What It’s Really Like Being An Entrepreneur

I’ve been an entrepreneur since 1999. I’ve lived through 2 recessions and have fired more people than I care to even think about.

There have been long stretches where I felt like I had PTSD. Maybe I did. I never go to a therapist. I just take anti-depression medication.

Being an entrepreneur is intense. Wild money swings. Sheer terror. Complete devastation of self-belief and worth.

Clearly I’m not painting a pretty picture here. But I feel it’s important to tell you those things before I tell you this:

The alternative sounds 10 times worse. I don’t know how long I could survive in a job. I suspect if I didn’t kill myself I would at least be emotionally and spiritually gutted. A job to me is just a cage.

I would rather be the king of a pile of shit than be a drone in a fancy office.

I tell you this because I’m pretty confident that is how you need to feel if you want to become an entrepreneur. The alternative should look and feel like death to you.

Chances are quite good you will make less money and work harder than your peers that climb the corporate ladder.

That’s not always the case certainly. There are many people that will never make the money you make. But if you are a go-getter / achiever, chances are you run with similar types of people. I see friend after friend living extravagant, fancy lives as I sit in my two bedroom apartment and go camping each summer in my old popup camper.

I’m quite sure I probably could be making more money as a marketing executive somewhere.

But there are two things you need to realize about that:

  1. I’ve also known many people that get pushed out of their cushy executive lives.
  2. I am not at all confident that anyone would actually hire me for one of those jobs. I have, more than once, been called a “loose cannon.” I’m proud of that label. But I also know that it probably makes me look uncontrollable. Which is probably true. You would never put a guy like me in your organization unless you wanted it turned upside down, probably with very little input from you.

I was inspired to write this because I was thinking about how being an entrepreneur often makes people go crazy.

There’s a local ice cream shop guy that is obsessed with people “illegally” parking in his parking lot. It’s usually chained up so no one can use it, including his own customers.

The property manager of our building has become obsessed with a broken down car in front of our building. It’s ALL he can talk about.

And me, well, I’ve got 3 or 4 (I’m not really sure of the number at this point) homeless people living in the basement of my building. So there’s that.

It’s just a crazy way to live your life.

But ultimately, you have given yourself the gift of freedom.

We often talk about freedom in America. And, really, I don’t think people give that word much of a thought. But I do. I think about freedom all the time.

I am constantly trying to break free from the constraints that society constantly tries to put on me. I am a perpetual rebellious teenager.

And that’s what being an entrepreneur is. Being free is worth sacrificing almost everything else in exchange for it.

If freedom isn’t that important to you then it’s very possible being an entrepreneur might not be the best path for your life.


  1. Ryan Scanlon December 22, 2016
    • Sage December 22, 2016

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