Why Aren’t You Working “On” The Business?
Categories: Entrepreneurship

In my twenties I was pretty rotten at dating. I’d go on dates and only reveal the parts of my personality I thought my date would be approve of. We’d hit it off, things would start to get serious, then as more and more of my true self began to bubble to the surface, my new beaux would realize I wasn’t the person he started dating. 

This would start a typical unraveling that would end with me reminding myself that once again, I had been rejected. When, in fact, the root cause of this rejections was my lack of authenticity, honesty, and transparency. But it was far easier for my unconscious mind to blame it all on someone else’s behavior than it was to recognize my own unhealthy patterns. 

So why am I sharing how terrible of a dater I was? Fair question. The point I’m trying to illustrate is similar to the one I see with lots of entrepreneurs who tell me they’re not able to work “on” the business because they’re too busy working “in” the business.

As founders, we spend a good portion of our day in the weeds getting our hands dirty. In the beginning this is required. But over time we tell ourselves a story that we’re the “only person that can correctly do task xyz.” Or maybe we’re simply the creative type and we tell ourselves, “I do it because I love building things.” 

But if was that simple, why would we consistently put ourselves through so much emotional suffering to simply complete xyz task or build something new? This is sort of like asking an alcoholic, “Well, if you’re really that thirsty, why don’t you just drink a case of water?” We’re just as addicted as they are…just to something harder to see.

What if we’re doing it all for a completely different reason? Maybe crossing a task off your list or creating something new is actually less about the task itself and more about why you’re doing the task to begin with. Maybe it’s less about getting the task done and more about hustling for your worthiness. 

Peeling back the layers of what we’re doing and investigating why we’re doing it is often referred to as shadow work? We all have a shadow. (P.S. If you think you don’t, yours is probably even bigger ;))  And in that shadow lurks the unconscious behaviors that cause us to act in ways we don’t even understand.

My less-than-stellar dating habits were developed a long time ago as a safety mechanism. Showing my authentic self as a gay kid in a small central-Nebraska town in the mid-90’s was dangerous and liable to get me hurt. It wasn’t until I had done a lot of my own shadow work that I realized I was actually the cause of my own dating issues and that being rejected or abandoned was simply a story I was telling myself.  

So I’d invite you to ask yourself why you’re working so hard “in” the business versus “on” the business? Could it be that crossing tasks off your list makes you feel good because when you did that as a kid you got a gold star or extra ice cream? Or maybe you love the joy of closing a big sales deal because you were taught that winning at sports was the best way to receive praise and affection (from family, friends or even strangers).

In the end, our subconscious mind is sort of like water and electricity. It prefers the path of least resistance. A study published by the University College London puts it this way,

Imagine you are in an orchard, trying to decide which of the many apples to pick. On what do you base your decision? Most research into this type of decision-making has focused on how the brain uses visual information – about features such as colour, size and shape – to make a choice. But what about the effort required to obtain the apple? Does an apple at the top of the tree look more or less tempting than the low-hanging fruit?

This study goes on to suggest that our brain will trick us into believing the low-hanging fruit looks more appealing. Not because it’s actually the ripest, but because it’s the easiest to acquire.

Shadow work is a tricky business though. We can’t see our shadow anymore than we can tap into our unconscious mind. These thought patterns and behaviors are highly adaptive and sometimes they’re all we’ve ever known. We only know we’ve been hanging out in the dark after we’re presented with light. 

Holding up a mirror to your unconscious mind is the “easiest” (and usually unpleasant) way to begin exploring these hidden patterns. For starters grab a pen and paper (really, a real pen and paper – not a keyboard) and answer a few of these questions to get you started:

  • What do you think are the worst character traits a person can have?
  • How do you think people see you, describe you, or feel about you?
  • What really triggers you, makes you angry or sad?
  • Who do you envy and why?
  • What person or institution has hurt you the most in your life?
  • What memories bring you shame?
  • Who regularly (or last) belittles or downplays your emotions?
  • Which relationships in your life no longer serve you?
  • What do you most dislike about yourself?
  • What do you wish people understood about you?

Now take these answers and say to yourself, “If you spot it, you got it.” All too frequently the things that make us crazy looking at other people are actually traits we don’t like in ourselves. Going deeper into this work usually requires the help of another human. Someone patient, curious, and safe enough where we can be totally honest and unguarded. Sometimes that’s a good friend, a therapist, a coach, or a clergy member.

The path to emotional sobriety is a tricky one so I can’t urge you enough to begin examining your shadow. And remember, the closer we move towards the light, the more of our shadow we get to see.


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