and watered it.  Being an entrepreneur is definitely about closing deals in your boxers or answering emails in front of ESPN but its also a ton of sleepless nights, bouts with anxiety and a level of sacrifice that would make ramen noodles seem like a treat (the first health insurance plan that I had was literally marketed for both low income and sole proprietors).  Like Ari Gold implied and Turtle quickly learned, there are no short cuts, cheat sheets and most importantly, guarantees to being a successful entrepreneur.  If you are one of the few that want to jump off that cliff and join us in the loony bin, prepare yourself because the day you walk on our lawn will be the last day that you think its greener.


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