Life is challenging – and being an entrepreneur often intensifies those challenges. Doing, thinking, planning, anticipating, living in the past, and projecting into the future all create stress, worry, and fear. How will we meet that deadline? Will we make our quarterly numbers? Will we ever exit? Did I make the right decision? Can we raise the next round of capital? Can we compete in our sector? And many other anxieties, real or imagined.

Does this sound familiar? I’m guessing the answer is “Yes.”

The Human Condition

It’s the human condition to be plagued by this compulsive thinking. By some estimates, Westerners in developed societies have roughly 50,000-80,000 thoughts per day – that’s about one every second of our waking hours. Think that’s bad? About 80% of those thoughts are negative. Worse still, 80-90% of them are repetitive. How pointless and destructive to our mental and physical health. What a colossal waste of time and our precious mental energy. Wouldn’t we all prefer to spend that energy on something productive and beneficial? (Like successfully running our companies and nurturing our relationships.)

I view this compulsive frenetic grinding and rehashing of negative thinking (some call it the “monkey mind”) as a bona fide form of mental illness. I’ve learned that when I’m not in free will choice, I suffer. If I kept hammering compulsively without the ability to stop after finishing driving a nail, you’d be right to think I was suffering somehow.

A Thought Experiment

A number of years ago, I took a moment to sit in a quiet room with my eyes closed. I wanted to see just how long I could sit in mental stillness without a thought – absolute stillness, not any thought at all. To choose to be truly still and calm, not to think. I barely lasted a second or two. (Try it yourself. It’s really hard.)

I had had enough of this suffering. But what could I do? I did a 10-day silent retreat in vipassana (awareness meditation), which was definitely powerful. But I was really impelled to another of the core Buddhist mediation practices called samatha, or concentration meditation, as taught and practiced by Theravadan Buddhists for centuries. 

I read and re-read The Jhanas, a how-to book by Ajahn Brahm, which strongly called to me. The Art of Disappearing by Ajahn Brahm is a very readable discussion of the philosophy behind samatha, and is extremely powerful.

Then I went on an 11-day silent retreat in October 2016 with Tina Rasmussen and Stephen Snyder (, two among the first certified Western masters in this practice. It was transformative and revelatory. 

A Cure for the Common Monkey Mind

Samatha practice develops a skill for mental stillness, a letting-go of all of that compulsive thinking. With stillness, profound joy arises both in the mind and physically in the body. I’ve been practicing samatha for more than the past 1,100 consecutive days since that retreat, and it continues to have a profound impact on my life. 

I’m calmer and more focused. I’m less anxious and stressed. I’m more productive and effective. I sleep better. And all that makes me a better entrepreneur, leader, and business partner than I ever have been. Sound good?

Most important, now I have a skill that I can tap into absolutely anywhere and anytime to relieve my compulsive thinking and self-inflicted suffering. Just as important, I can access peace, joy, and energy at will. I meditate in airports, cars, hotel lobbies, forests, as well as at home to create stillness, peace, and joy for 30-90 minutes every day. Definitely good.

The ROI is Compelling

I’m planning to write more about my amazing experience in the hope that you’ll be inspired to explore samatha as well as you seek to be a better person and business leader. 

Your comments and questions are encouraged.

Read more about the author, Stephen Kuhn:

Stephen Kuhn

Experienced tech and finance executive, serial entrepreneur, board member, and investor. Operations, finance, business development. UC Berkeley.


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