The Founder Freedom Fallacy

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  • Published on August 5, 2021
  • Last Updated March 18, 2022
  • In News

Freedom is a huge motivating factor for most founders. Almost every entrepreneur I work with dreams of freedom. 

Iโ€™m not talking about the kind of freedom that an ordinary person might desire. Iโ€™m talking about Mel Gibson in Braveheart type โ€œF-R-E-E-D-O-M!!โ€

Unfortunately, such dreams may remain dreams alone. The day-to-day realities of freedom and entrepreneurship are often diametrically opposed.

Sadly, most entrepreneurs learn the hard way. They donโ€™t find out until theyโ€™re neck-deep in starting their business, that achieving the level of freedom theyโ€™re looking for is a fallacy that cannot be realized until much later when the business is successful.


The definition of โ€œFreedomโ€ for entrepreneurs usually comes in a few common flavors. Business owners want the freedom to set their own work schedule; The freedom to make all the money they want; The freedom not to report to a boss. 

These are all fantastic north-star goals. Yet far too often they get traded in for more pressing needs and immediate concerns, never to be seen again.

What we donโ€™t learn until much later โ€”if not too lateโ€” is that being โ€œin controlโ€ is actually the one thing that causes us to feel out of control. Subsequently we become trapped by the very thing we thought would save us.

Itโ€™s totally understandable why freedom is a sought-after experience. Everyone wants to be independent and live an autonomous life.


According to a report by The Journal of Personality and Social Psychology, โ€œautonomyโ€ ranks as the number one driver to happiness, which they define as, โ€œthe feeling that your life โ€”its activities and habitsโ€” are self-chosen and self-endorsedโ€. 

So, as founders, we often think that being โ€œin controlโ€ of our company is the key to the autonomy we need to find the happiness we desire. But this is where most people get tripped up. 

The most exquisite paradox of them all is as soon as weโ€™re willing to give it all up, we can have it all. The challenge is not collecting it all, itโ€™s deciding when to hold on and when to let go. 

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