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The Brutal Truth About The Lifestyle of Entrepreneurship

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What I am about to tell you is as unfair as it gets.

If your company is struggling, or not progressing as quickly as you would like, whose responsibility is it?


You work the hardest.

You care the most.

You put in the most hours.

You are the most dedicated.

You are the most passionate.

You put in the money, strain your personal life (if you have one), deplete your finances (if you still have any),strain your relationships (if you have any), cry, drink, don’t sleep, don’t date, and spend every waking moment on the business.

Is anyone else willing to make the sacrifices you make every day?

No one said being an entrepreneur was fair.

Early stage companies need to accomplish a lot with limited resources, and this can lead to organizational chaos.

This chaos is characterized by common problems:

  • Too much to do
  • Lack of financial resources
  • Lack of human resources
  • Lack of established priorities
  • Lack of clarity with internal and external constituents
  • Emotional and reactive decision-making
  • Frustration with existing resources
  • Reactive day-to-day management

The definition of chaos is:

1) “Complete confusion and disorder: a state in which behaviour and events are not controlled by anything.”

2) “The state of the universe before there was any order.”

Starting a business is like driving in New York City.

All taxi drivers swerve from lane to lane.

Taxi drivers with passengers drive fast and erratically (to get their passengers to the destination as quickly as possible).

Meanwhile, taxi drivers without passengers drive slow and erratically (to be in a position to pounce on an available fare).

Now add the constant wail of sirens from police cars and fire engines and the inevitable garbage truck.


Imagine if you took away all structures of order—lights, lane lines, speed limits and traffic signs—and threw in jaywalking pedestrians, a couple of skateboarders, a dog walker with an unwieldy pack of hounds, and a good oil slick.

It becomes a game of Frogger on steroids.



Being an Entrepreneur and Accepting Your Role

Now you know what it feels like being an entrepreneur—if you didn’t already.

Without the appropriate tools to manage, entrepreneurship is a like driving in New York City without any lane lines, speed limits, stop signs, or traffic signals.

Sounds about right, doesn’t it?

You probably believe the cause of this chaos is that your business is unique or faces a unique set of obstacles, you’re developing a new market, or you don’t have the resources to operate like a more established business.

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It is common for us entrepreneurs to blame the chaos on others: the lack of money, the lack of resources, the lack of a defined market, or one of the many other excuses for not fixing the chaos.

When you believe passionately in your idea and chaos ensues, it’s easy to blame everyone and everything else.

After all, you think you are doing the right thing.

This may be ego, insecurity or over-confidence in your ability.

The natural reaction is, “How dare you challenge me?

Without me, this business would be nothing.”

We all say, “It’s not me, it’s you.”

Customers don’t understand.

Employees don’t work hard enough.

Employees aren’t talented enough.

Vendors don’t perform.

Advisors aren’t committed.

Investors haven’t seen something like this before.

Friends don’t care as much as we do.

Family can’t understand what it feels like to walk a mile in our shoes.

There’s maybe some truth in each of these complaints.

But what is important is why you are getting negative results in the first place.

Want to know the cause?

You may be ticking off a hundred reasons in your head as you read this sentence.

But ultimately, there is only one.

And that is YOU.


In addition to being the most dedicated, you are also the most emotional, the most tired, the most reactive, the most frustrated, the most (insert what you are feeling right now).

You get the picture.

The pressure, emotion and intensity of being an entrepreneur is often accompanied by a lack of perspective, and a failure to apply to your own behaviour a set of basic principles that will prevent a chaotic business environment.

The same drive, self-assurance, and creativity that enable you to create vision, are often the same characteristics that prevent you from bringing that vision to life.

Isn’t that a relief?

You thought you had hundreds of problems to fix and you only have one—YOU.

At first glance, this may seem like a huge slap in the face.

On the contrary, it is the realization that will unlock your potential and create new skills and opportunities to move your business forward.

Don’t look at this as fixing something that is wrong with you.

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It’s natural that you are in over your head.

Being an entrepreneur is a humbling experience.

Your friends say to you, “You get to be your own boss.”

You think to yourself, “It must be cool to make the donuts at Dunkin Donuts.”

On Being an Entrepreneur and Managing Chaos

Accepting that your company is failing because of you is a tough pill to swallow.

But once you take the medicine, and put the job of “learner” on your resume, you can do great things.

Accept this truth, and it will set you free.

With that in mind:

  • Why is there too much to do? Because you need to set the priorities and align your resources to those priorities.
  • Why do you lack financial resources? Because you need to raise enough money to keep the company properly funded.
  • Why do you lack human resources? Because you need to raise the capital necessary to build the right team.
  • Why do you not have established priorities? Because you need to understand how a company that has to do everything, can still prioritize one thing over another.
  • Why do internal and external constituents lack clarity? Because you need to avoid communicating in a way that is confusing and verbose.
  • Why are you frustrated with existing resources? Because you need to understand their role, establish their job, and align their skills to the appropriate tasks.
  • Why do you make reactive and emotional decisions? Because you are reactive and emotional.
  • Why is the management of your company reactive? Because you need to build a plan.

It’s tough, but once you realize the power of changing your perspective, the challenge becomes exciting.

The responsibility becomes liberating and not so different from the satisfaction you feel being accountable for inventing a great idea, or trendsetting product.

Great Leaders Are Great Learners

There’s a powerful book called Leading at the Speed of Growth: Journey from Entrepreneur to CEO by Katherine Catlin and Jana Matthews.

It addresses the long-standing belief that entrepreneurs who start a business do not possess the skills to help a business grow.

It challenges this notion and argues that entrepreneurs have enormous talent that simply needs to be applied differently at various stages of the business.

In other words, the unique talents entrepreneurs possess—drive, passion, creativity, the stomach for risk and uncertainty—can’t remain static or be applied with cookie cutter repetition to distinct and evolving stages of your business.

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No matter how much talent you bring to the table, to achieve success, you can’t remain satisfied with your own status quo.

Your skills and perspective must be adaptable and flexible as you grow your business.

This had a profound impact on me.

It was as though someone said to me:

“If you are as good as you think you are, you need to change.

Being an entrepreneur, this really challenged me—though I’m sure it was my ego talking.

Then I realized how much a change in my own perspective could help my company.

What an opportunity.

I also didn’t realize was how empowering it was to be challenged, to acknowledge shortcomings, and to grow.

Change in the midst of calm seas is one thing.

Change in the middle of a hurricane is another.

If you can come out the other side, imagine what that would feel like?

When someone asks you, “How is your company going?

you probably answer with a description that includes the word crazy or chaotic or nutty, or something unprintable.

Wouldn’t it be something to be able to say, “We have our shit together”?

When my company was acquired, one of the sales team members of the company that acquired us said to me, “Every time I interact with your business or your people, you are organized, structured and efficient.”

What a message to be able to share with your team.

It still makes me proud.

There is a famous line in the John Lennon song “Borrowed Time”—“The more I see the less I know.”

Once you accept this, it is easier to see that your perspective is both the cause of your company’s problems, and its best opportunity for success!

Embrace the gift of growth and learning.

You may tap potential you didn’t know you had.

Bottom line: it is your job to fix these issues.

You are the leader.

Being an entrepreneur, you must manage the chaos, whether it is the pressure, passion, pleasure or pain, a lack of experience or lack of perspective doesn’t matter.

It is YOUR job to fix it.

But while you’re doing hard work, remember that you are the greatest tool you have to transform chaos into order; to bring your vision to life—and to see it grow successfully.

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