The Guide to Wholehearted Leadership
Become a decade-long founder by unlocking your X Factor
When I started my company, I was pretty freakin’ authentic. I had my ambitious, Type-A work side but I was also goofy and a love bug. It was just my cofounder and I, so there was no hiding any part of me. Even when we were a jolly group of four people at 500 Startups, I let this empathic, lover free -- we started having weekly meals together where we could hang and be ourselves.
As we climbed to 20 people, I could feel a shift in myself. I started looking at leaders of scaled companies and thought, “I think I’m supposed to be more professional. I need to look and act more like them.” Each new person who joined the team didn’t know me the way my cofounder did. I felt that to gain more credibility, I had to be a little more polished. It was interesting but didn’t feel fully like me.
At 50 people, my errant comments on features or projects would create changes to the product roadmaps. I would get feedback from leaders that I had to watch what I said because I was the CEO, and people gave extra weight to my opinion. I felt like I was under a microscope. As the pressure mounted, I leaned more on the “leadership” side of me who was controlled and decisive. I assumed she inspired confidence.
I also de-emphasized the goofy, empathic side of me. I moved her out of the sunlight. She would come out in controlled ways: at team off-sites or dinners. She was alive with my friends and family, but decreasingly a part of my daily life. In the darkness she started to wither.
What a stifled x factor looks like
I work with clients who tell me they feel constantly tired and drained. They generally feel less excited about work. Stress levels are high. They attribute it to working long hours spread across many years. But even when they go on vacation, they still don’t feel recovered. I believe the underlying source of this burnout for many leaders is psychological, not physical.
Sometimes as they reflect on their culture, they realize they don’t even like the culture of their company. THEY feel like an outsider to the team they built. The culture doesn’t feel totally like them.
So what gives?
We are suffocating a huge part of ourselves to play a role. And it’s costing us energy.
Our abandoned side wants back in
There are (at least) two sides to every leader.
The first side is focused, ambitious, and driven. The side of us that gets stuff done. I’ll call this the Business Side. We put this aspect on a pedestal, bring this face to work, and build our companies around it. As the company scales, this side feels even more important -- it’s our work face, our professional energy, whatever you want to call it.
The second side isn’t focused on efficiency or productivity. It’s often more childlike, a part that we embodied at a younger age. It is playful and open to possibility. Ironically, this is often the part that births the idea for a business. I’ll call this the Creative Side.
Here are the archetypes I’ve witnessed in leaders I’ve coached and been friends with:
• The Empath - This part cares deeply about people, can read the room, and is in touch with their and others emotions. They are considered People People, and they have a superpower of being able to read and connect with people.
• The Artist - This part prioritizes beauty and truth, and it often has appreciation for aesthetics. It can be a more introverted part that creates well on its own.
• The Magician - This is an intuitive side that operates more from gut instinct and openness to possibility. It’s more playful, and can often drive insights that are predictive and almost psychic.
• The Fun Lover - This part loves music, food, and whatever vices it enjoys. It can come out with sales teams, but generally it’s not viewed as “productive” so it gets shoved for evening activities.
As a company scales, leaders accept the Creative Side less and finds it more threatening. We label it as immature or childish. We tamp it down, build more frameworks to manage uncertainty, and we try to choke it off.
Integrate your two sides into one whole leader
The ambitious, Type A personality type is pretty common in business people. It’s competent but bland. It is necessary but not sufficient to inspirational leadership.
It is the union or integration of our Business Side and our Creative Side that is our actual x factor. This powerful combination gives us aliveness and takes leaders from competent to extraordinary.
A few years into building my company, I began to recognize that I was stifling the Creative Side of me. Ironically, it was the part that made me human to others and inspired people to follow me down the chaotic startup path. With the help of my cofounder and coach, I brought my creative side (the Empath archetype) into the culture of the company. We initially called ourselves a love company, where care for people and connection lived at the heart of it. But this wasn’t integration, it was still favoring one side over the other. While it served us well initially, it didn’t make enough space for the hard-charging Business Side that I longed for.
As I matured and the business scaled, the integration became more balanced: we became a love AND excellence company. We believed that the two complement one another. You couldn’t love someone without holding them to a high standard, but you couldn’t expect excellence from them if you didn’t treat them with human respect and care. Each of these pillars had its own values, giving us a framework for 6 values under 2 pillars. If you’re interested in me publishing our Cultural Operating System, please leave a comment below!
Build a culture you want to work at
This integrated culture carried me through our acquisition in 2020.
People often ask me how I did it - how I ran my company for 10 years? And the core of the answer was in this integration of both sides of me. I was stoked to be a brand ambassador for a culture that was truly representative of the best parts of me and what I wanted to bring into the world. I loved how this alignment pushed us to challenge the standard Silicon Valley narrative of treating people like machines and squeezing every last drop out of people.
What could you bring into the world if you could bring your full self to your work?
What would excite you about that?
What blocks you from that?
Whatever story you might have about the deficiency of your Creative Side, I promise that it too has wisdom and aliveness to share. I hope you’ll let it loose on the world.
I appreciate you!
If you appreciate this conversation on identity and leadership, would you be willing to share this post with one other person?
If you’re managing your inner work alongside your outer work of building a company, you may benefit from my coaching work. If you book a consult, I’m happy to chat more.
yes pls!