Your Biggest Obstacle? You

I recently had a call with one of our CEOs. It was one of the best VC-and-CEO conversations I’ve ever had. I told him that I think I had identified his biggest impediment: it is he.

My exec. coach has coined the phrase “The Inner Saboteur”. In other words, this is the inner voice in your head that may sabotage your self-esteem. Someone praises an accomplishment, but your Inner Saboteur attributes the success to “luck.” You’re late to a meeting, and the Inner Saboteur calls you “stupid.” You skip a work out and have dessert that night, and the Inner Saboteur calls you “weak”.

In this CEO’s case, I’ve been pushing him to add to his executive team. He is moving but it has taken time. So, I told him today: “You’re worthy of a world-class executive team.”

There was a long pause.

We chatted for a long time. I shared with him what my Inner Saboteur tells me. I then predicted what I thought his Inner Saboteur was telling him.

“Wow,” he said. “I’m going to cry. It is almost as though you’re standing there next to me and you’re able to read my mind.”

I write about this to share what I’ve observed in my life and in others: you are your own biggest impediment, most likely. You criticize yourself harshly. You say things to yourself that you probably wouldn’t say to an enemy. You don’t practice self-compassion (more here).

And, over time, your sense of self-worth can erode. You may become reliant on what your boss, parents, life partner, romantic interest and friends say about you. Or, you may seek to target activities that generate the most praise for you. You’re now susceptible to grading yourself always (your net worth, your weight, your possessions, your looks) on a curve.


Instead, consider a point of view that is different. Seek activities about which you’re passionate vs. whether others will “approve” of them. Tie your self-worth to the fact that you’re a unique individual: there has never been anyone like you before, nor will there ever be anyone like you in the future. Seek and live a life of integrity and authenticity.

When entrepreneurs can achieve unconditional self-esteem, I find that they are happy. And, more likely than not, career success follows.

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