Freedom’s Just Another Word for Nothing Left to Lose

These words, written by Kris Kristofferson and immortalized by Janice Joplin in her rendition of Me and Bobby McGee, frequently roll through my head. 

Why did I become an entrepreneur?


I’m restless. Every job I had before becoming an entrepreneur left me dissatisfied. Certain that my ideas were better than those being implemented by the executives around me, always subject to committee consensus and diluted by compromise, I convinced myself that if I had complete control I could achieve much better outcomes. 

I believed that starting a company, having a blank page in front of me, meant total freedom and independence and a chance to determine my own destiny. That’s the reward for taking on so much risk, or so we tell ourselves. But is it true?

American culture celebrates the power of the loner, the super man, a gun slinger who comes in and cleans up the town, saves the day and then disappears into the sunset. Having been fed this narrative since birth, we grow up believing in the power of one. We idolize those free individuals – Jack Reacher, the Lone Ranger, Batman – who get to decide every day where they go and choose the problems they want to solve. We admire their lack of entanglements and the power they seemingly derive from that.

It is called mythology for a reason.

As soon as you start something tangible, hire people, raise money and engage in partnerships, freedom evaporates. You’ve created an ecosystem. People now depend on you for their livelihood. 

Being the ultimate decision maker has never made me feel free, unless freedom weighs six tons and squeezes the air out of your lungs.

Recognizing that my idealized version of freedom didn’t exist in entrepreneurship was a wake-up call. Once I created my company, I felt the opposite of freedom. 

I felt trapped. 

I’d made many, many assurances, to myself, to investors, employees and to others about how great the company would be, how we would grow, make customers happy, change the world, etc.

So how do you cope with it?

When you jump into entrepreneurship, you are in it. There are only two ways out, to quit or to take it to a positive conclusion, grow your company into something that can be handed off to another person or organization when you no longer feel equipped to deal with it. The other alternative is to stay in, recognize it for what it is and push your dream forward. Don’t run from the dependencies and expectations. 

Accept that this is not freedom because there is much to lose.



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