The Entrepreneur’s “Not Enough” Trap–And How To Avoid it

A leadership coach for some of Silicon Valley’s top startup CEOs reveals how to hack your mind for success, satisfaction, and putting fear out to pasture.

The Entrepreneur’s “Not Enough” Trap–And How To Avoid it

As a leadership coach for some of Silicon Valley’s leading startup CEOs, I get a peek into the internal workings of some of the most brilliant and accomplished entrepreneurial minds in the world. And one of the things I’m finding there is giving me cause for alarm.


Driven by “Not Enough”

One of the primary drivers of the frenetic striving and Herculean accomplishments of the world’s most successful entrepreneurs is a deep sense of not being good enough. Not smart enough, not brave enough, not creative enough. Somehow, in some way, not enough. This sense of lack, and the compulsion to anesthetize it through achievement, combined with the right combination of smarts, guts, and ecosystem are creating a boom in the startup world. Billions of dollars and hundreds of thousands of jobs are being created. And that’s a great thing.

But the dark underbelly of this startup boom is that too often companies are getting built in a way that leaves founders and team members drained, exhausted, and ultimately, unfulfilled. It’s the result of building a company because you think you have something to prove. It leads to a near constant state of anxiety and fear of failure with fleeting moments of celebration. And it doesn’t have to be that way.

Wired for Fear

Human brains are predominately wired for fear. It makes sense evolutionarily that in a world of lions, tigers, and bears, those with the most sensitivity to danger would have the best chance to survive and reproduce. The mental constructs “I’m not enough” and “I don’t have enough” are brilliant survival programs for creating a near constant state of vigilance and drive to succeed.

But we no longer live in that world. We have conquered all of our natural predators and civilized our society at such a rate that our brains are fairly outmoded for our modern world. So too, is the way we operate as creators and builders of businesses.


Driven by Love

As society’s innovators, entrepreneurs have a great opportunity to pave the way for a new way of conducting themselves and their businesses–shifting from a context of “not enough,” fear, and lack to one of sufficiency, love, and inspiration. The pioneers are among us.

When you conjure up an image of Sir Richard Branson, what most likely comes to mind is a man who loves his life. You picture him grinning ear to ear, laughing heartily, and warmly shaking someone’s hand or giving them a hug. He’s a man who savors life, and whose entrepreneurial endeavors themselves appear to be acts of love and creative expression. Herb Kelleher, founder and chairman of Southwest Airlines, is another entrepreneur who clearly built a company from a place of love and service. Southwest is renowned for their extraordinary culture, and the caring they show for each member of their team and their customers. Their ticker symbol is LUV. Their examples serve as a shining counter-example to the norm among entrepreneurs.

Moving Beyond Fear

When I challenge my clients to believe they are enough just as they are, they often reply that they’re afraid to lose their drive to succeed. They worry that if they felt the sense of peace and appreciation that comes with believing who you are is enough than they would become couch potatoes (or worse, failed entrepreneurs). What they initially fail to realize is that there is another, more powerful source of motivation: love. When you imagine contributing to another person, or a group of people, in a meaningful way you can’t help but feel a stirring in your heart and an energy in your core that pulls you into action. And from this inspired place, your level of focus, creativity, and energy is far greater than when you’re driven by fear and lack.

When you experience your work as contribution to others, you handle setbacks and obstacles in stride instead of seeing every bump in the road as a potential to expose you as the fraud you believe you are. When you operate from love, you’re at your most creative, imagining the future you want to create rather than resisting the present you’re currently in. You focus on how much value you’re delivering, not just how much you’re capturing.


So, you ask, how do I shift from operating from a place of fear and lack to one of love and inspiration? One moment at a time.

Practices to Shift from Fear & Lack to Love & Inspiration

Extend Your Breathing

I once had a meditation teacher tell me that you can change your entire experience of life if you extend your exhale by one second. Just one second. The breath serves as both an indicator and a signal for our nervous system that we’re in danger. When you slow down your breath, you send a signal to your nervous system that everything is okay, and free up your mind for creative activities.

Focus on Your Contribution

Notice the all-too-common tendency to judge and evaluate your own performance. “Why did I say that?” “That email was way too long.” “Why didn’t I ask for the deal?” We spend a good portion of our mental lives criticizing ourselves for falling short of the ideal we hold ourselves to. One great way to instantly transcend this inner conversation is to focus on the contribution you’re making in others’ lives. Imagine the person or people you’re impacting, and what their life was like before you or your company touched their lives. Now create a clear picture of what their life has been like since, and notice the positive difference that you created. Typically, you’ll begin to feel inspired to create more of the same.

Imagine the Future You Want

One of the most pernicious traps we fall into as entrepreneurs is shifting our focus from the inspiring future we want to the frustrating reality that we’re not there yet. We essentially collapse the imagined future into the present, and wish things were different than they are right now. When you resist reality, reality wins every time. Instead, put the future rightfully where it belongs, in the future. Rather than begrudging how far you have to go or wishing you were already there, simply imagine the future you want, enjoy the inspiration and excitement that comes, and take the next practical step forward.

For startups, the culture of the company is largely forged by the inner experience of the founders. Entrepreneurs, it’s time to elevate your inner game for the sake of the people who will be impacted by you and the companies you build. When you choose to believe that you are good enough, and experience the lightness, joy, and love that naturally occurs from that place, you will build an extraordinary company that not only makes you rich, but also enriches people’s lives.

Dave Kashen serves as founder and leadership coach/trainer at San Francisco-based Unleashed, a premier leadership & culture development firm for startups. Previously, he was cofounder of Wellsphere, and worked for SPO Partners and Goldman Sachs. He also writes the awesome culture blog, and you can follow him on Twitter @awesomeculture.


[Image: Flickr user Hans Splinter]