The Weight of Your Shadow on Your Company

At a Glance:

• What is our shadow

• How it weighs on our organization

• Five questions to connect with your shadow 

My last newsletter, about channeling deeper motivations to create meaningful ventures, led to some beautiful connections and stories. 

One of the most inspiring new connections was with Julie Penner, a Boulder-based venture capital investor, coach, advisor, and writer who lives at the intersection of inner work and entrepreneurial success. She focuses on areas like conscious leadership, the enneagram, secular Buddhism, and internal family systems (you may remember IFS from an earlier newsletter). 

She’s my people. 

Julie has written extensively about founder motivations, so I dug in with her on how to show up as our best selves. That conversation led to a critical topic: “Why understanding our shadow is required for future leaders.” 

The Shadow

Carl Jung (also in many of my newsletters) illuminated the power of the shadow on our lives and the importance of making peace with it. For him, these subconscious, repressed traits, desires, and impulses that we deem “out of bounds” with ourselves and our society are the keys to self-awareness and feeling alive.

For leaders, it’s critical. Julie explained: “While drivers like ambition and defiance can fuel a startup’s early growth, they become liabilities if founders are unaware of their impact on those around them and how they shape the company’s culture.” 

We all have a shadow self with the power to drive our actions. For me, it was using business success to gain back power and admiration: “F**k you, watch what I can do!” 

Whether it is anger, fear, jealousy, or shame, it’s an incessant background drumbeat behind our actions and a cloud over decisions. 

Why it’s Important

As Julie says, “Founders who acknowledge their shadow traits and integrate them wisely build meaningful companies and enjoy the ride. They harness their ambition while mitigating the self-destructive aspects of their personalities.” 

She shared stories of spite as an example of that fuel: people who suffered deep injustices of prejudice along gender, color, or identity. Sometimes, the founder worked through their shadow’s influence, and the company transformed and succeeded. In other cases, the founder’s repressed anger never shifted, and the weight of that drive hampered the company. 

Sometimes, companies hire other execs or “hired-gun CEOs” to balance founders who cannot make peace with their shadow. This can work, but often, when you neutralize or remove the “spiritual and historical foundation” of the company, the culture changes to reflect the shift in values. For the team, it becomes a job, not a mission. 

As AI levels the playing field, companies must find ways to support the flourishing of their team and customers. They must channel creativity and uniqueness or suffer a race to the bottom with other vanilla companies. 

Founders who can’t get past their shadow’s influence will never create a meaningful, connected organization. 

Inviting Your Shadow to Tea

In the last newsletter, I had questions to help channel your deepest motivation. But it doesn’t happen without welcoming your shadow. 

In the Buddhist tradition, this is described as “Inviting Mara to Tea,” with Mara being the demon who sought to distract and tempt the Buddha from enlightenment. This means learning to love your shadow.  

I asked Julie, “What questions do you ask founders to find their shadow’s influence?” 

Like all inner change, the real work is emotional and somatic, not intellectual, but these questions serve as a road sign to point in the direction of the work. They are meant to be challenging and contemplative. If there’s something here that you don’t want to answer or face, it’s a good indication that a shadow is lurking. 

1. What’s something that was challenging for you as a child?

2. What do people sometimes misunderstand about you?

3. What erodes trust with you? How can someone lose your trust?

4. What’s a behavior that deeply annoys or irritates you? How did you react when you last witnessed it?

5. What would you do differently if you could do your life so far over again? 

With love,

Dave

Know someone struggling with their shadow and how it’s holding them back? Share this newsletter with them. 

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