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The Myth of the “Lifestyle Entrepreneur”

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There is a false dream being overly sold today. 

It’s is the facade of The Lifestyle Entrepreneur. 

It typically includes messages like work from anywhere, set your own schedule, be your own boss, drive a Bentley, and make passive income without doing anything. 

It’s a damaging dream because it’s a lie. 

My problem is not with the promotion of all the things you can have, such as some of those listed above. 

All of those things can become true…eventually. And there are lots of different types of pay for performance business models that can yield them over time. 

My problem isn’t with the dream they are selling, my problem is the dishonesty about what it takes to get there. 

Because the reality is that anyone who has built a successful business has worked their freaking butt off with really long hours, for a really long time. 

They have sacrificed and saved, they have hustled and worked, and they have been beaten down over and over and over again long before they ever had any of those things. 

Real achievers have tried and failed. They started over and got slammed. They kept at it when it never looked like they would make it. But they stayed committed, they fought, they bounced back and went through piles and piles of muck and mounds of setbacks. 

They’ve had a thousand opportunities to embrace any number of justifiable excuses that would have been accepted by any other reasonable person – yet they turned their back on those “outs.”

Every “Lifestyle Entrepreneur” I know that has actually made it is someone who has worked relentlessly to get where they are and they make no mistake about what it’s taken to get there.  

The people who have successfully built businesses are easy to spot because they are the ones who are talking about the truth. 

They are talking about how hard you have to work to get there. They are talking about all of the rejection you have to endure. They are talking about how many times they failed. 

Successful people have unmistakably learned that you do what you have to do until you’ve earned the right do what you want to do. 

So while they may have some shiny toys, big brands, and large followings, they would never promote how easy it is to get there because they know full well that it’s a lie. 

Robert Herjavec from the Shark Tank said it pretty well when he said, “If you are under the illusion that you can start a business and run it at your life’s schedule, you are mistaken. The business is like a starving puppy-when it needs to eat, then it needs to eat regardless of what you have going on personally.”

Gary Vaynerchuk also captured it nicely when he dropped this truth bomb, “people leave companies to start their own business thinking that it will somehow be easier. They are badly mistaken. What they will quickly realize is that if you thought your old boss was bad, in order for your own business to succeed, your new boss had better be a slave driver.”

So if you’re allowing yourself to be convinced that there is some easy path that you’ve missed out on – don’t be. 

If you’re scrolling through social media looking at the manicured versions of other people’s lives thinking they’ve figured out something that you haven’t – quit that. 

If you’re selling yourself that if you’re being asked to work hard you’re in the wrong business – stop it. 

Because chances are that if you’re doing anything that is hard, then it probably also has integrated into it a path to many of the great things you want. 

But it won’t come easy. 

And it won’t come fast. 

And it sure isn’t going to come from jaunting gleefully around the world working only 20 hours a week. 

Quit buying into the lies. 

Quit allowing yourself to be deceived. 

And instead, put your head down and go back to work. 

When you get tired, suck it up and go back to work. 

Then, when you’re ready to quit, go back to work. 

After you’re sure you can’t take anymore go back to work. 

Once you’re completely empty, keep going back to work. 

And one day, after you’ve done that, in one direction, for a really long time, you’ll look up and realize that the “Lifestyle” you thought you missed out on became your actual reality.  

  • Olabisi Lawal

    Awesome and revealing! This is nothing but the truth. Thanks Rory

  • Ze’ev Smason

    Job 5:7: “Human beings are born to work.”

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