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Screw Being Your Own Boss

In: Business 101,

“I started my own business so I could be my own boss!”  Meh meh meh meh meh!  *high-pitched little girl's voice*

No, you didn't.

You might think you did, but you definitely didn't.

Want to know why?

Because being your own boss is infinitely harder than having a boss. And by infinitely (which, by the way, is a pain in the ass to spell), I mean 17,929,531.9045 times harder. Yes, that's exact math. Although I suppose it's more than that, since we're talking about INFINITY. So it's not exact math. If this were still the 90's, I'd tell you to sue me. But since it's not the 90's, I'll tell you to blow me, instead. Because that's classy.

The next time I hear someone say that they want to be their own boss, I'm going to take the nearest rotten pork chop and slap them across the face with it. Because that's kind of what it's like being your own boss.

Gone are the days when you just take orders and go home at 5pm to your cozy little cottage to watch Desperate Housewives while shoving Twizzlers down your throat.

Being your own boss means a humongous fucking time investment.

Being your own boss means mega responsibility.

Being your own boss means that the work is never done.

Being your own boss means rules, regulations, taxes, paperwork.

Being your own boss means you can't just zone out.

Being your own boss means your livelihood.

Being your own boss means your dignity.

And dammit…

Being your own boss means that sometimes, when the hottest guy on the face of the planet wants to bone, you have to say no.

So why do we do it, then?

Because being your own boss also means freedom, of course. But not just the kind of freedom you're thinking of, like the kind where you hop on planes and roam the planet and do whatever you want. (Though, that's an awfully nice bonus.)

We're talking creative freedom.

Freedom to experiment and play with opportunity in ways like you never have before. Freedom to dip your little red toenail into the unknown, and stir things up a bit. Freedom to prove to yourself that you're more than just a job title. 

And the freedom to be you in ways you've never been before.

Opportunity, man.


With the internet, you've got so much more than you realize.

Not just to “be your own boss,” but to do something that fucking matters.

Because at the end of the day, that's really why you want to quit your job.

Isn't it?

Enter your email address and I'll rummage around in my bag of tricks for JUST the thing.



Fuck Plan B. You’re on the A Team.

His name is Oskar. He’s Rastafarian. I met him when I first came to Costa Rica in 2004 and watched him trying to sell his paintings day after day on the beach, sweating, struggling to speak English to the tourists who passed by, working from dusk until the wee hours of the night to make […]

In: Business 101,


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84 thoughts on "Screw Being Your Own Boss"

  1. Esha Addy says:

    Such an awesome post. Being the boss is the double edge sword. But, I rather be the damn person that controls my destiny and not some lifeless robot called a job. You think being your own boss is risky wait when that so called secure job drop “DEUCES” on you. 

    By the way Ash you are awesomeYou have helped me find my true voice. No longer are the days of being the perfect lil solider for dick-head non leading bosses. 

    1. Anonymous says:

      YEAH!!!!!!!!!!  It’s go time, baby. 😉