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I’ve uploaded a previous podcast episode that I did with Vinay Hiremath about having a chip on your shoulder and whether that’s a healthy thing or not. If you are interested in what I write below I’d recommend listening to that above.

It seems to be a rule of a successful enterprise that the ones most motivated to succeed by external measures have a chip on their shoulder from childhood experiences that motivate them to do whatever it takes to prove the world wrong.

In proving the world wrong we are playing out something that happened when we were younger as if it were happening right now. We are trying to prove the offending party wrong, whether that was our parents, the high school bully, or our first lover.

This is very personal for me as I grew up in a family with enough chips on our shoulders to build a wooden bridge across the San Francisco Bay. I have been struggling for many years with gigantic chips on my shoulders that have defined my identity in many ways that I find useful and a whole lot more which I do not.

In the episode above, Vinay recognizes his own chips on his shoulders and gives nuance to the discussion by saying that whenever he hires for the company he co-founded (Loom), he actually looks for someone with something to prove to the world.

But he doesn't leave it at that. He also looks at whether they are aware of their desire to prove something to the world. If someone is not aware that they have a giant chip on their shoulder then it can lead them to be a massive jerk.

Self-knowledge seems to be the key to channeling the rebellious energy of our past into a productive and effective future.

I uncovered a lot of wisdom in my life from hearing Vinay's thoughts on this subject. Since this episode a few months ago, with the help of a coach, I have gone further and started to explore the following questions:

Is it possible to integrate the chip on my shoulder totally while still achieving external metrics of success? To not let it run my life?

Can my desire for success come from a sense of abundance and serving rather than proving the world wrong?

What I've been finding is that the chip on my shoulder has lead me to invest energy in building an identity named Stewart who had a difficult childhood and overcame that childhood and was right.

There is nothing inherently wrong with this identity but I do believe that investing energy into this identity makes me less than agile or antifragile when it comes to certain situations.

My benchmark for a healthy or effective human interaction is one where I'm able to respond to the conditions of the moment rather than to how my identity should be acting in a given situation to maintain consistency.

To really listen deeply to what the other person is needing in that moment or what I myself need (not the identity). To respond from a place from the unknown potential of what could be as opposed to what should be.

I believe an identity gets in the way of that type of listening and so I'm going to try and get to the root of all the chips on my shoulders. To find freedom in all things!

*PS - The history of the term “chip on your shoulder” is very interesting.



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