Inside Out Leadership

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The secret to leadership

Authentic leadership, we’ve all heard the phrase. Truth be told, It’s this special kind of leadership superpower that we all possess, but most people hide without even knowing they're doing it.

Leadership doesn't have to be hard. Seem too good to be true?

“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness, that most frightens us. We ask ourselves, Who am I to be brilliant, gorgeous, talented, fabulous? Actually, who are you not to be? Your playing small doesn’t serve the world. There’s nothing enlightened about shrinking so that other people won’t feel insecure around you.” – Marianne Williamson

Authentic Leaders Are More Effective Leaders

Leading authentically isn’t about warm fuzzies. It’s about effectiveness. 

Most leaders work really hard to lead. They study what the best leaders do and try their best to emulate them. They hustle maniacally, and yet they consistently struggle. Work is a constant battle, as they try mightily to enroll people in their mission and make an impact. 

And then there are a few leaders for whom everything seems easy. Things just tend to work out in their favor. Spend any amount of time around one of these people, and you know the difference between people who do leadership, and people who simply are leaders.

Authentic leaders aren’t trying to be anything at all. They wear what they want. They say what they feel. They don’t hide the messy parts of themselves, and they don’t worry about what people will think. They just are inexorably themselves, and they happen to be dedicating their lives to something. You can’t fake authentic leadership. It’s not a mantle you can put on. It’s an alignment between who you are on the inside and who you are on the outside. These people, true authentic leaders, fully aligned inside and out, you want to follow them. Everyone does.

Authentic leadership gets misunderstood as something moral. Something that you should do, because it’s the right thing for some or another reason. But it’s not a moral issue.

Authentic leaders are simply more effective leaders. 

Leadership is a function of energy. This is why we call the best leaders a “force of nature,” because their energy exerts a powerful effect on their surroundings. We all have this energy within us, innately, like a light shining from deep within. But most of us learn early on that we need to be one particular way or another to be “successful,” and so we begin to filter this light to better match the ideal we have in our heads. Like a slide on one of those old school overhead projectors, we filter out the parts of ourselves that don’t look like the hard charging alpha male, or the compassionate leader, or whatever leadership archetype we’re holding in our subconscious, and in so doing make ourselves less powerful.

Trust Yourself

The most powerful, effective leaders are those whose light shines through fully, without filter. They do not concern themselves with pleasing one constituency or another. With looking the part to their investors, or being strong for their employees. They don’t question whether they should be this way or that way in a meeting. They let every last “should” go in favor of simply letting their light shine through in its fullness. 

Said another way, they trust themselves.

It’s these wonderful people, those who have figured out who they are, and lead fully as that person, who I am calling authentic leaders. 

And you don’t have to be one. 

Nobody will think less of you if you decide to be a “good CEO” or a “great leader” (in fact most of society will appreciate you more, because you’ll more thoroughly look the part of whatever you’re doing. Society loves conformity). But if you try to be someone, your effectiveness as a leader will always be limited. Every time you try to change yourself into something more (effective, successful, sexy, etc), you’re putting another filter on the projector, and you dim your light. 

“There is a vitality, a life force, an energy, a quickening that is translated through you into action. And because there is only one of you in all time, this expression is unique and if you block it, it will never exist through any other medium, and be lost. The world will not have it. It is not your business to determine how good it is, nor how valuable, nor how it compares with other expressions. It is your business to keep the channel open.” – Martha Graham

I spent most of my career as a CEO trying to be somebody. I had an image in my head of who my employees wanted me to be (a cross between Steve Jobs and Ashton Kutcher), and who my investors wanted me to be (Adam Neumann, which says something about my cap table), and I tried my damndest to be that person for them. Sometimes I was, when I had it all together. But even at the best times, it felt forced. And most of the time, I felt like a fraud. Like a duck, on the surface I was calm and collected, but underneath, I was paddling manically to simply stay afloat. 

I learned that you can have all the trappings of a successful life, and still feel like something is wrong. I learned that, even when you win the game, you can feel like a loser. In working with many of the fastest growing CEOs in tech, I now know that many successful people feel this way. The solution is not more stuff or more success. The solution is to figure out who you really are, underneath all the roles you’re playing, and to commit to being that person in the world, without reservation. 

I look back now at the moment I left the company I founded and scaled, one of the hardest moments of my life, and I’m grateful. For 15 years I was sure that who I was was a hotshot tech CEO, a “big deal,” and in leaving I was forced to confront the fact that I had never been that. Not really. It was just a role I’d been playing, a role I lost myself in. And in learning that, I removed a filter and allowed a bit more of my light to shine through. Had I never left my company, I’d probably still be living America’s idea of success, chasing another dollar or belt notch and thinking it would fix me. 

You don’t have to live this way. 

Authentic Leadership Is A Choice You Make

No matter where you are in your leadership journey, no matter how thoroughly enmeshed you are with your company and your identity as a leader, you don’t have to wait until you have no choice. You can choose to let your authentic leadership shine through now. 

It’s undoubtedly more fun. Less stress. Fewer things to remember. But more than that, leading authentically simply works better.  You don’t have to recruit people because the right people simply come out of the woodwork to find you. You don’t have to hide skeletons in your closet when pitching investors, because they see that you believe in what you’re building, warts and all. You’re way more successful, with way less work (I’ve finally learned the incredible power of serendipity). I work 30 hours per week now and make more than I ever did as a CEO. 

I imagine that for some of you this sounds too good to be true. 

It’s not. It’s your birthright. 

You just have to let go of the person you think you should be, and reconcile with what’s underneath.

“The way to rule the universe is to expose your heart so that others can see your heart beating, see your red flesh, and see the blood pulsating through your veins and arteries.“ – Chogyam Trungpa

If that sounds scary, that’s because it is. Being unique in the face of a society that wants conformity is fucking scary. It’s way easier to simply learn the dress code and put on your suit (or for tech CEOs, your hoodie).  

But on the other side of that fear is the life you were meant to live. The force of nature you were meant to be. And the most effective leader you can be.

How do you do this? 

Let’s talk.