The Olive Vineyard: An Entrepreneurial Metaphor


When I was practicing law  I had a conversation with one of my clients that, looking back, I would say was the most inspirational event that happened to me in my five years as a lawyer.

I’ll never forget the message that he shared with me, and I can honestly say that the idea he shared has profoundly influenced me.

The client was an entrepreneur and had been involved in various ventures throughout his life – some very successful and others not so much. He was in his mid-forties, and his most recent venture has been successful enough to basically “solve the money game” in his words – that is, he had enough money, at the age of 45 to retire if he wanted to.

He was in my office because I was helping him with a simple real estate investment transaction. After several meetings with him where I built rapport, I asked him what he was going to do with his life going forward. He told me that he would continue to start, build and sell businesses – not because he needed the money, but because he enjoyed the process.

He said that having enough money to retire, in his mind, just meant that he had the security to ensure that he did what he wanted to do for the rest of his life – and he didn’t want to sit around, golf, garden, do what “retirees” stereotypically do – he wanted to do what he liked to do, and that was be an entrepreneur.

I thought that was really, really cool, and I thought about that concept as it applied to my own life.  At the time I was building a business on the side of my law practice (the business which is now a significant venture) but I thought that the philosophy was a very sound one.

You live to live – you don’t live to retire. You figure out what you want to do with your time and then you spend all your time doing it, regardless of money. 

This philosophy was both simple and smart. I at once became interested in duplicating his philosophy in my life, and I worked even harder to build our business so that I could spend my time doing only what I wanted to do (which is my case is what I now spend every day doing: being an entrepreneur, writing and public speaking).

Now this idea was profound, but it wasn’t the most profound thing that he shared with me that day. The most profound thing that he shared with me was the reason WHY he loved being an entrepreneur:

Because it allowed him to witness the process of creation.

Then he shared a specific example, using one of his current business ventures. A couple years prior to our meeting he had purchased an olive vineyard in California that was in receivership. He saw value in it, so he took a calculated risk, now his venture was making a profit, but what was even more fulfilling for him was watching the process.

He said that in the vineyard he had the chance to watch the little trees grow, and in the process nurture and cultivate them – give them TLC, and the process of watching them grow from vulnerable little trees, to strong secure, olive-yielding structures was very internally rewarding – so much so that he said that he would keep the operation even if it wasn’t turning a profit.

That was the most profound idea that impressed me that day:

Watching, and being involved in, the act of creation is intrinsically meaningful.

Years later, having created many things including several businesses, several websites, a book (and another on the way), hundreds of unique blog posts and videos, several workshops and seminars, and many other things, I can 100% say that not only is witnessing, and being involved in, the act of creation intrinsically meaningful, it is super addictive as well.

So go find yourself an olive vineyard (metaphorically speaking, or an actual one if you feel so inclined). Give it time and TLC and watch how it changes your life.

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