The Brutal Truth About The Lifestyle of Entrepreneurship

The lifestyle of an entrepreneur looks amazing from the outside (and it truly is great in many ways)!

Being an entrepreneur means the freedom to create your own schedule, the ability to make big decisions, and the possibility of more income than you would make at work.

What could be better than making money while driving your kids to school or the puppy to doggy daycare?

How about opening up your laptop and working anywhere… including the beach!

However, there are some downsides to the lifestyle of an entrepreneur.

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 must work the hardest.

Care the most.

Put in the most hours.

You should be the most dedicated.

You should be the most passionate.

It is you who puts in the money, strains your personal life (if you have one), depletes your finances (if you still have any), and strains your relationships (if you have any).

The lifestyle of an entrepreneur includes a lot of crying, maybe drinking, not sleeping, no time for dating, and spending every waking moment on the business.

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

No one said living the lifestyle of an entrepreneur was fair

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

Common problems characterize this chaos:

  • 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 their destination as quickly as possible).

Meanwhile, taxi drivers without passengers drive slowly and erratically (to be able 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 taking away all structures of order—lights, lane lines, speed limits, and traffic signs—and throwing in jaywalking pedestrians, a couple of skateboarders, a dog walker with an unwieldy pack of hounds, and a good oil slick.

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It becomes a game of Frogger on steroids.


Being an Entrepreneur and Accepting Your Role

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

Without the appropriate management tools, entrepreneurship is like driving in New York City without 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.

Maybe you’re developing a new market, or you don’t have the resources to operate like a more established business.

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.”

Common thoughts you will have as an entrepreneur

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.

Your family can’t understand what walking a mile in your shoes feels like.

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?

As you read this sentence, you may be ticking off a hundred reasons in your head.

But ultimately, there is only one.

And that is YOU.


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

You get the picture.

The pressure, emotion, and intensity of being an entrepreneur are often accompanied by a lack of perspective and a failure to apply basic principles to your behavior, preventing a chaotic business environment.

The same drive, self-assurance, and creativity that enable you to create a 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 only have one—YOU.

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

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

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

Naturally, you are in over your head.

Being an entrepreneur is a humbling experience.

Your friends tell 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 about the lifestyle of an entrepreneur, and it will set you free.

With that in mind:

  • Why is there too much to do? Because you need to set 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 adequately 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 confusing and verbose way.
  • 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 the challenge becomes exciting once you realize the power of changing your perspective.

The responsibility becomes liberating and not so different from the satisfaction of 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 needs to be applied differently at various stages of the business.

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In other words, entrepreneurs’ unique talents—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.

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 told 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 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.

Imagine what that would feel like if you could come out the other side.

When someone asks you, “How is your company going?” you probably answer with a description that includes the words crazy, chaotic, 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 songBorrowed Time”—“The more I see the less I know.”

Once you accept this, it is easier to see that your perspective is 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.

This is the reality of the lifestyle of an entrepreneur.

Being an entrepreneur, you must manage the chaos.

Whether it is the pressure, passion, pleasure, or pain, a lack of experience or 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, bring your vision to life—and see it grow successfully.

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